Sold my soul to Uncle Sam for a college degree and a five year stint which turned into a career which returned a retirement check every month. While active duty, I flew with a warbird museum, but started by washing planes and sweeping floors and turning wrenches. Managed to get to keep my dad's Cub for a couple of years when I was in Oklahoma as a Major. During that time, I bought a Tripacer project. My dad and I (mostly him) converted it to a V6STOL homebuilt. Owned it for a couple of years for a relatively low investment of $12,000 all in, including Ford 3.8L engine and reduction unit. During this time, I also restored and sold former Army jeeps.
After retirement, I went to work at a full time job which paid slightly less than I was making as an Army Lt Colonel and traveling a bunch. It left little time for flying, but paid off after a few years. My wife, an Army brat, is a school teacher who has taught school in Oklahoma (twice), Germany, Texas and Tennessee. Fortunately, both kids received great to good college scholarships. I've owned houses at several assignments and managed to make money on all of them. I'm about to pay for #1 daughter's wedding, but started saving for college and wedding when she was born, so it is already paid for. Daughter #2 school and wedding is already banked.
About a year ago, I took a less job with same corporation with slight pay cut to have no travel and more free time...of course, both my kids are adults and out of the house know and I missed much of their growing up which regretfully, was just how it worked out. Fortunately, I have a great relationship with both and a great wife.
Now, I'm flying more and enjoying my planes. Just sold one. I've owned five total. Owned three at one time twice, which isn't smart, but found something I really wanted and had the means and bought another before I could sell something else. None of my planes are terribly expensive. All three combined were probably worth $100K.
To do this, we keep and drive vehicles for several years...most of which have no monthly payments. My wife has had new cars, but me and the kids drive got used vehicles. Not extreme high mileage, but used and driven for years. We have had conservative houses mostly. Current house is fairly large and we built a pool because this is home...having now lived here 13 years. We do hope to downsize in 2-3 years and be mortgage free afterwards. I'll be 57 by then and retiring to a fun, part-time job...giving me time to fly more. The corporate grind which I got because of college degree and military experience is what will allow that, along with stock options (which I mostly held), investments and military retirement check and zero debt.
The key to it all? spend less than you make. Save some. Invest some. Don't borrow too much. Don't expect everything early. If it is worth having, it is worth waiting and working for.
Jim R
Collierville, TN
N7155H--1946 Piper J-3 Cub
N3368K--1946 Globe GC-1B Swift
N4WJ--1994 Van's RV-4