I hope you’re having a lovely start to your weekend.

What I’ve been up to:

• Write of Passage 11 finished on Wednesday! It's always busy and overwhelming and exhausting at points, but so rewarding and sad when it's over.

• I published an essay helping Alex Dobrenko with linkedin (using my expertise from being a business undergrad well-steeped in linkedin excellence). It's the first time I tried to write something funny. Hitting publish I felt like I was at the top of a roller coaster for about three hours, but the response has been beyond my expectations.

• This morning I caught a 4:45am flight (don't ask) to Bariloche, one of the top-rated towns in Patagonia.

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

Kurt Vile on spiritual longing and God:

"I think there was always a yearning in me for something else, something beyond myself, from which I felt excluded.

I always felt desirous of those who had a religious dimension to their lives. There was always a yearning. I have come to see that maybe the search is the religious experience - the desire to believe and the longing for meaning, the moving towards the ineffable.

When it comes down to it, maybe faith is just a decision like any other. Perhaps God is the search itself."

📚 book passage i loved:

"No tree, it is said, can grow to heaven unless its roots reach down to hell."

― Aion: Researches into the Phenomenology of the Self by Carl Jung

Jung believed the first step to enlightenment is the encounter with the shadow.

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💡 idea from me: the last saturday mornings

This will be the last saturday mornings newsletter I send.

I started saturday mornings in May of 2021. I was uninterested in school, unfulfilled in internships, and reading for hours each day. Writing became my outlet to share ideas I found fascinating.

Like most big life moments, beginning my Substack feels fated. It’s hard to put my finger on an inflection point. It just happened. 

Two and a half years later, there are over 800 of you here. 

You have shaped me into a better human being with your time, your attention, your kind words, your love. 

You have made me smarter by engaging with my ideas, sharing your thoughts, teaching me new perspectives.

You have helped me find work I find meaningful. 

There’s still ample anxiety and doubt and days I question what the hell I’m doing. 

“dude writing on Substack seriously your gameplan? are u a joke? get a job for sucks sake” inner Tommy says, who can be a bit of an asshole. 

I’m still afraid. But I know I’m on the path. Where the hardship is heavy but worth carrying. That’s all I can ask for.

To cut to the chase (idk why it’s a chase that saying makes no sense) I won’t be sending out writing anymore… in this format.

If my weekend newsletters are the horse and my mid-week essays are the man (lol) my new essays will be a centaur (or is it minotaur??). 

The top will be a personal essay. At the bottom, I’ll have those life update bullets my Mom loves, as well as a quote or question or poem I thought was exceptional. I’ll also include my best photo each week as I continue my foray into photography. Sent out every Saturday morning (my favourite time of the week since I was a little boy).

See the stunning sketch I made:

This week, I deleted Twitter and Instagram. Stopped my daily travel video logs. I canceled plans to make book summary podcasts. I’m not taking any new courses. 

I dream of simplicity. I won’t ever get there if I don’t (painfully) cut back. 

My “main thing” is writing high-quality essays on Substack. Writing is more nourishing than curating quotes and questions, and you seem to resonate more with my essays than my newsletters.

I’m only sharing one post a week. For now. The more I reduce, the more powerful concentration of myself I can pour into each piece I produce.

Less but better. 

I want to spend more time with each essay. Write more words, rewrite more words, scrap more words. So when I do share something with you, it’s really the best I can do. 

As I pour more of my heart into my work, I’m also finding it more exhausting. I was texting a friend about how scared I was Wednesday after publishing. Then I woke up Thursday morning like “I have to do this again???”

And my job with Noah Kagan will get busier as we get closer to the launch of his book Jan 30/2024 (exciting news coming in the New Year on that…)

I’m slowly learning creativity demands rest, kindness, self-care. Cutting back is alien to me. My instinct is to do more. But my writing suffers when I work myself to smithereens. 

A friend I admire told me he’s only doing three things: reading, meditating, and BJJ.

It made me ask, “What are my three things, if I could only pick three?”

Writing and reading aren’t going anywhere. My third… probably photography. Journaling counts as writing. And my lecture series counts as reading. It’s not cheating I swear. I also want to practice guitar and exercise/yoga every day and learn a martial art. 

Damn… reduction is even harder than seduction. Both are a work in progress. 

Growing an audience is exciting, something I dreamed of for a long time. But also scary. I don’t want to lose sight of myself.

Moving forward, I’m obsessed with questions like: 

• How do I make my writing beautiful? 

• How do I craft more compelling stories? 

• How do I make my essays an aesthetic experience? 

In the end, I hope this all results in writing you love. Writing that makes you think, writing that makes you feel, writing that makes you smile. 

Like any new chapter, to turn the page is to experience both euphoria and terror. At the same time. 2023 has been quite the year and I have an inkling 2024 will be even better.

I’m just learning to focus, to say no. I’m just starting to read humanity’s great books. I’m just beginning to show up more as myself on the page.

I’m just hitting my stride.

Psst. I’m sharing a lot of fun-stream-of-conciousness type writing every day on Substack Notes. So if you have a Tommy-shaped hole in your heart, follow me over there & we can go back and forth on ideas and hopes and dreams and secrets and what’s keeping us up at night.

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❓ question i’m asking:

What am I devoted to?

This week, I listened to a Dharma talk on desire & devotion.

It reminded me of an idea from DFW: We all worship. We're all devoted to something.

We only get to choose what we worship.

📸 photo of the week:

My best photo from Week 7 of learning photography in public.

Turned up the pink tint because i want to see the world with rose-colored glasses.

See my best four photos on Substack Notes.

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

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3- Get in Touch. If my writing resonated or if you just want to be friends, please reach out. Reply to this email or leave a comment! (I respond to everyone)

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You got all my love,

Tommy

I hope you’re having a lovely start to your weekend.

What I’ve been up to:

• I published an essay on graduating & growing up. It's an ode to friendship and a love letter to my friends.

• I'm organizing an IRL weekend "Airbnb in the woods" type writing retreat in early 2024! If you're interested in going to the retreat or sponsoring the event (or may know someone who would), you can read the full manifesto and apply here.

• My Dad and brother left Buenos Aires to tour the rest of Argentina. I'm still hanging out here for the next bit. It's the furthest I've been from home and still adjusting to being alone, but all around it's going well :)

• If Noah Kahan makes these songs I’d like to formally take credit now.

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

Poet W. H. Auden on laughter and love:

"Among those whom I like or admire, I can find no common denominator. But among those whom I love, I can: all of them make me laugh.” ​

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📚 book passage i loved:

"A man's eye reveals his quality.

It shows how much of a man there is within us. We declare ourselves by the light that gleams under our eyebrows. Petty spirits merely wink; great spirits emit a flash of lightning. If there is no brilliance under the eyelid, there is no thought in the brain, no love in the heart.

A man who loves exerts his will, and a man who exerts his will radiates light and brilliance."

― Toilers of the Sea by Victor Hugo

💡 idea from me: my dogdamn bus ticket

“No… No visa”. 

My eyebrows scrunch, my hands convulse, my neck flashes hot.

Earlier that morning, my Dad and brother caught a flight north to Salta, leaving me in the Airbnb (and in the second biggest city in the continent) alone. Despite my sleep-deprived state, I wanted to clear a few things off my plate. Hoping it would put my mind more at ease. 

The biggest was my bus ticket. 

It’s not for a few weeks, but I read online that if I don’t have a printed copy, I won’t be let on the bus. Nightmare. Printing is a headache in Canada, where I speak the language, so I wasn’t necessarily frothing to figure it out here. 

I close the door to our Airbnb one last time, put the key back in the lockbox, and step out the front door in my wool sweater. 

Rain is falling in silver sheets. “Oh… Great”. 

I head down the sidewalk, ducking under store canopies, towards what looked like a business center I had passed every day on my way to the gym. But, only 30 seconds into my walk I notice a small convenience store on the other side of the street, with a sign above “Impresions”. 

I run over to get a closer look and see a printer through the front window. “Okay, maybe this won’t be so bad”. 

The store is empty except for a middle-aged woman behind the counter. I slide open the door a crack, stick my head in and mumur a hopeful “¿Hablas inglés?”

“A little,” she smiles.

I step in and start to explain how I need to print my bus ticket.

“No a problem. Send it here and I will print for you,” pointing to a laminated sign taped to the plexiglass with an email address. 

I pull out my phone with the tickets already loaded. I flip on my eSIM data, go to Gmail and hit send. The blue circle spins and spins and spins… and then stops spinning. I’m standing in this small store two feet away from the woman who’s staring at me.

“You gotta be kidding me. It says it’s fucking connected.” 

The woman’s husband had come out of the back of the store. He got everything by the look on my face. I point towards the door and open my mouth, but he spoke. “The connection is bad in here,” in a warm tone. “Try outside”.

I know my data is a lost cause, but I may be able to get wifi from my Airbnb on the sidewalk. 

I step back out into the rain, hopping between puddles until I get to the entryway that is now so familiar. I huddle under the narrow porch canopy, pull out my phone, go to Settings. The wifi network pops up. I hit connect. It connects. I go to my email. Nothing loads. I try to Google something. Nothing works. I go back to the wifi. It says “No Connection”. 

It’s chilly outside but my palms start to sweat. 

I forget the network. I find the 5G wifi. I hit connect. It connects. I go to my email. It loads. I go to my Google Drive and find the ticket. I go back to Gmail. “Wait, I don’t have the email?”

I’m close to giving up. Very close. But I take a deep breath.

Then another. 

I trudge back to the print shop, walk in, and try to subtly take a photo of the email address (although it’s a small shop and I wasn’t subtle at all).

I head back into the rain, back to the Airbnb. But, halfway across the street, I hear a voice. I turn around and see the husband standing in the rain, waving me back in.

“You can use our wifi to connect,” he says as I walk through the door.

I hand him my phone and he takes his glasses off his forehead and puts them on. Pepper gray hair crowns the top of his head. He’s wearing a worn-down button-up shirt, green with thick folds of canvas, sleeves rolled up his burly forearms to his elbows. My phone looks miniature and metallic in his big, leathery hands.

He finds the network and punches in the password with his pointer finger. It connects. 

I type in the email address and send the ticket. The wife gets the email and prints it out and hands it to me. Just a single page.

A sign on the counter says “IMPRESIONES … $60”. 

“Visa?” I ask.

“No… No Visa.” 

“The bank charges us a big fee to use a credit card,” he explains. “It’s too expensive for only $60. You don’t have cash?”

I slowly shake my head no. 

“What’s the minimum amount to use a Visa?” I ask.

“300 pesos.”

“Let’s just do 500,” I reply in relief. It’s almost 10 times the price, but still 60 cents CAD. They had been kind and the economy isn’t doing well and I was grateful to have the bus ticket finally printed.

The man looks me in the eyes above his glasses that are bridged on his nose. Nods. Picks up the credit card machine, punches in the amount, takes my Visa, and taps it. I hear a reassuring beep. Tension releases from my shoulders like a hiss of air from a tire.

He rips off the receipt and hands it back with the card. I shove both in my pocket.

The man asks where I’m from.

“Canada… Toronto actually.” 

“Toronto,” he echoes, tasting the words in his mouth.

I tell him I’m very far from home but I love Buenos Aires. 

He asks me if I know where to get cash and warns me about the people who offer to exchange money on the street because they may give me fake pesos and recommends I go to an official exchange place instead and tells me where to find them. 

We chat for a minute or two more and then I thank both of them. I step out. The rain had stopped and the sun had begun to peek out from behind dark clouds. 

As I head down the street, I reach in my pocket for my card to put it back in my wallet.

I see the receipt. Before I crumple it up to toss it in the trash, I skim it. My eyes stop in their tracks. 

“300 pesos” it reads.

I refuse to believe there is no hope for our world.

