How to Deal with Loneliness as a Founder?

BUT if there might be the slightest idea of a medical condition, get professional help.

Also, hire and empower people to take off some of your work and responsibilities. For many years I didn’t have a proper vacation as I was trying to be always available and this is not the healthy way.

If you can, consider hiring a CEO/COO or get a cofounder.

What kept me going was to carve out some personal time for non-professional relationships. Since you say you can’t have these sorts of conversations with your current network of friends you should probably expand that network until you find people that you can be open with.

I moved in with my girlfriend and we built a really solid relationship.

I invested more time in friendships that I had neglected for a few years.

I also started playing a team sport which did wonders for me both physically and socially. If you’re not much of a sportsman try golf.

It takes a while to build those things though so in the meantime you might try seeing a therapist. Paying someone to listen while you vent out loud in a safe environment is actually helpful and will make you feel better. I never saw myself as the type of person who would go to a psychotherapist but now I feel that my preconceptions about that were totally wrong.

Also if you have the money for it consider getting a cleaner to free yourself of as many domestic chores as possible.

But definitely do something before the problem gets worse. Building your company is just one facet in building the life you want but if you ignore everything else you risk building a prison for yourself instead.

Being a founder is inherently isolating because you probably work extreme hours, and are not a peer relationship with anyone else in the company apart from perhaps others in the C-suite due to the inherent power differential.

You say you can't quit, but I think you should rephrase that. You essentially acknowledge this yourself: you can quit, but doing so would have consequences. Turn that into an equation, and verbalize it / write it down. I'm not sure why, but it feels different than just thinking about it. On one side you have $X million dollars, and on the other side you have the costs associated with it: burnout, unhappiness, but also providing employment to others (not all negatives, fill out the equation as per your perspective)

Then break that down a little further: you might be able to address burnout (give yourself some odds, and a cost in time/energy for that attempt), quantify exactly how unhappy you are and how that's trending, and then acknowledge that regardless of how your company performs, your employees will (very likely) find other jobs. Most will do it anyway even if your company survives.

Your sides of the equation might look a little different, but the basic approach is to just divide it into an equation and start pulling apart the components. If you're unhappy but it's getting better, perhaps that's not so bad. If you're unhappy and are on the verge of suicide, it's worth thinking strongly about if it's time to move on.

From my understanding the general advice on burnout is that you should expect it to take months to recover from, but individual cases vary greatly.

On the subject of loneliness, I'd try focusing on non-professional relationships. There's too much power-play in professional relationships, even when there's no current exchange of value.

Perhaps most importantly, in your personal relationships, don't say what you do or be a bit vague. Be extremely modest. "I'm a founder of a company" becomes "I work at a startup" or "I'm in XYZ industry". Try to find people who enjoy being around you for your personality, not what you are.

Personally I went the other way and found hobbies I can do individually. There's a reason so many people in software turn to woodworking afterwards. There's a sense of progression, zero bureaucracy, and it feels like artisanship.

Successful succession is a first order priority of successful leadership. Working toward it might or might not mitigate your loneliness, but building a structure to make a successor successful will give you another option for moving on and solve a critical business problem.

The worst outcome will be about the same as the average outcome in the absence of a succession structure. Good luck.

If you really feel that you can't talk to people in the company about your emotional state; then maybe approach it from another angle. Say "We need a plan in case I get hit by a bus tomorrow", and listen to their input. Part of your problem is you are worried that everything will fall apart without you.

Join some Discord groups, maybe you'll find one with people you can befriend. I got lucky with one that play a lot of board games online, which I also enjoy doing. And the movie group now has a discord too.

If nothing else, I find I can dull the loneliness a bit (when I have it) by having Youtube or Twitch in the background sometimes.

While it may seem like there is something wrong with you, having and maintaining friendships relationship is an actual skill, which you just simply haven't had time to develop. Just like with everything, its gonna suck at first, requiring you to take time to do things that you may not enjoy, however it gets easier with practice.

Start with going to therapy and work from there.