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Episode 24

Episode 24: The Path Not Taken: Cultivating Confident Decision-Making


To join, or not to join, to re-enlist, or not to reenlist…Throughout our lives we encounter many situations, both personal and professional, that place us at crossroads, unsure of which path to pursue. In this episode of Veteran Led, John Berry explains the pivotal role of mindset, conquering fear, and aligning with our personal beliefs and values in guiding us through these challenging moments, enabling us to make informed and confident decisions.


Welcome fellow veterans. From the tip of the spear to in the rear with the gear, I went from active-duty Infantry to reserve-component logistician. I’m your host, CEO, entrepreneur, trial lawyer, and Lieutenant Colonel Retired, John Berry. The military lessons that I learned helped me grow an eight-figure business that has maintained consistent annual double-digit growth, landing on the Inc. 5000 list of fastest growing companies in America every year for the past seven years and has allowed me to continue to serve America’s heroes.

We all know the poor soul who almost enlisted, who almost joined the military. And then there are those of us who had only one active duty tour. There are others who stayed in longer. And there are those who stayed in for over 20 years. The question comes up time and time again, do I re-enlist? Do I stay in? And there’s a path that you can take, and there’s a path that you don’t take. And it seems that the grass may always be greener on the other side, so long as you fertilize it, and you water it, and you’re willing to commit to it.

I had the great fortune, in 2014, when I went to my Pre-Battalion Command Course. When I showed up, I was still on the same career trajectory from the lieutenants in my IOBC class. We went from being lieutenants together to now we’re all getting ready to go to battalion command and some were even from my first duty station, and we had great conversations. While I had only had two deployments during my time, many of them had six, seven or eight deployments. And we talked about our futures and our families, and some talked about being in for as long as they could and others said, “Hey, after battalion command, I’m getting out and here’s my plan.”

And we talked about the sacrifices and whether having a family early or having a family later was better. And some of them had families young. Some of them decided they would wait until they retired to have a family, to raise children so that they could be around; they didn’t want to have a family where they had to deploy. I know how difficult that can be. My daughter was four months old during my first deployment. So we talked about all of those things and the important decisions we have to make about our futures. The discussion we have about staying in or getting out is a discussion we have that goes beyond the military.

Throughout our lives, we hit many milestones where we have to decide whether we’re going to stay in or get out. We have to decide whether we’re going to stay in the military or get out. We have to decide whether we’re going to stay in our career field or get out and try something new. We even have to make those decisions about relationships. Are we going to stay in this relationship or are we going to get out? And that may be a romantic relationship, that could even be with a peer group. These are not my peers anymore. I don’t want to be around these peers. I want to be around peers who want a bigger, better future.

These are all important decisions, and as leaders, we have to counsel subordinate leaders when they hit important milestones. We have to have that crucial conversation about what’s going to happen next. What do you want to do next? What does your future look like? What are your goals? If we’re not doing that as leaders, we are failing them.

And then we have to have that other conversation with our subordinates and with ourselves. What’s holding us back from those opportunities that we want? Are our relationships holding us back? Are our beliefs holding us back? Are our values holding us back? The values that we have early in life sometimes change, sometimes they evolve. As we grow and mature, our perspectives change. And that’s okay.

We have to be willing to understand that as human beings, we don’t just come to the world with one set of values that are forever in stone. Instead, we evolve, we develop, and we grow. And that’s important because there are individuals with what Carol Dweck calls “fixed mindsets” and “growth mindsets.” And the people with fixed mindsets want to keep things the same. These are generally intelligent people who love being told they’re intelligent. They don’t want to fail. They’re afraid of failing. Whereas those with growth mindsets are okay with failing. They understand that they are going to grow. They’re okay with being told, “You’re not that smart” because they know they can get smarter.

