The Curse of Conscientiousness

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I lasted just 18 months in my first job at JP Morgan, where I was supposed to help bankers manage money for their uber-rich clients. "Help" is too strong a word, since they didn't seem to think I was contributing much at all. My resignation was a response to a Performance Improvement Plan, a corporate euphemism for "shape up or ship out."

Contrary to what my title suggested, the job was 0% "analyzing markets" and 100% keeping track of processes, documents, and client requests. I can't overstate how objectively bad I was at all of it. I didn't show up to the office on time, develop a system to track deadlines, or clear my mailbox effectively. In an industry ridden with regulatory compliance requests, my lack of attention to detail added fuel to the fire. I repeatedly failed at the most basic tasks and couldn't find it in me to try any harder to improve. Years later, but unsurprisingly in retrospect, I was handed an ADHD diagnosis, a couple of decades overdue.

Regardless of the underlying reasons, I was always ambitious but not particularly conscientious. This has been a handicap for most of my career, but also a blessing in disguise. A conscientious person underperforming and miserable in an entry-level banking job would instinctively try harder until achieving basic competence and finding a baseline level of peace, albeit not happiness, with their situation. My approach was to put in some effort, but not enough, until it all came crashing down. This turned out to be an adaptive strategy, as my incompetence propelled me from one job to another until I found a role where my strengths more than compensated for my weaknesses.

I later discovered that most of my more conscientious peers experienced a foreign failure mode. Years later, they had climbed the ranks at their first company or moved to a competitor in the same industry. While impressive to me personally, as I could never have done this even if I wanted to, I’m skeptical that the randomness of the "spray and pray" process used to land one's first job effectively maps them to the career path that best leverages their strengths.

Almost by definition, highly conscientious people are probably decent enough fits for many more career paths. They probably have an easier and consequently better time in jobs that aren't a perfect match for them. So one could argue that the incentive to go around looking for better paths is somewhat lower. But it's unlikely that this behavior is rational, given the role that inertia and status quo bias play. As

Annie Duke

highlights in her essay on quitting:

This is the issue with grit. It can get you to stick to hard things that are worthwhile, but it can also get you to stick to hard things that are no longer worthwhile – like after your fibula snaps at mile eight. Throughout our lives, it turns out we are not very good listeners when the world tells us that we should stop.

There are a host of reasons why we ignore obvious signals to quit, not the least of which is that quitting has a nearly universal negative connotation. If someone called you a quitter, would you ever consider it a compliment?

The sunk cost fallacy and status quo bias are closely linked - we are famously bad at cutting our losses and moving on, since it means actualizing the loss and leveling with momentary unpleasantness. The prospect of deferring this unpleasantness by doubling down will never cease to be appealing, especially when quitting also induces uncertainty, another one of our renowned enemies. Given that the decision to quit is like stepping into a quagmire of biases, you should be skeptical of whether your decision to carry on is really a rational one, especially if you have built your identity around resilience or “doing hard things”.

Voluntary or not, quitting paid off for me. At JP Morgan, hours spent in the office were clearly net negative to my conscious experience. Now, work is so comfortably net positive that the only reason I don't describe it as "enjoyable" is to refrain from being annoying to friends in less enviable jobs. The difference might be less stark for some people, but it's easy to underestimate the net present value of a better fit. Even in a 9 to 5 job, work constitutes about a third of your waking life. Moreover, careers are long and most people I speak with are barely a quarter of the way through, and the rewards of modest improvement can be larger than they seem.

Some might worry about the forces pushing in the opposite direction, questioning if we're sometimes too quick to give up or if we should be concerned about our quest for novelty. It depends. My fiance, who happens to be one of these high C people, was not remotely worried that a quest for novelty was behind her desire to quit. It’s a much more rational worry for someone like me, who has had trouble sticking with things and completing projects. But even so, choosing the wrong career is a ridiculously expensive way to build a habit of sticking through things.

This is why young, talented people, regardless of ideology or philosophy, should take a leaf out of the Effective Altruism playbook. In the past few months, I've spoken with over 50 people, mostly early in their careers, about half of whom identify as EAs. On average, EAs seem more willing to approach their careers "like scientists," as 80,000 Hours puts it, testing one hypothesis at a time while being mindful of overstaying. This mindset is not only socially accepted but considered wise in EA circles, and EA organizations are more inclined to hire based on potential, placing less emphasis on directly transferable experience, provided the candidate shares their values. (Note: I’m not necessarily endorsing this from an organizational effectiveness standpoint)

Regardless, the younger you are, the stronger the case for ruthless hypothesis testing. I've never done this hardcore version myself, since my flaws did the work for me, but I'm bullish on the idea of young graduates adopting a self-enforced policy of "Quit in 12 months unless this job is a great fit." This changes defaults and guards against status quo bias. You can be confident that you're not quitting "only because it was hard." If you decide to stay, you owe yourself an explanation; if you quit, you don't.

I recognize this is easier said than done. Parts of the corporate world can be overly resume-focused, often without good reason. Interviews might question why you "jumped around so much." Quitting also means giving up linear growth opportunities on your initial path. It might involve starting a soft search for your next role a few months into your current one. As a society, we should certainly do more to facilitate this kind of career exploration for our brightest minds.

Ultimately, enjoyment and competence are likely correlated (barring edge cases like your friend's mediocre guitar playing). Unless you were destined for the pinnacle of your first or second job, losing a couple of years seems a small price for exploring options that could vastly improve your life and career. As the CEO of your life, recognize that most of the value lies ahead. When you're young, your job is to identify paths that maximize this value.

About the newsletter

In Optima & Outliers, I'll be digging into the big questions about talent, innovation, and progress that keep me up at night. From the micro-foundations of agglomeration effects to the impact of LLMs on productivity, each edition will investigate the ideas, institutions, and incentives that determine how talent is identified, developed, and deployed.

About Me

Vaishnav manages Probably Good's 1-on-1 career advising service and is part of MIT's Sculpting Evolution group (now SecureBio), working on global catastrophic biorisk reduction. He holds an MBA from MIT Sloan and an undergraduate degree in Computer Science from Nanyang Technological University (Singapore).