Ask HN: What if nothing works out?

Look, for every 100 people that venture into entrepreneurship, less than 10 make it, that is why there is so much money to be made. You should be proud of your effort, the only time you should be pissed at yourself is if you didn't commit 100%, in the long run we are all dead!

Sure some things change. I can't be as reckless or risky now as I was when I was 20. Perhaps this IS my last attempt, but I doubt it. If it is I hope I can find just as much joy in something equally as productive as entrepreneurship.

Ok, just kidding.

I knew it was the right move when I realized I was learning 5 times as much in the startup.

Nothing matters more to your career than the development of your brain.

And if you're not excited by what you're learning, if its become stale and dreary, make a change.

Most of the people I knew in the late 90s "new media" sphere are no longer involved in Web development or Internet media at all.. and certainly wouldn't be hanging around forums for those kinds of people. Their stories are stuck with them in their new roles as bank managers, fashion journalists, and mechanics (the founders of Boo.com, for example, are now a fashion designer and an investment advisor).

I doubt the strongest "failed and never got back on the saddle" stories would come from asking on HN. People who died in the entrepreneurial space are most likely not here.

Update: An idea, perhaps, would be to find people from famous Internet companies or "up and coming" lists and track down where they ended up.

If you meant corporate life by 'career', my startup experience landed me in better and better jobs.

If you define your success by something that you have been unsuccessful at for years, it seems to me you will get depressed sooner or later.

Saying that, most careers are dead. Obviously in some areas there will always be a direct path of experience where a true career will exist, but the days where you went from junior to intermediate to senior to manager to vp etc are dying fast, especially with companies people who frequent HN are likely to want to work with. Do you want to take a job where they say you didn't do two years as senior developer or marketing assistant etc so you can't have the job?

More and more companies are starting to recognize the experience gained in the field and it is easier than ever to move between fields and jump "stages". Not all companies are like that yet, in fact maybe most aren't yet, but as they lose good candidates to companies that are then they will change.

So I wouldn't worry about what happens if everything fails, if you're willing to try the life of an entrepreneur then survival post that is going to be easy.

I have failed w/two different startups, one very recent. The first time it was great for my career in monetary terms. The second - I don't know what will happen, but I don't regret doing it.

Working on a failed startup is draining. Your whole life is tied up in it, and if the company fails it seems like a phantom limb for awhile.

To directly answer your question - past entrepreneurship should be a big plus to any company worth working for.

You know you want to try something else, why not another startup?

When I left the company I started, I intended to start another one almost immediately. But then I didn't. Partially this was because of assorted conceptual and administrative issues, but partially it was because I realized how burned out I was. I'd been living this thing for five years, breathing life into it as part of a very small team, starting with literally no budget. Business is hard, and it was often soul-destroying - I discovered that other people were considerably more cut-throat than I was willing to be, and consistently underestimated how low people could go. And on top of the business itself, I was up to my eyeballs in code most of the time. Over time, I lost perspective. Within a space of a couple of months, though, two immediate family members were told they were seriously ill, and my sister became long-term disabled, and I was snapped back to reality.

It wasn't that entrepreneurship wasn't for me, as such, I don't think. It was that the specific kind of entrepreneurship I was living didn't fit my hopes or goals, and was eclipsing everything else in my life in a very negative way. I didn't think I could fit the care-giving that would potentially be required with the demands of the job. They're still going strong, but I wanted to live a different kind of life, closer to what Tony Stubblebine writes about on his blog. (Tony's the smartest guy I know on the topic.) That was always my intention, but we diverged.

It's certainly positively affected my career. Since leaving, I've spoken at Harvard, been published by IBM and have worked in a bunch of really interesting situations, with fantastic people, on a consultancy basis. Before the startup, I was a ground-level developer, so that's a win. But I'll certainly start a company again, at some point, if only because I'm the kind of person who loves to make things, and to do things on my own terms.

I'd ask yourself carefully if it's entrepreneurship that's not for you, or the situations you've been in.

(By the way, my family's health situation is vastly improved - but I think the thought experiment of what would happen if you needed to be a care-giver is a good one.)

One thing it did for me is that for a while, I was hesitant just jumping into any idea, because I know now how much it can take out of you (years of work before you know it).

Go find something you enjoy doing, and then find people willing to pay for it. Enjoy your life. Don't go searching for the next big thing.

Then, when you least expect it, you will have an itch that needs scratching, that might be of value to other people, and you will be rested and ready to try again.

It will all work out if your are persistent.

http://www.youtube.com/watch?v=iA7RKwhrOT0

Personally I pay a lot of attention to stories on HN when they mention failure (complete and not just cosmetic how we failed and then won type stories).

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 ha...