A couple years back, I wrote a little bit about starting my own company. I worked on it for a few months, and then, for a number of reasons, put the project on hold. When we moved to Boston last fall, I looked around briefly for jobs, but quickly decided that if I didn’t pick up that project again, I’d look back and regret it. That sentiment seems to be a common one within the startup community (I’ve heard a couple of entrepreneurs say it) and it’s worth examining a little bit further.

I went last night to the Dragon Hardware Hangout, where someone asked a question along the lines of: “How do you know when you have a good idea? Something worth pursuing?” It’s a really good question, and not quite as easy to answer as it might first seem. There are some ideas that are just so obviously good that it’s really a no-brainer to turn it into a business. But in reality, those are few and far between — if an idea is so clearly good, chances are other people either would have done it already, and/or multiple other people are already working on it. The other ideas fall into two (other) categories: things that might make for good startup businesses, and things that just obviously wouldn’t make for good businesses. And it’s the “mabyes” that are tricky.

So how do you figure out if your idea (assuming it falls into that “maybe” bin) is really worth your time, blood, sweat and tears? You can (and definitely should) try to do some due diligence, to work out if your idea is technically feasible and whether there’s a real market for it. But that kind of analysis can only take you so far: it might actually be difficult to get hard numbers on your potential customers at first; you might be in the right ballpark but need to shift your idea a bit before it would sell; the technical feasibility might be hard to evaluate without spending some time on it; and so on. Ultimately, it’s the kind of thing that’s really quite hard to prove or guarantee ahead of time, and instead comes down to your own willingness to accept some risk, and then later on, also convince other people to accept risk (either as investors, collaborators, or even just early adopters). And the dark side to this is that you are constantly reevaluating your decisions. Some of that self-questioning is healthy — Did I really listen to my customers? Am I making the right product? Are there (easy) things I missed that could make a big impact? — but some can fall closer to self-doubt, and it can be a real challenge to keep going, especially when things aren’t going so well. And you don’t always have external validation (especially in the beginning), either, which can amplify that self-doubt.

So that’s it — other people can help you get closer to answering the “Is my idea a good one?” question, but it’s not really possible (most of the time) to definitively predict that an idea is a winner; you have to take at least a little leap and find out empirically. It comes down to you and how you handle risk, uncertainty, and failure, as well as your ability to be self-critical without turning negative. It’s the thing that’s surprised me the most, so far, about starting up a company — how much emotional self-management it involves, even without throwing other people (or money, for that matter) into the mix.

My project is gradually coming out of stealth mode and I’m making lots of progress, even with the aforementioned challenges. If you’re interested in what I’m doing — creating a lab automation system for biologists — you can head on over to the FlySorter website.