I think it's important to remember that in the world of the Internet, "running your own business" doesn't have to be "a startup." I'm 32, and had a similar real

I think it's important to remember that in the world of the Internet, "running your own business" doesn't have to be "a startup." I'm 32, and had a similar realization a couple years back. I hated having bosses. I don't know if my ideas were the best, but I feel like I tend to have good gut instincts. I was tired of not having control of what I was doing. I worked at a small web shop, a big ad agency, and a tiny remote-only web thing. I saw what people were doing, and what was out there, and knew that I knew enough that I could survive. The hardest part was making the leap. To say "OK, I design and develop websites under my own flag," and then to find people. Having worked in the industry for a while, I had contacts, and so far (knock on wood) I haven't really had to do a lot of marketing. It's all mostly word-of-mouth. Build something, do a great job, get remembered/recommended, repeat. Even though when you first get started you'll take a couple projects you might not be thrilled with to get your feet underneath you, soon enough you'll be raising your rates, getting to say no to projects your not interested, and maybe even working on small product-like projects too to mix in with your client-work. That's what I'm doing, I also co-lead development of a little CMS called Statamic. I use it on a lot of my clients' sites (if they're OK with it), and using it lets me improve it, while improving it helps me sell it. It's not glamorous. It will probably never net me a 7-figure-profit for a year. But it's fun, challenging, and rewarding. You don't have to build a product that makes hundreds or thousands of people happy. You can build one site for one person and they'll be just as thrilled. And on top of that, all the challenges of business are there too. You get to pay taxes and everything. :) You also mentioned family obligations. For me, being self-employed helps with that too. If something comes up, I can walk away from my desk and go help out — whether it's picking up the kids, or just meeting my wife for lunch if she's having a bad day. Self-employment is risk, but it's a calculated risk that balances with freedom. If I want to make more, I take on more projects. The hardest part I've found is turning that off. ("You mean working 80 hours pays me 80 hours!? SIGN ME UP!" — that just leads to burn out.) Anyway, I know Hacker News is more startup-focused, and that you're probably more interested in that, but I wanted to throw my two cents in that there are other things you can do relating to the Internet that are just as interesting and just as rewarding.