I lost everything I owned three years after leaving the Navy, including my marriage. Then I picked myself up, dusted off, and built a new life outside of my service. It was a tough, lonely, and sometimes scary, road. As we are experiencing one of the largest migrations of combat veterans to civilian life since World War II, it is my goal to share my own transition experience with the hope I can make it a bit easier for others by learning from my mistakes.

It’s tough going from a predictable routine and a group of people you can trust to an unscripted life on the outside. It must be similar to being in prison for ten years and getting out with no routine and in a strange world. For me, it was hard because when I left the Navy and the SEAL community, I had just made chief petty officer (E-7) and many were resentful that I was leaving mid-career. They saw my leaving as wasting an E-7 billet. There were more than a few rumbling voices at command. But, I’ve always had a strong opinion about doing 110% of something straight to the end, and if that meant putting my all into the job and getting promoted early, only to leave it all behind, then so be it.

I didn’t get too much support when I left, outside of my immediate family. Many veterans do not and that’s unfortunate because I think a lot of vets end up drifting off into bad places because there’s a genuine lack of community outside the military once you leave. If you’re thinking of the known veteran groups, most just aren’t relevant to the modern vet in transition. I keep hearing about the “Brotherhood,” but it really exists in a small part at the unit level only. It is heavily glamorized in film, TV, and social media — mostly by those who never served or worse, veterans who can’t leave their career behind and are clinging to some false narrative.

I’ll summarize my story as quickly as possible below, and then get on to the top ten transition tips I think will be most helpful to my fellow veterans.

My Story

I left the Navy in the summer of 2006 just after my youngest son was born. I extended to make sure we had good healthcare in place. Aside from paying for college, another huge benefit to serving is the healthcare is really good. You’ll not have the same healthcare on the outside but I’ll get to that later. My plan was to do overseas contracting for a year and to start a business on the side. My best friend, Glen Doherty, recruited me to a special program and I was approved for deployment during my paid leave in the military and already had my first deployment date to Iraq.

I did several deployments over the first year and a half which allowed me to save enough money to support my family. I enrolled in school to take several business courses and started writing my first business plan for a racetrack facility with government training. We spent a year just looking for land and eventually found a nice parcel. After we got the project approved through the local government, the economy completely collapsed under the mortgage loan crisis. (Watch “The Big Short,” a great movie that explains what happened.) Our funding dried up, and to make matters worse, an environmental group sued the county over the environmental report, and the project was dead. Welcome to development in the People’s Republic of California.

Then, just to make things more interesting, my marriage ended. We tried to work on things but realized we’d be better off apart and thankfully, have developed a deep connection and friendship for our kids’ sake. I’ll write more on this later because if you have children, it’s worth making the investment and sacrifice to maintain a good relationship with your co-parent. And contrary to many stories I’ve heard, divorce can have a positive outcome. So there I was, no business, no money (in fact, I was in debt), and no family. I went from being an involved dad to one who saw his kids on the weekends. It was rough but, one of the greatest gifts I took from working as a sniper instructor was the time I spent with some of the best and brightest with a positive mental outlook. This saved me a lot of pain, and it was an extremely humbling experience all-around. I cried many nights alone as a 30-something who went from the top of my career as a Navy SEAL to losing it all on the outside.

I ended up taking a few odd jobs, then landed at an amazing division of L-3 Communications in San Diego. I had incredible co-workers and an amazing woman boss, and they trained me up as a business development executive. I did this for about two years as I was starting to write and blog on the side.

Shortly after taking the job, I submitted a book proposal to publishers in New York. Everyone turned the book down except one editor, Marc Resnic at St. Martin’s Press, who liked my story. The book would go on to sell well and it made the New York Times bestseller list. At the time it sold, there was very little in the market in the form of Navy SEAL books and nobody really knew about the SEAL Teams or cared. This has obviously changed. In fact, there are more SEAL books than I can count these days.

Since then, I’ve built a business around blogs, podcasts, and e-commerce. It’s had ups and downs like every business but continues to this day, eight years later. I’ve also had the privilege of being appointed to the U.S. Small Business Administration’s Veterans Advisory Board. This was a great experience and really opened my eyes to the things the SBA could, and should, be doing for veterans.

