It was eleven years ago I hung up my reflective belt and ventured into the civilian wilderness. I had joined the US Air Force at age 17 and retired at 40. It was all I had done or known in my adult life to that point.
In the time since, I’ve graduated from law school, built and sold a business, and led huge operations teams as a senior manager for a premier global retailer.
Triggered by watching The Greatest Generation dramatized in the first two episodes of the epic Masters of the Air, I’ve been reflecting. My ghost has been whispering lessons to me and encouraging me to share them with you.
So here they are, my lessons. Because taking avoidable beatings when someone else already took them is just dumb. That’s what we call practice bleeding.
BTW, these are unnumbered because I refuse to become one of those “7 tips for the best sliced bread” people. I’m going to un-chamber rounds until my brain is empty. I can’t be bothered with whether that yields a round or random number of thoughts.
As you transition from military to civilian life, remember:
Nobody Cares. In military circles, we tend to respect the achievements of others in our circles, because we can relate to them. “Congrats Dude! Supreme Allied Deputy Division Chief of Strategic Tactical Operations as only an A1C … that’s cool!” But just as you’ve never been a civilian before, your counterparts have never been military. They’ve lived a different reality. Likely nothing has compelled them to learn about or connect to or even comprehend your experience. If you walk through the door expecting anyone to care about your rank, quals, deployments, or medals, you’re just begging for a kick in the teeth. I will never forget the feedback I got from a promotion panel where I was initially unsuccessful. The critique was that I talked too much about my experience prior to Amazon. “We couldn’t clearly see how that would translate into this environment.” What meant the world to me and made me a leader was foreign gibberish to these people. Understand rapidly that you’re just another new kid joining a team, nothing more. Don’t expect people to get you. With time, as you build relationships, people will come to understand what you’re about. And if you’re doing it right, vice versa.
Your Peers Will Screw You. In military organizations, most people believe that when the team wins, everyone wins. And most, not all, have a basic foundation of honor. These are checks on self-interested behavior. And they don’t really exist in the civilian world. It’s much more zero-sum. It’s much more cutthroat. This doesn’t mean you should go into civilian employment packing a loaded holdout piece, but it does mean you shouldn’t assume as much trust or mutual support in a new team until it’s proven. Shakespeare captured the timeliness reality that a grin and handshake are not reliable indicators: “one may smile and smile and be a villain.” I got shanked a few times because I didn’t know the game I was in. As I told my kids when teaching street smarts, a little paranoia goes a long way. Make it your mission to survive long enough and rise high enough to thump this decrepit attitude out of your organization.
Your Team Will Screw You. For all the challenges they face, military commanders have it pretty good. Everyone is there because they volunteered. They’re all well-trained. There is a higher purpose and value system. Civilian environments are different. Not everyone wants to be there. Many are there for lack of a better option. Some are shits, proactively undermining what you’re trying to do. And there are many more radicalized individuals who cannot be reached, no matter how well-meaning or authentic your message. My first leadership role in civilian life was marred by a string of safety lapses. My initial response was an appeal to shared values. Then I realized some of my people didn’t share those values. A few sackings later, our safety record improved and I had learned, luckily without a serious incident, that some employees just want to watch the world burn.
They Don’t Know What Triggers You, and Vice Versa. Veterans from a common era of conflict tend to share common triggers. Certain ideas and sensations that take them to old places, usually not good ones. There’s no reason for your civilian teammates to have any idea what these are, so be prepared to rock up and deal with an unintended triggering occasionally. You’ll also find that they don’t share your love of violent imagery or gallows humor, so you may traumatize them just by being yourself. I came off a call in 2017 remarking the guy on the call had really “torqued me off” and that I wanted to “set fire to his lawn.” My team were mortified. In all things, actively deescalate your language, preserving just enough for comedic effect.
Ordering People Around Won’t Work. While authority is part of civilian work, it plays a smaller role. “Because I said so” will get you nothing but a chortle. You have to actually explain yourself and get people to actually want to do stuff. This doesn’t mean you can never use pure direction. But in many ways, when you go to authority, you have already lost … because at that moment your people will feel powerless. To feel powerful again, they will min-run, doing just enough to not get fired. The creative ones will actively look for chances to undermine. I said to a guy once “do this, I don’t have time to explain.” To which he replied “if you can’t explain, must not be important.” Which was totally fair.
The Blade is Always On Your Neck. Military service comes with job security. In fact, you usually can’t quit even if you try. You can totally flush the idea of job security in civilian life. Burn it and bury the ashes. You are never truly safe. A few bad months and you might play your way out of a job. A few bad quarters for the company (or even just its share price) and you might be jobless through no fault of your own. One bad boss and you might get mercy killed before you can truly suffer. These are mainly healthy things. The pressure keeps you frosty to learn fast and deliver results. The uncertainty makes you a more agile life planner. But you shouldn’t feel safe. If you do, brush your fingers across that ripcord again and remember you might need it at any moment. By the time I’d been at Amazon for 7 years, I was more tenured than 98% of the company. Turnover is a fact of life, and an adjustment for those of us accustomed to a stable environment.
