one do in their 20s to avoid regrets in future

Jim Stone

You can do anything, but you can’t do everything.

That’s the pithy version. A little more accurately . . .  you have a very large number of things you can do with your life, but you can’t do more than one or two to a high level of excellence.

This has many correlates:

1. Don’t “follow your passion” when you’re 20: Often people who aim to follow their passions will develop new passions whenever their current track becomes difficult. This can lead to a life of jumping around too much and never getting truly good at anything.

2. . . . build career capital instead: Cal Newport gives this advice in So Good They Can’t Ignore You, and (applied to most people) I heartily agree. When you’re 20, you don’t know all the things there are to be passionate about. You will also find that your deepest passions will come when you’re truly good at something.  Get good and connected first, and then, when you are 35, you will naturally find yourself following passions much more compelling than the silly little things you called “passions” when you were 20.

3. Don’t seek autonomy too soon.  Develop excellence in your field, get some connections, get a good feel for your industry, and squirrel away some “frak you” money before trying to set out on your own. It will usually work out better that way.

4. Focus on what Paul Graham calls “upwind skills”. (What You’ll Wish You’d Known) Upwind skills are things like writing, mathematics, design and programming. These skills take time to build (so it’s better to start sooner rather than later), and they will keep your options open more than other areas of focus.

If you study mathematics, your knowledge and skills can likely be applied to dozens of fields down the road, depending on where your opportunities lie.  If you focus on French Lit, your options will be limited.

I’m not advising you to avoid French Lit so much as encouraging you to make sure you learn to write, learn to program, learn mathematics, or learn design. At the least you should pick one of those four areas to develop throughout your 20s, and if you develop more than one of them to a high level of competence, you will probably stay in high demand right up to the edge of the Singularity :)

5. Be less judgmental. When you see a doctor who doesn’t know how to troubleshoot his car problems, don’t scoff. Sure you COULD become a doctor if you wanted to. And you COULD become a master mechanic if you wanted to, but you likely won’t become both.  You’ll learn soon enough that you, too, will need to specialize, and can’t become good at everything.  So stop projecting in your daydreams to a future self that is good at writing, programming, medicine, design, history, and auto mechanics. Just because you have a passing knowledge of those things at 20 doesn’t mean you’ll be an expert in all of them when you’re 35. So don’t judge the practitioner of X who shows a poor knowledge of Y.  Instead appreciate how he or she does X.



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