Ask HN: How do you know if leaving your 1st software job will make you happier?

Three years in I think our company is, on average, as good as the best 'out there', but when individuals hit rough patches (stress, poor growth, low autonomy, etc.) they often start looking for a new job. Even if they decide to stay put, they sometimes plow on with low morale, berating themselves for not trying a new gig.

I believe other good software companies would have just as many problems - though maybe not the same ones as us - and that some of my despairing colleagues would be happier if they had that mindset, focusing on making the most of the opportunities they have and driving change instead of pining for a nirvana. But maybe my expected cosmic background shittiness is too high, I'm romanticising pointless suffering, and we should actually all bugger off.

How can first timers make better judgements about their situations - both in terms of being grateful for what's good around them and critical of the genuinely bad?

PS: For those who have been at one company for most of their career, but who felt like quitting for one or more reasons, did things get better or did you just accept the tradeoffs?

Have you ever truly regretted quitting a job - why?

Money aside, did you ever leave a job you were happy with to find one where you were even more happy? Did that work?

I've never regretted quitting a job. The pay rises have often been surprising - the funniest one was returning as a contractor to a workplace I'd gotten bored and frustrated with as a junior/intermediate engineer, getting paid 3x what I was paid before. That was eye opening, and a lesson about negotiation and market rates I wish I'd learned years earlier.

If you are interested in switching track into management or technical leadership, and have no prior experience in those roles, it may be much easier to do this while staying within one org for a longer period of time, assuming the org has such roles to fill (growing company etc) and they are open to mentoring you.

Another aspect is that different colleagues' subjective experience of the same work situation can vary wildly. I've joined teams as a contractor in somewhat challenging corporate environments and projects and had a lot of fun, where some of my colleagues who had already been there for several years had a lot of emotional baggage, and would react to day-to-day situations with much frustration and pessimism. Even if the company is objectively a pretty good place to work, individual workers can end up completely sick of the company's particular problems / politics / failures.

If you ever find yourself obsessing over thoughts related to work, and it impacts your mental health and enjoyment of life outside of work -- that is perhaps a signal of looming burnout, and that it could be a great time to take care of yourself and find a different job. Even switching to a job that is worse on paper in some respects can be mentally like a holiday if it lets you completely refresh and clock off work each week with no mental baggage. Sometimes in larger orgs it is possible to get some of these benefits if you can jump sideways onto a different project.

I have, once. About 10 years ago. But I ended up returning to the company I left and keeping the 20% pay raise I got when I came back. I was happier my second time at the company, after having experienced a truly toxic work environment when I had left.

I stuck around another 9 years. Just left in December. New job starts Monday. Confident I won't regret it this time.

And truly the right reasons are whatever you want them to be. It could be solely pay, wanting to try something new, or being tired of your current job. If you're sick of your current job, as you've noticed with your coworkers, it doesn't really go away. Sometimes the only way to see how good you have it is to leave and experience it yourself. You either stay miserable or take a chance elsewhere.

Just make sure you leave in good standing and you likely could even come back down the line, hiring is infinitely easier when you've worked with the candidate before.