I got a job.

Why have I sought my path with fervent care,

If not in hope to bring my brothers here?

— Goethe

The Departure (Thomas Cole, 1838)

They say the three biggest decisions in life are who you're with (partner), what you do (career), and where you live.

A few months ago, I wrote about where to live. This essay is about how I chose a career. I've also written about my philosophy for work here.

Part One

Recently, several people asked me what I do for work and how I make a living. Despite the temptation to give a veiled answer in a velvet tone, like "a little of this, a little of that," last week, I signed a full-time job offer. My first “real job” in four years. But it was a long, confusing, and arduous path to get here.

Here, I want to tell you the story of how I decided what work I wanted to do.

In my last year of university, after realizing I didn't want to go to Wall Street, following a series of intense finance internships and a period of spiritual seeking, I decided I wanted to be a writer. I had already been writing a newsletter on Substack for a year, in the cracks and crevices of the day, but now I wanted to be an uppercase-W, real-deal Writer. Nothing captivated me more than the world of books and ideas. Becoming a writer seemed the only way to make a full-time profession out of my full-time obsession. I was convinced that if I could make it work financially, writing for a living would be the dream.

After I graduated, thinking I was above a corporate career path, I landed a part-time remote job for $30/hour working with Noah Kagan, an entrepreneur and business influencer, on his book Million Dollar Weekend. I spent a year bouncing between home and away, visiting the Canadian Rockies, Brazil and Argentina, then Thailand and Japan. I would write for a few hours in the morning, then work on the book in the afternoon. Yet, even with ample time for my own interests, I still scraped and clawed for more. A few hours wasn’t enough. I had an almost primal urge to command complete control over my time.

When the book launched in January 2024 and work wrapped up in April, I turned down the offer to join his YouTube team, as well as three other offers from popular entrepreneur-influencers who were writing books. I didn't want to be a "book marketing guy". I probably could've spun a decent business out of it, but I had no interest in floating over the globe like a pale ghost, getting very good at selling books that I wouldn't read myself. No, I wanted to be a Writer.

After two years of yearning, never thinking it’d actually happen, I finally found myself free to pursue writing. I wouldn't be making money, but it didn't matter. I would be living out my dream, pushing it to the cliff’s edge and seeing if it would fly.

To keep costs down, I mostly lived at home. The two trips I took—two months in Newfoundland and one month in BC—were both through Workaway. In exchange for five hours of work, I could stay with a host family for free and write in the quiet corners of the day.

In June, after a year of planning, I turned on paid subscriptions. I even hired a marketing consultant to make sure the launch would be lucrative. With "conservative assumptions," I projected that in two to three years, Substack would generate enough income to live off.

But, to my surprise and chagrin, writing full-time wasn't anything like I thought it would be.

I had complete freedom over my time. But instead of feeling liberated, the boundlessness soon became daunting. It was entirely up to me to structure each day and keep the discipline to stick to it. Weekdays were no different than weekends. I could choose to do nothing, and nobody would care. Life was so weightless that I was floating away.

Eventually, I learned to set a writing cadence that worked. But when the words I wrote became the point and purpose of my day, the standard by which I measured a day's success and justified my existence, the pressure became Marianic. A bad day's writing became a bad day.

There was a certain emptiness that rose into my soul like a gas and diffused despair. An emptiness from making my mind, my thoughts and ideas and feelings, the sole center of my life. I saw a future of this downward spiral of introspection, lost in the labyrinth of my mind, peeling back the layers of the onion until there was nothing left but abyss. Dante’s critique of Odysseus was a clear warning: wandering forms character, but one can wander too far.

And, I continually stubbed my toe on the brute reality that I could only write for two, maybe two and a half, hours a day before my brain began to melt. I was living the life of a retired 70-year old, writing and reading and baking, strolling through meadows of milkweed and watching clouds pass. Sitting in a coffee shop in the middle of a Tuesday afternoon, surrounded by old men reading the newspaper, the subconscious guilt tattooed on the back of my brain was a reminder that I hadn't done my years of service to society.

And that, in all honesty, was the worst part: I didn't feel useful. I didn't feel my work was making a real contribution in the world. Yes, people were lavish in their appreciation of my essays, which still makes me smile like a kid in a candy store, but I didn’t feel I deserved their kindness. Writing is fundamentally a self-serving act. I write entirely to find out what I'm thinking, what I see, what I want, and what I fear. Writing is an act of ego. There's no way around it.

