Assuming you are doing pretty well and are happy with your current standard of living, what would you need to maintain your standard of living in retirement? Knowing you are on track to accumulate a nest egg to support that lifestyle is a big win. Gold medals go to those who have accumulated enough assets, or passive income streams, to be in a position to retire well.

Hang in there, Adam. I’m in the similar boat as you. I’m 51, looking to retire @55 when my son goes to college (his tuition is already saved in separate 529 account). @4% withdraw rate, we have enough assets to generate passive incomes of $250K+, and our annual living expense is <$100K. Neither me or wife have pension or medical coverage, but we do have 401K and some prior HSA savings.
Great post. One thing I’d challenge you on: owning a car. I’ve had one since I was 17, and LOVE having a car to get me from point A to point B. Thing is, I want FI more. So I yesterday donated my car to charity, and am now walking/bussing/Zipcar-ing my way around. No repair costs, insurance, gas, oil changes…no saving for a new car. Goodbye Saturn SL1, Hello Carsharing
The doctor or lawyer, for instance, could use her or his income to invest in a medical start-up or buy shares of medical companies he understands such as Johnson & Johnson. Over time, the nature of compounding, dollar cost averaging, and reinvesting dividends can result in her or his portfolio generating substantial passive income. The downside is that it can take decades to achieve enough to truly improve your standard of living. However, it is still the surest path to wealth based on the historical performance of business ownership and stocks.