Ask HN: Is it me or ...?

I absolutely agree with you! After 10 years of work I only realized in the last few ones that those things you listed are the only to care about. Personally I always try to learn and apply to new projects, and not giving over 100% makes me feel quite comfortable even in those difficult relations expressed in the main thread. It's really important when you work for a company for a long time: you may learn all the dynamics between your colleagues but you cannot avoid some kind of behaviours...

That's a very inspiring reply, thank you :-)

Personally, I'd say some combination of 2, 4 and 5.

No company is perfect, even if you're the sole owner & employee. "Inability to close deals" is extremely vague, so I don't want to jump to conclusions, but deals fall through all the time. It could be a sub-par sales team, it could be market conditions, it could be a million things, but that's just a part of business in general.

Short-sighted decisions are also tricky. What you call short-sighted might be necessary for a longer-term strategy. Long-term strategies are great, but sometimes $10 now is more important than $100 next week. If it's a code thing, sometimes you need to have a feature done immediately for contractual reasons, even if it's going to require more work down the road.

Petty management techniques are a pain in the ass, but if it takes you over a year to find them, there's not a ton you can do before looking at your next job to ensure that doesn't happen.

Overly frequent pivots also can be tricky. If you don't see profit/upswing anytime soon, you might be forced to pivot if you can't raise money on reasonable terms. Unless you're privy to board meetings and whatnot, it's hard to say.

There aren't many perfect jobs out there. Like other posters have said, you might be happiest if you can save enough to do your own thing for awhile. But keep in mind that in one way or another, you're probably going to have to deal with other businesses, even if you're running your own show. Deals will fall through, your business plan might not go according to script, you might be forced to make short-sighted decisions just to keep the lights on / keep a client / what-have-you.

One thing I might caution about is quitting too many jobs. I'm not in the valley, but here in Boston, a reputation can follow you. If you get a name for being a perpetual flight-risk, it can be hard to shake. Granted leaving after a year or two at each one probably isn't the worst, but as your career develops, it might make it more difficult if you want to become a leader within a company.

Exactly. The OP said "after one or two years". That can be a lifetime for an early stage startup. Things change, and every day you're re-signing up for your job by going to work. It can be tricky to evaluate the current landscape objectively and independently of the landscape a year or two ago.

Chances are a year or two ago things were much simpler... There's a fair chance that was because a year or two ago the team was ignoring or just not-expecting the challenges you have today. Startups often mortgage their future this way... Year one is lots of work, but in my career it's never been the hardest part. Not by a long shot.

I think there's a lot of value in being the person who's valuable year three when folks are tired and struggling to find traction and maintain culture than it is to be valuable year one. Being valuable year one is easy, frankly.

If you have any friends that freelance, reach out to them. If they're successful, they'll know about more projects than they can take on, and may be willing to refer some over to you.

They may have also been approached by consulting companies that have more work to do than they can handle, and are looking for independent consultants to help with the load. The rates on those projects are usually a little less than your normal rate, but quite good for getting into the groove of things early on.

You can also reach out to local consulting companies yourself and make yourself available to them.

If you have the choice between a short-term client that wants you 40 hours a week and a long-term client that wants you 10 hours a week, take the long-term client. They'll reduce the risk of being in business for yourself, and you can take on other part-time contracts in addition. When you've got the benefit of a long term engagement, you can experiment with your pricing more with the remaining time. I end up giving a pretty significant discount to the companies I'm engaged with over the long term, as my rates on new projects are constantly going up.