And so our beliefs, our values, and our mindset all play a role into where we go in life. Unfortunately, fear plays a big role in our decision-making, especially for those of us that have accomplished a lot of great things. Early on in my career as a lawyer, I wanted to be the best possible lawyer I can be. I didn’t even think about growing the organization. I thought about serving my clients and I thought about what I could do to win, to get them the best possible result and to build a great team, but I didn’t want a big team. I just wanted to hit specific targeted goals that I had, but they were achievable.

And I achieved those goals at age 40. And then I had to decide. What is next? Do I keep going where I’m going? Do I keep the same goals, or do I do something bigger? In our lives, we all reach a point where we have the successes that we want, where we hit those goals, and the question becomes, can we get even bigger? Can we grow even bigger goals and opportunities? Or do we start dying? For me, I didn’t even consider the goals of growing a bigger, greater organization until I had hit those individual technician or practitioner goals as a lawyer.

There were certain organizations that I wanted to qualify for. There were certain cases I wanted to win, certain opportunities that I wanted to have that I had to earn my place at the table. After I hit these goals, I thought somehow my life would slow down and become comfortable, that I would be accomplished and I could be happy watching TV, just relaxing. And look, I know plenty of people that are, I know plenty of very successful people who hit the pinnacle of their career, late thirties, early forties and have coasted and they are very happy because they spend their time with their family, they spend their time doing what they value, but I don’t have the same values.
And it goes back to when I was 10 years old and had a paper route. I have always been entrepreneurial. I had to realize that that’s who I was. I wasn’t going to grow into that complacent person that many of my peers had become. I wasn’t like them. I was different. And that’s okay. The problem was I didn’t have peers that were different like me. In many ways I was a freak, right? People were saying, well, why aren’t you happy? Why aren’t you satisfied? You’ve got some great professional accomplishments. You’ve done a great job as a lawyer. You did a good job as a military officer. Now’s the time to enjoy your family. Now is the time to settle down, slow it down, enjoy it. Enjoy the people, enjoy the time.

And I tried to do that, but that just wasn’t me. And that doesn’t mean I don’t love my family and want to spend time with them, I absolutely do. But it is in my nature. It is who I am. That I want to continue to grow teams. That I want to help others build a bigger, better future. That I want to build a community. This is my purpose. This is who I am. And I’ve heard from many of the veterans listening, I’ve had conversations with some of you, that that is not for you. And that’s okay. For many of you, you’ve lived accomplished lives. You’ve done great things. And at this point, you’ve earned your opportunity to slow it down.

That just is not me. Here I am almost 50 years old, and I have not slowed down. In fact, I feel things ramping up and it’s a great feeling, but I understand that that’s not for everybody. But the thing that concerns me is when I talk to some of my peers who have had great successful lives who say, “Well, John, I’d love to do what you’re trying to do, but what if you fail? Or what if I fail?” And for me, I’m okay with failure.

As we talked about before the fixed mindset and the growth mindset, those with a fixed mindset worry that if they fail now in their late forties, they will be called failures for the rest of their lives, which simply isn’t realistic. Whereas if I fail, it’s a growth opportunity. I will learn something new. And when we talk about failure, let’s really define failure. Failure is you lose everything. You lose all your money. You lose your relationships. What happens next? How are you going to take care of your family?

My answer is that if I take the wrong path and I fail, I still have a few things going for me. Number one, I’m a veteran. There are plenty of resources out there to help veterans. You are a veteran. You earn those resources by the blood, sweat, and tears that you sacrificed for this country. Those resources are here for you, and you should be proud to take them. I talked to so many veterans who don’t want to ask for help or ask for the resources, but they’re there for you. And as a country, we should be proud anytime any veteran ever uses those resources.

The second thing is that as a leader, even if you fail, your subordinate leaders, your supervisors, they’re still out there and they’re willing to help you. And I’ve asked for help a lot. I have failed a lot. And the thing that has kept me going is those relationships, but not that people have supported me necessarily financially or with labor, but that they gave me the moral support that said, “John, I’m willing to help in any way I can. What do you need?” Sometimes that’s all I need to hear.