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❓ question i’m asking:

Where am I not communicating out of fear, but that’s creating the very problems I’m afraid of?

📸 photo of the week:

My best photo from Week 6 learning photography in public. See my best four photos on Twitter.

Bonus PDF

Okay you got to the bottom so I know you’re cool.

Last month, I was going to set up this elaborate referral program & try to get you to run through it like a rat in a maze like James Clear told me to (sorry James) but I realized I don’t wanna do that cuz I love you too much.

The main bonus was going to be a really valuable PDF I spent 3 years curating titled, "Great Poems Most People Have Never Read"

A lot of poetry is lame but this poetry is the opposite of lame.

Reply “Tommy” to this email and (if you’re feeling up for it) your favorite thing to do on Saturday morning.

I’ll just send it to ya.

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

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3- Get in Touch. If my writing resonated or if you just want to be friends, please reach out. Reply to this email or leave a comment! (i respond to everyone… and i definitely need friends)

Pura vida,

Tommy

I hope you’re having a lovely start to your weekend.

What I’ve been up to:

• This week has been my busiest in a while. Many 12-hour work days :( There's just a lot to do.

• When I sit at my computer all day, I burn my brain into a confused submission and feel spacy, until I get outside for a few hours. I feel like I don’t have a body. It's not my ideal existence. But I'm learning.

• I published the longest essay I've ever written on my experience switching from meditation to Morning Pages. I didn’t think anyone would read it. But the response has been so heart-warming.

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

Writer and philosopher G. K. Chesterton on love:

“There is the great lesson of 'Beauty and the Beast,' that a thing must be loved before it is lovable.”

📚 book passage i loved:

“I haven’t meditated, and I know I have been afraid that meditation might open up lots of things that could delay the passage of this craft I’m rowing. It is an intentional limitation in order to go in a direction and get there. And I have gotten there, and I know it…

Each of us has individual capacities. The real trick is knowing the machinery of the boat in which you are crossing the channel.”

― A Joseph Campbell Companion by Diane K. Osbon

Psst. This quote from Campbell was the crux of my essay this week.

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💡 idea from me: your inner child

Early one morning, I sat down at my desk, cracked open my worn leather journal, and started drawing a design for a guitar stand.

Back at home in September, I dug out my Mom’s old Yamaha Folk guitar from the cellar. Dusted off the cobwebs. Taught myself a few chords.

The case is heavy and clunky and ugly. But the guitar is beautiful. I decided I would build a stand for it. For aesthetic beauty. But also to work on a meaningful project with my hands and learn a bit of woodworking in the process.

One night last week, lying in bed, trying to fall asleep, a vision for the design of the guitar stand beamed into my brain (God only knows why).

It took me a few days, but eventually, I couldn’t ignore it any longer.

I haven’t drawn a design in at least a decade.

But when I was a child, I’d sit at our dining room table with piles of printer paper and a big blue basket of sharpened Crayola pencil crayons, and draw for hours. 

I wanted nothing more than a tree house in our backyard. I must’ve drawn a hundred variations—with rope ladders and trapdoors and secret passageways and drawbridges and slides. I was so insistent on building one, I remember mapping out each step of the process to make it easier on my parents (all in 10 steps on a single sheet of paper… couldn’t be simpler). I made a list of all the materials needed, down to the number of screws. 

More than anything about my childhood I remember this obsession with design, which still feels crystal clear despite its remoteness in time. 

When Carl Jung wanted to follow his bliss, he asked himself, "What was the game I enjoyed when I was a child?" 

Jung remembered he loved to design towns out of little stones. He bought a property and began to build a home. It was a lot of work and utterly unnecessary because he already had a home. But for Jung, it was sheer play.

“What did you do as a child that made the hours pass like minutes? Herein lies the key to your earthly pursuits.”

It’s funny how as adults we start to slowly transition back into the things we loved as children. The path to bliss is kindling the joy & wonder of a child with the wisdom & maturity of an adult. A fusion of imagination and practicality.

As I’m sitting at my desk drawing, my brother—who knows me more than anyone in the world—is writing beside me. He leans over, sees my page, and says “Hey, it’s just like when you were a kid”.

I have zero carpentry skills but I’m building that guitar stand.

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❓ question i’m asking:

When was the last time I asked for help?

📸 photo of the week:

My best photo from Week 5 learning photography in public. See my best four photos on Twitter.

I’ve also fallen in love with the 1920’s Norman Rockwell autumn aesthetic:

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

3- Get in Touch. If my writing resonated or if you just want to be friends, please reach out. Reply to this email, leave a comment, or find me on Twitter!

I respond to every single reader.

Much love,

Tommy

I hope you’re having a great start to your weekend.

What I’ve been up to:

• I've been busy as ever writing essays, working on a resource library and bonus bundles for Noah's book, and being a student/editor for Write of Passage.

• I'm working my way through Jordan Peterson's Biblical Lecture Series on Genesis.

• I published the most popular thing I've ever written on my love for lighted windows.

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

Scottish novelist Robert Louis Stevenson on keeping your soul alive:

“To know what you prefer instead of humbly saying Amen to what the world tells you you ought to prefer, is to have kept your soul alive.”

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🖋️ poem i adored:

💡 idea from me: a journal entry

You found your wool sweater with that one burn hole in the sleeve from last summer. Dug out your Blundstone boots from the basement, mud still caked on the heels. Put on your worn-out blue jeans. 

You always said Fall was your season.

Hot coffee. Frosty grass. The blue and gritty sky. Golden light crowning the tops of trees. Leaves piled up on sidewalk curbs. Road hockey games. 

Then you remember you haven’t been home for Thanksgiving for two years. And you forget what color your Blundstones are.

~~~

You bought a plane ticket to Argentina. Because that’s what young geographically-independent people seem to do. There was a time you thought travel would solve your problems. 

You still work all day. Sit down at your desk, let your coffee go cold, microwave it every 30 minutes. The hours melt together into one Google-suite-induced haze. You look up and it’s almost evening. Your brother has to drag you out to explore. 

Most days, you feel calmer. You’ve started to book bus tickets, flights, hostels in advance. You used to leave it to the last minute. It used to make you anxious. That makes you a little proud of yourself which feels strange, also silly.

You learned to bake scones. Your family is amazed. You retort that recipes are easy to follow and you don’t get how it’s so impressive. Then you tried to make gnocchi but it fell apart in your hands. No one told you how hard it was. The recipe lied. 

Your hair is growing longer. Your Mom jokes over Facetime you should cut it, but she’s not really joking. You say it makes you look more like a creative spirit. You hope one day it will cover your eyes.

You journal more than you used to. You hope the words will run out, but they don’t. The pen never catches up to your thoughts. There’s always something left unsaid. 

You found Gregory Alan Isakov. You listen to his one album on repeat. It reminds you of home. Of a person you could be.

~~~

You dream of Paris and cold winters. You think the cold will clear your head. 

You keep adding to your list of places to travel to. A note in your phone creatively titled “Travel ✈️”. You keep daydreaming. Of beauty and simplicity and natural light — a reduced life, where nothing is missing. 

The truth is, you’re scared. You’re scared of going big, of actually committing, so you take on more things. Insurance, maybe.

But you have no one to complain to. You’re exactly where you wanted to be. You’re living the days you once fantasized, not stuck in a 40th-floor cubicle. Your Dad says you’re living the dream. He’s right.

~~~

You met some of your idols. You realized they’re human, just like you. Your dreams feel closer but still too far away. 

You say you’re scared of failure but you’re more terrified of success. You say you want to be noticed but you’re afraid of being seen. You hate the spotlight. Something you wrote went semi-viral on twitter and it scared the hell out of you. People on the Internet are mean.

Each week you worry you’re going to run out of things to say. But you still show up every day. Honest. Earnest. You still open your heart. Bleed. You’re better at showing up as yourself on the page, being vulnerable, but sometimes you think no one cares.

You were told the discipline will lead to something but what if it doesn’t.

You said you’re done thinking about the future but it still nags at you. Life still feels so undecided. Unshaped. You’re not sure if you’ve grown more tolerant of uncertainty or just become numb to it. “Maybe it’s the same thing,” you think. 

~~~

You’re getting older now. You’re not allowed to shrug, say I’m still a student. 

You thought you’d have it figured out by now. You thought you’d have more answers. You’re tired of asking the same questions. 

It’s just like you to think that the hard work will all pay off. It’s just like you to think that fullness lies around the next corner. You’re starting to see the holes in your own logic. You can poke your fingers through. 

Your boss tells you he needs more out of you. You mumble some excuse and thank him for his feedback. But deep down you want to keep you for yourself. 

Everyone seems to want more of you. You’re not sure how much you have left to give.

You smile. You send emails with one exclamation mark at the beginning and one at the end. You try to say kind things. Even when you don’t feel so kind. You try to care. But you’re getting worse at it. 

You don’t get why you have to build Excel spreadsheets and fire off emails when you could be reading Plato’s Republic and trying to understand the Christian foundations of the world and what it means to be human and how to cope with the fact you will die soon. It doesn’t make sense. 

Nothing seems as interesting as your own thoughts. You worry you’re becoming unemployable. If only you had a trust fund, you joke. 

You started to think about God. You see Him everywhere. You’re not sure if you’re religious but you’re no atheist anymore. You worry your family will think you’ve become a Bible banger. But you just want answers. You just want Truth.

~~~

You find that jean jacket in the closet you love, the one with the fur around the collar your high school girlfriend bought you. You realize you’re wearing all denim, but no longer care.

You step out to the crisp morning air. The breeze smells like damp earth and fresh beginnings.

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❓ question i’m asking:

From poet Mary Oliver:

Listen, are you breathing just a little, and calling it life?

📸 photo of the week:

My best photo from Week 3 learning photography in public. See my best four photos on Twitter.

I also spent all Sunday making a mood board. It’s the new lock screen on my phone. If you’re curious, I wrote about it.

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

3- Get in Touch. If my writing resonated or if you just want to be friends, please reach out. Reply to this email, leave a comment, or find me on Twitter!

I respond to every single reader.

Much love,

Tommy

I hope you’re having a great start to your weekend.

What I’ve been up to:

• Write of Passage is underway and I've been busy writing, editing, and attending live sessions. Although it's my 3rd time around, the course changes each time. With such amazing people in the community, it continues to reward me for every ounce of effort I put in.

• I published my first WoP essay on creating more agency in my life.

• I'm exploring a little bit of Buenos Aires each day & eating plenty of pastries (they put dulce de leche on everything). While it's not good for my body, it's good for my soul and that has to count for something.

Good luck to my Mom and sister running their second half marathon this year together :)

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

American essayist Ralph Waldo Emerson on how we show our character:

“People do not seem to realise that their opinion of the world is also a confession of character.”

📚 book passage i loved:

Many times in my life I have been ashamed because I caught my soul not daring to do what supreme folly—life’s essence—was calling me to do.

― Zorba the Greek by Nikos Kazantzakis

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💡 idea from me: the future doesn’t exist

Written in December 2022 (Version 1)

*Revised in October 2023

My brother and I have a running joke that "the future doesn't exist".

We planned this trip to Argentina for months and wanted to be here so badly and now we're here. And Buenos Aires is an unbelievable city. Yet, we catch ourselves fantasizing about coming home for the holidays, planning our next trip.

"The future doesn't exist" is a little reminder that we need to be here while we're here. 

~~~

There seems to be a deep-rooted human desire to be somewhere we're not. A desire to be"anywhere, but here."

Living in Canada most of my life, I drooled over vagabonding across Europe. Then I actually did it. Last year, I spent 26 weeks abroad. But, despite doing what I had coveted for so many years, I often missed the familiarity and comfort of home.

The backpackers I met in hostels, in renowned cities like Rome, Prague, or Vienna, would rave about all the places they want to visit next, forgetting the grandiosity of the place they're in.

