Five years ago this week I left an incredible job at a great company to co-found my own business with Jenny and Walter — Jackson Fish Market. Leaving the security of a big company and a job that most people would kill for was incredibly counter-intuitive. And building your own business is way way harder than you may imagine. The press loves to talk about amazing success and spectacular failure, but people who are plugging away building their businesses one (virtual?) brick at a time do so mostly outside the spotlight. Luckily, there’s no magic to this effort of building your own business. Every time I learn a lesson (which I do almost daily) the inevitable conclusion is that more hard work is required. And that’s something I can do.

But the question still remains, why leave the great job at the big stable company to work your ass off in anonymity with no guarantees of ever recouping your lost wages? There are many reasons people give for this, but I’ll give you mine, and it’s the same as the day we started JFM five years ago.

Anyone familiar with the innovator’s dilemma knows that companies who’ve achieved incredible success doing one thing have trouble shifting gears. And in my experience, conservative thinking, and those who come up with reasons to say no are the ones who are trusted to be in positions of responsibility. Nobody usually gets fired for saying “no” to a risky idea. There’s almost never proof that it was the wrong call so there are almost never any consequences to folks who say no. And as a bonus, saying no makes you seem more like a grownup at a big company. Big successful companies like people who seem like grownups. After all, the company has a franchise to protect. You don’t put people with wacky ideas in charge of protecting something valuable. And in truth, ideas are a dime a dozen, so why not have some grownups there to weed out the good from the bad? The thinking is sound on paper.

In running my own business I have learned that the only way we make progress is by trying 100 things. For every 100, 2 usually show some promise. We then come up with 100 new ideas based on the learnings of the 98 failures and of the 2 modest successes and try to make some more forward progress. This is an awful lot of work, but there’s no magic to it. And that’s reassuring as I never got an owl from Hogwarts.

But at most big successful companies, where your job is to protect the franchise, trying 100 things and having 98 of them fail is career suicide. In fact, investing in only 2 ideas and having 100% of them show only modest returns is a “career limiting event”. The internal ecosystem is brutal. And if you don’t have a runaway hit out of the gate, your project is usually done. Interest flags, and the project is tagged as failure. Nobody wants to be associated with it. So let’s say you even manage to get your idea going internally, there will be an endless amount of people tweaking, tuning, and “improving” your idea to make sure that it has the best shot of success. And this is important, because inside the big company, the perceived cost of failure is enormous. (Whether the real cost is so large I’m not entirely sure.) And because everyone is so worried about failing (or as they put it – “giving your idea the best chance to succeed”) the amount of time the company invests in your idea goes up. As the investment goes up, so do the stakes. And the cycle reinforces itself.

This cycle is familiar to many. But here’s what I consider the worst part. The point of trying things even though most of them will fail is to learn something, iterate, and keep trying. By the time the original idea has been through so many cycles of peer and executive feedback, it usually is so far from what the originator conceived that the only thing they learned is not to let people fuck with their ideas anymore. And not because the idea would have been successful. But because at this point, they haven’t learned anything. At the end of the day, the originator keeps saying to themselves, “if we’d just done this the way I conceived originally, maybe it would have been successful”. Maybe it would have. Maybe not. But at least there would have been learning.

I left the generosity and stability of a large successful company so that my failures could be my own. I geniunely want to be good at what I do. The only way I know how to improve is to learn from my mistakes. But they must be my mistakes, or I’m not learning. Thanks to the incredible patience of my business partners, I now learn on a daily basis. ;) Creating your own business is treading water in a sea of failure until you’ve built something small that can float. I’m so grateful that I’ve had the time and latitude to build our cozy little rowboat called Jackson Fish Market. Don’t be surprised if after a few thousand more failed experiments it turns into a pretty nice sailboat.