The Sunk Cost Fallacy of Your Career

Plus a special announcement!

I’m a big fan of putting down a book if I don’t like it. Sure, some stories take a while to get into and I’ll give most a good 50-page chance. I don’t even need anything to happen in those first fifty pages! But if the voice of the book and the narrator’s style isn’t clicking, I’m happy to move on. I only have so much time to read for pleasure and when I do I want it to be, well, pleasurable (by which I mean making me cry or laugh or feel utterly gutted and questioning my life).

Last year, I kept track of how many books I read for the first time. This had the unfortunate side-effect of compelling me to finish books that I started even when I didn’t enjoy them. And though I did up my number, I mostly just white-knuckled through a lot of mediocre books. This year (thank god!) I’m back to not tracking. Since Jan, I’ve dipped into passages of old books, bopped around essay collections, and only finished novels I enjoyed. Truly refreshing.

Not feeling the need to finish something just because you started it is one of the most freeing concepts I’ve ever grasped, one that, especially as an inherently competitive person with obsessive-compulsive tendencies, does not come easy, and one that changed how I view my career and, in turn, my entire life.

The “sunk cost fallacy,” for those unfamiliar with the term, is the phenomenon whereby a person is reluctant to abandon a strategy or course of action because they have invested heavily in it, even when it is clear that abandonment would be more beneficial. A common example of this is the assumption that you should finish a movie or a book that you’re not enjoying because you’ve already put in that initial time. This is a faulty assumption (a “fallacy”) because the only thing you’re likely to get from that decision is… even more wasted time. We’re likely to continue something if we’ve already invested in it, even when it goes against evidence that it’s still the best decision.

It's scary to let go of something you’ve put time and work into. When it comes to professional success this can be exceptionally true. Not only do our jobs pay the bills, they’re often fundamental plugs for the leaky boat that is our self worth. Leaving them midway can feel like a kind of death of self. And so we assume we have to stay in a single lane, keep doing the work we’ve always done. Capitalism relies on this consistency, because competition, the beating heart of the system, requires training, preparation, and time. And so in order to be successful, we learn to view our careers as a track or a tree—something to stay on and climb up—afraid if we jump off, all that training and preparation will be lost and go to waste.

And this is true to an extent. We do have to build skills and gain experience in order to be competitive in the job market. If you really want to be a doctor, for example, the first few years of med school are not a sunk cost (unless you no longer want to be a doctor), they are just an unpleasant part of achieving your goal. But the idea that all of us have to consistently climb a very specific path in one specific direction just because we have already clocked time is simply not true. If you’ve built skills and experience in a particular field, that experience cannot be taken from you. If we have the means, the perceived risk of taking a career break to pursue something else is much higher than the actual risk.

From a very young age, my career felt like a glass house, like the smallest mistake would bring it all crashing down. I chose my college, my major, my first job with the care of a surgeon, wanting everything to be pristine in order to make money, pay back my debt, and support my family. When I got an itch to write in my 30s, I tried to ignore it. I had spent so many years and so much money establishing myself as a certain type of professional. At the time I had gone back to business school, shifted towards “social impact” work, and had a dream title at a dream organization. To then try to maybe become a writer felt insane. In my mind “the arts” were for people who read Proust in college and grew up with dishwashers. People who were encouraged to just flow and feel, not plan and optimize at all costs, people who had parents with safety nets. Artists were a different species, and I was not one of them.

Still, I scribbled every weekend and after work. In secret at first, mortified to tell anyone that I considered my thoughts important enough to spend the time it took for me to write them down.

I was thirty-three when I took my first writing class. I was so nervous that I almost turned around at the door, terrified I’d have to read my writing out loud and people would laugh or, worse, exchange nervous glances, too embarrassed on my behalf to make any audible noises. But that single workshop introduced me to my first “writer friend,” who then introduced me to more writer friends, who then encouraged me to take more classes, where I then made more friends and started, eventually, to accept the idea that since I was now writing somewhat constantly I was maybe sort of a writer myself. So when I realized it would take many, many years and an unfathomable amount of rejection to publish an actual book, I did not run away in despair feeling like a total fraud, but kept writing, because that was, I had learned over many years, simply what writers did.

And through that process something fundamental shifted in how I thought about my career. What if instead of a precious glass house, it was more like a bouncy castle that I could actually have some fun with?

I’ve noticed the most common thing getting in the way of mid-career professionals itching to pursue a creative passion is the fear that if they leave their job, they’ll lose everything they’ve worked for. But what I’ve found—personally and in watching many friends who have also taken long breaks from traditional career paths—is that you will very much not lose the years of experience you’ve worked hard to gain, you will not lose the titles that continue to sit neatly on your resume, and you will not lose the skills you’ve developed and will continue to develop in whatever non-traditional next step you may or may not plunge yourself into.

What you will lose is a few years of climbing. Maybe you save enough money to take some time off, then return to the job market and land the exact title you had before you left. Maybe that makes you feel bad about yourself because maybe the guy who used to report to you now has a better title than you and so you feel like a little kid getting held back in school. But here’s the beauty: we are not little kids shuffling through a very specific track to get on with our lives. We are IN our lives and we can do whatever the hell we want with them! Sacrificing a few years in an unpleasant career to make room for a whole new part of your personhood—a part that could not possibly translate to the hellscape that is LinkedIn and thank god—has its own inherent value. And opening ourselves up to different forms of value can be life-changing if we allow ourselves to silence the ingrained comparisons that capitalism so brutally instills.

I didn’t leave my job as soon as I discovered writing, I couldn’t possibly. I do not have retirement level savings, or a rich spouse. And I didn’t leave tech entirely when I started writing seriously or when I sold my debut novel. Instead, I adjusted the way I viewed my career. I took extended breaks when I could, and stopped trying to climb in a traditional sense, got more creative with the roles I took, then reset my priorities and expectations to make room for new goals. Of course this depends on the particular industry and job market (which across the board right now is dire). But I’ve spoken to many people eager to pursue something creative, who could easily get another job if they needed to, but are still afraid because of the time they’ve already put in.

Instead of our careers being a tree to climb, they can be a playground to hop around. Clocking many miserable years is no reason to push through more miserable years. And anyway, that misery will probably be waiting for you if and when you need it.

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Special Announcement!

I’m piloting a workshop! From Corporate to Creative Writer is a 4 week workshop designed for professionals who want to get started and / or progress in a creative writing practice, while making meaningful connections along the way.

Over the course of a month, we'll have in-depth discussions about different paths to publication and the steps involved, examine how a professional career and a creative practice can co-exist, and unlock how to make progress and stay accountable in a way that fits with your lifestyle and goals.

Logistics:

• One-hour sessions once a week for 4 weeks; includes a brief presentation, class exercise, and group discussion

• Two 30-minute individual sessions, at the beginning and end of the month to discuss goals

• A detailed edit of any piece of writing, up to 8 pages

• $500 per person (this is a discounted price for early cohorts)

Note: You will NOT be required to share your writing with other people in the class.

Learn more and answer a few short questions if interested!