5 Books to Read During Your Military Transition

Estimated reading time: 8 minutes

In going through your military transition, there can be a lot of questions: What do you want to do next in your life? What will be your next career? 

I’m a big believer in reading, broadly and deeply. If you ever listen to really successful people, they almost always have some type of consistent reading habit. Warren Buffet, the famed investor and Oracle of Omaha, famously reads five to six hours per day. Bill Gates is known to read 50 books a year. Correlation does not mean causation, but you can’t help but think there is something in their process. 

And beyond the objective questions of what type of career and where you will live, there is the ever-important question of what will be your purpose? It’s easy to understand your purpose in the military, but it can be harder to determine after you take off the uniform. 

The good news is that you don’t have to try and figure this all out in a vacuum. People have gone before you, veterans and non-veterans alike, and have put forth the effort to think about these very questions. 

Some of these books listed were ones that I read and found useful during my own transition. Others I haven’t yet read—they’re on my list and routinely show up as recommendations for people amidst a career change.  

Shoe Dog, Phil Knight

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I recommend this book more than any others to people. It is so NOT a business book. It is a story of a young man with an idea, a passion to make something that others wanted, and a drive to eschew the “normal” path and craft his own.

This is also a good book for this crowd because Knight was a veteran. He was working on Nike while serving in the reserves.

Knight tells the story of selling shoes out of the back of his car at track meets in Oregon, to taking Nike to an IPO in 1980. Along the way, there were friendships forged and lost. Friends who died and children born. Parents who invested their savings into their child’s company, believing that it had to be worth it if their son or daughter was involved. And on trying to figure out what the hell to call the now-iconic “swoosh.”

A passage to which I often go states:

“We wanted, as all great businesses do, to create, to contribute, and we dared to say so aloud. When you make something, when you improve something, when you deliver something, when you add some new thing or service to the lives of strangers, making them happier, or healthier, or safer, or better, and when you do it all crisply and efficiently, smartly, the way everything should be done but so seldom is- you’re participating more fully in the whole grand human drama. More than simply alive, you’re helping others to live more fully, and if that’s a business, all right, call me a businessman. Maybe it will grow on me.”

In your military transition, it can be easy to feel like you are “selling out” or becoming some corporate shill after you take off the uniform. But bringing the mindset described above into business can help you internalize your purpose in the civilian sector. 

The 4-Hour Workweek, Tim Ferriss

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If you haven’t heard of this book, I have to wonder if you’ve been hiding under a rock. Sorry, not sorry. 

Yes, this book gives you some incredibly direct and tactile tools that you can directly apply to building a business. And yes, plenty of people have used it as a playbook to build businesses from which they became independently wealthy.

But that’s not why I put it on here on a list of books for your military transition.

There are two key aspects of this book that cause me to want to put it on this list.

First, the idea that you can design a life around what you want to do. To veterans, this is a relatively new concept. We were not really afforded this luxury while we served. But once you leave the uniform, the possibilities of how you can set up your life are infinite. Following this mindset, I am currently writing this post while seated on a roof in Quito, Ecuador during my world travels before starting my MBA this fall. 

The second reason I put this on here is because of the last part of the book, what Tim usually refers to as his most important: thinking about what you are going to do with your life when you have the time, freedom, and resources to do whatever you want.

How will you continue to contribute to the world? If you could design the ideal life for yourself, what would you do and to what purpose? Have an endgame in mind. Work toward a purpose and when you have the ability, find a way to contribute to humanity.

What Color Is Your Parachute?, Richard N. Bolles

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This book has sold 10 million copies in 28 countries. It was named to Time Magazine’s list of 100 best non-fiction books of all time. If that isn’t enough reason to check it out, it was also selected by the Library of Congress’ Center for the Book as one of 25 books that have shaped people’s lives. 

Likely the biggest challenge for veterans in the transition process is figuring out what will be their place after the military transition. How do you translate what you learned from the military into marketable skills in the private sector? How do you think about what your passions, skills, and traits are that you can offer the world? This book is designed to help you process these questions. 

The Third Door, Alex Banayan

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In the military, we are taught to follow the chain of command — an attribute that can be valued outside the military. But there are ways to reach out to people and level-up your circumstances without going through the traditional method. 

While I was a young LT, the army went through a process of reviewing the records of active-duty officers for past discretions, as they wanted to cut out what they deemed “low-quality officers.” Our battalion fire support officer received a notice that he was being removed from the army for something that happened when he was a brand-new officer. Not being one to accept the circumstances presented to him, he skipped over every level and emailed the Chief of Staff of the Army directly to appeal the decision. It took him a few tries to get a response, but eventually he got one. The army ultimately reviewed him again and decided to repeal their initial decision. 

This book examines high-achievers to show that they reached a lot of their success because they refused to accept the “conventional path”. They all found a way to reach people who they wanted to meet or who could make a decision they needed. 

Especially as a transitioning veteran, there are a lot of people who want to help. Services like American Corporate Partners or Veterati are great ways to start growing your network, but you can also reach out of the traditional pathways to reach the people with whom you want to connect. 

So Good They Can’t Ignore You, Cal Newport

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Cal Newport is a serious thinker. He’s a regular on business and self-improvement podcasts and is highly regarded for his thoughts on productivity.

This book aims to break the myth of “follow your passion.” His argument is that if you work hard enough, the opportunities will come to you. And when the opportunities come, that is when you start to be passionate about what you are doing.

As you start your next chapter after your military transition, you have the power to create the life you want, centered around work that fulfills you—but it may not come right away. This book can help you understand and appreciate the journey that is part of creating work that you love.



Broadly speaking, there are two major themes presented by these books:

  1. Work on identifying your purpose. Focus on what matters to you and how you can achieve that.
  2. It’s possible to go outside the normal path to create the life you want.

I hope you read broadly and think deeply during your military transition to think about what it is you want to do next in life and how you want to contribute to the world. There’s no reason you can’t shape the life you want after serving in uniform.

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Related:

Top 10 Career Change Books on Amazon

The hardest decision I’ve ever made

Why I Didn’t Go Into The Reserves