If OP is reading the comments, I’d highly recommend developing a meditation practice. As you’ve already experienced, the quality of one’s experience of life is determined by one’s mind, regardless of possessions, achievements, etc. And meditation is the best way to “train” the mind.
Go for it. You will fail a lot. But where there’s a will there’s a way. And the “end” is so worth it.
Similar story: I was working in software, and over the years I literally felt pain to think about working for someone else for the rest of my life. After lots of side projects alone and with friends, with VC—backable and bootstrapped ambitions, I could just feel it in my bones that solo-bootstrapped B2C-software-entrepreneurship was the best fit for my skill strengths and weaknesses, temperament, and desired lifestyle.
1. I left corporate at $3K monthly (not recurring).
2. 0 pivots on the idea that ended up “working”, but countless other side projects before AND after that idea.
3. $0 for many years. Then decided to monetize (one time purchase) a project that had decent usage and traffic. Then a few thousand a month for a year. Moved to subscription pricing and improved it a ton based on my vision and customer feedback. Now a little under $10K/m recurring after a few years from the previous milestone and growing steadily.
4. I never want to go back to working for someone else again.
5. Solo
6. See above. Two critical aspects IMO.
1. I did a lot of side projects. I had a lot of “at bats”. And each time I learned more. I developed more skills sure, but also arguably more importantly learned more about myself: what I wanted and what I could do. And you only need one hit. Doesn’t even have to be a home run.
2. Product and marketing/sales intuition are critical. I wasn’t even a software engineer, but was a technical product person. You can’t just build an impressive technical system. You have to build a product that users love (product vision/sense) and get it in front of them (marketing/sales), with extremely limited time and money (ruthless prioritization).
When you say maxed out deductibles for collision and comprehensive, do you mean you picked the highest deductible? Or lowest deductible which would mean max coverage but also premium? I’ve always wondered about the value of collision and comprehensive, since it seems to be one of the more expensive parts of car insurance