Always loved that quote. In my old financial world, it was used for fund managers who invested a significant portion of their own money in the fund to underline their commitment and responsibility.
With these actions they moved themselves out of the usual comfort zone. Screw ups, hurt, but with failure comes quicker learning.
Too many people never have “skin in the game” in their own lives. Afraid of taking risks. Afraid of failure. The play the blame game and its always the fault of others. So, they end up living the same days, the same months, the same year, over and over again. Same diet, same friends, same thinking. They know on the 1st of Jan what they will do on the 31st of Dec in a few years.
If that’s what you love, who am I to judge, however I haven’t met many people who are really happy living like that.
No doubt you will occasionally fail when you start putting skin in the game. But failure is only a failure if you name it as such. Otherwise its simple learning and a way not to do it next time. You know the difference between a Gold medallist figure skater and one finishing 5th or 6th? A few thousand times spend less on their butt when falling and training a complicated jump. Skin in the game almost literally! Yes, you read correctly, a few thousand times. (see Talent is overrated by Geoff Colvin, p.187)
Bronnie Ware, a palliative nurse interviewed people on their death beds what where the top things people regretted NOT doing, and the No1 was not living their dreams and aspirations.
Hence, I would encourage you to put “skin in the game”, get off your butt and out of your comfort zone. You can’t win a game that you don’t even play.