"irreparable damage to my career."

I am trying to help you with my comment but it is going to be straight. You sound like someone who wants to have the cake and eat it too. If you have the itch so bad, you need to do something about it at some point and there never will be a right time. Trust me on that. Yes, you can take calculated risks etc but overall, there will never be that perfect day.

"Irreparable damage" is too strong of a phrase. That tells me that your itch is not that bad and it is more of a nice thing to do because many others do it. Don't think of it that way. If you truly want to do your own thing, think of it this way. What if you never do it ? Will you be ok with it on your death bed ? If not, do something now. If it doesn't matter that much to you, you are most likely better off just working for someone else.

Having said all this, if you are not sure about how to start your own thing, the next best thing is to join a small company/startup where you learn and are very close to the bottom line. Lot of startups/small companies (under 50 employees) would love to hire failed entrepreneurs.

Source: I have been doing my own thing for almost a decade now after working jobs for a decade. If you are a failed entrepreneur, hit me up. Always open to chatting.

I had a failed business venture and when I was truly ready to give up I found a listing for a job at a startup company that was trying to do something similar to what I was trying to do and I was working for them in about three weeks.

If I was hiring for a startup I’d be more inclined to hire someone who tried to start something and failed that I would be to hire somebody who worked at Facebook and Google and had internalized the processes there.

People might have a different attitude at a big company but I think startups appreciate people who can wear many hats and will figure out how to get something done whether or not it fits the job description exactly.

I was an employee, then did my own thing for 6 years, then recently went and got a job again.

I felt no push-back at all for doing my own thing; in fact, I think it was a positive for most people.

If it was only 6 months instead of 6 years then maybe that would have made a difference (?), but generally I've found that people saw it as a positive sign that I was able to be self directed, work in ambiguous circumstances, etc.

Also as pointed out elsewhere here, the ease of getting a job is often a lot more about your network and who you know rather than your exact experience.

Good luck!

I doubt it would do much harm to your career unless your business ends up facilitating child molestation at scale or something and that’s what you see when you Google the name of the business.

But, the fact that you’ve been thinking about it for 10 years; are asking for permission from a group of strangers; and are already thinking about an exit plan before you’ve even started the business suggests that entrepreneurship may not be for you.

It will obviously be a higher risk proposition than working for someone else. If not having a big brand name on your resume for a few years sounds scary to you, trust me, that will be the least of your worries.

How old are you?

Ageism would be one of my top concerns with regard to re-employment. It is also one of the biggest factors prompting techies to try doing their own thing.

Take a good look at your co-workers. What percentage are beyond middle age? This should give you some indication of your employment prospects going forward.