It's not only travel.

City slickers visit small towns and ache at how picturesque the countryside is, while the townsfolk are scratching and clawing to escape.

Single people crave the connection and companionship of a relationship, while those in relationships pine for the freedom of being single.

The masses hunger for the luxury and opulence of money, while the rich are burdened by meaninglessness and shackled by golden chains.

Peter Thiel once worked for a prestigious law firm in New York City, where the hours were long and the competition was cutthroat. He recounts, "On the outside, everybody wanted to get in. On the inside, everybody wanted to get out."

When I had a straightforward career path, I fantasized about the coming-of-age experience of wandering and being a little lost and figuring my life out. Now my path is less predictable, I ache for certainty.

~~~

There's an annoying cliché that "we want what we don't have". But, it's more than that. You could almost say: "we want the opposite of what we have".

Books or advice or a "stern talking to" don't seem to help. Wisdom doesn't transmit well through words. It only blooms through experience.

I have a friend. Let's call him Jeff. A few years ago, Jeff decided he needed to break into finance. He glorified the 80-hour weeks, cocktail lunches, bulky bonuses. A mutual friend was worried Jeff was losing sight of himself. No matter what he said, Jeff wouldn't listen. Jeff was convinced a job in finance was the missing puzzle piece of his life. Eventually, after months of stress and strain, Jeff got the job in banking he wanted. Within days, reality hit him like a brick wall. His illusions shattered. Within weeks, he wanted out.

We create ideals of the things we don't have. They seem perfect in our minds. They promise the fullness of being we lack and long for. But, because we haven't experienced them, they lack detail. Yet, reality has a surprising amount of detail.

The jagged edges are forgotten or smoothed over. We don't consider the lower back pain from the 14th hour of hunching in a swivel-chair and mastering the shortcuts of Microsoft Excel, the stiff steel springs of hostel beds, the pervading loneliness spending Saturday night staring at the ceiling.

No books or lectures or podcasts can supplement the detail reality has.

~~~

We will spend our lives learning hard things the hard way.

All the mistakes, all the falling off, all falling away and stubbing our toes, seems necessary. I had to gallivant around Europe to realize Hemmingway was right all along: “you can't get away from yourself by moving from one place to another.” I had to fall out of a relationship to learn my problems are just as stubborn when I'm single. I had to waste hours fantasizing about the future, how glorious it would be, to see how the future never came.

As numb as we are to words of wisdom, we always find our way back to their truths after learning their lessons the hard way.

Instead of wanting to be "anywhere, but here", I'm reminding myself: "I'd rather be here, than anywhere".

Besides, the future doesn't exist yet.

Psst. If you enjoy my writing, it’d sure be cool if you subscribed :)

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❓ question i’m asking:

What is prayer?

📸 photo of the week:

My best photo from Week 3 learning photography in public. See my best four photos on Twitter.

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

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3- Get in Touch. If my writing resonated or if you just want to be friends, please reach out. Reply to this email, leave a comment, or find me on Twitter!

I respond to every single comment (find one I didn’t I dare u).

Much love,

Tommy

I hope you’re having a great start to your weekend.

What I’ve been up to:

• I arrived in Buenos Aires, Argentina late Sunday night. I've been excited to visit ever since I read the 4-Hour Workweek in early 2020. I'm trying to do a new thing every day and avoid falling into a rut. So far, I have loved it here. Top 3 cities I've visited.

• Write of Passage kicked off Monday. I'll be busy as I add an Editor and partial Student role to my plate.

• I published an essay Tuesday painting the landscape of my ideal life in the countryside. (My BIG essay I'm working with Alex Dobrenko on is taking longer than anticipated and still far from publishing... yet I think it'll be worth the wait).

Early take on Buenos Aires: cheap steak, beautiful people, French architecture, bakeries on every corner, vibrant flower stands, cozy cafes, safe streets, warm weather.

Happy Thanksgiving to Canada :)

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

American writer, Joseph Campbell, offers perspective:

“Life is pain; life is suffering; and life is horror — but, by God, you’re alive.”

📚 book passage i loved:

“Wisdom cannot be imparted. Wisdom that a wise man attempts to impart always sounds like foolishness to someone else...

Knowledge can be communicated, but not wisdom. One can find it, live it, do wonders through it, but one cannot communicate and teach it.”

― Siddhartha by Hermann Hesse

💡 idea from me: how my nice week went to shit

It has been a tough week.

I have been busy, stretched thin, like too little butter scraped over too much bread, and have edited this little, not enough to edit out my attempt to sound Oxford-ian (and remove useless sentences like this).

I was hesitant to write this.

One thing I wish more of my favourite Substack writers did was humanize themselves. Balance their beautiful becoming with some ugly reality. I’m not much for podiums (In fact, I fell off an Olympic podium in Lake Placid).

Netwon said every action has an equal and opposite reaction. So perhaps sharing my journey on the struggle bus may do you some good.

~~~

I haven't been sleeping much. I get into bed by 10pm but my mind races. Ideas run back and forth in my head like a blind man knocking over furniture. I try to focus on my breath, clear my mind, 4-7-8 myself into a sleepy submission. But it lasts sparse seconds. My head constructs a to-do list and writes tweets that sound smart and drafts emails to send. It must be an hour or two before I finally enter the kingdom of sleep. Except it has felt like less of a kingdom and more of a jail cell.

I wake in the dark hours of the morning. My sheets soaked in sweat. Blankets kicked onto the floor. Tired but unable to return to rest. I lay in bed until dawn. With dreams that slowly return to memory like a strange polaroid still developing. Dreams I dare not whisper to a bright-eyed old man through a curtain. I try to nap in the middle of the day but I am never able to fall asleep.

I think I'm getting sick. My forehead has been running hot like a car radiator. My throat is sore and scratchy. I've been popping Tylenols like tic-tacs.

I'm still writing, working, exercising. “No zero days,” they say.

Chasing my to-do list like a dog chases cars. Never able to catch up (and not sure what to do with myself if I ever did). Like the White Rabbit Alice meets in Wonderland: always in a hurry, time always just out of reach.

In typical Tommy fashion, I have piled more onto my plate this month with no intention of taking anything off.

Write of Passage is underway until early November. As an editor and student, it adds 20 hours of working screen time to my week. But I still want to keep up with my journaling and the Artist's Way and publish this newsletter as well as high-quality weekly essays you'll love & resonate with and this huge meaningful essay I'm working on with Alex, and start Jordan Peterson's Genesis Lectures and continue to share ideas on Twitter (so I get more followers and then finally my anxiety will vanish and I'll feel validated) and get all my work for Noah done and my daily photos and the video logs I'm sharing on Instagram. Plus Jack wants to get out and explore Buenos Aires more while we're here, and he's right, but I could sit at the desk and work the whole goddamn day.

I haven't been reading much, which is sad to admit. When I finish up my work by the evening, my brain is too burnt to process anything meaningful. 

I know I'll have to make some hard discerning decisions of what to cut. I know I'll have to shoot some of my desires in the head. At least for this month, this season. "Hard decisions, easy life," they say.

More realistically, my desires will be torn from me.

That's the thing about trade-offs. There's no precise right way to make them such that all my wants will be satisfied. I'm slowly starting to accept that trade-offs mean some of my wants certainly won't be satisfied.

I think people underrate how intensely painful focus is. It nearly kills me to say "no" to the good things, so I can say "yes" to the great things. Or just so I can have time to not go crazy. I don’t want a backburner, I want four frontburners.

"Less but more," they say.

I get frustrated with myself. I fantasize about this simple, sweet, reduced life where I have this rich existence outside of my laptop. Yet I tend to take on so much "laptop stuff".

I get frustrated with my meek human abilities. How dare it fall ill? Why is my head so muddled past 7pm? Does it know how much work must be done?

I'm just beginning to get better at listening to my body—admitting when I am tired or burnt out and need a break without feeling guilt.

~~~

These were disjoint thoughts, as are so many of my thoughts these days.

My new plant sits beside me on my desk. I forgot to water it for two days because I was busy. Its leaves started to wither and drop. But this morning I took it to the faucet and gave it a nice sprinkling of water, like Spring Argentine rain, and placed it on the windowsill to bathe in sunlight.

Already, its leaves are beginning to rise.

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❓ question i’m asking:

If my only goal today was making my day tomorrow excellent, what kinds of stuff would I do?

📸 photo of the week:

My favourite photo from week two of learning photography in public.

Sorry for the bad quality. If I still had my iPhone 8 it would be much better.

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

3- Get in Touch. If my writing resonated or if you just want to be friends, please reach out. Reply to this email, leave a comment, or find me on Twitter! I respond to everyone.

Much love,

Tommy

I hope you’re having a lovely start to your weekend.

What I’ve been up to:

• I've spent the past week writing, working, and exploring Rio de Janeiro with my brother. We went to a Brazilian steakhouse, hung out with monkeys in a park, wandered through stunning botanical gardens, had a traditional feijoada lunch, toured downtown, took a cable car to the top of Sugarloaf Mountain, dove under crashing waves in the Atlantic ocean, and saw the iconic Christ the Redeemer statue. It’s been strange integrating work with travel but figuring it out as I go!

• In the evenings, I've spent more time than I'd care to admit making Pinterest boards for aesthetic home design. Super fun. I'm slowly recovering a visual sensitivity I haven't kindled since I was a child.

• Today, we're packing up and heading to the airport to fly to Buenos Aires where I'll be spending all of October. Write of Passage starts Monday and I'm fired up.

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

U.S. President Harry Truman on the risks of recognition:

"It is amazing what you can accomplish if you do not care who gets the credit."

📚 book passage i loved:

“The world is indeed full of peril, and in it there are many dark places;

but still there is much that is fair, and though in all lands love is now mingled with grief, it grows perhaps the greater.”

― The Fellowship of the Ring by J.R.R. Tolkien

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💡 idea from me: notes on rio de janeiro

I've spent the past 10 days in Rio which is the most time I've spent in any city outside of Canada (besides when I lived in Porto for three weeks or Pamplona for four months).

Here are my notes:

Safety.

For most of my adult life, up until about two months ago, I believed Rio was an extremely dangerous city. Like a "drug trafficking get shot in the street don't even bother thinking about visiting" city.

It continues to amaze me how little I know about the world, yet how much I default assume/pretend to know. (Aside: I had the same thought looking at the biodiversity of wild cactuses in the botanical gardens. So much of the world remains a mystery.)

Like any city, there are parts you don't want to visit, especially at night, and I'm more cautious here than I would be in Toronto. But overall it has felt very safe.

There is an evident police presence. I counted at least four different police forces. Policemen patrolling every few blocks (but mostly scrolling on their smartphones).

The biggest risk to tourists is having your iPhone snatched if you're flailing it around on a busy beach boardwalk. Of course, the simple solution is to not flail your iPhone around on a busy beach boardwalk.

If you read the travel advisory or watch the news, with "high crime rates and regular incidents of violence," you'd think Rio is a violent battleground (I got scared again reading it) when it’s actually a pretty well-off city. A lot of good, normal people just going about their lives.

Although important warnings, these information sources take a seed of danger and plant it into a garden of fear.

It’s a bit sad. If we're led to believe the world outside our front door is a violent and dangerous place, we shut our blinds and stay inside. We begin to believe human nature is violent and dangerous and the earth is a hellish landscape and we're not far from descending into fiery Armageddon.

The only place that seems safe is our home, because we know it through experience, while everywhere else seems dangerous, because we're told it is.

In general, I think we're ruled far less by objective facts and far more by cultural narratives than we care to admit.

Hesitant to conflate safety with general kindness, people here have been kinder and warmer and friendlier than almost any city I've visited. From our first Uber driver joking about Canada being "muy frío," to a grocery store cashier (with excellent English) noting what a beautiful country Canada is and how he'd like to visit Montreal one day, to Pedro at the gym letting us workout the first time for free, to the doorman in our building who always says good morning.

