I’d do the basics of paying off my house and doing some renovations on it. Or buy and move into a slightly bigger one in the same area. Maybe buy/rent a condo right next to Wrigley Field. Nothing fancy, but I would like to be able to stay near the park.

After I put most into safe investments I would have some fun.

I’d find some financial advisors and give each of them a million to invest for me. Then fire the one who performs the worst after a period of time. Then put that money to a new investor and repeat.

I’d buy a small warehouse to turn into an auto shop to house and work on the cars I buy. Which would be daily drivers, so things like a Miata and a classic mustang. The only fancy car I’d buy, and drive, is a Catterham. This would be my main hobby, so I don’t consider it a waste of money. Repairing/restoring cars and selling them.

I’d set off on a road trip and love to be able to just see and experience everything without worrying about how much hotels, food, and gas cost. If it weren’t for girlfriend and her daughter I’d consider even just living in a van for a while. Spend a year and go to literally every Cubs game.