If you upgrade your life and lose it, you're back where you started, not worse off. The speaker argues you should pursue what matters to you anyway, building value by serving people and solving problems, rather than staying small because you're afraid of falling.
One of the craziest things I hear is that people are afraid to increase their lifestyle. If you increase your lifestyle and then you lose that thing, you just go back to where you are now. You can invest in things that serve your values and make you really happy. And if you lose those things, that's okay. You just go back to where you started. If you want to have nice things, increase your value in the marketplace, serve more people and solve a problem and stretch for that life that you've always wanted, there's no reason to take everyone else's advice and stay mediocre so that you don't lose. That's just crazy.
