This is sort of a funny question because it's one where answers arising from the brashness of youth just sound brash. The strains of, "The power is all in your hands," just don't ring as true when you actually have to sing them to someone who's trying to make life decisions. I had a recent failure, and I've crafted an exit strategy for just such occasions. Here's my pitch:

I've been an entrepreneur for most of my life. Aside from a brief stint at IBM where mostly people looked at me funny for two years, I've done ridiculously financially risky things just because I enjoy taking risks and seeing if I can make them come out. I'm like a compulsive gambler who bets the rent every month, except I place longer-term bets than the craps table, and I've beat the house more than half the time.

I published my first piece of code at 7, and it was for a TRS-80. Like most risk addicts, the #1 predictor of getting hooked is early success. Even if you're predisposed to being an adrenaline junkie, if you hurt yourself trying the first few times, you're done. Needless to say, the heroin of early success has a particularly acute effect on a 7 year old.

I tried a lot of stuff over time, some of it way out of my league, some not worth trying, some just dumb, and some a bad fit for the exigent circumstances of life and market. Those were the losers, and I've been kicked in the balls hard many times by betting on losing ideas, bad plans, lousy partners, conniving vendors, bad customers, and, more than anything, my own personal triumph of hope over cold, hard experience.

I also have just enough successes to keep me hooked. But on average, I'm not a whole lot better off financially than many of my 9-to-5er friends. My years where I turned over a lot of personal income are offset by the years when I don't, for sure. So for me, it just isn't about wealth. It's about the one place where I have the 9-to-5ers beat: that where they say, "Wouldn't it be cool if somebody..." I live my life being able to say, "Isn't it cool that I did?" But that's not the life for everybody. Most folks need the sense of security and uniform societal justification that being one more cog in the machine brings. I've never personally valued or had either.

So I totally blew a startup project I was working on for over a year. All but abandoned it a couple months ago. It was just too complex to fund, and it was a regulatory nightmare. I personally lost most of my net worth on the miscalculation. Oops. (On the bright side, I didn't lose anybody else's money, so I came out with as many friends as I went in with.)

And, of course, it flamed out at the height of the biggest recession in generations, so I was left fairly idle. I moped. I piddled. I taught myself to cook. I toyed with other backburner ideas I've let simmer for a long time. I did a fair bit of nothing and pretended it wasn't awful and painful and embarrassing and deflating and demoralizing. I'd trot out Michael Jordan's, "I've missed more than 9000 shots..." quote in my head and try to ignore that he was Michael Jordan and I wasn't.

The other day, I was talking with a recruiter friend of mine, and he said that it would be easy to get me a real job (gasp, choke). Suggested that I join his big company, do something simple, and let them pay for grad school in some subject area that I enjoy but doesn't necessarily have any commercial value. Get paid to hang with folks and just think for a few years. So I considered it. I even began the application process.

Then, I talked to a line manager at the company my recruiter friend works for (because I do my homework), and the guy related to me how much trouble they have managing the line because they have very weak procedures and no training on the line as to how they'd develop procedures.

My response was: "Well heck, I've been wanting to do some Android development, and you guys all have Android phones. I'll just build you an app to support your line management. I'll learn Android on a non-trivial project, and you'll get to know me."

The point (and I do have one) is that even my personal risk management behaviors are colored by entrepreneurial behaviors. I'm thinking of taking a 35-hour per week job to pay me to go hang out at a school and pay the rent, and I somehow manage to turn my job interview into new development and a mini-enterprise applications project. It's just who I am now.

I have a lot of respect for people who walk away from the startup game and go act like normies - I know tons of 'em, and I know that almost all of them miss the exhilaration and the sense that every time they come to work, they have a chance to move the needle. I can't seem to let myself give up that rush, and I really don't want to. I have no problem picking up high-paying work when I need it, but that's a function of having cultivated skills that have value no matter what kind of job I take - startup or secure (consulting, of course). I'm confident that if push came to shove and I needed to walk away, I could. I have a steady stream of job offers to prove it.

Churchill said that success is going from failure to failure without loss of enthusiasm. Of course, he won his war, so he would say that. And forums like HN are rich in first-attempt winners because there's an audience for them. So they've been as immunized to failure as a published 7-year-old. If you get into startups and totally flame out, assuming you can tolerate failure like a fully-formed adult (seriously, be sure you can), you might end up taking a pay cut if you decide to leave for higher ground. You might end up leaving for something deadly boring. But any losses you incur will probably be temporary, relatively minor, and non-fatal.

Or maybe you'll get hooked, and your life will just stay interesting. If you live by the Chinese curse, "May you live in interesting times," then don't do it. If you think that's a blessing and not a curse, go for it.