No matter where you go, I’ve found people are just people. Everywhere in the world people laugh, dance, drink, move their bodies, eat good food, tell stories, express love. Seeing this across cultures makes you appreciate it more.

Beach Culture.

If you pay attention, most cities whisper a subtle message. Rio whispers: Go to the beach.

Rio's beaches are the hub of social life when people aren't working and, because the beaches are always busy, it seems like people are never working.

I see the influence of "beach culture" everywhere. From the clothing to the beach body aesthetics and tanned golden skin, down to how storefronts are designed to be open with outdoor seating so patrons can visit sandy and partially clothed.

The wealthiest (and safest) neighborhoods are all along the beach and real estate prices are the highest because everyone wants to live there. It's a sign of prestige. While the favelas (the poverty-stricken and dangerous housing areas) are secluded up in the steep mountains.

There's even a fairly strict beach etiquette: what to bring to sit on (not towels), what to wear, what to drink.

On Sunday, I took the subway into the city. Our train was empty but the one heading to the beach was packed like a can of sardines. The downtown core was an eerie ghost town. Everyone had left the city and gone to the beach.

In Rio's main cathedral, during service, attendance was scarce.

As DFW wrote: There is no such thing as not worshipping. Everybody worships. The only choice we get is what to worship.

Here, people seem to worship at the beach.

Architecture.

The most startling difference in Rio versus European cities I've visited: the lack of a sense of history. It doesn't feel old, but it also doesn't feel modern. Somewhere in the middle. There aren't many old buildings and hardly any (noticeable) churches.

Most of the original colonial buildings have been knocked down and replaced by taller apartment buildings, which are currently being knocked down and replaced by more modern apartment buildings.

In places trying to improve the standard of living and catch up to the modern world, an emphasis on history often falls by the wayside. People are careening towards the future, not reminiscing about the past. As Maslow tells us, survival cares little for actualization.

My tagline for Rio de Janeiro would be: If you love the beach, you'll love it here.

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❓ question i’m asking:

What’s the most beautiful life I can imagine for myself?

Am I making the decisions that would get me there?

📸 photo of the week:

My best photo from last week. I shared my best four photos as well as my approach to learning photography as a beginner on Twitter.

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

3- Get in Touch. If my writing resonated or if you just want to be friends, please reach out. Reply to this email, leave a comment, or find me on Twitter! I respond to everyone.

Much love,

Tommy

I hope you’re having a great start to your weekend.

What I’ve been up to:

• After hearing how Jennifer Roberts, a professor of art and architecture at Harvard, offers this challenge to her students I went to the Art Gallery of Ontario alone on Sunday to stare at a single painting for 75 minutes.

• The Noah Kahan concert on Sunday was splendid. Dare I say, best concert I've been to. (1) Noah Kahan, (2) Tragically Hip, (3) The Lumineers.

• On Wednesday I flew to Rio de Janeiro, Brazil with my brother! I'll be in Rio for 10 days then Buenos Aires/Patagonia until mid-November. I guess that makes me a digital nomad (although I cringe at the word). I'm curious to see if travel-working is everything it's cracked up to be.

• I've spent the past few days settling in, working, and exploring Rio. If you want to follow along, I'm sharing daily video logs and my best photos on Instagram (@tommy_dixon__).

• I'm putting a ton of time into this new essay. My intention was to share it Tuesday, but it won't be ready (currently +7,000 words and a huge mess). However, once done, I think it'll be something I'm very proud of and hopefully something you love... I want it to be the most raw and real thing I've written. (Spoiler: it’s on my addiction to work.)

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

American philosopher John Rawls on true fairness:

“The fairest rules are those to which everyone would agree if they did not know how much power they would have."

📚 book passage i loved:

You enter the forest at the darkest point, where there is no path.

When there is a way or path, it is someone else's path.

You are not on your own path.

If you follow someone else's way, you are not going to realize your potential.

― A Joseph Campbell Companion by Joseph Campbell (edited by Diane K. Osbon)

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💡 idea from me: homesickness

Waiting at the gate in Toronto's Pearson Airport, I already felt very far from home.

Thoughts began to fire in my mind like loose canons. Am I really going to South America for two months? It’s so far away. Home isn’t so bad. Plus Fall foliage in Ontario is gorgeous. And Mom's been making some great dinners. Why am I leaving?

I always get like this. I miss people, places the most at the moment of departure. That's when my homesickness sinks in the deepest.

Memories flash back. Giving my Mom a last hug as she climbs into the car and tries not to cry, leaving me in my university dorm. Glancing back at A as I board the train, the words "I'll see you in 10 weeks" still tasting sad in my mouth. Closing my bedroom door after a final glance before leaving to live in Spain last Fall.

Now, waiting at the gate at Pearson.

The irony is, there's no escaping homesickness. Either homesick or sick of being home. Wanting to leave, then missing its familiar comforts.

I moved back home in April. But I've had the felt sense I can't remain there. I’d be limiting myself. "If I stay home literally, I'll stay home metaphorically," I wrote in my journal one morning.

It's easy to grow complacent, static, even lazy at home. Comfortable but constricted. Not expanding. Not meeting new people, challenging my beliefs, opening my eyes. Downloading scripts from family instead of writing my own.

I need to become my own person. Throw myself into the deep end, learn to swim. Stop fearing the ocean. Maybe it's because I'm the youngest.

I went through the early stages of the Hero's Journey. First, hearing the call the adventure. The sense I have to leave home, journey from a known to an unknown world. That there’s something more “out there”. Then, wanting to refuse the call. In early August, I thought this whole thing was crazy. I wanted to run to safety. Cancel the trip, get a full-time job, move downtown like all my friends. But I didn't. Despite the fear, I knew somewhere deep down I had to stay true. I had an adventure ahead.

As I was saying to my brother the other night, "this is it". This is the lifestyle, the freedom, the flexibility we glorified. Being able to work on a laptop from anywhere in the world. We're here. We're doing it. We're living the exact thing we want to be living.

I could be doing anything this Fall. Stoking a fire in a cabin in Vermont, hiking oceanside cliffs in Vancouver, staying home. Instead, I chose to be here.

I wish I could tell you it's the utopia it seems to be on Instagram. That salvation lies in remote work and geographical flexibility. I wish I didn't sound so indifferent.

I suspect I'll learn the same lesson as every time I travel: that if I can't be happy everywhere, I won't be happy anywhere. That a plane ticket won’t solve my problems. That I can't get away from myself by moving from one place to another.

Yet, I trust my decision to leave home, step outside of my comfort zone, do what is difficult.

As Rilke says so wisely in one of his last letters: We know little, but that we must attach ourselves to what is difficult is a certainty that never deserts us. It is good to be lonely, for loneliness is difficult. The fact that a thing is difficult must be for us the more reason for doing it.

Here in Rio, it's muggy and hot. The final few days of winter. There's a man down on the street corner outside my window selling cartons of eggs. He’s been at it all morning. I doubt we speak the same language but I'm heading down to buy some.

Goodbye for now.

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❓ question i’m asking:

Am I so caught up in the relentless hamster wheel of consumption that I can no longer hear myself think?

📸 photo of the week:

I committed to taking at-least-one-photo-a-day until the end of the year.

I'll share my best photo each week here.

P.S. My good friend Nic Hurrell is launching a new cohort for his course, Sprouter Monday. I offered to share it with you because (i) I trust anything Nic puts out will be high-quality, (ii) people have found it transformational, and (iii) he walks the talk.

Sprouter is “A program for heart-led individuals empowering them to act on their ambitions within a month without being plagued by fear. It teaches the methods world-class athletes and performers use to be at their best.”

Online courses won’t solve all your problems, but I’ve gotten a lot more from them than from university.

If you’re interested, shoot him an email nichurrell@icloud.com

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

3- Get in Touch. If my writing resonated or if you just want to be friends, do reach out. Reply to this email, leave a comment, or find me on Twitter!

Much love,

Tommy

I hope you’re having a beautiful start to your weekend.

What I’ve been up to:

• I'm working with a writing coach! The very talented Alex Dobrenko is helping me with my next essay. If I pour even more of myself into my work, I want to see what I can create.

• I finished Devotions, a collection of poems by Mary Oliver. She’s my favourite poet yet. I also read my second Joseph Campbell book in a row and promptly bought a third. Sue me.

• I'm seeing Noah Kahan in Toronto tomorrow and I'm pretttyyyy pumped.

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

American writer William Faulkner on his productivity:

“A bus station is where a bus stops. A train station is where a train stops. On my desk, I have a work station...”

📚 book passage i loved:

The little prince went off to see the roses again.

'You're not at all like my rose; you're nothing special yet,' he told them.

...

'Of course, any ordinary person walking past my rose would think she was just like you. But she is much more important than all of you put together, because she's the one I watered. She's the one I sheltered under a glass dome, she's the one I protected with the screen. She's the one whose caterpillars I killed (except for the two or three for the butterflies). She's the one I listened to complaining, or boasting, or even sometimes being silent. Because she's my rose.'

― The Little Prince by Antoine de Saint-Exupéry

🖋️ poem i adored:

💡 idea from me: fate & freedom

I went for a walk yesterday afternoon, the first colours of Autumn beginning to show.

Flurries of red and yellow fading into ochre and brown, the trees bathed in dull golden light, as the last of the bugs leave their homes again. Crisp air breathing new life into my lungs. Clouds gathering thick in the West, silver seeds of cool cleansed rain beginning to fall.

There's something symbolic about nature coming to life with a final burst of colour before fading away into death.

Fall has always been my favourite season. Reading nooks and mugs of tea and sweater weather and candles and apple picking and hints of the holidays. What's not to love?

As I walked, I reflected back on my year. How little I knew of what was to unfold. How much life has been calling me to open to the unknown, to receive the unexpected. How foolish I felt to set plans with any semblance of confidence they would play out.

I thought about how much control I really have in shaping the narrative of my life.

I try so hard to make the right decisions. I get caught up in the fantasy of executing my life perfectly. Crafting a life -- if I'm only thoughtful and intentional and patient enough -- where all my needs are met and none are forgotten.

But I look back at the past few years and get the subtle sense that I was swept along to this point. Led through the labyrinth of life by a thread of fate, not bushwhacking my own trail. I can't recall any crossroads, big decisions, going right instead of left.

It more feels like I fell into things.

Both of my long-term relationships arose unexpectedly, without any intention. I found Substack and Write of Passage through a perfectly timed phone call with a friend I met by chance. My job with Noah Kagan I'm still scratching my head about.

I set things in motion, sure, but momentum takes a life of its own.

So do we happen onto life, or does life happen onto us? How much is under our control? And how much is fated?

The questions bounced around my brain as my pace slowed, my steps became smooth, timed, rhythmic.

I have a friend who sees life as a hyper complex video game that God has already coded. You have some freedom of choice, where to run around and stuff, but the storyline is fixed. All you have to do is hit play and watch.

It's kinda wild how you can make one decision and it can be years before you understand how meaningfully that altered the trajectory of your life. It's ever wild-er how it's these small passings, these chance events, these tiny moments that ultimately shape our lives in momentous ways. We just don't know which ones and we don't know how.

It's never more acute than when I hear stories of how my friend's parents met. A party they almost didn’t go to, a table at a restaurant they almost didn’t sit in, a class they almost didn’t take… becomes a family they never started, a home they never bought, a person they never raised.

As the saying goes, life can only be understood backward. But it must be lived forward.

Tolkien seemed to believe we retain a degree of freedom but much of our fate is decided, out of our hands.

"Do not trouble your hearts overmuch with thought of the road tonight. Maybe the paths that you each shall tread are already laid before your feet, though you do not see them".

