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  • Writer's pictureChris Lanier

New Day, New Jet: 3 Things to Consider When Transitioning from the Military

Updated: Feb 28, 2019


I hate flying in the simulator. The first few rides in pilot training were exciting, but since then I rate the experience somewhere between sitting in the DMV and getting my teeth cleaned. That sounds harsh, but I'm no unicorn. It's unlikely you'll find many pilots that relish strapping into these marvels of engineering while the instructor dials up death and disaster for hours. After experiencing engine failures, fires, and a host of other problems, tortured pilots quickly become familiar with the phrase,"new day, new jet." It's what the instructor says when the emergency scenario has been presented and pilots have taken corrective action. Usually there's some immediate feedback on how they handled the scenario followed by a complete simulator reset where all of the problems (fire, engine failure, blown tires, etc.) are removed. When the pilot is ready to go again, the instructor utters the phrase..."new day, new jet" then resets for the next scenario. As in, all your aircraft problems are removed...go forth and fly beautifully.

Since retiring from the U.S. Air Force 6 months ago, I've thought about how that phrase aptly encapsulates the planning for transition. While by no means an emergency, retirement or separation is a one-off event that military personnel undertake with simulation as the only preparation. The military does a fantastic job providing comprehensive transition resources (Transition Assistance Program) for members, but they can't do the hardest work for you: imagining what career and circumstances will maximize your happiness. Former Secretary of Defense James Mattis once remarked that the most important 6 inches on the battlefield is the space between your ears. I think he was alluding to the role of imagination, preparation, and planning to success on the battlefield. The same could be said about deciding what your "new day, new jet" is going to look like when your military service is over. Creating space on your calendar to imagine and plan your transition scenarios with as much granularity as possible is the key to determining which one is the best fit for you and your family. In my case, I spent over 22 years not thinking in sufficient detail about what I would do when the ultimate "new day, new jet" reset occurred. I was slow to connect how big details (where to live, what job to pursue, income required, time off) interlocked with smaller ones (local economics, school districts, quality of life). As a result, the perceived speed and stress of my impending retirement seemed to accelerate like an overloaded truck heading down a steep grade. Decisions made about whether to downshift, hit the brakes, or take the runaway truck ramp were all made on the fly with the smell of hot brakes permeating the air...not an ideal scenario. And that my friends, is why I want to share 3 things that might help guide your structured thinking on your transition from the military.


Service to Country: I failed to realize how important it was to me.

1. What brings you happiness? How does that align with your new career?

I read Simon Sinek's Start With Why when I was leading a small organization a few years ago and it had an outsize influence on that organization and me. A couple of months into my post Air Force job search, I found myself thinking about the core ideas of that book again. I highly recommend that you read Mr. Sinek's work, but I think a couple of illustrative examples will give you the gist of what finding your "why" is all about. Apple has long been know for "thinking differently." From the Mac Operating System to the iPhone, the company has never been afraid to innovate and create. "Think different" shows up in virtually every product design. As a result, it has inspired a legion of loyal Apple users that connect with the core "why" of thinking differently. Harley Davidson is another great example. Rugged American individualism is at the heart of the brand. It's hard to hear Harley Davidson and not have imagery of leather and tattoos pop into your head. In fact, some people identify with that brand and "why" so strongly they get the company logo tattooed on their arm.

For me, I didn't understand the gravitas and purpose that military service provided for me. It was a huge component of my why. Equally important to me has been contributing to an organization that provides unparalleled customer service in an environment where everyone has fun and wants to show up to work. Whether as a worker or a leader, I've always wanted to be part of an organization where people are afraid they're missing out if they aren't there,...not looking for an excuse to not show up. You are lucky if you have been part of such an organization. You'll not be fully happy with anything less once you have experienced it. What are those core things that drive your happiness? It's something you should spend some time thinking about.

I would like to offer one important caveat. Your work doesn't have to share perfect alignment with your "why." In other words, your work doesn't have to bring you happiness. I have many friends whose happiness is centered on their philanthropic pursuits outside of work or time spent with family. However, I don't think you'll be happy somewhere if there is significant misalignment or contradiction with your core principles and "why." Optimally, your "why" will align with your new career. But at the very least, there shouldn't be disharmony. Tangential to this concept of finding happiness outside of work is joining a company or pursuing a career that allows to you the time to pursue your "why" if there's not great mapping. I think many that pursue commercial aviation after military service find themselves with lots of time to pursue their passions outside of the cockpit. This freedom effectively affirms their decision; because they're able to pursue their core "why"even if it's not directly related to the flying they do at work.

Here's a helpful link if you want to devote some time to discovering your "why." It's not a complex concept, but it will require some introspection.


The devil is in the details. What will life really look like with your new career?

2. What happens when your dreams collide with reality? Chair fly your possibilities.

"Chair flying" is a term used by pilots to describe the process of visualizing details and maneuvers associated with an upcoming flight. It's a great way to enhance your performance. The rigor involved varies considerably from person to person. Some pilots will use a toilet plunger to simulate the flight controls as they close their eyes and imagine the speed and flight attitudes required for maneuvers. Other pilots will mentally rehearse upcoming flights as they shower, dress, and drive to the airport. Regardless of how elaborate the process is, the core concept is the same: think in advance about what you plan to do before you undertake it and you'll likely execute more smoothly. My flight experience has certainly reinforced that notion.