Your People Feel That Blade Too. The job security of military service affords a leader much of the psychological safety they need to get people buying into vision and values. Unless they are unionized, your people don’t have that feeling in civilian life, so it’s extra tough getting them to feel a sense of belonging. To trust their environment enough to let their guard down and give their best. All you can do is what you can do, which is to talk straight, be someone they can trust, be authentic. This will encourage them to feel as safe as they can in an inherently volatile commercial environment. The other thing you can do is deliver killer results to make their jobs safer. In the buildings I ran for Amazon, we beat projections and earned ourselves a larger share of network volume. This meant I could retain more people.
Shit Still Rolls Downhill. If an executive on the other side of the planet expresses a momentary flicker of curiosity about a marginal triviality, it will become a padlocked target for the whole company until another flicker occurs. In its downward travel from the c-suite bozosphere to the operational trench where you reside, it will be amplified, distorted, and condensed into a horrific meteor eclipsing all other facts and conditions of the universe. You’ve seen this before, and you thought it was a military thing, but it’s just a thing. I recall a time when an Amazon executive got interested in why trucks weren’t being unloaded more promptly. Entire worlds were laid waste to fix this one metric, defeating its underlying purpose in a hundred different ways while inflicting pure misery on every flea that ever nipped the ass of anyone touching inbound operations. It was a planet-wide shitquake rumbled by a dude asking a superficial question on a call. So dig in. You will never escape this unless you climb the mountain and become the one who rolls things down it.
Despite Not Being Special, You’re Still a Novelty. When Veteran’s Day rolls around, you become a convenient walking advertisement for your company’s commitment to diversity. Expect to be nudge-pimped by corporate shit merchants. You won’t swerve this fate, but if you don’t secure yourself a free t-shirt in the process, you were objectified for nothing. OK, maybe a lanyard or a water bottle. All depends on how cheap you are.
You Have to Speak English. With the values and culture of military service, there is a shorthand between teammates. Communication is eased. This doesn’t exist on the other side. You have to spell out your intent. Allow more time for communication to unfold. Don’t assume you’ll be instantly understood. Beg for questions and answer them. I made the mistake several times of spitting a complex idea toward my team and assuming they absorbed it because their blank stares seemed so knowing. Only to find out later through performance gaps that it was pure bilge to them.
Better Money, But Tighter Handcuffs. In the military, people in the same pay grade make the same money. The useless quarter-wit is paid the same as the striving astrophysicist. Civilian employment is different. Pay is tethered to performance. Do better than peers, make more. But don’t get twisted thinking the company is paying you more as recognition for past deeds or out of the goodness of their hearts. It’s about expectations. With extra compensation comes the weight of more throughput. You will be on the hook to justify your salary, and the more generous your package, the less excuse you will have for even a momentary perception that you’re relaxed. I remember the euphoria of the nice bump I received for promotion to General Manager. Followed within hours by a call with my boss reminding me I needed to deliver to that higher level.
Get Over Yourself. Military service happens in an authority culture. Rank and position insulate individuals against challenges from subordinates. The military preference is to disagree in private whenever possible. Being respectful to others is part of professionalism. The result is coddled leaders with fragile egos and thin skins, who are then savaged in the normal course of civilian business. Challenges are encouraged. They are often public and are not always well-mannered. Respectful behavior is not really a requirement for executives or senior leaders in a commercial environment, so it is not expected or incentivized in company cultures. If you have fallen into the comfort trap of bubble-wrapping your ego, taking a “how dare you” attitude toward disrespect or a “don’t you know who I am” response to disobedience, you’re in for a hell of a shock. One way civilian employment is healthier is its preference for open and fact-driven debate about what’s best for the business. Embrace this.
Don’t Defer Too Much. Because you’re from a culture of respect and decorum, you’ll tend to disagree in a reserved manner, or take differences offline. This will contrast you with peers who will antagonize, interrupt, and derail as tactics to lodge disagreement. Calibrate. Get comfortable being difficult right out in the open when it serves a purpose, so you’re not perceived as timid. But don’t over-index and become obnoxious. The military tendency to avoid conflict until it becomes necessary but then unleash decisive force will be seen as nuclear volatility by your colleagues. In my early years at Amazon, I’d sit on disagreement too long, decide to go active, and then loose a barrage of scathing argument flattening the debate into a grease spot. “This guy is crazy!” It can be fun to be unpredictable, but it’s a net negative compared to a controlled but tenacious contest of ideas.
