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Why Are You Going Where You’re Going?

Think about the time you decided what you were going to be when you grew up. I’m not talking about ideas you had growing up or in school, but when you legitimately made a decision and started taking steps to get there. How did you know? Why did you pick this direction? Would you pick it again? How do you know if you were right? If you weren’t, did you aim too high, too low, or in the completely wrong direction? 

For my part, I knew I wanted to go into the Air Force since I was in high school and as soon as I learned my vision improved since early childhood, I wanted to be a pilot. The Air Force piece was mostly for altruistic reasons plus a solid college funding strategy. The pilot piece was for the typical reasons of excitement and mission. I expected I would do a 20 year career and then go off to the airline industry and fly my days out as a civilian. From an Air Force perspective, I never envisioned myself as a staff officer or commander, I really just wanted to fly and execute the mission. I thought that was my destination.

In my 13th year in the Air Force, I was on track. Up until that point, I was flying as much as anyone could. This was partially due to denying an opportunity to be a Wing Executive Officer during my 2nd assignment and also letting my commander know I did not want to leave the squadron to go to school for a year. Then, my career path was bumped off course… my destination changed. My then commander persuaded me to do a staff job and convinced me that I would make a good commander. My plan suddenly didn’t look the way I intended and I had less control over what it would look like in the future. 

In the end, I’m glad it happened the way it did. I spent the next 7 years leading, managing, advising, engaging with senior leaders, and on rare occasions I did fly. My original destination in the Air Force may have been short-sighted or maybe I didn’t consider all I had to offer. There was certainly some imposter syndrome going on. As it happened, those last several years in the Air Force were filled with rewarding experiences and lasting memories not necessarily better than my flying experiences, certainly not worse, and at least equally as valuable. 

I retired from the Air Force after 21 years and landed a job with FedEx, so on paper it appears my plan is intact. However, about a year before I retired, I had a revelation I don’t believe I would have had if my career path did not change course those years before. First, flying in the Air Force came with a great sense of duty, mission, and pride… things I didn’t expect commercial flying to match. Second, after having the experience of leading people and working so closely with them, I grew to enjoy it and knew I would miss that when I took the uniform off. I began to take stock in these two components and how they seemed opposed to my future employment. 

I talked with one of my closest friends about my paradox who also works for FedEx and what he told me dialed my looming anxiety back significantly. He told me many, if not most, pilots he knew at the company had some “side hustle” to fill whatever satisfaction jar flying airplanes didn’t fill. Several examples of people who did remote engineering work, loan officers, community volunteers, etc. So suddenly flying in retirement seemed less like a destination and more like an opportunity to give me time and space to do other things, but what?

I was fortunate enough to participate in the Pursue Your Purpose program with the Commit Foundation, a non-profit that helps Special Operations Service Members make the transition to civilian life. Over those few months with my Executive Coach, it became increasingly clear, even to my coach, that flying was not going to be enough for me. That program highlighted for me how much I valued my experiences in leadership positions when I had opportunities to help the people I worked with achieve their goals and contribute to a successful organization. While he had all of the appropriate tools to be a coach, I recognized I really enjoyed doing similar things and put the pieces together. I wanted to do what he does. 

I’m in a space for the first time in my adult life that if I don’t enjoy what I’m doing, I can go find something else. So if that is the case, it can’t be a destination at all… just a path. So if we’re talking about careers as paths rather than destinations, I believe it is hard to say if you took the wrong or right one, and it is never too late to change. 

My goals now are to leverage my strengths, prioritize my family, and make the most out of my time (hobbies, exercise, travel, etc.). I believe if I can do this, wherever the destination is, I’ll be happy when I get there.