For me personally….

I defined my lifestyle goals: the sort of car I wanted, the sort of girlfriend and friends I wished to have, the type of home and neighborhood I desired, the variety of hobbies and activities I wished to engage in, etc. I told myself that when I reached a net worth that would support that lifestyle until I die, I’d retire. And that’s what I did. It was a fun ride it didn’t involve having to take on partners or investors, etc. It’s a modest life but a fulfilling one. I’m glad I chose that path.

But there are others in my social circle who had much higher standards. First class travel wasn’t enough. They want the private jet. A 9 girlfriend isn’t enough. They want a model-quality wife. They want the mansion in Connecticut, the country club membership, lots of kids, each going to private school, exotic vacations, etc. They want to leave a “legacy” and have their name on hospital buildings. Those guys are aiming so high that they really need the additional capital and coordination of business partners and investors. They need to take their company public. They need to spend an additional fifteen years achieving their billion dollar dreams.

You have to figure out which class you fall into, I guess. I don’t really know you, but you seem like the type who values life enjoyment, spending time with friends and family, improving your skills, etc. rather than becoming a wine industry superstar on the cover of business magazines. If you can do reach your life goals without taking on a partner or outside investors and working yourself to death, that’s definitely the path you want, in my opinion.