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An experienced developer does not lack for job offers. You can spend your entire life taking people up on those offers and never get around to doing your own thing. For most people on Earth, historically, that's not a bad place to be: it beats the hell out of starving. But if you have the luxury to do it, I think it's less impulsive than you imagine.

> An experienced developer does not lack for job offers.

I won't suggest that I know whether or not the original poster made a good decision, but assuming that an experienced developer will have job opportunities on tap is naively short-sighted.

The current market in the Bay Area won't last forever. A lot of people today either weren't around in the late 90s or have chosen to forget what happened. In a matter of months, lots of developers went from having a seemingly unlimited number of high-paying jobs to choose from to collecting unemployment.

Even if the next down cycle isn't the same as Bust 1.0, a lot of the angel and VC-backed startups in the Bay Area currently eager to pay six figures for even mediocre talent aren't going to survive, and when they're replaced by fewer and fewer startups, many developers will be ill-prepared.

Ageed.

Is the OP an experienced developer?

(How many years does he have in a production setting? Would it be worth getting those critical 5 years of experience, despite bouts of boredom?)

> you chose to jump into nothing rather than parlay your way to something else. Seems a little impulsive. Impulsive is a red flag

Sounds impulsive, but doesn't have to be. It's possible to make that jump after long and thorough consideration. It took me years and a couple of jobs before I finally dared to quit and start my own thing. Not everything I did with my own thing worked out well; spent a lot of time finding my own way, wasted a lot of time, made almost no money in my first year. I did some freelance work, now working on a bigger freelance gig, but I'm really hitting my stride now, and can't wait to go back to my own projects.

I'm not a natural entrepreneur. It took me ages to make this step. Nobody in my extended family has their own company; they all work for a salary. Nobody likes this kind of risk, but I love it. I love the freedom and the uncertainty. I love the risk.

It was a tough decision, and it still seems impulsive compared to a steady salary, but it was the second best decision of my life. (The best was marrying my wife, but that one was surprisingly easy.)

You say, "after spending my 20s earning enough to justify it" like it's a distinguishing mark. It seems to me like Loren has enough savings to say he has "earned enough to justify it" too. Just what do you think makes your situation different? If nothing, I think you should at least be consistent in your appraisals of your and his situations.

Earning enough experience and savings (just shy of a decade in quant finance). I claim those years do make a difference. I further claim this time off sounds like lost time rather than experience building.

Everybody gets bored and frustrated with work. Up & quit after a year and sell it as wisdom on HN? Fuck that.

I tend to be fairly transparent and vocal. Sometimes it gets me into trouble, but usually it works out for the best. If a potential employer asks why I left my job (which I entirely expect), I will be straightforward. Heck, I'll even send them a link to the blog post.

I'll tell them how I don't think sticking to what is easy is the best approach to building a successful business, even though it feels safe. I'll tell them how I think it's important to always be moving, and take calculated risks to push forward. I'll tell them how I learned (from mistakes) that it's okay to release an impefect product - because trying to get it perfect on the first time around will kill you.

I told my past employer all of this. They disagreed. And that's fine. They were smart guys, and they worked hard. Everyone has their own methods and ideas. We just weren't the right fit. But I'll try hard to make sure the next employer is.

I think in the long run you'll be fine. Red flags are a lot less important than ability to solve the company's problems. As much as it pains me to say it, once you move out of the startup arena into large company territory time off matters even less because most people who will interview you know very little about specific technologies and just want the hiring phase to be over with. Some won't even ask you about your time away from work. Those that do will give you a "heh, that's interesting" and move on to the next question.

Generalizing is usually pretty pointless but if I were banking on getting a programming job, were debt free, and okay with not being especially picky about what company I work for after the experiment should it come to that, I wouldn't worry too much about possible red flags.

In life you have to prioritize things. If your highest priority is running your own business or taking time off from work to try something new, then your next job after that really has to fall down the priority list. You can't have everything assured and hope to be successful. Edit: MOST PEOPLE can't have everything assured and hope to be successful. Of course there are exceptions to every rule, but most of the time you do have to experience trade-offs to be successful. I'm not advocating taking huge risks, and most of the time there are smart ways to mitigate risk, but in the end I think a lot of people are arguing you should mind your red flags and try to stay focused on getting your dream job after the hiatus. I'm simply saying that isn't realistic if you want to focus on being successful in a different line of work. I've always believed you can really only be truly committed to one career at a time.

I tend to be fairly transparent and vocal. Sometimes it gets me into trouble, but usually it works out for the best.

Good. Me too. Gets me in trouble all the time; I'll never change.

And I agree with you motivation for leaving... I just would have rather read "I quit X to start Y." I don't care what "Y" is. Might not have made front page. Hmm, karma or cash... which is better?

Y == "For the next three or six months, I'm just going to work on interesting things."

I just hope "interesting things" != internet pornography