I sometimes think that one factor in success as a business or as a human being has a lot to do with what kind of problems you’re comfortable solving – and how you get better at addressing the stuff that falls outside that comfort zone.

History is littered with revolutionaries who couldn’t run the country they’d overthrown, Generals who’ve insisted on re-fighting the last war, talented programmers who were promoted to becoming ineffective (and very unhappy) managers, and, of course, there’s the countless companies that just couldn’t make the leap when technology or cultural change rendered their comfy old business model moot.

Seems like there’s a thread here that’s worth thinking about.

How do you get better at knowing when you’re trying to solve the wrong problem?

It’s something I’ve been thinking about a lot lately as I take what had been mostly a hobby and try to “Go Pro” with it. For me, that’s meant a lot of stumbles around moving from being a one-man show into what may eventually become a small company (who knows?). I’m finding it really challenging to stop solving the problems I’m comfortable solving, and to ask for and accept help with the stuff I suck at or that doesn’t represent the best use of my time.

I think this applies to almost everybody, from the time they’re born, right? You figure out a few things, you do some informal experiments with reality, and then you try to suss out the patterns that won’t get you hit by a car or carted off to jail. But the old patterns almost always stop doing the trick at some point or in some unexpected context. For example, that bawling and tantrum-throwing that got you a hug in kindergarten may not endear you to your company’s board.

The best advice I’ve gleaned so far is to try and stay cognizant of diminishing returns. Just because I know how to do basic sysadmin work doesn’t mean I’m the best person to work on it. And conversely, just because I loathe the idea of becoming a “manager” doesn’t mean I can afford to put off learning the skills forever.