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The Best Career Plan Is No Plan
If you Google “how to make a career plan,” you will be immediately filled with regret.
The specific advice you encounter will vary depending on which website’s SEO experts are the most up-to-date on Google’s latest algorithm changes, but the gist will be the same. It’ll usually involve a lot of deep introspection to figure out your skills and “passions,” a lot of mapping out where you want to be at some distant point in time and trying to ascertain the best path to get there. If you’re especially unlucky, the phrase “five-year plan” might appear.
I think this advice is all terrible. I advocate for its diametric opposite: listen to your gut, operate on impulse, and don’t think too hard about anything that’s more than a year out. Daydream and imagine, for sure, but don’t plan too much. The best career plan is no plan.
Before I get into it, some hopefully obvious caveats. This advice applies mostly to people at the beginning-ish of their career—say, people under 30. It also clearly doesn’t apply if you’re interested in a career that can only be obtained through long-term planning, like being a doctor, astronaut, or totalitarian dictator.
For the rest of us, though, trying to plan a career too much is at best useless, at worst actively counterproductive.
We don’t know what we’re good at.
Even several years into our careers, most of us don’t have the full picture of what we’re actually good at, because we probably have too narrow an understanding of the possible range of things one can be good at.
It’s usually not hard to tell early on if you’re good at math or writing or computer programming. But many, if not most, of the skills that are valuable in a job are much harder to define. This is not a new idea—we’re all familiar with the concept of “soft skills”—but even those are usually defined much too generically: teamwork, public speaking, critical thinking, etc. The truly valuable soft skills are much more niche, things like:
Accurately perceiving which people in an organization have real power, regardless of what the org chart says
Convincing others to do what you want without coming off as sinister or manipulative
Finding the exact edge of the safe-for-work line such that you can be genuinely funny in the workplace without being lame or inappropriate
(These are all drawn from my own experience and will be different for everyone. The point is there are 10,000 such examples.)
The only way to discover which of these kinds of things you’re good at is through experimentation and experience—and even then the results will be different at different jobs and at different times in your life. Any attempt to come up with a list of “what you’re good at” in a vacuum is doomed to fail.
We barely know what we want now, let alone what we’ll want in the future.
It’s often impossible to predict which career opportunity will actually align with your desires, so there’s no point putting too much energy into any one choice. The things that make a job great usually aren’t the things you’d put on a pro/con list: they’re things like the amazing friend you make there, or the unexpected new skill you pick up, or the personal growth you go through when shit really hits the fan. Assuming switching costs are relatively low (which they usually are), better to just try something and adjust as needed later.
The longer your time horizon, the fuzzier the picture of your desires gets. A decade from now, you might be an entirely different person—so what good is it trying to plan that person’s career now? A good heuristic is to think back on your past. Would the you of ten years ago have picked the right career for the current you? If the answer is no, you probably shouldn’t try to do too much career planning for the you of ten years from now either.
Your “career” is an illusion.
With apologies to Margaret Thatcher, “There is no such thing as a career. There is only a series of individual jobs.”
In my experience, most people stress way too much about their overall career arc, trying fruitlessly to fit every choice into the so-called “big picture.” The thing is, your “career” is an illusion that only makes sense in reverse. Do enough interesting things and chances are they’ll become a career whether you try to make them one or not. And even if they don’t—even if you end up as a true all-over-the-place dilettante—so what? You still did a bunch of cool stuff.
Paradoxically, you might find that whatever it is you’re seeking comes to you easier if you pursue it with 10% less intentionality. As Viktor Frankl said:
Don’t aim at success—the more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side effect of one’s dedication.
We optimize the wrong decisions.
I’ve noticed that when people extensively analyze a career decision, they usually apply an excessive amount of focus to an unnecessarily narrow decision point. As Rob Henderson writes, we tend to spend too much time on decisions with equally satisfying outcomes:
When shown a disfavored food alongside a favored food, people chose fast. When shown a favored food alongside another favored food, people took a while. But this is irrational (at least in the economic sense)...people misallocate their time, spending too much on those choice problems in which the relative reward is low.
Historically, when people have asked me for career advice, they’ve usually been choosing between options that are not actually that different—i.e. two startup jobs. They’ve typically spent much less time (often no time at all) considering whether they should, say, just live on the beach and be a bartender for a year. I’m not saying that’d be a good idea—in most cases, it probably wouldn’t be. But if you’re going to exert extra energy on a decision, consider the possibility that you might be better off broadening the decision space instead of just trying to make the same decision “better.”
Plans are worthless, and so is planning.
Dwight Eisenhower famously said, “Plans are worthless, but planning is everything.” But whatever plans he made for his career very much did not involve becoming president. In fact, for most of his life he kept his political views so closely guarded that in 1951, both the Democrats and the Republicans tried to recruit him as their candidate. He rebuffed their entrees repeatedly, and ended up becoming the Republican nominee only after an extensive “Draft Eisenhower” movement formed and convinced him that the political circumstances of the time had created a genuine duty for him to run.
If he didn’t need a career plan, you don’t need one either. Embrace chance, stay open to opportunity, and see where the wind takes you. Odds are, it’ll be somewhere better and more interesting than anywhere you would’ve thought of on your own.