I'm a 40 year old with two kids living in San Francisco, and I actually know a lot of people in my position who work for startups. It's not as big a career ris

I'm a 40 year old with two kids living in San Francisco, and I actually know a lot of people in my position who work for startups. It's not as big a career risk as people thing, especially in high tech, where career stability is more valuable than job stability. The people who work for startups tend to have a lot of connections and very sharp skills - qualities that make it easy for them to find a new job quickly. There are a few downsides. The startups they tend to work for aren't the "rundown apartment eating ramen" kind of deals. They pay decent salaries, though they do offer more upside in exchange for lack of job stability (though like I said, job stability isn't such a big deal if you have a reserve fund and have very sharp skills). Even so, working for this sort of startup is more like having a job, more casual than a typical bigco but nowhere near as liberating as the PG-style ycombinator startup. Quasi "stable" startups aren't necessarily any better than a job in bigco, and the more they resemble a bigco in terms of pay and benefits, the more likely they are to behave like a bigco toward employees. Both types of organizations do display a wide range of workstyles. Also, I don't know how it will be as these folks get older. I've found "age discrimination" per se to be overstated so far in my life, but that doesn't mean age won't make for a poor cultural fit. Plus, I am "only" 40... so who knows, I may feel it more later. When you have two kids at home, certain types of startups (the kind that might use the term "brogramming", for instance) generally aren't going to be a good fit for a 40+ year old with kids and a mortgage. I know a programmer in his 50s with teenage kids - the sort of dude who is super sharp in terms of intelligence and technical prowess, physically trim, and a little edgy. He works with these sorts of companies, but he says he sometimes looks toward more of a consulting arrangement. Lastly, these folks could be at risk in a true meltdown. The last time I saw this was when during the dot-com bust, when genuinely talented programmers just couldn't get a gig. The big companies did shed some people, so I can't say bigco is necessarily safer, but there was little doubt that if you needed a stable income, a large organization was better shelter from the storm. This sort of true bust is rare, but it does happen. That said, if I did lose my job, I'd rather have the kind of network and technical skillset more common among a startup type than a bigco type who had gotten too comfortable over the last decade... My lesson learned so far is that everything does carry some risk, and that in some ways a bigco career can carry greater risks than a series of startups... there isn't a single hard and fast rule for this.