Founders, Fortes, and Figuring It Out

When people talk about working for a startup, they’ll often say that you have to wear lots of hats. That’s totally true. What’s a little less explicitly discussed is the fact that sometimes the hats don’t fit very well. Or maybe you’ve never worn this particular hat, and it seems awfully complicated to put on. And not only that — you know that once you get it on, it’s going to make you look (in your mind, at least) pretty stupid and incompetent. No matter — you don that hat, anyway. Someone’s gotta do it, if this startup is going to go anywhere. That someone is you.

This can be super uncomfortable.

It’s not just about time pressures, and the constant feeling that you’re juggling a million different priorities and demands on your time. That’s all to be expected. The to-do list grows faster than you can check things off of it, especially if you’re trying to make this hustle happen on the side. (Side note: Notion is saving my sanity.)

It’s also because maybe you’re a complete newbie at something that is now your responsibility. This means 1) you’ve just gotta figure it out — which means, of course, that it’s going to take some time for you to get up to speed — time which (as previously noted) is in short supply, and 2) you’re not going to be very good at it, at first.

For someone who’s a little further along in their career, this can be pretty challenging. You’re used to feeling like you know what you’re doing, and not so used to feeling completely out of your depth. You’re smart enough to recognize that your efforts are embarrassingly novice… but (at least if you’re a bootstrapper like me and my team) you’re going to have to try to be ok with it, and say that whatever you’ve managed to do is “good enough,” because you don’t have the money to hire someone who actually knows what they’re doing.

IMO, this is a big part of why some people make good founders, and others aren’t so well-suited to it. You have to learn to love the great many “opportunities” you’ll have to get out of your comfort zone. (I use quotation marks there because I’ve found that language and framing is a really powerful tool for me, mentally. It’s not “I have to” — it’s “I get to” — and yes, some days this is easier said than internalized.)

It’s about being ready to take on whatever the world throws your way — finding a way to make it happen, and taking it all in stride. You will grow as a professional and as a person — and you’ll also grow closer to your co-founders. It’s amazing how your heart will swell when someone else on your team volunteers to wear a hat that you were really, really dreading having to force onto your head. You may have moments like this:

And as uncomfortable as it can be right now to have a head full of ill-fitting, ugly, needy, but necessary hats, you’ll know that someday, perhaps when you’re wearing one single hat that fits you perfectly, you just might look back and think of these as the good old days…

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