For Transitioning Military Leaders
The first civilian role is rarely the perfect role. It is where you learn how companies work, what kind of people you want around you, and what tradeoffs you are willing to make.
I have had the privilege of mentoring a lot of service members as they prepare for life after the military. This page is my first attempt to put the advice I repeat most often in one place.
The Core Idea
Coming directly out of the military, it is hard to benchmark corporate titles. A vice president in one industry may have the scope of an individual contributor in another. A manager title at one company may be a better career platform than a director title somewhere else.
Your first civilian job is less important than it feels right now. What matters more is whether you are surrounded by people who care enough to give you honest feedback, help you understand the game you are now playing, and invest in your development.
Some companies have earned strong reputations for leadership development and for teaching veterans how business works. Those can be great places to learn for a year or two while you build context, confidence, and a better map of what is available.
Transition Principles
The details change by person, family situation, finances, and ambition. These principles tend to hold up.
Early in the transition, you need people who will tell you the truth, explain context you do not yet have, and help you build civilian pattern recognition. A slightly less glamorous role with a strong manager may beat a prestigious title with no support.
Most of us leave the military with a narrow picture of civilian work. You may know about lawyers, accountants, marketing, operations, and project management, but not the full range of jobs that actually exist. Your first few years are partly about discovery.
Career, finances, and personal life form a three-legged stool. If one leg grows only by weakening the others, life gets unstable. Some people should sprint. Others should take a steady 40-hour role while they build a resume and learn civilian life.
More Lessons
Relationships matter deeply, but they exist inside a business system. Part of the transition is learning how that system actually works.
Relationships often matter more than org charts, process documents, or performance systems. Build them carefully. Be the kind of person people want to help, trust, and keep close.
But sometimes a company downsizes, restructures, changes strategies, or conducts large layoffs. When that happens, the decision may stop being personal and become business.
That can be unsettling if you are coming from the military, where large personnel decisions may feel more structured or predictable. I saw this firsthand at USAA, where major restructuring exercises happened shortly after I joined. People watched who went into the SVP's office, who was invited, who was not, who spent the most time there, and what it all meant. Everyone speculated by the water cooler.
When entire divisions are affected, the outcome may be largely outside your control. Build strong relationships, do excellent work, and stay aware of the business context. Just remember that sometimes a decision is not about you individually.
Figure out whether your company primarily rewards visible performance and rapid impact, or whether it rewards stability, tenure, predictability, and trust built over time. Neither model is inherently good or bad.
Meritocracy has a positive connotation. When I was a young hotshot, I naturally assumed that charging up the hill today should be rewarded immediately. But early velocity is not always the same thing as sustained future performance.
Some organizations intentionally reward people who have proven they can be steady, predictable, loyal, and durable over time. That can be frustrating if you expect every win to translate immediately into advancement, but it is not irrational.
The key is to know which company you are in. If the system does not match your preferences, you have two choices: start looking for a better fit, or reset your expectations.
A Personal Example
When I left the military, I thought I wanted operations because that sounded like where business mattered most. I thought continuous improvement would be great. I thought becoming a certified project manager might be the logical next move.
Those would have been poor fits for me. I respect that kind of work, but I do not think I would have had the patience for it day after day. My time at USAA helped me meet people across a broader set of business functions. Graduate school and McKinsey then expanded my understanding of what different careers could look like and, just as importantly, what I did not want.
That is why I encourage veterans to treat the first step as a learning platform, not a final verdict on their potential.
Free Mentorship
I am opening a limited number of free mentorship conversations for veterans who are actively planning their transition or are in the first few years of civilian work.
Tell me where you are in the transition, what you are considering, and what feels unclear.
We will talk through roles, industries, managers, development programs, compensation, geography, and family constraints.
The goal is not a generic pep talk. It is a clearer next move, better questions to ask, and a more honest view of your options.
Send a short note with your branch, role, expected transition date, current location, the paths you are considering, and the biggest decision you are trying to make.
This is free. I cannot promise I can help everyone, but I will prioritize people where a focused conversation can be useful.