In the previous episode, I brought up the sergeant major who asked me to participate in the 50 mile march and help raise money. Now I was not comfortable asking anybody for anything, but as I reached out to people that I knew, people that I’d helped in the past, they were so receptive, they wanted to help. Some of them believed in the 50 Mile March mission and they wanted to help all veterans. Other ones believed in me, and they just said, “John, you’ve helped me. I want to help you.” And there was so much reciprocity out there. If you’re a leader, you have helped people and the people you help want the opportunity to pay it back. You have been a hero to them, and they want desperately to be a hero to you.

As I conclude this, I want to talk about something that is really important to me. For many of you, you’ve known service members who have committed suicide. I’ve had three under my command commit suicide. And as a leader, you feel responsible. One of the things that bothered me was that each one of them at some point had reached out and I had spoken with them, and I didn’t understand what they were going through.

A few years ago, a soldier reached out to me and at this point I was on high alert, and he started telling me about a lot of things that had gone wrong in his life. He felt defeated. He felt a loss of purpose. And I tried to steer him into the, what was going well for him, and he couldn’t say a lot. Finally, I said, “Well, what would great look like in your life right now? Tell me if you could do anything, what would you do?” And he lit up a little bit and started talking about something that he really wanted to do. I said, “Well, what would happen if you failed? Would it be the end?” And he said, “No, it wouldn’t be the end.”

And then he said, “You know what? I’m gonna do this. You’re right. I have nothing to lose. I have failed here. I have failed there. I failed so much that it doesn’t really matter. I’m going to go ahead and do this.” And I don’t know if I saved a life that day, but I’m proud to say that I took the time to have that conversation for someone that was, I think, facing a lot of failure and afraid of failing again.

But I have found that the more we fail, the more we just get used to it. The more beatings we take, the more resilient we become. And that as leaders is something that we, we have to watch out for in our team members, for our peers, for our friends. We know what failure looks like. As military leaders, we have all failed. We’ve all been at points in our careers where we fail bad. Other people were affected. We’re responsible and we feel that, and we feel that in our souls because as leaders that was our responsibility, our charge.

So when team members or veterans come to us and ask for help, it’s our obligation to help them. And if they want to talk about failure and they’re feeling failure, it’s our job to lift them up and say, “What’s the worst thing that happens if you fail? No one can take away that you are a United States military veteran. You’re the top 1%. You served when other people wouldn’t. Thank you.”

After Action Review:
1. One of the biggest decisions we make is whether to stay in or to get out, whether that’s in the military, a civilian profession, or a relationship.
2. We continue to grow, develop, and evolve. Who you were at 18 when you were enlisted, or 22 when you were commissioned, may not be the same person you are when you get out of the military. Our values change.
3. As a veteran, there are always people there to support you.

Three down:
1. If you have a fixed mindset as opposed to a growth mindset, you will be risk averse and you will be concerned about failure and growth will always be a challenge.
2. No matter what we do in life, we will fail from time to time and the more we fail, the more we learn.
3. Not every opportunity is a good opportunity. We have to examine our relationships, our beliefs, and our values.

Thank you for joining us today on Veteran Led, where we pursue our mission of promoting veteran leadership in business, strengthening the veteran community, and getting veterans all of the benefits that they earned. If you know a leader who should be on the Veteran Led podcast, report to our online community by searching @veteranled on your favorite social channels and posting in the comments. We want to hear how your military challenges prepared you to lead your industry or community, and we will let the world know. And of course, hit subscribe and join me next time on Veteran Led.

Berry Law

The attorneys at Berry Law are dedicated to helping injured Veterans. With extensive experience working with VA disability claims, Berry Law can help you with your disability appeals.

This material is for informational purposes only. It does not create an attorney-client relationship between the Firm and the reader, and does not constitute legal advice. Legal advice must be tailored to the specific circumstances of each case, and the contents of this blog are not a substitute for legal counsel.

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