That's not a bad plan, hypnoman. You will never be a sharper pilot than when you are instructing. And yes, the profession is basically a crapshoot. Planning and preparation is important, but luck plays just as big a hand.
My career path worked for me but was not the most direct path to an airline or corporate flying job. In fact, it is likely impossible to follow now. In answer to your question, however, if I had to do it over again I wouldn't change a thing.
My parents ran a little sod airport and we also had an airstrip on the farm, so I grew up around airplanes. One of the many advantages to that is that I still fly the same Cub I learned to fly in six decades ago. After high school, I went to tech school for a year to get my A&P Mechanic certificate. When I was a kid, I thought that the best flying job in the world was cropdusting. I was right, by the way; I did that for the first five years of my career and it is hands down the most fulfilling job I've ever had. It also provided enough stories in that brief time to last a whole career. I was twenty-four years old and could see that I was going to be thirty years old with 9,000 hours of single-engine VFR time, so I thought I better diversify.
I had zero interest in the airlines and jets and thought that I had been born fifty years too late to enjoy the heyday of aviation, so I went about about seeking to relive it. I picked up instrument and multi-engine ratings and went to work flying for a cargo outfit that flew just-in-time freight for the automotive industry. They operated fourteen junk Beech 18s single pilot. I knew how to fly overloaded tailwheel airplanes and radial engines from the cropdusting, but what I knew about weather flying would fit in a thimble. The only reason I'm still alive is that a Twin Beech is such a stable instrument platform and will fly with a big load of ice. The company had two fatal accidents while I was with them. I spent about 2500 hours in the recips and 1500 hours in the PT-6 conversions [Westwind conversions] before moving into DC-3s for another cargo outfit. I was in hog heaven. After about 2000 hours in them, I had an epiphany one night in February at Fargo. I was trying to get 5 gallons of very cold and viscose 60 weight oil in the left engine oil tank while trying to avoid frostbite and being blown off the wing at the time. I decided that I had had enough nostalgia to last me for a while and needed a job where someone other than the flight crew loaded and serviced the airplane.
The next stop was flying 727s for an airline. Nice airplane, but boring as hell; the only stations we operated to were BOS, LGA, BWI, MCO, and SJU. I wasn't there long before a furlough but immediately went to work for another cargo outfit, this time on the 727. I stayed there for seven years, mostly on the DC-8 and ending on the 747. That job averaged about 21 days a month on the road. The wife and I were thinking about having a kid and I thought I at least ought to be around for the conception, so I took a job flying Gulfstreams for a charter/management company that got me home more often.
I did that for seven years and then went to NetJets international flying Gulfstreams again. That was a nice company to work for and I stayed there seventeen years before retiring in 2022.
I get the jumping out of airplanes by the way. I have 4000 jumps, met my wife [a more experienced skydiver] at a drop zone, and our daughter just passed 2000 jumps.
So you’re saying you’ve flown a few hours in your time.
Sounds like you’ve had a great career. Hopefully none of your 4000 jumps were requirements of the job. 4000 jumps and 3999 different employers.
Thanks for sharing your story. It’s inspiring to know that this career can take someone in so many different directions.