The unknown is where beauty and surprise emerge. Our plans for life are never as wonderfully, painfully true as life's plans for us. I could never craft a life in my mind as beautiful as my life proves to become.

Perhaps — as my friend argued — that's why it’s crafted by God.

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❓ question i’m asking:

A question from Nietzsche on Eternal Recurrence:

What if a demon were to visit you and announce that you must relive your life exactly as it is, with all its joys and sorrows, for all eternity?

Would you greet this prospect with joy or despair?

Nietzsche says forget the "live each moment as if it were your last" nonsense.

How would you live if you were destined to relive everything for eternity?

Differently?

📸 photo of the week:

My definition of "made it".

A wall of books and floor-to-ceiling windows.

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

3- Get in Touch. If my writing resonated or if you just want to be friends, do reach out. Reply to this email, leave a comment, or find me on Twitter!

Leave a comment

Love you more,

Tommy

I hope you’re having a beautiful start to your weekend.

Is it too early to get a pumpkin spice latte? (asking for a friend)

What I’ve been up to:

• I've been working my way through David Perell's 7-part lecture series on the French philosopher René Girard. Girard's ideas are as terrifying as they are brilliant.

• I started teaching myself guitar. I've been thinking a lot about cultivating hobbies. Trying new things. Especially in the evenings—learning a skill instead of plugging in and zoning out. It's the difference between pleasure and enjoyment.

• I bought a Fitbit. I've read about how the modern world only values what we can quantify. Hence, the decline of emphasis on aesthetic beauty in architecture and cities. But, if this is true, how can you quantify things important to you to place more value on them? (A Fitbit measures exercise and sleep).

• Write of Passage is starting to pick up and I'm pretty pumped.

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

American poet Charles Bukowski on being alone:

“And when nobody wakes you up in the morning, and when nobody waits for you at night, and when you can do whatever you want.

What do you call it, freedom or loneliness?”

📚 book passage i loved:

“We are what we pretend to be, so we must be careful about what we pretend to be.”

― Mother Night by Kurt Vonnegut

💡 idea from me: fear at the centre

Near the end of my in-home meditation retreat, a day of complete solitude and silence, 8 hours of meditation, I was taking a nap.

(Because all that breathing is tiring, you know?)

In a half-asleep, half-awake, somewhat conscious haze, I experienced a sudden revelation: at the heart of all suffering, all my suffering, was fear.

Fear of not living as well as I could. Fear of the terms life has given me. Fear of nothingness for an indeterminate unconscious eternity.

For those brief moments, I felt like a small, terrified child again.

Scared to live, scared to die.

Or, as philosopher Ernest Becker would call it, fear of insignificance and fear of impermanence.

My friend Nic and I came to the same realization that fear lies underneath all negative emotion. Once you peel back the layers, fear is at the core.

It's an ancient idea. Fear and desire are the two emotions by which all life is governed.

Adam felt fear, Even felt desire—transcending fear and desire is the path back into the Garden of Eden. They are the two guardians at the gate to the tree of immortal life, Buddha seated under it. In Dante's Divine Comedy, hell is the place of those fixed to their fears and desires, who can't pass through to eternity.

The challenge with epiphanies, illuminations, sudden moments of clarity is not having them but handling them.

If they're true. Loving them. Keeping them. Cultivating them.

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❓ question i’m asking:

Where in my life can I integrate rather than atomize?

When we engage in activities that integrate multiple facets of our lives, it leads to more happiness versus when we individuate and optimize everything we do.

It's the difference between going for an hour bike ride with friends vs. 20-minute Peloton sprints. Working at a coffee shop with co-workers vs. deep work sessions with "focus music" pounding through noise-canceling headphones. A long drawn-out dinner with family vs. chugging Soylent at your desk in-between Microsoft Excel shortcuts.

Unintuitively, slowness and inefficiency are more enjoyable than speed and efficiency.

As Nat Eliason writes, "The more creatively we can integrate the various parts of life that matter to us, the more satisfied we’ll be in our day to day. The more we atomize, the more lonely and overwhelmed we start to feel."

Integrated living is more rewarding than atomic living.

📸 photo of the week:

This caught my eye while I was touring the historic Banff Springs Hotel.

I loved the intense attention to detail. The gold embossing. The time and energy and devotion poured into a mail chute.

While mail is no longer our primary means of communication, it’s a far cry from the current aesthetic.

The Lion and Unicorn is the coat of arms of the United Kingdom.

Created in 1603, when the King of Scotland became King of England. The lion (England) and unicorn (Scotland) represents the union of two opposites — two formerly warring nations.

Dieu et mon droit imprinted underneath (which means 'God and my right') implies the King has a God-given right to rule.

I love how you can learn about the decline of beauty, Canada’s colonization, the history of England, and the link between power and divinity, just by studying a mail chute.

Reality has a surprising amount of detail. Anything becomes interesting if you zoom in enough.

Thank you for reading! It means a lot to me :)

1- Leave a Like. If you enjoyed this, please click the little ❤️ below. It’ll help other people find this post.

2- Spread the Love. If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

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3- Get in Touch. If my writing resonated or if you just want to be friends, do reach out. Reply to this email, leave a comment, or find me on Twitter!

Much love,

Tommy

I hope you’re having a beautiful start to your weekend.

August is over. Wow. Summer has slipped by and now fades into Fall.

What I’ve been up to:

• I spent my final few days out west with family, visited the spa of the Banff Springs Hotel (fancy right?), and went on a pretty intense hike, summiting Cirque Peak at 3,000m elevation.

• I flew back to Toronto, went to the CNE with my Mom, and then got back to business. It's nice to be back in routine after two weeks without much writing or work. Book stuff with Noah is ramping up, and I have travel plans to iron out and some big essays to write.

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

An email from Steve Jobs, sent to himself, on how much we all need each other:

"I grow little of the food I eat, and of the little I do grow I did not breed or perfect the seeds.

I do not make any of my own clothing.

I speak a language I did not invent or refine.

I did not discover the mathematics I use.

I am protected by freedoms and laws I did not conceive of or legislate, and do not enforce or adjudicate.

I am moved by music I did not create myself.

When I needed medical attention, I was helpless to help myself survive.

I did not invent the transistor, the microprocessor, object oriented programming, or most of the technology I work with.

I love and admire my species, living and dead, and am totally dependent on them for my life and well being."

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📚 book passage i loved:

“Do not think that the person trying to console you lives effortlessly among the simple, quiet words that sometimes make you feel better. His life is full of troubles and sadness and falls far short of them.

But if it were any different he could never have found the words that he did.”

― Letters to a Young Poet by Rainer Maria Rilke

I tried to capture the same idea in my essay on The Illusion of Writing.

💡 idea from me: meditation mutiny

This year, I’ve leaned into meditation more than ever.

For a four-month stretch, I was meditating 30-45 minutes a day and even did a full-day in-home meditation retreat.

Last week, I was talking to my Uncle about my plans to go on a 10-day silent retreat.

He asked if it would be good for me. And I said "yes, I think so".

Then he asked if meditation is one of those things that you do for decades. And I said "yes, it requires consistent practice over your lifetime and the truly transformative experiences seem to require thousands of hours".

And then he asked what if I took those thousand hours and instead did charity work? Think of the impact I’d make on other people (a lot more than sitting cross-legged on a cushion)? And wouldn’t I get the same effect? A transcendence of the self? Forgetting myself and how much I think I matter? And I said "yes, that’s a pretty good point, I’m gonna write about that".

I’ve noticed how meditation feeds into itself. The most avid meditators I know only want to meditate more.

I have a friend who said her first 10-day retreat felt like "a single snowflake out of a thousand." Her three years of in-home practice before was nothing. Inconsequential.

I’ve experienced how meditation can be isolating. Create distance, separation. I’ve seen it happen to others.

I have another friend (crazy right?) who meditates two hours a day and has done several silent retreats. While he seems fulfilled and calm and spiritually attuned, I’ve noticed his growing alienation from the world. How it has become increasingly impossible to resonate with other people, including his family, when he occupies such a different plane of consciousness. I admire him but it also makes me a bit sad.

I’ve learned how deep meditation can go. Sensed it myself.

At Rabbit-hole-athon, one person studied cessation experiences: “the end of thought or feeling”. The meditator can effectively disconnect their mind, turn consciousness off, and enter a trance-like state. With “a total absence of sensation and awareness.” With no concept of space or time. For many hours (some for six days!)

At times, spirituality feels beautiful and true and inviting. Other times, it scares the heck out of me.

Full of wonder and mystery but infinitely complex and seismically above my head.

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❓ question i’m asking:

Did the person actually tell you no or did you just assume they would?

I'm great at fabricating fictional "no's".

One benefit of working with Noah Kagan is I've gotten much more comfortable just asking for things.

📸 photo of the week:

Thank you for reading! It means a lot to me :)

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

Beyond that, click the ❤️ button on this post so more people can discover it.

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

With love,

Tommy

I hope you’re having a great start to your weekend.

What I’ve been up to:

• I published an essay on feeling overwhelmed by how much I want to learn/see/do in this lifetime. From the responses, it was heartwarming to know many of you feel the same.

• I did a few day hikes around Canmore/Banff, then drove four hours north to Jasper for a 3-day backcountry hike on the Skyline Trail. Walking on a ridgeline at 2,400m elevation, above the clouds and beside the glaciers, was divine.

• I headed back to Canmore for a few more days of hiking. After five days without reception, I could viscerally feel my stress level rise as hundreds of emails and notifications and newsletters poured in and I flailed to catch up on all I'd missed. I'm reminded how difficult it is to truly disconnect.

As Paul Graham said, some cities speak to you, send a message. Canmore whispers: “Get Outside”.

Here are the most interesting ideas I've explored this week.

Thanks for stopping by :)

✍️ quote i’m pondering:

Buddhist monk Thích Nhất Hạnh on the miracle of life:

“People usually consider walking on water or in thin air a miracle. But I think the real miracle is not to walk either on water or in thin air, but to walk on earth.

Every day we are engaged in a miracle which we don’t even recognize: a blue sky, white clouds, green leaves, the black, curious eyes of a child—our own two eyes.

All is a miracle.”

📚 book passage i loved:

“The influence of a vital person vitalizes.

People have this notion of changing the world by changing the rules. No — any world is a living world if it is alive. The thing is to bring it to life.

And the way to bring it to life is to become alive yourself.”

― The Power of Myth by Joseph Campbell

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💡 idea from me: on journaling

I met a 74 year old man in Salzburg who has journaled every day of his life since he was my age.

It’s become a part of his daily motions, no different than having coffee or brushing his teeth.

He has a library of notebooks stored safely on an oak bookshelf. A record of his life. His children, now adults, sometimes ask to read old journal entries. Their 6th birthday or when they left for university or their wedding day.

This summer, I've been journaling almost every day. Beginning to feel the daily routine turn ritual. Roll over like a wave and pull me under.

Mostly in the mornings. Mostly stream of consciousness. Whatever floats to the top of my mind and demands documentation in blue ink. No filter. No judgment. I just sit in front of the blank page and listen.

Journaling is one of the best ways for me to meet my thoughts and feel my feelings.

Writing is thinking. I never know what I think until I write it down. I come to conclusions as my hand works its way across the page. Often, I surprise myself.

I stop trying to outsmart my emotions, and surrender to them instead.

I declutter my mind. Trap thoughts on the page. Leave them there so I can move on with my day. I never write things down so I can remember. I always write things down so I can forget.

Reading old journal entries, I learn the timelessness of problems. How they stubbornly reappear in different forms. How, despite my maturation, I'm still the same person. The same dog with the same few bones. The inner child never disappears despite the illusion of distance.

September 3, 2018. My first day of university. Nearly 5 years ago. I read the words "trust yourself and your abilities" in smudged pencil and chuckle.

❓ question i’m asking:

When was the last time you did something you’ve never done before?

