How to stay positive in your start-up even though you know you are making a million mistakes

I frequently browse hacker news for start-up advice, and as much as I love the community and though I find the advice immensely useful, I also find it incredibly intimidating and terrifying. Whenever I look something up, it occurs to me that there are at least 5 to 10 things I’m probably doing wrong that the various posts are discussing, and that I also probably can’t do anything about it in the short term. I have to then stare at that, gulp, try to smile and then carry on, because best that I can tell, there is simply no way to build a start-up without making all these mistakes, constantly, and not only getting over them but optimistically charging on into a million more. As much as I enjoy the more practical advice, I thought I’d share some about this experience and how I cope with it, as I firmly believe this more emotional side of start-ups is equally, if not more, important. And it helps to know there is someone else out there, alone, cranking away, screwing everything up but carrying on anyway and maybe on the way to making something great.

First, a little about me. I’m currently a single founder (gulp, I know). I’m not a programmer — my career has been in big management consulting and hedge funds. But I taught myself coding anyway and am cranking away towards a prototype and trying to find first customers as much as I am able. I quit my full-time job around 3 months ago and am trying to bootstrap until I have enough traction to recruit cofounders or raise a good round.

Maybe you are already reading that and thinking, this guy is a disaster. Partly I’d agree with you. I just re-read Paul Graham’s essay on 18 mistakes that start-ups make and I’m super worried about more than half of them:

Single founder: I’m a single founder and that’s super hard and everyone is right about it being a bad idea. But I don’t have close friends that want to take the dive and I don’t have a million close (and talented) friends in the first place (I’m a proud introvert).

Derivative idea: My product is sort of a derivative idea but half the time I think it is and half the time I think it’s not.

Obstinacy: I care deeply about what I’m working on, and want to solve a problem I personally have. But this makes me worried I’m being obstinate and won’t want to change it.

Choosing the wrong platform: I’m just hacking a product together and learning new languages along the way so I’m pretty sure my platform sucks.

Slowness in launching: I’m a single founder so it’s hard to do, well, everything.

Raising too little money: No one wants to invest in a single founder. Ycombinator hates single founders. I don’t want to get on the fundraising treadmill early if I don’t have to.

Hiring bad programmers: I haven’t hired anyone yet but I have gotten interest in a few people I know in being co-founders. Since I know I need a cofounder, I’m tempted to hire them, but they aren’t technical at all and we don’t have a super solid friendship yet. Still, I’m biased to want to hire them to get a cofounder. But then maybe I’m hiring bad programmers. And asking for fights between founders.

The list of worries goes on. But here’s the thing. I’m going to keep going anyway. And I have to believe that even though I am probably screwing up half this stuff, that it’s okay, and that it’s worth it, and that I just have to keep putting one foot in front of the other. For all the disasters that could happen, probably the only one that will assuredly destroy me will be if I start believing I’m already sunk. Still, this is a daily emotional battle. Here’s a few things I do to help keep my head high:

1. Watching videos and reading stories of other start-ups and founders. Even the super successful ones made a million mistakes, too. Some of my favorites include the one about when Blogger was back down to one person, and when Pinterest was floundering for 3 years with 2 non-technical founders before they got traction.
2. Uplifting music. I think taking the dive into a start-up is a little like artists taking the dive into art, going all out for the passion of it and not looking back. They sing about this a lot, and it helps.
3. Exercise and meditating.
4. Participating in the start-up community. Most early stage start-ups are struggling somehow and it helps to share and talk about it. I started a local meet up group (I’m in Oakland) and I’m a big fan of Hacker News.
5. Talking to friends and family. Sometimes you just got too stuck in your own head.
6. Talking to customers. While this also can be a big downer if people hate what you are working on, usually they wind up being positive and helpful and give you inspiration even if it’s not quite right yet.

If anyone else is out there still in the early stage, I hope you keep going, and stay strong, and screw it all up and then fix it. The only mistake that will sink you is if you stop trying.