And, not to forget, there was the fact I wasn't making enough money to buy groceries. I learned it’s very hard to get people to pay for writing, especially without being pushy or clickbaity. Monetizing creative production is difficult¹. The economics of any creative endeavour are almost impossible to make work, especially in the first two decades. Creative success asks for a lifetime and won't accept anything less; almost no one succeeds right out of the gate. Most artists don't do their best work till their 40s or 50s, sometimes later.

To be an artist is to commit to at least a decade of obscurity. At least a decade of persistence and sweat and devotion, until one day, unexpectedly, it pays off.

Besides, I knew if I started to treat writing as a career, and relied on it to afford groceries or a mortgage or car payments, my work would suffer and I would suffer more and the people who love me would suffer most. Pinning financial goals to each essay would make me deeply unhappy. Soon enough, my writing would mold around money, aiming for virality instead of a patient quality.

When I began to read about the lives of my favorite writers, it wasn't pretty. Many were manic depressives, lonely alcoholics, and romantics with reckless abandon. They often couldn't keep a job or couldn't keep out of trouble. Many were poor as pennies, relying on family or rich, pitying patrons to survive. And they all had egos bigger than the moon.

Were they writers because they were manic, or manic because they were writers? I think the answer is both. Their mania and their creativity existed in an ecology, each fueling the other. There is a certain Faustian bargain writers make, where their excessive introspection and ruthless observation lends to a stunning landscape of the soul, but elevates their interiority to a dizzying height, from which all they can do is fall.

I decided I did not want to be a martyr for my art. I did not want my life to be a train wreck of torment and tragedy. Mostly, I want a normal and quiet life, filled with good work and green things. To build a beautiful home and fill it with love. To work in the garden on Saturday mornings and read books on Sunday afternoons. Walk about in the woods, raise children, make pancakes. In an age where fame accumulates at the extremes, a normal life is overlooked and underrated. Domesticity is not dull but life's true delight. "The most extraordinary thing in the world," Chesterton wrote, "is an ordinary man and an ordinary woman and their ordinary children."

I decided I would rather live a normal life, even if it meant I would never produce anything great.

Besides, a day job can fuel creative pursuits. I figured meeting some characters and having some real life experiences—instead of being locked away in an ivory tower of reasons and proofs—would only deepen my understanding of what it means to be human. In order to write about life, I must first live it.

And so there I was. I had no interest in being a starving artist. To reduce my lifestyle to that of an ascetic or rely on my parents or a partner to foot the bills and limit the opportunities for a family because of my own needs for a creative odyssey. It seemed selfish. I felt I had a duty to build wealth. But, I was also unwilling to go back into the crazy corporate world, where I knew I would get sucked up in the current. It'd be foolish to think I was strong enough to resist what everyone else around me was doing. And I was unwilling to give up on my intellectual and spiritual life in order to make a living. Not only would I become lost and depressed, I'd inevitably start to hate the confines of the job until I cut enough corners to get fired. I needed work where I still had time outside of the office to expand my mind and keep my heart open. To remember spreadsheets are less important than Shakespeare. To stay close with family, forge meaningful friendships, help the community, and take care of my health.

Once I decided to get a job, the first place people told me to look was in writing. On the surface, it makes sense. I love to write and I've gotten good after years of deliberate practice. But instinctively, I knew it would be creative suicide. A big part of the reason I love writing these essays is because I have autonomy. I decide what ideas are worth exploring and expanding. I decide what sentences to keep and which to cut and how much to abuse alliteration. Perhaps I am maternal about my words: devoted and fiercely protective. Writing about things I'm not interested in, while someone else makes me cut parts I love and keep parts I hate, would drive me nuts. It is, as a writer friend said, "prostituting yourself out". And, after a full day of writing for work, my interest in writing for pleasure would be close to zero. I wanted my job to be entirely separate from writing.

