If the third option of hiring someone to do your day to day really was impossible, this would never end. I would strongly recommend getting someone to come on b

If the third option of hiring someone to do your day to day really was impossible, this would never end. I would strongly recommend getting someone to come on board and start trying to take off some of the load / get up to speed. It might take a long time but either you're going to quit and ruin it anyway, it's going to kill you and that'll ruin it anyway, or that has to happen eventually. Start now. I get why it's hard: attracting someone who's committed, getting the incentives right for them to not feel the same way in 2 years, etc. But it's really worth focusing on attacking those specific issues as soon as you feel up to it. Even if the person just takes over some QA work / automation / simpler features and fixes, etc. Doesn't necessarily require an unreasonable amount of domain knowledge but if it frees up a couple of hours a day for you, you could take a hike in the mornings and stop feeling like crying about what you're not experiencing every day (or whatever it is you'd love to do instead of work). More immediately - it sounds like you need a vacation. I've been there with the whole fantasizing-about-walmart-construction-sites-and-grocery-stores but it's a dead-end in the long-run. Every job will wear on you and come with it's own set of hardship. Mentally less stressful? Possibly. But think of the very different set of people you'll interact with - possibly a huge culture shock. Think of what a bad day at work might look like at a construction site. In the rain and cold, a little physically injured, maybe having to deal with a client that's trying to screw your crew over on the contract? Probably making less money? And dealing with all the comes with? It's not much of a greener pasture once you get into it. I would bet what you're really in need of is a break and a change of scenery for a little while. If you can make that happen (and again - you need to or this is all destined for failure at some point), try that and see how you feel when you come back. By all means keep talking to people who have been there to get input - probably a lot of us on HN. Don't take all of it as gospel, but you're definitely not the only person to go through this, and you won't be the only person to figure out a way through it.