I recommend that you chair fly your post military career possibilities. It's not enough to simply list your possibilities with a simple "pro" and "con" column. You need to find a quiet space (or coffee shop w/killer Americano), close your eyes, and chair fly your day-to-day existence. Depending on how busy you are, this might take days or even weeks to accomplish. With regard to computers, have you ever heard the adage "garbage in, garbage out?" In short, it means that a computer can't provide a correct solution if it was provided erroneous inputs from the outset. Chair flying your future career possibilities is a bit like that. If your model contains incorrect or incomplete data then it's going to give you an inaccurate picture of what your future could look like. Use as many resources as you can to try and create a complete and accurate picture of each possible career and location. Pro Tip: Most people think about the big questions. You will only have an accurate assessment if you are willing to invest the time to think about the small details. Here are some examples:

How well does this job align with my "why" and happiness? <big question>

>Less Obvious

Does the company culture and mission run counter to my "why"?

If it doesn't align with my "why", does it offer time for me to pursue my passion?

If I'm pursing my passion outside of work, can I do it where the job is located?

How predicable will my schedule and vacation time be? How will that impact my family?

Where is the job located? <big question>

> Less Obvious

Can I afford to live there? <You MUST do a hypothetical budget>

How long will my commute be? <Do you hate traffic?>

How are the schools? <Will that influence where I can afford to buy? Commute?>

Does the area offer activities that my family likes?

Is my family excited about the possibility of living there?

Opportunities for my spouse to pursue their career? <How long is their commute?>

Is the job located near your extended family? <big question>

>Less Obvious

How often do you want to visit your extended family?

Do you think you will need to be a caregiver to your mother or father soon?

How easy is driving or airline travel from your possible location to family?

It might seem tedious, but realistically imagining what your day-to-day life might look like in each of the possible scenarios will really help you narrow down what seems like an overwhelming number of options. I'll share a couple of examples from my own journey to help illustrate the point. About 1 year from my planned retirement I had no plans to continue flying. I always figured that I'd finish my Air Force career and then start a small business of some type. I'd grown up watching my father and mother successfully operate one and it seemed like hard but rewarding work. In terms of the big questions,...I think we'd nailed some of them down as a family. We wanted to live near the beach and mountains. And we'd always wanted to live in a small to medium sized city with a vibrant downtown and civic scene. I think we sort of flipped it around a little bit from most folks that are retiring. We picked our planned retirement location first (San Luis Obispo, CA) and then I figured I'd get something that aligned with my "why" once we got there. But as I started to take a closer look at various business ownership and employment opportunities I found that it was a tough market. There was a business that I was interested in purchasing and operating,...but it didn't cash flow enough to support our family. In fact, there weren't many employment opportunities outside of flying that could support the budget required to live in our chosen location. So I decided I would continue to fly in some capacity.

Deciding to continue flying opened up an entirely new set of decisions to make. What type of flying; cargo or passengers? Would I need to go fly for a regional airline first to get some recent hours? What about corporate aviation; what does that career path look like? It was a short few months as I worked through imagining what life would look like in each of those scenarios. I ultimately found a small private aviation company called ACI Jet ( in our new hometown. It was a perfect fit for our family,...but it wasn't the obvious choice until I compared all the options in great detail. If I'd simply stuck to the "big questions" I might have set our family down a different path. And that is the point that I would like to reemphasize. There will certainly be multiple paths open to most folks transitioning from the the military. But only a detailed consideration of each, chair flying them if you will, can realistically help you rule them in or out and help determine the best fit for you and your family.


Great friends want to see you succeed. Leverage your network and theirs!

3. Do you have any friends that can offer advice or help? Sure you do...use them!

About 10 months before I retired I had a good friend visit me. We talked about many things, but at some point I told him that I wasn't planning on flying when I retired. He looked at me quizzically and said,"really, you're just going to throw your experience in the trash can?" That conversation stuck with me for a few more months as I fleshed out all the possible options for my next chapter. I eventually reconsidered my post military plans in light of where we wanted to live and the options available. In retrospect, that conversation played a valuable role in my transition from the military. It helped me realize that I should keep all options open and begin talking with more friends.

Once I decided to continue pursuing aviation after the Air Force, I had many friends come out of the woodwork to help me with the transition. I hadn't spoken with some of them in over 5 years. It helped reduce my stress considerably to talk with those that were many months or years ahead of me on the journey. They offered everything from concrete steps (get this certification, this is where to submit your resume, etc.) to simply serving as a sounding board as I chair flew options (Have you considered the commute? Do you mind flying a lot at night? Etc.). My takeaway from those conversations: involve your friends and peers and leverage their networks for information and perspective. I joined Linked In many years ago and always viewed it as a great place to read up on current trends in leadership and business. But I quickly found that I was either directly connected to, or a friend or two away from any company I was considering for my next career. If you aren't building your Linked In network right now,...then please establish an account after reading this post.

I would also encourage you to talk with your friends about what they have found to be the most challenging part of the transition. The insight I gained about pursuing your passion outside of your "job" was reinforced after a conversation with a friend talking about those themes,...and I have seen him share that advice in wider circles. But to gain that perspective you need to join those professional networking circles,...or create some of your own.


Our family has loved this new chapter of our story. It's not perfect; but it's a great fit. I think that's about all you can look for as you transition...the best fit. Don't compare yourself to others or chase their dreams. Make sure you truly understand what brings you and your family the greatest happiness. Then give yourself the time and thinking space to fully imagine how well your future career options will help achieve that happiness. Your friends will gladly help you bridge the gap between your dreams and that reality. They certainly helped me. So whip out your calendar and pencil in some blank space to chair fly your future possibilities. I think it'll help you when the time comes to execute one of them.

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