When I reflect back on my free agent career, it strikes me that I more or less did everything wrong. I mean, I don’t actually believe that when I look at it analytically. But it does feel that way, knowing what I know now. Starting a software company from scratch invites plenty of missteps.
In the lead into last Friday’s reader question post, I talked about starting this blog as a journal of sorts. That’s a good example of what I’m talking about. In the end, I built an audience, established a brand, and wound up in a good place. But if I could go back in time 7 years and give myself advice, my path would have been more direct.
It goes beyond blogging, of course. That was one example, but it applies generally to my entire approach to starting my software development/consulting company. I did things that worked out, but it hardly seems optimized in retrospect.
You’re probably thinking that this applies to everyone. Hindsight is 20/20 and all that. And you’re right, which is exactly my point. I dove in with severely imperfect knowledge, made a lot of mistakes, and it still worked out pretty well.
If you pursue the free agent life, you’ll flail, make mistakes, and have some false starts. But you’ll recover, figure it out, and do fine, even if it sometimes seems like you’re drowning in the moment.
Flat Squirrels and Driving Directions
Perhaps you’ve heard an expression. “Be decisive. The road of life is paved with flat squirrels who couldn’t make a decision.” Don’t blame me for the macabre nature — I didn’t make it up.
I like part of the sentiment, but I think it misses the mark slightly. If you picture a terrified squirrel in the road, its biggest problem is thousands of tons of steel and plastic death bearing down on it. It starts left, then moves right, then freezes and then… well, you get it. Indecision costs it dearly, but only once it has a large problem already.
This probably doesn’t describe you in most situations that call for more decisiveness. We face paralysis by analysis, rather than paralysis by mortal terror. Have you ever sat in your car, debating whether to take the highway or side roads during rush hour? Have you ever sat there debating this for so long that you get to your destination later than if you had simply picked either option and started immediately? (Come on, I bet you have.)
This makes for a better analogy for our lives, especially when it comes to starting something new. We put off action out of fear of taking a sub-optimal path. But, at some point, even a sub-optimal path beats sitting in your car fretting.