Ask HN: How do you “stay foolish”?

In Steve Jobs’ 2005 Stanford commencement speech, his parting words to graduating students was to “Stay Hungry. Stay Foolish.”

I have been foolish in many ways much to my financial detriment. The most foolish thing I’ve done is buy, fix and sell over 10 houses for $500k profit, getting burned out, and wasting all the profit in the following years chasing foolish investments. I’m burned out from dealing with all the unreliable idiots to the point where I will likely not buy another house again even as a personal residence.

I was also foolish enough to buy early into bitcoins and not lose them. This was probably my most profitable foolish move although it doesn't make up for all my other moves.

Every passing year it’s getting harder and harder to stay foolish.

What have you done to stay foolish?