I've noticed how inertia can be a governing force in my life.

Sam Altman: Not only does doing new things seem to slow down the perception of time, increase happiness, and keep life interesting, but it seems to prevent people from calcifying in the ways that they think. Aim to do something big, new, and risky every year in your personal and professional life.

📸 photo of the week:

Thank you for reading! It means a lot to me :)

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

Beyond that, click the ❤️ button on this post so more people can discover it.

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

With love,

Tommy

I hope you’re having a beautiful start to your weekend.

What I’ve been up to:

• I wrote a short essay on solitude and togetherness. Connection isn't a topic I've explored much in my writing, so it was a lot of fun.

• I flew to Alberta early Wednesday morning for two weeks of backcountry hiking in the Rocky Mountains. I’m spending two days in beautiful Canmore with family, before heading into the mountains with my brother and a friend.

Here are the most interesting ideas I've explored this week.

✍️ quote i’m pondering:

Spiritual teacher Ram Dass on bearing the burden of being:

“You can do it like it’s a great weight on you, or you can do it like a dance.”

📚 book passage i loved:

For still there are so many things

that I have never seen:

in every wood in every spring

there is a different green.

I sit beside the fire and think

of people long ago,

and people who will see a world

that I shall never know.

― The Fellowship of the Ring by J.R.R. Tolkien

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💡 idea from me: notes on money

August 7, 2023 — 6am

Driving through the West Virginia mountains, I started talking with J about money as the sun crept above the trees.

Initially, like many young ambitious people my age, I wanted to be rich. I wanted a mansion, a fortress of blue Italian suits, an AMEX platinum card, a Rolls-Royce, maybe a villa in Spain. Just the basics, you know?

I made decisions that oriented me toward a high-income career. (Although money wasn't my motivator, status was.)

Then, at some point in 2021, I fell into the camp of "I don't need money and people who want to get rich are chasing the wrong things and it won’t make them happy and I know better".

Maybe it was Seneca brainwashing me (although turns out he was a hypocrite... Seneca was loaded).

I realized I don't need to be rich--and probably won't be--to live a good life. I pivoted away from a high-income path to pursue what felt like a calling. Namely, writing.

This year my perspective has changed. There's nothing wrong with wanting to get rich. Done ethically, it’s better than chasing status. I actually think accumulating a lot of money early on in life can expedite the process of finding peace.

If I start a family one day, I want to be able to provide. Part of that is making a sturdy income. I've felt a bit selfish in my decision to "pursue a calling". It feels millennial, detached from reality.

Money is also a powerful tool to create experiences that bring joy to others which brings joy to me. I've felt glimmers of it when I bring friends to my cottage.

As my friend writes:

The only idea of happiness that consistently works for me is making someone happy. Or just knowing that someone I care for is happy. It’s happiness by reflection. Borrowed happiness. And that’s all I need: borrowing back a little of the happiness that I’d help generate, or that someone I love has.

I still hold onto fantasies of taking my brother and sister on a vacation or having a big property where my family can commune and spend quality time together or funding a project that makes someone’s dream come to life.

okay here comes the help-self part:

I was obsessed with money, finance, and investing for three years.

I realized I have many thoughts about money I think are worth sharing. Hopefully one or two are insightful.

Here are my notes on money:

1. 90% of personal finance can be boiled down to: spend less than you make, save the difference, invest consistently in broad-based index ETFs with low fees.

2. Choosing to be joyfully unoptimized in my finances freed up a lot of time and mental energy to invest in things I care more about (writing, reading, meditation, etc.)

3. Lifestyle creep (upgrading your lifestyle proportionately with increases in income) should be avoided at all costs. Keep your personal burn rate low.

4. I have a sneaking suspicion that you have to make a lot of money (or spend time around rich people) before you actually believe money doesn’t buy happiness.

5. Whether or not money can buy happiness, it can buy freedom. The best reason to accumulate wealth is to buy yourself freedom from anything you don’t want to do, and freedom to do things you do want to do. Morgan Housel: Money’s greatest intrinsic value is its ability to give you control over your time.

6. Money won’t solve all your problems but it will solve all your money problems. Then you’re left with only problems money won’t solve.

7. People can be incredibly intelligent academically or professionally, but incredibly stupid with their own money. (Even if they work in finance.)

8. All the super-rich old people wish they were young and broke again.

9. Being poor is not having little, but wanting more.

10. Financial freedom is less about making all the right moves and more about avoiding big mistakes (i.e. car, house, partner, get-rich-quick schemes).

11. Avoid get-rich-quick schemes. There are no get-rich-quick schemes. That's just someone else getting rich off you.

12. Avoid big crazes. The more FOMO you have about missing out, the more you should avoid it. The more aggressively someone tries to convince you they're right, the more insecure they are about their belief (and thus seeking validation).

13. FOMO is a terrible emotion to let affect financial decisions (spending or investing).

14. You don’t have to make money back how you lost it.

15. You probably inherited your money habits from your parents. If you want a different outcome, you need different habits.

16. Always have a bit of cash in your wallet. You never know when you'll need it. (Says my Dad).

17. Focusing too much on money can lead to making less money.

18. Set aside a % of your money into a separate "Dumb Mistakes" savings account. Next time you lose or break or damage something, pay for it through the account and forgive yourself.

19. Will Durant: Don't let restaurants lure you; they are the vampires of the stomach; they will burden your flesh in proportion as they tighten your purse.

20. Inheritance makes people do crazy things.

21. Lack of money is stressful. Studies show economic stress impedes cognitive bandwidth. Do whatever you have to do to not worry about money. Sam Altman: having enough money so that you don’t stress about paying rent does more to change your well-being than having enough money to buy your own jet.

22. My north star is to have enough money that I don’t worry about money. (Although I've met middle-aged men with a lot of money who say the same thing).

on spending:

1. My most trusty spending rule: wait a week and see if I still want it.

2. Buying something to remove a negative will make you happier than buying something to add a positive.

3. Spend lavishly on what you love, cut ruthlessly on everything else.

4. A scarcity mindset is independent of income. There are multi-millionaires who don't let themselves buy Greek yogurt.

5. Don't buy things to impress other people. It doesn't work.

6. Allow yourself to spend more money than you're comfortable with on cool experiences. Especially if you can't do them when you're older. Sam Altman: in your 20s, I think it’s ok to take a “Give me financial discipline, but not just yet” attitude. All the money in the world will never get back time that passed you by.

7. Spending money on experiences isn't always better. Try spending money on different oddball things and find what brings you joy.

8. The more you hate your job, the more of your paycheck you'll feel justified spending.

9. Every time we spend money, we make a statement about what we value. There’s no clearer indication.

10. Things you use for a significant fraction of your life (bed: 1/3rd, office-chair: 1/4th) are worth investing in.

11. When buying things, time and money trade off against each other. If you’re low on money, take more time to find deals (sales, in-store specials, buying used, hacks, etc). If you’re low on time, just buy things quickly online.

12. Buy most things used. You save money and the environment.

13. Buying high-quality is better for the planet than buying low-quality. But, buying nothing is best of all.

on investing:

1. The best investments are “buy and forget.”

2. People forget to factor in the time and the psychological toll of investments. Daily stress and 15 minutes reading reports every evening may not be worth the extra 1-2% return.

3. 98% of people should not invest in stocks. The 2% who should are not legally allowed to.

on real estate:

1. Buying isn't always better than renting. A lot of people have been financially ruined from buying. They just don't sell courses about it. Do the math yourself (and include opportunity cost).

2. Rule of thumb: buy if you're *pretty certain* you'll stay for at least 5-10 years.

3. Buying can make you fragile, while renting can make you antifragile.

4. "Lock it and leave it" flexibility is huge if you travel often.

and finally:

1. Personal finances are personal. Everyone has different definitions, goals, risk tolerances. You probably shouldn't take financial advice from most people. Especially people on the Internet :)

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❓ question i’m asking:

How much of what I want is on the other side of a few hard conversations?

📸 photo of the week:

A lot of people know Banff, but Canmore is a hidden gem.

Thank you for reading! It means a lot to me :)

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

Beyond that, click the ❤️ button on this post so more people can discover it.

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

With love,

Tommy

I hope you’re having a great start to your weekend.

What I’ve been up to:

• I wrapped up the Rabbit-hole-athon retreat (met some awesome people), went for a four-hour hike through a lush North Carolina forest, met a nonchalant black bear, then drove back to Toronto.

• I published a new essay called The Illusion of Writing. Writers always sound like they have things figured out, but there’s often a mess behind the polished facade. It's an idea I've been thinking about for months and I was happy to get it out.

• I'm planning on foraying into photography next month. (Made the social commitment, can't back out now...) Partly for the vibes, but partly because it teaches you to notice what is beautiful and aesthetic in your surroundings. Any beginner recommendations? Let me know!

Here are the most interesting ideas I've explored this week.

Enjoy.

✍️ quote i’m pondering:

American writer John C. Maxwell on why people change:

People change in four seasons: when they hurt enough they have to, when they see enough they are inspired to, when they learn enough that they want to, and when they receive enough that they are able to.

It’s simplistic, but there’s something about the idea of experience accumulating until you hit a breaking point that feels true to me.

📚 book passage i loved:

"All I wanted to do in the end was advise you to go through your development quietly and seriously; you cannot disrupt it more than by looking outwards and expecting answers from without to questions that only your innermost instinct in your quietest moments will perhaps be able to answer."

― Letters to a Young Poet by Rainer Maria Rilke

💡 idea from me: nature as sacred

In 1852, the United States Government wanted to buy a plot of tribal land for new immigrants to settle on.

A politician wrote a letter to Chief Seattle, the leader of the native people of those lands, with this request.

His reply was nothing short of marvelous (emphasis my own):

"The President in Washington sends word that he wishes to buy our land. But how can you buy or sell the sky? The land? The idea is strange to us. If we do not own the freshness of the air and the sparkle of the water, how can you buy them?

"Every part of this earth is sacred to my people. Every shining pine needle, every sandy shore, every mist in the dark woods, every meadow, every humming insect. All are holy in the memory and experience of my people.

"We know the sap which courses through the trees as we know the blood that courses through our veins. We are part of the earth and it is part of us. The perfumed flowers are our sisters. The bear, the deer, the great eagle, these are our brothers. The rocky crests, the juices in the meadow, the body heat of the pony, and man, all belong to the same family.

"The shining water that moves in the streams and rivers is not just water, but the blood of our ancestors. If we sell you our land, you must remember that it is sacred. Each ghostly reflection in the clear waters of the lakes tells of events and memories in the life of my people. The water's murmur is the voice of my father's father.

"The rivers are our brothers. They quench our thirst. They carry our canoes and feed our children. So you must give to the rivers the kindness you would give any brother.

"If we sell you our land, remember that the air is precious to us, that the air shares its spirit with all the life it supports. The wind that gave our grandfather his first breath also receives his last sigh. The wind also gives our children the spirit of life. So if we sell you our land, you must keep it apart and sacred, as a place where man can go to taste the wind that is sweetened by the meadow flowers.

"Will you teach your children what we have taught our children? That the earth is our mother? What befalls the earth befalls all the sons of the earth.

"This we know: the earth does not belong to man, man belongs to the earth. All things are connected like the blood that unites us all. Man did not weave the web of life, he is merely a strand in it. Whatever he does to the web, he does to himself.

"One thing we know: our god is also your god. The earth is precious to him and to harm the earth is to heap contempt on its creator.

"Your destiny is a mystery to us. What will happen when the buffalo are all slaughtered? The wild horses tamed? What will happen when the secret corners of the forest are heavy with the scent of many men and the view of the ripe hills is blotted by talking wires? Where will the thicket be? Gone! Where will the eagle be? Gone! And what is it to say goodbye to the swift pony and the hunt? The end of living and the beginning of survival.

