It's probably not surprising that a lot of people working in software have at the very least a side hustle of some kind. Mine came about long before I had "software developer" on my business card (what's a business card?). I have friends that have done after-hours consulting, some have tried to bootstrap startups... lots of situations that involve some kind of entrepreneurial endeavor.
I've been asked so many times why I don't have my own business, to which I respond that I do, it's just not mortgage paying, but mostly it's because I'm a lousy entrepreneur. It's not that I have some shortage of ideas, it's just that the world distracts me with far too many things.
Maybe I had a better shot before I had a child, but now, Simon is both a great consumer of my energy and a reason to try and retain some level of consistency and risk avoidance. With the ASD and ADHD concerns, decent health insurance is also important. I adore my little guy, but the amount of patience it takes in the day to day is extraordinary, and I'm still not very good at reminding myself to be patient. That's a lot of energy.
Having a day job is certainly a challenge, too. I've had a few intervals where I have worked on my own projects between jobs, the last one being in the second quarter of 2013, when I ended a crazy good contract and hung out as we plotted the move to Florida. Each of those, I've really failed to turn an idea into something that was shipped. Well, I take that back. I built a quilting community that I hoped Diana would work with and promote, but the truth is that it was not very well conceived and not mobile friendly, so it had little chance of working out. But during full-time work, it's hard to think about hustling something on the side, and this has become more and more true as the level of work has increased, especially in the last five or six years as jobs have been more management oriented.
I also have concern about the way that entrepreneurs often kill themselves for the work, but I'm not sure if that's really necessary or a symptom of type-A overachievers. Most people who start a business seem to really neglect everything else in their lives, and I wouldn't want to do that. However, as is the case when working for The Man, some people do that as a choice. I've worked with some founders who set no work-life boundaries, and the payoff for not doing so is negligible or non-existent. So this one I guess is an asterisk.
But if there's a real concern, it's around the one that means hiring people comes with enormous responsibility. When you hire people in a small startup situation, your leadership and direction is what ultimately puts food on their table. If you can't make the business generate enough money to pay them, you will disrupt their lives in a serious and potentially harmful way. That makes me incomprehensibly uncomfortable, in part because I've been on the receiving end of that scenario.
I never set out to make my hobby (the coaster web sites) into a business, but in the heyday of web advertising I could pay my mortgage with it and then some. It's unfortunate that I still get the traffic but not the money, because of the way the ad market has changed and gone half-mobile for less money. Again, that was not a business by design, because if I were to start something new, it would be with the intention of asking for money from people. That's a different game than making content and having people accidentally see it and fill your bank account, and it's a game that I fundamentally understand but have so little interest in.
Of course, the biggest obstacle is probably that I mostly don't believe very much in any of my ideas. A lot of my ideas over the years have been more content based ideas, which might be fun to an extent but don't make great businesses.
The thing is, I don't mind working for The Man, and I know that's the reason that a lot of people start their own business. The Man has at times really screwed me (often because of the economy), but he's also provided a lot of opportunity for me that I didn't fundamentally have to create. Maybe there is something in me that I'm super passionate about that will become a business. I don't feel like it's critical to my well being, and I'm happy to let it happen organically when and if it's viable.