Tell HN: Turned 44 today and I'm lost

Been professionally developing since my teens. Was the first person in the history of my university who was both a fulltime student and full time employee. Exceeded in all expectations at every job. Became the founding CTO of a start-up, put my heart and soul into it, and we sold for low 8 figures. Started a second company with some of the same people but directions started to diverge and I left. I moved to a different state for another job. Became a freelancer for a while. One of the guys who was at both start-ups recruited me into his current company with a total comp far exceeding what I asked for. All mortgages, car notes, and credit cards are paid off and our investments are enough for our day-to-day. I’m really only working for the health insurance.

But I've never been more unhappy and lost.

I used to joke that I would be dead by the time I was 40 though stopped because The Wife hated hearing it but I do feel like I have no plan past this point. Being in pandemic lock down during this time hasn't helped. I told my therapist that I feel like I've hit my mid-life crisis, though not your typical one as I'm not going out and buying a muscle car to cruise high schools. I know I'm depressed and have been for the majority of my life. Been in therapy for a while and tried various pills (didn't help), TMS (somewhat helped), and thinking about trying Ketamine.

I feel like I've hit my zenith already and it's just a slow decline from here on out. I’ve been dreading this day because it’s a sad reminder of that.

You know this sounds just as „just dont be depressed“?

Life is, or can be, about much more than work. You could be at mid-life crisis, it’s real and you’re exactly the right age.

Exercise, make sure your needs (quality time, intellectual engagement, emotional connections, nutritional, family quality) are being addressed. If you’re burnt out, take time for you. As codegeek wrote, consider volunteering. Making a meaningful difference, even small ways, to others is way more important than making bank once you’re adequately set.

If you can live a reasonable quality life without employment for the rest of your days, you’ve hit the lottery. Be totally psyched, and use your freedom. Wish I was in your shoes.

When you sold the first company, how did you pick the subject of the second company? Was it an opportunity, or was it something you really loved? Is there something you are really passionate about now? Could be anything… hobby, travel, certain pieces of tech, whatever. Think about it and try lots of things out. Maybe go back to things you enjoyed when you were a kid. In my experience, you need something, or a series of somethings, that really interest you and drive you. They might seem silly. They might seem dumb or done already. See if you can find something that you like to play with. Really play. Go from there.

None of us live forever but I think for many people, the ultimate hope is to make a difference, to leave the world slightly better than we found it, to invest our skills into progress and removing some of the evil we find around us.

If you can find what you really enjoy doing and turn that into an investment into the planet and its population then you get to arrive at your death bed really believing you did something valuable with your life.

As they say, few people wish to have earned more money or spent more time at work, they wish they invested in people, in communities, into the less fortunate etc.

Good luck. I'm two years older than you and still feeling like some of my best is yet to come!