There's a lot of hyperfocusing on the comment that you don't want your wife to know. From everyone on HN, you're the best judge of whether she should know or no

There's a lot of hyperfocusing on the comment that you don't want your wife to know. From everyone on HN, you're the best judge of whether she should know or not, so I have no choice but to trust your judgment on that. Something I find missing from your narrative is what exactly is making you unhappy -- the title of Founder? The pressure of the job and the impending sale? The mundane-ness of the technical details of the job? The fate of being handcuffed to this job (that you don't care for) after the sale? Are you financially constrained and feel tethered to the company to stay afloat? You mention the stress, but it doesn't sound like that's the kicker by itself. There's no magic bullet to fix all your worries in one go. So write down in order which parts of the whole situation you hate. You'd be surprised how many of those can be solved independently of the others. Maybe you can hire a personal assistant to sort through all your communications and scheduling and logistics, and can filter out the domain-knowledge-needed parts to you. Perhaps you can invest in transitioning various boring technical portions of your product to be outsource-able, so your in-house developers have only the more fun stuff to worry about. Consider the best and worst case outcomes for each of these options. Check the risk. Some of them will be worth it, some not. If you can improve your situation even a little bit, it's a step forward. I can relate to some of what you say. Luckily my cofounders are wonderful and take responsibility for lot of the shitty parts of the job of running a company, so I have a fun time mostly gallivanting in technical and product design spaces without stressing out much, and we're profitable and bootstrapped. All in all, my job doesn't really stress me out much, I work with great people, I love our product, I have lots of freedom and make enough money to use it to work out of a different country every other month. It sounds pretty great, but I have shared your fantasy of working as a grocery bagger or as a Starbucks barista or something. For me it's because I am in America on a work visa that won't allow me to be employed outside of my field of expertise and study, ie, engineering. So I fantasize about what I can't have, think how cool it would be to have the freedom to be an uber driver or a waiter or just simply be unemployed before I look for a new opportunity, even for just a month, without the threat of violating my visa agreement and risk deportation. A little reality check reminds me that I have these fantasies from a position of privilege -- all those people who's jobs I envy do not have the right, or freedom, or training to start and run a company building something they care about in the first place, and I happily return to my day job.