So, not in my early 40s and I haven't quit a high paying tech job, but I have done well creating apps. Years ago I decided not to go work at a large FANG compan

So, not in my early 40s and I haven't quit a high paying tech job, but I have done well creating apps. Years ago I decided not to go work at a large FANG company because I knew I would be miserable. Having the freedom to do your own thing is amazing. You will love it. But you need to switch from an employee mentality to an owner mentality. Assume you're not going to make $500k a year in the first few years (if ever). The main advantage you get is that you build up assets; say you create an app that nets 200 or 300k in income a year and run that for a few years. You can eventually sell that for a 2 to 5x multiple depending on the space it is in. Those gains are then generally taxed as capital gains, meaning you pay (lower) tax on them. Self employed people can take more deductions and pay less overall tax -- look at after tax income. Another thing to consider is, if your current compensation for a large part comes from stock based compensation, that these stocks will not keep going up forever. If you've been at Facebook for years and received stock at $20, it's not going to go another 10x in the next 2 to 3 years. Meaning you won't actually make 500k/yr (should that be the case) You will also need to learn how to invest. I don't think there are many entrepreneurs out there who don't invest their money. You're leaving a ton of money on the table and honestly, there is no excuse to have $1.1m sitting in cash in a bank account. But at current valuations perhaps wait until the stock market has a proper correction. Also, mobile games are hard. I know how to make money from apps, but games are insanely competitive. Have you considered looking into other things? Quality of life is worth more than anything, in my view. My father died at 55. Even though I've done well for someone in his late 20s, living and enjoying life / family is more important than money. Taking a moderate risk (on a 'lifestyle' business) might be enough -- there's no rule saying you need to shoot for the moon.