Your Composure Can Hurt You. You are used to staying calm and thinking clearly while the world is burning around you. This dampens your response mechanisms. You then risk sleeping through alarms when the trivial bullshit considered calamitous by others should be waking you up. Re-tune your sensors and understand what is a big deal in your industry, because issue-spotting is half of job performance. When reacting, be mindful that your calm demeanor could be misunderstood as a lack of urgency. I was part of a warehouse launch in 2016 where we struggled to receive goods, resulting in truck queues at our gate. Since most of us were new to the business, we didn’t get what a big deal this was until Jeff Bezos sent us an email. Fixing it then became a test of survival and blocked out the sun for 10 days. My penance for seeming relaxed was a requirement to send hourly updates to our director until it was corrected. Let’s just say I was more self-aware and situationally aware after that.
Don’t Expect Strong Leadership. Sport-bitching about the uselessness of commanders is a military pastime dating to the days of sandal-clad phalanxes. But it’s not unique to military service. Good leadership is hard to find everywhere, because it’s a damned difficult set of skills to master. Civilian companies don’t spend money developing leaders and don’t really herald classic leadership qualities. I had some good leaders at Amazon, but just as many who were searching haplessly for their first clue in the bottom of a wet paper bag they couldn’t lead their way out of. Control your hope, because it’s the hope that kills you.
Know Where the Line of Departure Is. Part of my rationale for 3-year degree program when I retired was to give myself a chance to become a bona fide civilian before entering the workforce. Only when I started working after graduation did I realize what a silly idea that was. Education, even under the unique heat lamp of law school, is not the arena. You control how you interact and collide with others. You’re only responsible for yourself and not delivering to a bottom line. I learned a lot in school, but the real adaptation started afterward, and would have been smoother and faster had I gone into it asking more questions. Do not put stock in “transition programs.” They mean well, but you can’t adapt to an environment until you’re in it.
I Don’t Care Who You Are, Max-to-Idle is Hard. I gave myself 6 months between retirement and my first day of school. I thought it would be a good idea to get used to a slower airspeed before turning to the next waypoint. What I didn’t realize is how mentally difficult that slowdown would prove. Suddenly I had loads of time on my hands and no responsibility, and it really messed with me. I struggled at first with how to redirect my energies without such a driving sense of purpose and clear mission. The plan to give my family more time was harebrained; they had their own lives and rhythms. I nearly drove myself and everyone around me into a ditch of insanity before finally realizing I needed a channel for all that excess airspeed until it could bleed off. That channel became my first writing project. This is a totally avoidable situation. Know what you’re going to do before your calendar goes from ludicrously overfull to oceanic white space. When I left Amazon, I knew about this trap and handled it much better.
Know When to Stop. Your military background means you naturally form a sense of loyalty to the organization where you work. It also means you have no idea how to quit. You see quitting as a weakness … as giving up. This is a dangerous mental model beyond the military context. All those years you served, leaving a bad unit was seldom an option. So you learned to suck it up. Sometimes, you negatively adapted to toxic environments because you had no choice. Carrying this skill into civilian life can trick you into riding a limping nag for too long. Staying in a bad situation degrades your physical and mental health. Keeping good money rolling is tempting, but if you take that idea too far you’re simply giving probate courts more to do after you’re gone. Last year, I left a job with a fantastic salary and willingly orphaned a few hundred k of share equity. I did this because I could feel the combination of a degrading company culture and its relentless demands shaving years off the end of my life. Thing is, I probably should have made the decision sooner, before confronting debilitating burnout. Separate emotion from logic and make systematic decisions about tenure and longevity.
My final thought … is that it’s all worth it. Nothing should dissuade you from embarking on the richly rewarding journey of private sector work. Your character and diligence make you a treasure for any employer, and you’ll be successful on the right terms no matter where you land.
Just go into it with open eyes, knowing how the terrain lays out. You’re still gonna take some knocks, but maybe fewer than I did with less pain.
I’ve been giving this advice to friends for a decade. And I always end our conversations the same way … by remarking that if I knew then what I know now, I would still find ways to screw up.
They’d just be different ones.
TC is a retired US Air Force commander and former Amazon GM. He is passionate about the success of veterans in the civilian workplace.
Another terrific post! You did a fantastic job parlaying your experiences; I shared many of the same. Your lessons carry wisdom that can benefit others navigating similar transitions. Thanks for sharing your journey and offering meaningful guidance. 👊
Great piece. I'm at 33 years, my dad is retired USAF, and my daughter is USAF, and as I near retirement in the next 4-5 years, I do struggle with what identity I will have for myself and further, purpose!
I shared your piece with our cadet wing here at Arizona State. Great lessons learned because at some point we will leave the military, and it will leave us behind.