How to know if you should stop doing startups?

> I can't help but wonder if the world really needs another Canva or Airtable or whatever

it probably doesn't and a business venture is a means to an end. I always thought the idea of 'doing startups' is kind of silly. Business as a recreational lifestyle produces mediocre entrepreneurship and probably stuff nobody needs.

there's nothing wrong with getting a job somewhere and working on something interesting that needs fixing, there's enough of it to go around.

You are clearly modestly competent at entrepreneurship and to the point where it's worth pursuing because of the high opportunity cost. I think it would be wise to take some time as a salaried employee while identifying and correcting the gaps in your skillset.

I'd suggest to get a job in a field you most passionate about. The role doesn't matter. Work there for 3-6 month to identify the problem that industry has. Then leave and build a company that solves it.

Get curious find something you're actually interested in. The Airtable people, bless them, were probably really curious about organizing data. But that's not you, ok.....in 50 years, what will be obvious in retrospect but you're curious about today? Crypto, VR, biotech, Siri, satellites, cars, solar panels, something else? You decide!

If you have 'solved' the money problem for your personal life and seems looking for 'purpose' and 'positive feeling reward' have you considered giving time to charity/community (specificaly 'local' ones near you live) ?

I think a common lacking in those (smale scale) organisations is sometime basic event/communication/money management, with often more enthousiasm than skills.

I don't know on the USA (I assume your from here) but hackerspaces and derivatives can allow you to keep in touch with the startup world while helping a lot of enthousiast people and being emotionaly rewarded.

Of course that mean taking a standard job to live. In Europe (dont know for USA) it can even help you land a real part time job after some time.

You should stop once your aspiration to continue is eclipsed by burnout. In other words, you've reached your final plateau, and are so stifled that you must descend.

Note that I am not saying that burnout alone should be cause for quits, far from it, but that you've reached a level of burnout where you are not assimilating what you've learned up to the point of that burnout to help you move past it.

Burnout is always telling us something, that there needs to be some change in our processes.

what is it that you like? building stuff? talking to people? money? power? I asked these questions when i was semi retired and what i found out is that i like building stuff. So now i build stuff, it doesn't matter to me if it is another canva, if it gets me some money i am happy, if i release it for free and someone uses it, i am happy. If no one uses it i am still...happy because i enjoyed the journey. Concentrate on journey and not the outcome.

I would read philosophy on the subject of sublimation. There are many profound writings and writers that have explored the idea. Nietzsche is one, Emerson another. I expect you will discover an agon that challenges your present value system, and this will become curiously interesting. Lead a hidden life with a private good in mind that runs in parallel to the life that is expected of you. But perhaps you are already well versed in these matters.

It sounds to me as if you need gift yourself some mental time off. You're clearly an entrepreneur, so I'd caution against getting a job, but you've not had a follow up hit and may have lost a little confidence in yourself and can't see the joy in trying to build something new.

You're in a fortunate position financially so I suggest you use that freedom to detach and replenish. Ask yourself, if I allow myself to do absolutely anything (or nothing) for the next 6 months what would it be? That's a pretty exciting thought right? Not only will you break the cycle of intellectualizing your situation, the process of self-permission will open up new ways of getting out of these ruts in the future.

If it were me, I'd switch off every device and read the Guardian's 100 best novels of all time.

Take a job if that feels like the right next step. As someone suggested join an earlier stage startup that has cracked product-market-fit, and you have an opportunity to create a strong relationship with the founders. You may start by leading engineering at such a company based on your experience here, that can transform into leading engineering+product into engineering+product+technical sales into COO etc. I know friends who have gone through similar journeys, and have achieved immense success both financially and spiritually by joining a caravan that is already on the road.

I’d recommend getting a job or at least starting the process. As you go through the motions you’ll be deciding if it’s something you actually want to do or if you want to keep pushing.

"Doing Startups" is not a thing. A startup should just be an outcome of something that you enjoy doing. If you are frustrated with the process, stop doing it. You seem to be in a very privileged position in which you have financial freedom. Don't restrict yourself by following what others define as "mediocre result and career". Do what you love and you'll see it will turn into a success.

Perhaps you should find someone that does have a good idea that you and others are excited about.

What do you care about? Which problems would you most like to see solved? By whose measure is "not having to work hard for the rest of your life" a mediocre result?

Consider getting in to hardware. Far more interesting.

have you considered joining an early stage startup?