Ask HN: When should you quit?

If isolation is an issue, perhaps there is a co-working space or public space at which you can work. If you don't want to work in public, maybe you just need to go to some meetups, professional organization, makerspace, or some other type of group where people come to socialize. You may want to try a mix of tech and non-tech type groups. I found when I was running my own business in my early 20s that a local user group provided a good way to meet new customers and interact with people. I also tried things like board game meetups, "young professional" groups, etc. even if I didn't like the people or never went back, I found it a good to break up my routine. I would also make sure to spend time outside, at the public library, just leave the apartment for lunch, etc.

I have often thought about leaving tech or going to a different area within tech, I can empathize that its scary to think you are a specialized cog that can't really do anything else. It may be helpful to reach out to a career professional for some advice - for example if you went to a college/university, they usually provide career counseling for alumni, local libraries also often have resources or people who may help. If you are thinking of staying in your own business, you may want to try your local Small Business Association chapter (or equivalent if you are outside of the US).

Remember, your greatest asset is often not what you know, but that you know how to think and make critical decisions. I am sure you have learned a new programming language or figured out how to deal with a bad customer. Those are skills which can be generalized and applied in other areas. It may be hard or scary to take the step on how to apply these skills in a different area, but you may be able to think of low risk ways of trying it out. Maybe there is some type of freelancing gig outside your realm or even outside of tech you could try. Some of the networking ideas about may help you bump into someone who needs your skills - even if its not paid work, they may buy you a coffee just to pick you mind.

I would also second some of the other comments on getting a mindless or corporate job for a while, taking a vacation, tech detox, etc.

In sum, the first step is to break out of your routine and try something. You may have heard of paralysis by analysis... sometime you have to just take that first step and not worry about having the perfect optimal, zero risk plan in place.

I'm 53 and have been working as a programmer since I was 17. I still love what I do but I've been where you are at several times. I'll tell you something you probably already know - it's impossible to make a good decision where you are at right now. For what it's worth I'd suggest taking a break and then deciding what to do once you have some distance and have shaken some of this off.

This is good advice - I did this when I turned 30 - spent my 30th on a beach in Chile having the time of my life - then spent the next 7 months backpacking around south america - and it was the best time of my life. After I came back I worked for a few months to save some $ then moved to the other side of the world - that gave me enough interesting stuff to keep doing something I wasnt so interested in anymore - but I found unusual work opportunities that never would have happened if id stayed in the same place

Don't worry man, lots of us (me too! I'm 33!) started companies while young. Shutting them down is liberating, not every effort comes to monumental financial success. Some say that the true measure of a person is how they respond to challenges. Knowing that there is no set direction in life, it's really healthy to embrace moments of reconsideration. Don't worry about deviating from some social obligation of fervently chasing dollars. Changing physical and social environments can be very powerful. If you have some money in the bank then I would highly recommend going to travel on the cheap to some different countries. Learn about where you go, explore. Try to limit the time while you are away spent with people from your own culture. It will help you relax, and stimulate you in new directions. You might even try something new that pops up on the way, and find new directions you might like to consider: Diving. Studying. Teaching. Writing. Art. Picking up a new language. Running a hospitality business. Maybe even someone who gives you a shared direction in life?

Personally I shut my first company in 2009 after getting some recognition from VCs and support from angels, found success working for others for awhile, did a few years of remote, and now - some 7 years later - I'm starting businesses for myself again. It took that long to re-energise. We don't even have our website complete yet, but yesterday just signed our first client for enough money to buy a nice shiny new mountain bike. I plan to let it grow slowly and organically, not stress and to ride that mountain bike at least as much time as I spent in the office coding. Wiser these days.

Spend a year or two getting as strong as you can physically. It is just as important as exercising your mind.