"When the last Red Man has vanished with his wilderness and his memory is only the shadow of a cloud moving across the prairie, will these shores and forests still be here? Will there be any of the spirit of my people left?

"We love this earth as a newborn loves its mother's heartbeat. So, if we sell you our land, love it as we have loved it. Care for it as we have cared for it. Hold in your mind the memory of the land as it is when you receive it. Preserve the land for all children and love it, as God loves us all.

"As we are part of the land, you too are part of the land. This earth is precious to us. It is also precious to you. One thing we know: there is only one God. No man, be he Red Man or White Man, can be apart. We are brothers after all."

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❓ question i’m asking:

Am I "running from" or "chasing toward"?

In other words: Am I driven by fear or inspiration?

📸 photo of the week:

I've been (slightly) obsessed with this collection of photos from Simon Sarris titled 'blissful days'.

You can see the full collection on Twitter here.

Thank you for reading! It means a lot to me :)

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

Beyond that, click the ❤️ button on this post so more people can discover it.

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

With love,

Tommy

I hope you’re having a lovely start to your weekend.

What I’ve been up to:

• I spent a ton of time on my latest essay on life changes—why they're hard and how I'm trying to cope.

• After a lot of hard work, my good friend CJ Kirk launched a coaching platform, Conquer Culture, to deliver his decades of coaching experience at scale.

• I'm in beautiful Black Mountain, North Carolina this weekend for Rabbit-hole-athon 3.0. "A learning retreat for technologists to dive into intellectual rabbit-holes".

Here are the most interesting ideas I've explored this week.

Enjoy.

✍️ quote i’m pondering:

Russian writer Aleksandr Solzhenitsyn on the duality of good and evil:

“The line separating good and evil passes not through states, nor between classes, nor between political parties—but right through every human heart…

To do evil a human must first believe that what he’s doing is good.”

📚 book passage i loved:

"Who is Igjugarjuk?" I said, barely able to imitate the pronunciation.

"Oh," replied Campbell, "he was the shaman of a Caribou Eskimo tribe in northern Canada, the one who told European visitors that the only true wisdom 'lives far from mankind, out in the great loneliness, and can be reached only through suffering. Privation and suffering alone open the mind to all that is hidden to others.' "

"Of course," I said, "Igjugarjuk."

― The Power of Myth by Joseph Campbell with Bill Moyers

This reminded me of something I heard recently: Whenever somebody has great wisdom, assume they earned it through great pain.

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💡 idea from me: making choices, big and small

Bit more of a casual, stream of consciousness post this week.

A few weeks ago, I wrote in my journal:

I’m starting to doubt that when it comes to life decisions there’s a “best choice” or even a “right choice”. Choices can't be measured, quantified. Life is too complex, unpredictable, spontaneous. Even if a "right choice" existed, there’s no way of knowing what it is.

You can make one decision and it can be years before you understand how meaningfully it altered the trajectory of your life.

My new thinking around decisions is something like: for the set of choices you're struggling to decide between (meaning they're all rational and reasonable and legal) there isn't a "right choice". Rather, you make what you choose "right" by committing to it, falling into it, and (paradoxically) not worrying about whether it was actually the right choice.

A friend sent me this book passage from The Unbearable Lightness of Being:

“There is no means of testing which decision is better, because there is no basis for comparison. We live everything as it comes, without warning, like an actor going on cold."

If I were to boil it down to a formula, part of a good decision is the thing itself (e.g. not marrying a serial killer) but the other important often ignored part is just owning your decision in its entirety and being satisfied with it (e.g. not thinking about other partners who could be better).

You almost have to say to yourself, "Despite the other choices I could have made this is the choice I did make and I'm going to trust it was the right one and live with it and stop thinking about the unactualized potentialities that I didn't bring into being."

(Wow that sounded pretty smart for an internal monologue).

I was at a friend's cottage last week and one night he mentioned how the famous Robert Frost poem, The Road Not Taken, is massively misunderstood.

You know the one:

Two roads diverged in a wood, and I—

I took the one less traveled by,

And that has made all the difference.

Frost wrote the poem to tease his chronically indecisive friend.

He's not advising him to take the uncommon path. He's poking fun at his friend’s tendency to terrorize himself at what might have been when there's no way of knowing. According to Frost, the two roads are “really about the same.” Interchangeable.

It matters less what we choose, but more that we choose. Make our choice and go forward with confidence and conviction. Indecision is the danger zone.

Like Satre thought, it's the contemplation of the near-infinite lives we could live that leads to anguish.

I think that's what makes commitment so meaningful (and optionality so overrated). You're closing off the vast infinite for the visible finite and then settling into it.

I liked this tweet I saw yesterday:

Everything might not turn out like you imagined, but it'll all end up okay. Because you will post rationalize your decisions and narrativize your conditions into a palatable story you can live with.

It'll all end up okay.

On another note, I went to some live jazz a few weeks ago. By accident actually. But it was so good that for those 30 minutes I forgot about life choices entirely.

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❓ question i’m asking:

A question from billionaire founder and investor Peter Thiel:

If you have a 10-year plan to get somewhere, ask yourself: Why can't I do this 6 months?

📸 photo of the week:

My three favourite “cozy cafe” paintings to make your weekend a little more beautiful:

Thank you for reading! It means a lot to me :)

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

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Beyond that, click the ❤️ button on this post so more people can discover it.

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

With love,

Tommy

I hope you’re having a great start to your weekend.

What I’ve been up to:

• I was sick for a bit. It felt like I temporarily inhabited the body of an 85 year old man. But I'm beginning to feel better.

• I've spent a few days at a good friend's cottage in Muskoka, Ontario. 

• One morning, I saw a black bear on my run. Up close, across the road, peeking out of the woods, looking right at me. I was stunned. But also appreciative that I can run somewhere black bears still live.

As always, here's an inside look at the most interesting ideas I've explored this week.

Enjoy.

✍️ quote i’m pondering:

Austrian poet Rainer Maria Rilke on fear as signal:

“Perhaps all the dragons in our lives are princesses who are only waiting to see us act, just once, with beauty and courage.

Perhaps everything that frightens us is, in its deepest essence, something helpless that wants our love.”

American writer Joseph Campbell echoes a similar idea:

"The cave you fear to enter holds the treasure you seek."

📚 book passage i loved:

“One of the most beautiful gifts in the world is the gift of encouragement.

When someone encourages you, that person helps you over a threshold you might otherwise never have crossed on your own.”

― Eternal Echoes by John O'Donohue

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💡 idea from me: on dreams

I keep having this dream where I’m in some bustling bright city.

I'm trying to find my way back to my hotel or apartment. I can't tell which. I walk down a street but I realize I’m lost. Without direction. I'm not able to find my way home. I don’t know where it is. I don’t know where I am. Often, I realize I've walked in the opposite direction. I have to start the long way back.

Then I wake up.

I've been writing down my dreams for the past few months. On and off. But I'm beginning to learn how they are laced with meaning. How my dreams reveal my relationship with myself: my fears, my desires, my self-image.

Many disregard dreams as trivial, silly, meaningless. But the symbols and stories that appear come from somewhere in my mind, for some reason. It’s not random.

Joseph Campbell (influenced by Freud and Jung) believed dreams are a portal to the unconscious. A canvas for the subconscious mind to project itself.

It's not always easy. My dreams dredge up the parts of myself and the parts of my life that I don't want to see into the light of consciousness.

Jung called it the shadow: the portion of our personality that is banished to the unconscious. The shadow isn't always what is evil, but what is hidden or ignored (from yourself and the world).

By facing our shadow and figuring out what dwells there, we become less susceptible to it. As Jung said, “A small evil becomes a big one through being disregarded and repressed… the most terrifying thing in the world is to accept oneself completely.”

To protect yourself from evil, you must understand it.

It's the same reason Harry Potter (with his forehead scar from Voldemort) and Frodo (with his Ringwraith wound) have a heightened sensitivity to and ability to ward off evil. They've been touched by evil—it left its mark on them. They know exactly what evil feels like.

The virtuous person isn't someone who is empty of evil, but someone who confronts and controls the evil within them.

It's also why Jordan Peterson's future authoring program has you describe the future you want to avoid:

Consider the multitude of your faults and the direction those faults could pull you in. Everyone has a sense of how they would fall apart in their own particular manner with their own particular weaknesses.

It's three to five years down the road and you let that part of your character dominate. What particular corner of hell are you now occupying?

Everyone has a sense of how we could blow up our lives if we succumb to temptation, if we aim down, if we bend to that which is evil within us.

I've written before about not becoming bitter. I can envision a path where I do. But by being consciously aware of exactly how my life could fall apart, I'm better equipped to avoid it. I know the pitfalls.

And because our shadow exists in the unconscious, dreams are one of the best ways to engage it.

Kristen Poeshn writes:

Simply writing down a tough dream, or sitting with the difficult emotions they brought up felt agonizing at best. But I’ve learned over the years that if I’m willing to meet the patterns coming up in my dreams, they’re much less likely to rollercoaster their way through my waking life.

The Sufi saint Radha Mohan Lal Ji once said, “One second of suffering in dreams is equal to years of suffering in waking life."

I'm not great with navigation (those who know me will be grinning) but I don't think that's what my dream is telling me. I think my dream is telling me that I lack clarity. Direction. I'm not clear on what I want and where I'm headed.

I'm kinda aware of it. But it's not something I like to think about. I tend to keep it in my brain’s peripheral vision. But noticing and journaling on these dreams has forced me to confront the pain of feeling a little lost in my conscious life.

And not all dreams are heavy.

Sometimes dreams reveal shadows, but sometimes they radiate light.

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❓ question i’m asking:

If someone took control of your life tomorrow, what’s the first thing they would change?

📸 photo of the week:

I guess I mostly take photos of poems these days…

Thank you for reading! It means a lot to me :)

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it.

Share

Beyond that, click the ❤️ button on this post so more people can discover it.

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

With love,

Tommy

I hope you’re having a lovely start to your weekend.

What I’ve been up to:

• On Saturday, I got dinner in Toronto with a few (awesome) people from the Write of Passage team. It's a company I'm very optimistic about.

• I wrote an essay telling the story of one of the most unforgettable experiences of my life—summiting a mountain to watch the sun rise—and how I’m trying to integrate the idea that life is about the journey.

• Prepping for a 2-week backcountry hiking trip in Alberta’s Rocky Mountains in August.

Here's an inside look at the most interesting ideas I've explored this week.

Enjoy.

✍️ quote i’m pondering:

Philosopher and author Albert Camus on resilience:

"In the depths of winter, I finally learned that within me there lay an invincible summer."

📚 book passage i loved:

“Regrets are illuminations come too late.”

― The Hero with a Thousand Faces by Joseph Campbell

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💡 idea from me: heaviness vs lightness

"You smile less than average."

A friend says to me casually as we sip espresso at a cobblestone cafe on Porto's Douro River.

Ouch.

It stings, but her comment is unflinchingly honest and painfully true.

Recently, I've been thinking about the duality of heaviness versus lightness. (I think we have a deep intuitive sense of what each means that transcends language and escapes definition.)

We all have a natural tilt: some of us are heavier by nature, some of us are lighter. One isn't better than the other. They're just different.

And it's not a binary (am I heavy or am I light?) but a continuum (how heavy or light am I?).

I tend to lean towards heaviness: thoughts with no bottoms, questions with no answers, intensity with no end.

We aspire to the opposite side of the duality: heavy people want to be lighter, light people want to be heavier. We seek balance.

When I look back at my journal entries from 2-3 years ago, I realize so many reminders to myself remain the same: to smile widely, to laugh loudly, to tread lightly. But I’ve found it can be an uphill battle.

And we seek our counter-qualities in other people, places, things.

All of my best friends, the people I'm pulled towards, are unequivocally light. They force me out of my head and into the world. Make me worry less and smile more. And stop taking things so damn seriously. They counterbalance my heaviness.

