The old adage of "If everywhere you go smells like shit then check your shoe" applies here. That's not to say you couldn't have worked at 3 actually bad companies that you should have left but it's at least a warning flag. I've had people with short job tenures back-to-back explain the reasoning and I've been perfectly satisfied with it but I've also had people give me reasons that sound very fake. Interestingly, the people that come across as "fake" are also the ones that give off a slight whiff of "I'm better than this job" or "This is only a stepping stone for me". Those things can both be true but if can't at least pretend to care then I'm not interested.

I mean have the story ready but you'll likely never get a chance to tell it. In this job market this is a "screen out without a phone call" criterion. I think it's shitty but it will likely be very hard to get interviews with this sort of recent employment streak.

Potentially, depending on where you are interviewing. I didn't write off anyone with multiple short tenures when I did hiring earlier this year but it was a red flag that I addressed in the first interview.

There is a wide cultural chasm between the startup world and established companies. The recruiters I have come across have very little real world experience. They are merely ticking boxes as handed down to them by management. So if management wants to hire people with a "solid" track record, then your startup experiences are going to be viewed negatively.

One option is to work for a large company with more opportunities negating the need to hop due to it going bad financially and more room to go up levels etc.

I mean, it does, but it's still got a good picture. It comes across as "I'll jump ship the moment a better offer comes along."

The problem with job-hoppers is that there are ones done for sensible reasons (I joined high-risk startups, but ultimately they failed, or got acquired or whatever) and ones who just treat the position as a placeholder until something better comes along, or until they get itchy feet etc.

It's hard during the hiring phase to tell the difference, so employers tend to err on the side of "why take the risk?" Especially in the current market where there are plenty of other applicants.

While it's perfectly understandable why you've responded to the changing environment of startups, the lack of holding a position for long enough is a career-limiting move.

It sucks, but the world isn't fair.

is it though? I see people hoping all the time. Sure you're bound to run into a situation where somebody will view that as a negative but the only way you can switch jobs every 2 years is if somebody hired you. Which means that by definition, there will be companies that don't care.

I guess in a tightening market you'll have more candidates without job hopping so you can use it as a criteria but if your company has legitimate vertical movement there's probably less to worry about. Of course though if you company staffs its ranks pretty entirely by hiring outside as opposed to internal promotion then you should expect to replace the role in a couple of years.

That's a weird thing about resumes... they're pretty much for life, so any move has to be explained/justified over and over again one or more decades later.

Any short-term quick win to get away from a bad boss of a few thousand $$$ could stop you from getting a great job much further down the track. Any move should always be thought of in terms of "how will this look on my resume?" (which won't show salary, office environment, etc.) and "how can I explain this?". "It was a good opportunity to learn about XYZ, which they didn't have at the previous company" sounds great. "I had to get away from XYZ" or "I wanted more job security" don't sound as good, especially if XYZ or the fact that the company was a startup with limited job security was evident from the start.

Often I'll also see someone who was in a job long-term (10 years+) but then has bounced through a few since leaving. That's a different kind of signal and requires a lot more exploration. You clearly -can- settle down, but you seem to be struggling to do that - why is that? I've had folk who are in the "don't tell me how to do my job, I've been doing it for decades" attitude which can be hard for others to work with, especially when "we do it differently here."

I would say riding a sinking ship is a negative for an employee - it's a world of pivots and rapid change. You shouldn't be too loyal to an idea, and likely that extends to loyalty to a company. For a founder level person, they are expected to see it through to the end, and do graceful shutdowns when it is doomed.

A question in their minds is whether candidates have the tenacity to stick through ups and downs of a company. This happens very frequently and I guess the employers are trying to gauge whether people will up and leave the moment things get difficult.

it may merit some nuanced explanation when such a question comes up.

What does that mean? The company on freefall? The company reversing WFH policies that are in your contract?

You have generalised a huge number of situations into one phrase and implied that employees should suffer it through. Would companies suffer it through "the moment things get difficult" with an employee if they had the chance of not suffering it through? No, they would just fire the employee.

You can only expect reciprocity in a business transaction. And that is what employment is.

When "things get difficult" is a catch-all of subjective nonsense and to paint it in a more charitable light is intellectually dishonest.

Whenever "things get difficult"—whatever that means—you can count on the recruiter not being around and is why their opinion does not count for much. Often companies will let referrals skip introductory recruiter call entirely. Recruiters are invaluable to form cohesive teams in a startup, but they're glorified secretaries for hiring managers at a large corporation.

Anyone that believes they can deduce a person's commitment to some abstract mission statement based on a few historical facts and a couple hours of interviews is not a serious thinker. It denies the genius 1000x engineer whom quit to move across the country and take care of a sick family member or two. And it denies people with the self-respect to say no to unethical demands by executives. This might be a minority of applicants, but claiming to hire the best necessarily means reducing the type II error rate to zero.

Some might say yes, thats a difficult situation while others might say how stupid that is to make a situation out of that.

The point was, the difficulty levels can vary and employers would like to know where an employee stands so as to gauge fit with the ups-and-downs of a particular context of that particular organization.

The startups were very chaotic and when I saw them fail to sell the companies 5 times, fail to secure more funding, layoff employees, no raises, no bonuses, failure to listen to employees, I could go on and on...

My explanation if someone asks is that I thought they were good opportunities but I was concerned about my job security after all of the issues and more I listed above.

If anything, I tend to judge people a little bit who stay in the same place more than 3-4 years in this industry. Staying somewhere that long you end up with very insular views and limited exposure to new tech and ideas outside of your bubble, and beyond that, I am a bit wary of someone who isn't motivated by the financial incentive of a diagonal upgrade every 2-3 years, or somehow doesn't see that potential. Being able to effectively advocate for yourself and by extension your ideas I see as an essential skill for SWE.

Also, I think failed startup experience is super valuable, perhaps more valuable in some cases than coincidentally riding a unicorn and now falsely believing that every little thing you did along the way (or your cherry-picked list of "favorite" things you did) is actually repeatable, useful advice and/or a blueprint for future success.

While I completely understand this point of view, I wonder if you are speaking as an employer or employee? If, as an employer, how do you cope with your 25% of your staff leaving every year? How do you build that institutional deep knowledge if your longest serving person has < 5 years under their belt?

I can really only view it from the view-point of an employer (so my comment comes from there.) Personally I've been in the same job for 33 years now (was my first job out of uni) but I've seen the company grow from 2 people to 50. Most of our staff have > 10 years with us, and a bunch > 20. They are highly skilled, and have a depth of knowledge about our products and customers that are unmatched. They earn salaries well higher than other companies would pay them.

50 people is of course very modest success - I'm not saying we're a unicorn, or even especially valuable. But from our view-point we're also not looking to hire folk who have short-term goals and are already looking for the next gig down the line. Obviously lots of job-hopping is a red flag for our recruitment process.

And that's the thing I guess. Another company would have a very different perspective, and be looking for a very different kind of person. And ultimately that's ok. We don't all need to fit the same mould.