Me, personally? My thought is that you should do what will have you learn the fastest. If you have a good job, try to stick it out 3+ years. You'll learn more.

Me, personally? My thought is that you should do what will have you learn the fastest. If you have a good job, try to stick it out 3+ years. You'll learn more. It's faster-than-linear (for a while) what you learn by sticking with a job. I'm trying to level up on machine learning, into the big leagues, and you don't get heavy-duty production experience if you're a rolling stone. There are things you learn from building and supporting a system over 2+ years that you don't if you move on before you have the time to really finish anything. If you're not learning, though, I'd say that you should hop. If you are, try to stick with it for 3 years at least, and 5-6 (with promotions) is ideal. Including consulting + career counseling I've seen a lot of companies (probably 40+ of which I have intimate knowledge) and good jobs are not the norm (maybe 30%). When you have a good thing, stay the course. I'd be pretty forgiving of a good candidate with a job-hopping history, but I'm also at the 99th percentile of progressivism on this sort of issue. I've seen people get utterly raped by the job hopper stigma, and many were people with normal careers by VC-land standards. How is it considered by hiring managers? One hop's not a big deal, but a pattern burns you. Finance and large companies look down on that, and after 30 you're going to be a lot less interested in the VC-funded startups (for one thing, they won't be able to afford you unless you're in management). I've seen consultants and startup people face this problem when trying to move into more conservative (stable) industries like finance. They weren't disloyal and had done nothing wrong, but having been in a world where 18-month tenures were normal and not unstigmatized (because the only way to move up in the startup world is to create bidding wars; internal promotion is rare amid the social damage wrought by 90-hour weeks) made them unable to get, e.g., proprietary trading firms (which are very paranoid about IP) to take chances on them. Here's a guideline: 0-4 months: -6 points (but take it off your CV because even the gap is less damaging) 5-8 months: -4 points 9-17 months: -2 points 18-29 months: 0 points 30-47 months: +3 points 48-71 months: +5 points w/ promotions, +1 w/out. 72+ months: +7 points w/ continuing promotions, -5 (yes, negative) w/out promotions.