You bring up whether I would be okay on my deathbed, and honestly I do think that if I don't do it I will regret it, but there are other things in life that I w

You bring up whether I would be okay on my deathbed, and honestly I do think that if I don't do it I will regret it, but there are other things in life that I would regret not doing as well. I'm trying to gauge if it would mean an uncomfortable year or two if it meant having a lifelong impact on my earning potential. I'm not sure I agree with you that joining a company of under 50 is the next best thing to entreprenuership. I've been there and it seems like you get a lot of the negatives (ambiguity on your role, disorganization, uncertainty on stability of business) without a lot of the benefits (freedom/flexibility to work on what you want and potential upside.) For the record, I am the kind of person who wants to have my cake and eat it too, (what's the point of having cake if I'm not going to eat it?)