My younger older brother wanted to be an opera singer and majored in vocal performance, doing a variety of jobs like landscaping, manual labor, selling insurance, directing church choirs (doesn't pay well at all but was tied with his sense of mission), etc. I think he was a great singer, perhaps even professional opera quality -- but in that world you need to be the top 2% of the top 2%, maybe, to make a living at it, and to be in the right place at the right time.

So with a wife and two kids and in his late 20's, he decided one day he was going to be a pilot. Already in precarious financial circumstances, he took out some huge loans to go to flight school. We all were concerned it might not turn out so well. He worked up to a pilot license, twin-engine license, flight instructor license, commercial license. He got a series of cargo jobs ... and >> they pay extremely low wages and require lots of odd hours and time waiting around away from home. << It wasn't easy, pay was low, for many many years. These outfits all make money by squeezing employee pay and by skimping on maintenance -- and he had a couple of emergency landings in the Arizona desert amongst the cacti and boulders.

He eventually got some jobs flying real people around for >> minor airlines <<, and bounced between those and other cargo jobs. Pay was still low. He also spent a stint in the Central African Republic helping a real nice Sudanese gentleman start an airline. There are lots of mining companies that need to fly around equipment and engineers even in a poverty-striken country, and lots of rich Portuguese folks wanting a real African dense-jungle hunting experience. The biggest risks for a while were precarious landing strips and corrupt government officials (they managed to pay zero bribes by just saying "no" to solicitations, holding out, and working their way up the hierarchy). A revolution came along to destroy the airline dream, and he was lucky the French military managed to pick him and other expats up from his neighborhood before the worst came along.

In his last "podunk" air cargo job, the airplane he was operating malfunctioned due to poor maintenance. The company wanted to pin the damage on him and his lack of procedure (he's very conscientious) and tried their best to break him on an unreasonable simulator test -- he managed to come out of that unscathed. Fortunately he'd just interviewed with America West and got the word the next day he was hired to fly 757's.

So it took my brother about 15 years to work from his first commercial job to becoming a full-fledged airline pilot in the majors ... and he had to work many marginal jobs for low pay in the interim. It's worked out well for him. He's flown 757's for various years on many routes, but most commonly now does Phoenix <--> Hawaii. There have been more challenges stemming from America West's acquisition pseudo-mergers with first the bankrupt US Airways, then the bankrupt American Airlines ... labor and seniority issues in the airlines are never easy, especially during mergers.

He's had time to get a Comp-Sci degree in the mean time while working "reserve" and started a decent-sized Salesforce consultancy and recruited some other family to work in that. (That consultancy kind of blew up ... working with family is hard, but that's a different story.) He flies and does Salesforce consulting now and is reasonably happy.