Startup for a few reasons, with an assumption you aren't married with kids. 1. You will never have the freedom you have when you are young. Once you are more

Startup for a few reasons, with an assumption you aren't married with kids. 1. You will never have the freedom you have when you are young. Once you are more established with family, kids etc it is harder to take risks, not impossible just harder. 2. You will learn more good and bad in a year at a startup then 3-4 years at an Enterprise. You will be forced to grow and do things you didn't know you could do, but you can. 3. Even with the cons, startups are one hell of a fun ride. Yes, at times it will suck, but better to have some excitement then be bored after your first 6 months at an enterprise job. Now, the other side of that is. Enterprises can still teach you a lot and let you grow some while giving you greater stability, it just takes longer. You will also get to see how screwy corporate cultures can be and some good parts too. There are just things about working in and around Enterprises that you can really only learn well by being inside and seeing the beast. If you want an easy life, and to retire fairly young in a more "guaranteed" way, you will be better off taking an Enterprise job, working 20-25 years and saving well. You'll be well compensated, can save and invest well to retire quite comfortably. Not to mention you will rarely be working crazy hours and can take your vacation regularly etc. Yes it will involve stress, but IMO 75% of the stress is the bureaucracy you have to learn to navigate. In the end no one can tell you the best choice. My brother and I both came from the same entrepreneurial family and I went on my own after some experience in Enterprise businesses and he stayed in the Enterprise space.