Lots of small risks, not the one big risk

If you try lots of small things and make tons of little experiments, you’ll gain valuable insight across the board. You’ll learn how to better optimize yourself, your company, etc… but you will also potentially run into a number of big wins when that small risk carried massive upside.

However, if you cling to the status quo and refuse to deviate except every now and then to take a big risk, you put yourself in a position where you potentially lose very much which will cause you to be more tentative for the next big risk.

More important than that is that some risks fail so you need to take lots of risks to get the big wins. By only taking the occasional big risk you severely reduce your likelihood of getting that big win by having less proverbial pots on the stove.

Make risk taking a way of life. Small risks with limited downside and a big upside. Just doing that has a big upside.

Think of it as a songwriter. You write hundreds of songs (each with the risk of flopping, but nobody talks about the songs that never get popular anyway), you write those hundreds of songs to get a few huge hits. A few huge hits later you’re the Beatles (or Rolling Stones, or Bruce Springsteen, or Whitney Houston, or Dr. Dre, or Usher, or Coldplay, or Adele, or Taylor Swift, etc...)