Working a ton, but not saving. Not investing. Living downtown for too many years. Going out to restaurants and bars multiple times a week. Buying a new iPhone every year. Not optimizing the career path for income (or, anything really). Never really going into debt beyond a (cheap) car payment, so it could be worse, but also not seeing personal capital grow.
Now, I'm hitting the stage where I feel this pull to try an independent venture; and maybe even leave the software industry. But I don't know how to do it financially. Its not just the runway in my bank account which could be measured in months; its the lifestyle.