So, that’s the short version. Now for some advice.

Top transition tips

Have a plan

A plan gives you purpose, and trust me, you’re going to need it to be your North Star. This helped me tremendously and pulled me through some dark times.


If you have the GI Bill, going to (or back to) school can be a great cushion transitioning back to civilian life and helping with the integration. The housing allowance given is more than enough to rent a nice place and cover living expenses.

Get a job

There’s nothing stopping you from interviewing for jobs on the outside before you separate. I had my first civilian paycheck before my military pay ran out and this is a comforting thing. The defense industry is a great place to start, because you’ll be incredibly relevant to most these companies and they pay well. There are also a lot of non-profits that have partnered with big industry to place veterans. This is a good place to look and Google is your friend.

Clean up your social media

Most companies will check your social media accounts whether you know it or not. They will also monitor your social media while you’re an active employee to make sure you’re not posting inappropriate content that is out of alignment with company values. I’ve experienced this first-hand. We gave gainful employment to a veteran, it didn’t work out, and that person goes off half-cocked on social media looking like a complete jerk. People are watching and making assessments all the time. My company now has a code of conduct around social media and everyone has to sign it.

Start or buy a business

If I had to do it all over again, I would have bought a business. There are so many good franchises and you can get a small government-backed loan through the SBA to start. I think most veterans have what it takes to manage and grow a small business. You have tremendous freedom and autonomy and this would be my number-one advice for veterans. Start your own business. There are literally tens of thousands of businesses for sale by people who just want to retire. They put their kids through college and the kids don’t want the business because they’ve gone on to be doctors or lawyers and the parents just want to sell to someone who’ll take care of their baby. In many of these cases, you can buy these with owner financing and use the business to pay off the debt and take home a good, solid six-figure income. Do your homework on this, take classes, and look at the SBA’s website.

Trust but verify

The military puts you in a system that forces trust and you come to take that for granted. It is NOT this way on the outside. We have to trust people, but don’t get taken advantage of. Always ask for references and proof points and follow up. I’ve seen too many veterans get scammed by loan sharks or crazy schemes.

Find a good mentor or two, or three…

You just have to ask. I have several mentors and they’ve been critical in many phases of my transition. Some want to give back to the military community and some I’ve had to approach with a value proposition. “What can I offer them in exchange? How can I be valuable to this person?” Sure, people will respect your service but nobody owes you anything. Remember that. It’s up to you to do the work and prove your value on the outside.

Learn which military skills do (and don’t) translate

It should be easy but I see veterans using skills that don’t translate all the time. Hazing (all forms), threatening to kick someone’s ass to settle a dispute (while gratifying at times, it’s a sure lose-lose), and worse. Several skills translate well: Showing up on time, doing what you say you’ll do, teamwork, strategy, execution, taking initiative, and problem-solving. These are a few skills that will serve you very well on the outside.

Build a solid external network

There are plenty of great professional organizations you can join. You need to join one because you have to start building a solid external network. The Masons, Entrepreneurs Organization (EO), start-up groups, sports clubs, Young Presidents Organization (YPO), and so on. EO and YPO have both been incredible for me since I lost a lot of military friends in the war, and largely wanted to surround myself with positive, business-minded, successful people. You are who you hang out with. Remember that.

Which brings me to the most important tip I can give you:

Live by the Golden Rule

This sounds simple, but you’d be surprised how many veterans I’ve seen shit on each other in public. My own community is the worst at this! It only makes them (and all of us vets) look extremely unprofessional, and is a huge red flag to potential employers or future business partners. They’ll just de-risk and decline you before you even know it. I’ve worked hard to reverse the veteran stigma that exits and it’s hard to keep defending this to the business community when folks act like children. We have to police ourselves. It makes it harder for other veterans to gain future employment when veterans do this. So, treat people professionally and respectfully at all times and it will come back to you in a big way. If in doubt, ask yourself this question, “Is what I’m doing going to reflect positively on the veteran community?” If the answer is no, don’t do it. The Golden Rule, live by it.

Thanks for listening and I hope my story and experience helps. If you know a transitioning veteran, please share this with them. I’m also glad to DM any veterans who have follow-up questions on my Instagram: @BrandontWebb.

See you on the outside.