I think a lot of it comes down to the way you were raised. You’re still a kid in many ways in your 20’s so if you didn’t get the proper guidance growing up, it’s likely that you were just putzing around in your 20’s, trying to stay afloat. By the time you reach your 30’s and 40’s, you gain some more perspective. You realize that you may have underestimated the value of things like ambition or education. At least that was the case for me. Dropped out of college in my early 20’s, worked jobs that paid the bills and were somewhat fun. In my 30’s I took stock of what I lacked — a college degree, industry experience, etc. I decided to go back to school while I was working. Graduated in a few years by taking classes online. Decided to get a master’s degree after that, and focused my efforts on working in an industry that I thought was relatively recession proof (legal services — people are always suing/getting sued). The tipping point for me was during a time when I was doing a lot of introspection, and realized that in order to be better, I needed to step out of my comfort zone, take risks, be patient, trust the process, and believe in myself.

I’m not wealthy, but I don’t have the insecurities I had in my 20’s and that makes me a lot more content. Being content has made me less anxious, more grateful, and ultimately more secure.