I took the leap at 39 resigning from a high pay/high stress executive role to get a CPL and fly GA. Still doing it 20 years later and loving it! As a lifestyle, passion, adventure choice it is a no-brainer. I would suggest having a financial buffer though. Comparing last full year as an executive to first full year as a commercial pilot was a 90% pay cut. Twenty years on I’m earning about 50% of my former career compensation.