A journey of several months, countless conversations, and many revelations.
January 2019
Fly to California on New Year's Eve. Spend New Years with your to-be cofounder and your Airbnb mates in Mountain View. Interview for a startup incubator the day before its winter class begins. Receive a rejection swiftly.
Ponder existence. Recluse yourself in a cabin far isolated from your friends, your family, and most importantly, the version of yourself you'd left behind. Run daily — 3 miles, 5 miles, listening to words of wisdom from some incredible teachers through an artform you're just beginning to appreciate.
Write constantly on Reading Supply. Pour your heart out onto digital paper, reconnecting with the creative side of yourself whose existence you'd forgotten.
Receive a surprise email from a contact at a famous venture capital firm. “What are you doing now?" he asks, noting the break in your LinkedIn timeline. Contemplating existence, you reply. He asks to get on the phone and talk further. “Let me introduce you to some companies we've invested in." Sure, you reply, thinking that even though you weren't interested in a job, it could be interesting to have some conversations. Think, then write, about mortality and career.
Get introduced to several companies. One of them has been working for a year on the exact product you'd pitched to the startup incubator several weeks ago.
Meet with all of the companies on your next trip to San Francisco — three in total. Two aren't a good fit. One asks you to interview. You think about it, then decline. You're not ready to reenter this world.
February
On Instagram, you see ads for a gorgeous backpack cropping up every time you tap through Stories. Think about creation, the creative process, and all that it entails. Reach out to the founder of the backpack company, ostensibly for a discount, but really wondering if you might be able to work together. He gets back shortly, and you meet up the next week.
Over matcha, realize that you have much more in common than you could have expected. Impressed with his drive, accomplishments, and balance between artistry and business sense, propose to work with him on a project for a month.
Your career mentor of the past year and a half asks you what you're doing. Working with this guy who makes backpacks, you say. He becomes known as backpack guy among your friends and acquaintances.
Your mentor introduces you to half a dozen companies he's in contact with. Accept the meetings, more curious to hear about these founders' journeys than you are about taking a job. One company is based in New York City, and has an audacious goal. They invite you to come visit them in the Big Apple and see if you like working with the team.
Envision yourself strolling among the red brick buildings in SoHo and rendezvousing with friends at the MoMa — the real one — on weekday evenings. Orchestra nights at Carnegie Hall and fashion shows on Madison. I could do this, you say to yourself. I could live there.
Visit the startup in New York. Enjoy your time with some wonderful people, but realize that your heart was in San Francisco all along — not the version you'd sullied with cynicism and disdain, but the one you'd constructed back in 2017 while running miles and miles through the hilly streets.
Stumble upon a post of aphorisms by Naval Ravikant, finding deep resonance with many of them. (“Wealth creation is an evolutionarily recent positive-sum game." "This is such a short and precious life that it’s really important that you don’t spend it being unhappy." "Don’t debate people in the media when you can debate them in the marketplace.")
Fly back to San Francisco, with renewed confidence and slightly more clarity on what it is that you want.
March
Write a spontaneous email to a founder you'd met almost exactly two years prior. Inquire about rumours that the company was doing incredibly well, unbeknownst to most. Meet with him a week later in the Mission. The team that had been three strong was now eleven. Interview with them for an unconventional role on a sunny afternoon. Appreciate their airy loft space and the golden sunlight streaming through the windows.
Talk to backpack guy about cofounding a new venture together. Very nearly accept. The venture is exciting and you trust his ability to execute. Hesitate — you're not sure why, but you want to see what else is out there first.
Spend an afternoon at a Korean spa in Palo Alto. Spend twenty, thirty, forty minutes in the Swedish dry sauna, until the heat seems to permeate your very existence and settle into the crevasses of your mind. Emerge into the sitting area with the distinct sense that you had to write. Stream of consciousness jot down four things you're looking for now: work with extraordinary people, accelerate personal growth, build financial runway, build something that resonates deeply. Fire off an email on a whim to a founder you've been talking to.
Realize you'd always be left wondering if you didn't see what it was like at the last startup you worked at. That some part of you still thought of those people as family, because the months you'd spent there had been transformational for you in all areas, and you attributed the growth in part to them. Talk to the founder. Meet with your friends and mentors who work there, as well as some new faces.
Do a whirlwind three day trial with another startup you find a whim. They're run by two guys your age, and have really promising traction. You'd be engineer number two. Shy away solely because they work a lot. Work life balance would not exist here. Know that in order to balance your own energies, you would need more time on your own than this opportunity would give you.
Whittle down your choices to the Mission startup and the company that felt like family. Notice, in a curious turn of events, that Naval Ravikant had been one of the first angel investors in the former.
It's like you're choosing between your high school sweetheart and a cool new boyfriend, your best friends quip. Laugh, and also acknowledge the truth of it.
Feel your heart begin to whisper its choice to you. Dig up journals from two months ago where you wrote a few descriptive items that seem to describe the Mission startup precisely. Think about unconventionality, risk, courage. Realize that among the four criteria you'd jotted down at the Korean spa, there was a single clear winner.
Realize that if you decided to return to your last company, it would be a decision made out of fear, rather than out of expansion and possibility.
Decide that you are not a person who makes decisions out of fear.
Decide to join the Mission startup, in spite of the uncertainty that it poses and the new environment it would put you in. Or, perhaps, because of it.
Fly back home to Canada the day after you sign the paperwork.
Know that the next time you're back in San Francisco, everything would be different.
And that was okay.
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