I graduated college a semester early to live in New York City. My dream was to write for a living, and I figured I would increase my chances of that happening through occupational osmosis — full immersion in environments where renowned print publishers roamed and signed writers for six-, even seven-figure contracts. I hoped that by being in the proximity of these heady literary fumes I might alchemize into a commercial sensation who never needed to work a JOB-job another day in her life.
I worked in low-paying print editorial jobs my first five years out of school, the kinds of roles that sounded amazing to anyone not living in New York City that I had to supplement with additional gigs to get by. It hardly mattered that my diet consisted of questionably safe, half-off sushi, bagels, pirogies, and Chinese takeout that I ordered for the complimentary soup-container-full of wine; I was getting exposure to the business of writing. I ignored how, reading so many manuscripts, copyediting so many articles, the thought of writing my own exhausted me.
There remained an uncomfortable juxtaposition of what I did for a living and how I wanted to live, and those closest to me who shared my values were starting to pick sides.
My boyfriend at the time worked in a law office by day to support his screenplay and novel writing. A few months after moving in together he went off the W2 grid completely to complete his novel, live in Italy, and refrain from ever having to pick up another item of clothing from the floor again — a decision that concluded our time living together. My next boyfriend, a painter, covered rent initially by living in his dojo, then later by waiting tables to afford his Hostel-style apartment, a studio with no furniture, just three mattresses for him and his two roommates and a shower curtain that hung in the kitchenette, denoting a bathroom.
There was tension between us, when I demurred from spending the night at his place, versus at my two-bedroom, one roommate abode. Something was shifting in me, and not just because I wanted to poo in private. I was kinda done with living like an artist.
There was also a realization that my “art,” in itself, fed off of the real world. As a book and magazine editor I worked with many brilliant authors who were successful writing about their non-literary pursuits. I recall one in particular, a former police officer, who wrote gripping crime novels featuring a female detective protagonist. Her experience shone in these novels. Celebrating the launch of what was to become her fourth New York Times best-seller, at a circus-themed launch party in her Tuxedo Park manse, eating popcorn from a vendor cart in her spacious dayroom, it occurred to me: Maybe there’s another way.
Only then did it dawn on me that I was taking the whole exposure via working in “the industry" thing too literally. Perhaps, if writing really was my jam I would need to do other things that merited writing about.
It also led to a lot of confusing fits and starts attempting to merge my passion with a paycheck.
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“If someone tells you to follow your passion, it means they’re already rich,” says Scott Galloway in his book, The Algebra of Wealth. "'Follow your passion’, he says in this Financial Times article about the book, "is Latin for ‘prepare to be exploited’.”
In her HBR article "Striking a Balance Between Your Passion and Your Paycheck” Erin Cech makes a similar argument in more practical terms:
“…following your passion can be hazardous, incurring significant financial risks. Finding a job aligned with your passion right out of school may require sacrifices of time and economic stability. Searching for jobs that don’t just fit your credentials and skills but feed your soul may take months or even years.
…Moreover, the ability to navigate these risks is not equally distributed. Passion-seekers from wealthy and upper-middle-class families are more likely to have the social springboards … that help them land work that is both in their passion and decently paid."
Galloway suggests pursuing occupational middle ground, "to find something you’re good at and apply the thousands of hours of grit and sacrifice necessary to become great at it.”
I was always painfully aware of this tension between passion and profit, and I nearly always took the profitable road — or I took the passionate road until a profitable road presented itself. I did eventually get a book contract, but, realizing that the $15k advance for six months of work would not cover my rent or food, I declined the offer, rationalizing that I’d get back to writing the book once my professional profile merited a higher advance, or (back to Scott Galloway’s point) I was too well-off to care what I was paid to write.
The problem with that approach is that the moment of pure financial self-satisfaction never really materializes. Initially my reason for putting work over passion was to pay rent; later that reason was to pay my mortgage, then college savings, then family travel, and then retirement. That "F-you I’m done working so hard” number we all have in our heads, it would seem, is written in sand.
Perhaps passion itself is a mirage, desired as an endgame you never actually expect to win. A friend of mine who left a very lucrative tech job was told by her financial advisor she didn’t need to work any more, and so she left her company to decompress and work on a novel. Part-way into her endeavor she reached out to me for advice, not on getting published, but on finding another job.
Just as ironically, in my 25+ years of profitable pursuits I did many things for free — bootstrapped companies, reviewed other people’s manuscripts, let many an aspiring entrepreneur “pick my brain,” wrote drips and drabs on social platforms that, if aggregated, could comprise an entire Wikipedia's worth of content.
Only when I played out the fantasy of having my passion-filled cake and eating it did I realize I had been sneaking bites of it this whole time, and I only appreciated the cake in the context of the salad days that preceded it. Life is not meant to consist of dessert alone. If it did, it would not be dessert; it would be sweet torture. It would be meaningless.
Guy Kawasaki said it best in our recent Optionality interview with him, in which he talks about Ikigai, a Japanese word that is supposed to denote what makes you wake up in the morning.
"I fear that people have taken too simplistic an approach to [Ikigai], because they have tried to make it into a Venn diagram … Don't get me wrong. That is an ideal place to be: I love what I do. I'm good at it. I can make money. God bless you.
But I think a better test for your Ikigai is when you do something that at least initially, you're not good at. And you might not enjoy so much because you're not good at it. And you cannot make money doing it.
So when you do something and continue to grit it out, when you're not making money, you're not good yet. And because you're not good, it's not exactly joyful. That's when you know you found your Ikigai.”
I translate the inverse of this to be true as well: If you ARE making money doing something you are good at, not passionate about, but it enables you to find your Ikigai, God bless.