I have experienced this feeling at numerous low points throughout my career. It took me more than 20 years to figure it out - hopefully I can help you get there

I have experienced this feeling at numerous low points throughout my career. It took me more than 20 years to figure it out - hopefully I can help you get there sooner. Let's take work and debt and money and all that out of the equation for a moment. What do you really want to do? Like, not an activity or a job... how do you want to see your life being led by you? Who do you want in your life? What do you want from the neighborhood you live in? What do you want from the house that you live in? Get to the brass tacks with this. Really understand the details. Try to envision what you want to do and how you want to live. Ignore the doubts and the voice that says, "No way, never'll happen." Figure out what the road looks like to get there, then start shaping your life to fit that road. As you look for a new job, ask yourself how that job will get you closer to your ideals. Will it relocate you? Will it give you the time for the things you want to do? Will it expose you to people who you want to be part of your journey? You may realize that, first, money isn't really as important as you think, then realize that you may be happier at a smaller company, or in a different industry, or at a bigger company, or... whatever. It brings things into focus. Why did you do the startup thing? What was your goal? Was it something fuzzy like, "Get rich"? Was it something startuppy like "Change the way people travel"? Was it personal, that you wanted to build a name for yourself and impress people? Was it because of the freedom it offered in terms of how you spend your time and energy? Be honest with yourself as you answer questions like these. Maybe a startup-style thing isn't the way to go for you - maybe do something like a lifestyle business (i.e. bootstrapped, organic growth, etc.) or consulting. As you dig into these answers, you may decide tech isn't even what you want to really be doing - maybe you want to start a food co-op in your town, or maybe you want to spend less time working and more time just being. Again, start changing your life choice by choice to begin to fit the ideal in your head. And, if you get there and the ideal ain't so ideal... start it again. And again. And again. It's all an adventure, and you should try to enjoy the ride as much as possible. Don't beat yourself up for your "failures". I promise you will recover if you just keep at it. I have seen so many lows at this point the floor and I are very good friends. I always bounce because I figure out a way to push through the depression and the anger and the self doubt and the loss of confidence and trust and find an answer and a path toward the answer. You, too, will bounce.