G.I. Jobs Virtual Job Fair   |   Apr 25

Virtual Job Fair   |   Apr 25

Overcoming the Fear of Failing: Life After the Military

overcoming the fear of failing

Fear is a great motivator. At least that’s what my drill sergeant used to tell me. It really is true. In many situations, fear is what keeps us alive. It keeps us aware of our surroundings. In those situations, fear is needed in order to keep us safe, but what happens when fear causes you to be too safe? What happens when fear keeps you from pursuing a once-in-a-lifetime opportunity? Overcoming the fear of failing is what will help you push through.

Recognize the Fear

When I began my path toward transition, I received a lot of advice. It seemed like everyone wanted to offer their input on the best way to make it through. I took advantage of every class that I possibly could. Sure, signing up for transition classes meant I didn’t have to be at work, but it also gave me a great chance to gain as much knowledge as I could.

I remember going to a class about franchising, which was a great class because I had always considered owning my own business. After talking to one of my co-workers after the class and talking about franchise ideas, he told me he thought franchising was a big gamble. “You’ve got a family to think about, Wheaton,” he said. “You have experience as a human resources specialist, and government jobs pay well. Plus, they are safe. What happens if you launch a business and fail?” I thought long and hard about his words. I did have a family to think about, and they needed to be my first thought.

After 12 years of service, I had gotten pretty good at my job. Continuing to do the same thing outside of the military only made sense, right? I knew I could succeed this way. At least I knew I’d be able to get a good job and support my family. But I also knew that deep down I wanted something else. I wanted to control my own time and call my own shots. But that brought along a crippling fear of failure that I knew I had to conquer if I wanted to do anything other than be a human resources specialist for the rest of my life.

Have a Plan B

There was one thing I knew I wanted to gain in transition, and that was the ability to enjoy my family and the community we lived in. Getting out and getting a job doing what I’ve done for the past 12 years was definitely the safest path. But it wasn’t the one that I wanted to end up in. So how would I get to the point where I could do what I really wanted to do, which was own and operate my own business? By having a Plan B. My Plan B would give me time to plan my steps while earning a living.


Sometimes having a Plan B means accepting an entry-level role as a steppingstone en route to your goal. And there’s absolutely nothing wrong with a position like this. This can be a great time to continue working toward your goals, gaining more knowledge and experience and working to overcome fears associated with getting out of your comfort zone.

Trust Your Instincts

There is always a level of risk associated with anything that you do. And transition is no different. Paratroopers know that every jump comes with risk, yet still they continue to stand up, hook up and shuffle to the door. Why? Because they trust their instincts and their training.

My transition led me to a great position doing what I did in the military, and it was a great opportunity. Still, my heart was calling me to pursue my dreams. I wanted to own my own business and I knew my instincts would lead me to my goal. Besides that, there are so many great resources for veteran entrepreneurs to get help and advice that failure does not have to be an option. Sure, there may be setbacks along the way, but failing does not have to be permanent and it definitely doesn’t have to hold you back. Don’t let the fear of failure keep you from going after something that your heart is telling you to pursue.

The fear of failing can lead us in many directions when it comes to transition. Whether you want to open your own business, change career fields or land a phenomenal job, recognizing the fear, having a Plan B, and trusting your instincts can help in overcoming the fear of failure.


Jamaal Wheaton is a transitioning Army veteran with more than 12 years of active duty service. He is founder and owner of The Wheaton Group, a public relations firm that specializes in being a voice for veteran and military-related issues. Jamaal shares his personal experience of transition with the hopes of helping others navigate the through their own transition.


military to civilian transition guide