The Albertson’s cashier says, “That will be $33.97.” I nervously swipe my credit card and the transaction clears. I instantly feel a wave of relief and realize that I won’t have to put any groceries back.

The last time I shopped here I had to put the ground beef back. Not this time. This 2002 fall afternoon had been challenging and this small win was exactly what I needed.

During flight school at Airline Training Academy, I worked six nights per week at Steak n’ Shake from 11 pm to 7 am as a server trying to make ends meet. Unfortunately, no matter what I did, there always seemed to be too much month at the end of the money. The reality is I was tired, broke, and years away from that changing.

When you’re a poor aviation student learning to fly during the day, serving tables all night at Steak n’ Shake, and studying every free moment, life is not easy. Some of the richer students I knew were busy binge drinking on the weekends. Not me, I was binge sleeping trying to make up for the missed nights. Life was tough, but I was learning valuable lessons.

In addition to serving tables, I worked a second job at an aircraft paint shop. I would hand sand the paint around the rivets that the orbital sanders could not reach. The hanger did not have air-conditioning and I’m pretty sure the paint dust I was breathing in wasn’t EPA or OSHA approved.

In exchange for the long hours in that hot hanger sanding away, I got free flight time. This was the same as hundred dollar bills for me. For an aspiring pilot, flight time is how you land jobs. I was trying to move forward.

The work paid off, but I also know I have been fortunate (see Lie #2 here). I was the second-youngest hire in history at NetJets flying the elite on a $20M private jet, founded and exited an education technology company by the age of 30, and grew and exited a multi-million-dollar travel brand by 36. It has been a wild ride and one I am thankful for.

Back when I was broke, I worried about money for my car payment, food, rent, and utilities. Fast-forward nearly twenty years – I swipe the credit card at the airport for a $14.97 breakfast without giving any thought to whether or not the transaction will clear. This is clearly a luxury.

I turn to my travel companion and say, “The credit card cleared, I’m blessed.” He thinks I’m joking, but I’m not.

There is money in the account. That worry has been removed. I am blessed.