Perhaps we can try to change things about ourselves. But perhaps there are some things so foundational to our nature that we must embrace them, and balance our imbalances through the environment we cultivate.

I can try to force myself to be lighter.

But I can also just spend more time around my friends.

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❓ question i’m asking:

A question from poet Mary Oliver on the natural world as a doorway to ourselves:

Who will behold the inner chamber who has not observe

with admiration, even with rapture, the outer stone?

Well, there is time left—

fields everywhere invite you into them.

📸 photo of the week:

The complexities of human emotions is one of those things that will never fail to surprise me.

Thank you for reading! It means a lot to me :)

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it. Beyond that, click the ❤️ button on this post so more people can discover it.

Share

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

Much love,

Tommy

I hope you’re having an excellent start to your weekend. We're already halfway through July. Crazy...

What I’ve been up to:

• I've been studying Joseph Campbell's magnum opus, The Hero With A Thousand Faces. Around 90 minutes every day: reading, re-reading, noting, journaling, watching interviews and lectures.

• I caught up with a good friend over sushi who's playing professional rugby. One thing I never appreciated was the sheer physical toll athletes undergo over the course of a season as well as the pressure within a team to perform flawlessly each week, their every movement filmed, dissected, and scrutinized.

• Back to back half marathons. 20km last Sunday, 21km tomorrow. I'm starting to seriously consider a marathon in September.

Here's an inside look at the most interesting ideas I've explored this week.

Enjoy.

✍️ quote i’m pondering:

Lebanese-American poet, Khalil Gibran, on seeking wholeness:

Do not love half lovers

Do not entertain half friends

Do not indulge in works of the half talented

Do not live half a life

and do not die a half death

📚 book passage i loved:

‘I do not think that any speech will help me. For I know what I should do, but I am afraid of doing it, Boromir: afraid.’

...

‘I think I know already what counsel you would give, Boromir,’ said Frodo. ‘And it would seem like wisdom but for the warning of my heart.’

‘Warning? Warning against what?’ said Boromir sharply.

‘Against delay. Against the way that seems easier. Against refusal of the burden that is laid on me.’

― The Fellowship of the Ring by J.R.R. Tolkien

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💡 idea from me: when was the last time?

When was the last time you lay on a grassy hill, and watched the clouds float by?

When was the last time you watched the sun rise from the gates of the east, pink mist melting into a golden dawn?

When was the last time you sat by a window during a storm, rain falling in sheets, wind straining the roots of trees, thunder booming through the heavens and echoing through your bones?

When was the last time you looked up to a star-filled sky and savored the silence, breathless with wonder?

When was the last time you gave a hug, that lasted a whole six seconds?

When was the last time your shoulders untensed? jaw unclenched? neck relaxed?

When was the last time your face wore its natural expression?

When was the last time you paused and noticed, and took it seriously, as if noticing was your job?

When was the last time you didn't hear the clocks ticking loudly, and failed to consider, what stretches beyond today?

When was the last time you were sufficiently grateful for the gifts you were given?

When was the last time you listened to your small voice, above all the traffic and ambition?

When was the last time you didn't hurry through the world, but walked slowly and bowed often?

When was the last time you smiled uncontrollably, as if there was nothing you could do to stop it?

When was the last time you truly felt alive?

For me, for many, life is busy, moments scarce. The mind is often occupied with more important things, than by happiness, and deep breathing.

Yet all you need is a glimpse, of these sweet things.

For in a glimpse, sleeps eternity.

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❓ question i’m asking:

A question from investor, entrepreneur and philosopher Jeremy Giffon on the paradox of success:

Why do successful people spend so much time doing things they hate?

David Perell elaborates: "You'd think people would more adamantly do things they enjoy. But nope. People are too caught up chasing status or deluding themselves about what they actually want to do."

People cling to who they think they should be, instead of surrendering who they actually are.

📸 photo of the week:

Current writing setup. There's something euphoric about the combination of black coffee and sparkling water. (Would also recommend Coffee Table Jazz on Spotify).

Thank you for reading!

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it. Beyond that, click the ❤️ button on this post so more people can discover it.

Share

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

With love,

Tommy

I hope you’re having an excellent start to your weekend.

What I’ve been up to:

• I finished Tolkien's Fellowship of the Ring, and began to read Joseph Campbell's The Hero With A Thousand Faces, to understand myth and The Hero's Journey. If you're looking for a short summary, I loved Vogler's Memo (which introduced Campbell's work to Hollywood).

• I published an essay curating the work of my favourite singer/songwriter, Noah Kahan. (Funny, because I work for Noah Kagan... small world.)

• On Thursday, I did my first at-home meditation retreat. 5 hours of sitting meditation and 3 hours of walking. I shared my schedule on Twitter.

Here's an inside look at the most interesting ideas I've explored this week.

Enjoy.

✍️ quote i’m pondering:

Japanese author, Genzaburo Yoshino, on following your heart:

“The things that you feel most deeply, from the very bottom of your heart, will never deceive you in the slightest.”

📚 book passage i loved:

'When I have a longing for something myself,' he said, 'do you know what I do?

I cram myself chockful of it, and so I get rid of it and don't think about it any longer. Or, if I do, it makes me retch.

Once when I was a kid—this'll show you—I was mad on cherries. I had no money, so I couldn't buy many at a time, and when I'd eaten all I could buy I still wanted more. Day and night I thought of nothing but cherries.

I foamed at the mouth; it was torture!

But one day I got mad, or ashamed, I don't know which. Anyway, I just felt cherries were doing what they liked with me and it was ludicrous. So what did I do? I got up one night, searched my father's pockets and found a silver mejidie and pinched it.

I was up early the next morning, went to a market gardener and bought a basket o' cherries. I settled down in a ditch and began eating. I stuffed and stuffed till I was all swollen out.

My stomach began to ache and I was sick.

Yes, boss, I was thoroughly sick, and from that day to this I've never wanted a cherry. I couldn't bear the sight of them. I was saved. I could say to any cherry: I don't need you any more.

And I did the same thing later with wine and tobacco. I still drink and smoke, but any second, If I want to, whoop! I can cut it out. I'm not ruled by passion.

It's the same with my country. I thought too much about it, so I stuffed myself up to the neck with it, spewed it up, and it's never troubled me since.'

― Zorba The Greek by Nikos Kazantzakis

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💡 idea from me: city struggles

If you asked me the main thing I've changed my mind about this year, my answer would be quick: cities.

For most of university, living in a city was perched on a pedestal. I'd be smack dab in the hustle and bustle. Walking distance from everything I need. Chasing ambition, meeting new people, establishing myself in the world.

But now I’m not so sure.

Walking through city streets after time spent in nature, I experience a sensory overload. I can feel my anxiety escalate with the swirl of sirens and screeching subways, the cacophony of cars and clanging construction. Amidst all the noise, I struggle to hear myself think.

Instead of engaging with the world, people seem to crave distraction. Phones travel first class in hands, headphones remain glued in ears, lines for nightclubs swell and snake into the streets.

Cities are breeding grounds for desire and graveyards for commitment. With so many options and so much stimulus, it's near-impossible to be satisfied with what you are doing because you're keenly aware of the near-infinite things you're not doing. There's a certain restlessness. Rootlessness.

A sense of speed permeates. Everyone is in a hurry. Everything moves too slowly.

Nicole writes about living in San Francisco:

Being 20 something in a big city is both agony and bliss. Everyone is lonely, everyone is obsessed, everyone is hungry. A collective era of being lost, hopeful, and distracted. Being overwhelmed with options, feeling unsure about choices. Feeling like everything matters and nothing matters at all.

I think this ties into a bigger idea: the location we live in has a very real impact on our happiness.

I've been living at my family's cottage this month. It's a simple cabin. But the rolling countryside, symphony of birds, and lush greenness feel therapeutic. My mind stills and flattens, like the lake a few paces from where I'm writing this.

In the serene stillness of nature, as Tolkien suggests throughout Lord of the Rings, we can connect to the wisdom of our unconscious, hear the whispers of intuition, feel the murmurings of the heart. Create clarity. Invite epiphany. Discover profound answers to troubling questions.

But I suppose, like anything in life, where you choose to live is a trade-off.

The city promises jobs, convenience, connection. The forest does not. The subtle-not-so-subtle suggestions I get to "get a real job," and abandon this writing fantasy, make me feel dangerously delusional. Insanely idealistic. My head lost in the clouds of the country, while the city is concrete inescapable reality. Especially as a 20-something year old. As A once told me after getting a great job and moving downtown, what else could I do?

Living in a city elevates ambition, offers opportunity, and sparks serendipity... but can also cloud your mind with desire and drown your intuition with noise.

The (exciting and terrifying) quest is to find a place where you feel at home. A place where you feel deliciously happy. A place that calls out, clear through the silence or high above the noise, "You belong here".

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❓ question i’m asking:

How much of my day is spent doing things out of obligation rather than out of interest?

Have interests sneakily turned into obligations?

📸 photo of the week:

Thank you for reading! It means a lot to me :)

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it. Beyond that, click the ❤️ button on this post so more people can discover it.

Share

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

Much love to you and yours,

Tommy

I hope you’re having an excellent start to your weekend.

What I’ve been up to:

• I published an essay Tuesday on the dangers of deservance. It's far from perfect, but I'm proud of the final product. Perhaps one of the best (and most honest) essays I've written.

• I'm spending the Canada Day long weekend in Niagara, Ontario with good friends.

Here's an inside look at the most interesting ideas I've explored this week.

Enjoy.

✍️ quote i’m pondering:

American poet and naturalist, Mary Oliver, on the spiritual background to her life:

It’s been one of the most important interests of my life, and continues to be.

And I have no answers, but have some suggestions: I know that a life is much richer with a spiritual part to it. And I also think nothing is more interesting.

📚 book passage i loved:

Do not trouble your hearts overmuch with the thought of the road tonight.

Maybe the paths that you each shall tread are already laid before your feet, though you do not see them.

― The Fellowship of the Ring by J.R.R. Tolkien

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💡 idea from me: compliments & kindness

When I was a boy, my grandfather told me I had shoulders like Gordie Howe.

Howe was a Canadian hockey legend, from the prairies of Saskatchewan. A man of titanic power. Built like a bull, muscle wrapped tight as steel.

At 5 years old, I clearly looked nothing like Gordie Howe. (Yet...) But I remember looking in the mirror, proud of myself. Smiling.

Now, as an adult, those words are one of the few things I still remember from that age.

Tolkien taught me language is powerful. Words matter. Words shape the world.

Sometimes small gestures can have a big impact. Sometimes people need to be told about their amazing qualities to see them for the first time themselves. Sometimes a compliment that took seconds to say, sticks with someone for decades.

As simple as looking someone in the eyes and saying you genuinely appreciate them.

As sophisticated as noticing potential in them they don’t see.

Leo Tolstoy: “Nothing can make our life, or the lives of other people, more beautiful than perpetual kindness.”

When you notice something you admire in someone, take a second and tell them.

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❓ question i’m asking:

Where am I spending energy trying to please someone who actually doesn't care? Where am I creating expectations that don't exist?

📸 photo of the week:

Last March, I spent two hours in the Maud Lewis exhibit in Halifax.

The repetition in her creative process was remarkable: Maud would paint the same scene, again and again, until she felt she got it right.

I also loved the personal thank-you notes she’d send to each of her customers.

Thank you for reading! It means a lot to me :)

Spread the love—If you want to support my work, the best way to do so is by sharing it with others who would enjoy it. Beyond that, click the ❤️ button on this post so more people can discover it.

Share

Get in touch—If my writing resonated or if you just want to be friends, please reach out 😊 Reply to this email, leave a comment, or find me on Twitter!

Much love to you and yours,

Tommy