The second option, one I seriously considered, was trying my hand at entrepreneurship. It's all the rage these days. I have thousands of subscribers on Substack, growing at a healthy clip, as well as experience at start-ups and a business education. I could whip up a course or coaching service and package it with a pretty bow and make more in a month than I’d make from writing in a year. I could also become a book consultant, charging authors $500 an hour to give them the "blueprint to success". Again, on the surface, it was alluring. I could live in Kyoto or Cape Town or Cambridge, work whenever I wanted, and still have time to write.

But here's the fatal flaw: I would no longer be a writer. I would no longer be devoting most of my time and mental real estate toward publishing exceptional essays. Writing, the thing I cherish, would get devoured and digested by the jaws of business. It just would. My writing would deteriorate as the top idea on my mind became selling rather than sentences, and with it, my respect for myself. Success would lead me away from the very thing that made me successful in the first place. Success, in short, would eat itself (more about this decision here).

Here's another uncool but true thing: I realized I'm not an entrepreneur. I don't have the risk tolerance. The unpredictability and volatility in income didn't seem like a rock I could build my house on.

Writing and selling require entirely different mindsets and modes of being in the world. Writing is internal, private. Selling is external, public. I have not seen a single person who has been able to successfully do both. No one can serve two masters. Yes, some entrepreneurs have written great books but, I would argue, they are fundamentally communicators, not writers. They are not obsessed with the craft of writing but rather with communicating their ideas about business or money or productivity in a clear and crisp way. A communicator will cut all the redundancies and repetition and recklessly weird combinations of words. A writer will leave them in. A communicator will think JFK could've simply said, "Ask what you can do for your country." It would have been more concise. A writer will ramble on about the shoulders of mountains and the lips of the waves and the toes of trees. A communicator only cares for the medicine. But a writer knows it must go down smooth; it must dissolve in the blood, infusing brain and heart and coursing through the veins until it is felt in the nerve endings. Ideas alone will only get you so far.

Despite the delusion, I still held firm to my faith in being a writer. Just like when I was a boy, filling the final few pages of my blue and red lined Hilroy notebook with poems of tragedy and stories of knights, until my hands hurt and my Dixon #2 pencil was dull.

For a while, I considered how demanding a job I wanted. Mary Oliver, who made nearly no money off her work, always took uninteresting jobs because she was worried an interesting job would distract her from poetry². On the other end of the extreme, I know a man who became a Wall Street investment banker in the 80s because he wanted to capture the mechanics of power in his work with crystal acuity, despite needing to wake up at 4am to still write. Eventually, I landed somewhere in the middle. I didn't want a menial or minimum wage job, because I'd soon get restless and because I wanted a salary I could provide for a family from. But I also didn't want 80-hour weeks, moving at head-splitting speeds, to preserve time for higher things.

Over the fires of contemplation, I forged my ideal: a stable, secure, 9-5 business job that would challenge but not consume me, to then pursue writing on the side. I was content with a moderate salary as long as there was room to grow. I also liked the idea of doing something "low status," because these opportunities tend to be overlooked and undervalued. Ideally, a job that I could continue over the long-term, compounding skill and trust and responsibility, until I can earn ownership of my time.

Now, I just had to find one.

Part Two

In February 2024, while I was still in the throes of all these discoveries, I had a glimmer of an idea that I wanted to work in wealth management in a small town. When I did an assessment of my strengths and weaknesses and the work I actually enjoyed doing, knowing I could fool myself and I could probably fool an employer but I could not fool reality, wealth management made good sense. I figured I could use my analytical thinking and interpersonal skills to help families toward financial freedom, without having to work eighty hours a week.

In November, when I came home from my travels and began to dig into these career questions, my hypothesis still held.

It's dangerous to give general advice, since advice generalizes poorly, but I want to explain the process that worked surprisingly well for me.

• I knew I wanted to work at a small firm with a promising future. I'd receive a lot of personal attention, see my work make a real impact on the company's bottom line, and perhaps get equity in the business. Especially as one of the first hires, if the company grows, I'd be in a position to take on responsibility and leadership. And small teams avoid much of the politics and bureaucracy and meetings that slow things down and stop good work from getting done.

• If I had to choose, I would take good people over good work. Good people can make boring work fun, while bad people can make good work intensely unenjoyable. I had to find intelligent, heartfelt, high-integrity people to work with. Ethical trade-offs exist in any industry, and I wanted to be with people who were not in the black, or even in the grey, but standing upright in the white. I wanted to be proud of how I made my living and able to sleep soundly at night. My motto became: Good work, done well, for the right reasons.

