People who are trying to make stuff often feel like we're failing. Ira Glass's articulation of the gap between taste and skill gets at this. He suggests making more stuff, for deadlines, for others, as a rhythm to push you to progress through that gap. But how do you keep up your morale during that push?

I'm a Recurse Center alumna, and that community often shares learning tips that are relevant to this struggle. For instance, I recommend Allison Kaptur's "Effective Learning Strategies for Programmers", which suggests reframing failure -- and reframing praise and success. Even if the tips I get via RC are programmer-centric, I can usually reuse them in other activities, such as growing my business. And earlier this year, in Ramsey Nasser's keynote The Unfortunate Value of Failure at !!Con 2016 (transcript & video), I heard a different nuance that really spoke to me. Here's the chunk of the captions/transcript that particularly resonated:

I have the same anxieties at 29 as a programmer that I did when I was a teenager. I don't feel measurably better about myself as a programmer over the last ten years, although it is objectively true that I'm a better programmer. Just looking at my GitHub repo, I can see rationally that I have actually improved, but I was trying to figure out why I didn't feel any better.

And my understanding of it... This may be different for other people, but this is my take on it. I don't think that my feeling about my skill as a programmer is actually tied to my skill at all. It's actually tied to the things that I'm trying to do, at whatever skill level I'm at. So when I was 19, I was just trying to make websites. And it was really hard. Right? And ten years later, I'm trying to write a symbolic compiler. And that's really hard. And the diff between what you're trying to do and what you're able to do is how you feel. And as I got better as a programmer, I just kept trying harder and harder things.

So the feeling is constant. Right? That's why there's no point where everything will just feel wonderful. Because I have to do this. I would have to just make basic websites for the rest of my life. And I would feel great. My anxiety would go away. I can whip up a website really, really quickly. But that's not actually what I'm excited about anymore. So my ambitions and the things that I'm excited about grow with my skill. And that's what keeps that feeling constant. That's what it's been for me. Like, right now, I'm running this whole presentation out of custom slide show software that I wrote, and I'm terrified that it's just gonna explode. Like, eat this presentation in front of everybody. And I hope it doesn't.

So if we can't eliminate it, I think we need to learn to love it. Right? We need to embrace it as part of the craft of programming. And not as this thing to be avoided. Failure... When you fail, that means you're pushing yourself. That means you're reaching beyond what you're capable of, because you want to be better. When you're failing, you're learning and you're growing. Right? You're sort of saying to yourself... Whatever you know now is great. It's wonderful. But there's more that you want. Right? It's a sense that you haven't given up on just absorbing as much as you can. When you're failing, you're exploring things that are in that grey area. That there may be interesting surprises there, or there may be things that you don't want, but you're willing... It's a sort of brave commitment to go there and to see what's out there. Failing is not wrong.

As a homeschooling parent once wrote: "The only thing that makes you smarter is doing hard things." (From the same parent: "I do think that one of the greatest educational gifts I can give her is confidence that she can seek out challenges and master them." and: "being out there on the edge of what you maybe-can't do. That's the place that you value, because that's where you stretch".)