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Well, I can say that I really feel for you since I have gone through painful breakups and you definitely feel lonely afterwards. Esp if its a spouse. Maybe you have old friends you can reach out to (some can actually be understanding)? If you feel depressed, it’s natural, but generally, if you care about your long term mental health, try seeking company, whether it’s old friends or just new friends (meet-ups, sports). I think this helps a lot. While work can be an obsession, try to break away to seek solace in your own immediate family (mom, dad?) or a sport/non-work hobby.

Sometimes, getting just a little distance from work can help. What I realized in my late 20’s, after the web 1.0 bust was that my startup wasn’t worth the sacrifice of my close relationships (gf) and realized like anything else, I needed to invest in healthy ways (time, energy, thoughtfulness) into those things as well as work. I’m still struggling with that since work can be an obsession, but I try to remind myself everyone how important my family relationships are….as I’ve gotten older, I care more and more about family….which probably would make me a shitty entrepreneur, but I suppose I’m ok with that trade off nowadays.

Second, I can see leaving a job if you don’t like it, but many entrepreneurs really need to examine themselves as to why they really want to work for themselves, is it because of rebellion to corp culture – boredom, or is it really because you want to start a biz – you can challenge yourself in other ways besides a startup. You can have a high paying job and start a business, so you don’t have to eat PBNJ sandwiches and live in a friends basement. I did it – never had ramen noodles for dinner. Wish you the best!

End game is “Sell a few subscriptions and raise money or partner with someone in our field to open more doors for us than a VC would, sell company or keep running it and finally be happy at what I do. Make more money, surf, run and get more involved in non-profits.” Help other entrepreneurs with life’s struggles, especially younger ones who do not know what’s in store for them.

What a thoughtless comment to say no one will care about him when he dies. I mean, beyond thoughtless.

As to the issue at hand, the what if ship has sailed. It’s full of people who have never done anything they wanted to do out of fear. Glad you missed it. Anyway, you are going through a lot, but I think you are asking the wrong question. The events would have happened with the high paying job or not. Can you honestly say there were no cracks in your marriage before the startup? I doubt it. However, I think you are focusing on the wrong thing really. There will be no startup if you are not healthy, so first order of business is to get yourself well. I understand that ability to focus on something else while things outside of your control are going haywire, but make sure that you are focusing on getting healthy. Did you note I did say the things going on are outside of your control. Note that well. You can be there for your wife and her dad, but what is going on is outside of your control. Cancer sucks for a reason. Either way, none of this has to do with you leaving your job, and clearly, you want to build something, so go for it, though I have to wonder why you didn’t do it on the side until you had tested it out? Don’t listen to the Silicon Hype which does not tell the realities of why you should keep your day job, if you get another one, until there is money.

And just keep this in your head – what entrepreneur HASN’T struggled to get to where he/she is today? Success is how much work you put into it. So keep working.