• I would prioritize where to live before what I did for work. Not to risk being unromantic, but a job is just a job. It won't make my life meaningless or meaningful. It is fundraising for the things I want to do, with a chance to build my character and contribute to other people's lives in the process by doing excellent work. On the other hand, where I live is the biggest enabler in achieving my goals. I could have the best remote job in the world, but if I was living in a miner’s hut in rural Manitoba, it would make finding a wife or being involved in a local church almost impossible. I wanted to move somewhere I could stay close to family, cultivate a circle of friends, and have access to amenities without needing a car. Somewhere without the concrete calamity of a city but still had vitality. Ideally, a place I could grow into, with farm fields on the outskirts where I could one day buy land.

• I've always had a moderate distaste for job boards. They seem an ineffective and inhumane way to find a career. Now with AI, where anyone can dash off a customized cover letter in five minutes, I can confidently say they are a waste of time. Instead, I made a spreadsheet with 10-20 places I'd like to live then, one by one, searched on Google Maps for businesses in the area that fit my ideal: small, independent wealth management firms.

• I found contact information on their website or LinkedIn and reached out to the top person at each firm (always go right to the top) with a part-templated, part-customized email, asking to do a short ‘informational interview’ to learn more about their business (thank you

  James Bailey
  ). My goal wasn't to ask for a job but simply to get in front of someone, feel them out, and learn something new. Through these calls, not only did I learn about the industry and whether it was actually a good fit for me, I discovered there were companies doing exactly the work I wanted to do. Out of the ~30 professionals I contacted, 20 agreed to speak with me (small firms don't get a ton of inbound traffic), which turned into a few follow-up calls and three job offers. Mind you, not one of these firms had a job posting³. Many weren't looking to hire at all, but a few vaguely knew they wanted to add somebody soon and were waiting for the right person to "come along".

I started in late November, took two weeks off for the holidays, and by the beginning of March, I had a job at a firm I admire in a city I'm excited about living in. I’d make 30-100% more money if I stuck with my old internships, but I don't really care. It's enough for me⁴.

Of course, what is impossible to compress or express here are the long days of waiting and wondering, starved of direction and craving clarity. What is hard to appreciate, in retrospect, was how clueless and hopeless and conflicted I felt for many months. I considered almost every future imaginable—book consultant, copywriter, carpenter, farmer, hermit—until I found one that fit.

Since signing the offer, I have already felt the pressure on my writing hiss out like a tire's inner tube. I have felt more freed to write whatever I think is interesting and good (like an indecently long piece about my career search) instead of giving into the gravitational pull of public opinion. There is a creative freedom, a weight lifted off the chest, from not depending on writing for meaning or money. The weight doesn’t disappear, but I am more free to carry it. Like if you gave Sisyphus a wheelbarrow.

Without long, unhurried days to write all morning and read all afternoon, I will need to redefine my relationship with this work. I expect most of my writing will be done in longer blocks on weekends. I can’t promise the same publishing cadence, but I can promise everything I publish will be my best and most earnest effort.

As with any practice, ebbs and flows and plateaus are part of the process. I plan to be writing till the day I die.

Walk slowly and pause often,

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1. I think this is because people have a felt sense that art should not be muddied by money. As if it doesn't belong to the artist but to all of us. A sense that it's both so humanly universal and intensely intimate, paying for it almost feels wrong. My soul touches your soul, my heart beats through your heart, our minds reach the same resonance despite the oceans of distance in time and space, and I’m going to charge you $7 for that?

No advance in technology will alter this stubborn instinct. Artists will always be grossly but gloriously underpaid. Their product and their payment are both spiritual, a currency of the soul.

2. “I was very careful never to take an interesting job. I took lots of jobs. But if you have an interesting job you get interested in it.

If anybody has a job and starts at 9, there’s no reason why they can’t get up at 4:30 or 5 and write for a couple of hours, and give their employers their second-best effort of the day — which is what I did.”

— Mary Oliver

3. The best jobs don't have a title or description because you get to co-create the role, working on interesting things that help move the company toward its goals.

4. The cost of living here is also 20-50% cheaper than a big city. It might not eliminate the wage difference, but it shrinks it substantially.