Ask any career mentor, financial planner, or parent for general life guidance, and they’ll probably give you variations of the same idea: invest time and resources now so that you can achieve successful outcomes in the long term. Whether that takes the form of trying to develop a career, putting money into an IRA, or investing in educating ourselves, the general reasoning is that if we work hard now, we’ll be better equipped to enjoy the fruits of our labor in the future.

This advice is generally true - investing effort now almost always leads to better outcomes later. But occasionally, it can also lead to an unexpected contradiction: sometimes, putting effort into achieving an outcome can take away from, rather than add to, the ability to enjoy that outcome’s benefits.

Take college admissions. Prestigious colleges make their value clear: if you come to our school, we can give you teaching, resources, and connections to better achieve your goals. These benefits are clearly valuable to a motivated student, so countless high school students compete to gain admission. The problem is, becoming a good candidate in the eyes of the college can require investing years of full-time work - doing specific extracurriculars, obsessing over a GPA, or researching the admissions metagame. Often, these activities help with getting into college, but take away from time that could be spent trying things out, developing interests, or figuring out what to work on - activities that would be helpful for making the most of college. So the end result is that the student that wins admission might be less well-suited to use the college’s resources than a student that hadn’t bothered with the admissions game in the first place.

Working ambitiously to acquire wealth might be another example. Everyone fantasizes about working hard, getting rich, and finally living a life of relaxation and luxury. But being ambitious and working hard likely makes one less able to enjoy the wealth they would get. Sacrificing free time to work takes away from learning how to spend leisure time and money. Moreover, ambition, by definition, makes it difficult to stay still, relax, and enjoy wealth once it has arrived. A relaxed person would probably be better suited towards enjoying being rich than a hardworking one.

An even more general example is how workers are encouraged to structure their careers around retirement. Most people give up their twenties, thirties, forties, and fifties to make enough money so that they can enjoy free time for the rest of their lives. But for many people, free time would have been best to have in able-bodied youth. So giving up time for money early in life might have been a bad trade.1 It might’ve been better if society encouraged working 20% less hours for 20% more years instead.

Many people realize these contradictions, but I think sometimes others don’t until the very end - until after they’ve worked hard to achieve an outcome they finally realize they don’t enjoy as much as they thought they would. Call it “enjoyment dissonance:” working towards an outcome without realizing doing so erodes the ability to enjoy that outcome.2

That dissonance can result in confusion and unhappiness for those that don’t realize it until later. Like the Harvard undergrad that feels pressured to do something prestigious, but doesn’t know what, since working to get into Harvard meant they didn’t get the chance to find out their true interests before college; or the wealthy person that’s restless, cracking under stress, and secretly wishes they were spending their days alone on a fishing boat; or the 67 year old that realizes retirement maybe isn’t all that great.3

Enjoyment dissonance comes from working towards outcomes without fully realizing the opportunity cost that comes from achieving them. This is especially easy to fall into when aiming for prestigious goals, since specific, measurable achievements - college acceptances (instead of general success), wealth (instead of fulfilling work), retirement age (instead of meaningful experiences) - don’t make obvious all the externalities that go into them.

To that end, it’s probably worthwhile to periodically reevaluate how your efforts influence the outcomes you’re working towards. What are you investing in? What are you hoping to get out of it, and how do your efforts change your ability to reap their rewards? Make sure the returns minus the efforts actually correlate with the successful outcome you want. If not, it might be time to find different things to work towards.

  1. Brings to mind the regretful phrase “in youth time and energy but no money, in middle age money and energy but no time, and in old age money and time but no energy.” ↩

  2. I’m not a huge fan of the name, but I still think there should be a term for this. Hence the bad name. Welcoming alternative suggestions. ↩

  3. These examples are all from real people I know, so even if they’re not representative of everyone, they’re hopefully accurate for a few. ↩