Long Story Short

(This episode is most certainly TL:DR)

• 82% of entrepreneurs silently battle impostor syndrome—even the most successful ones.

• From combat deployments to corporate jobs, to successful (and sometimes failed) businesses, I’ve felt like a fraud more times than I can count.

• I learned that action—not perfection—is the antidote to doubt.

• These 5 strategies helped me rewire my mindset and own my worth (Number 4 is my favorite).

• Read this if you've ever questioned whether you really belong in the room. (Spoiler: You do.)

Impostor syndrome is a silent killer of potential—that persistent feeling that you're a fraud despite evidence of your competence and accomplishments. It whispers that you're not good enough, that you don't belong, and that it's only a matter of time before everyone discovers you've been faking it all along.

Unlike simple self-doubt, impostor syndrome makes you attribute your success to luck, timing, or your ability to "fool" others about your capabilities. It creates a dangerous cycle: you work harder to prevent being "exposed," burn out, then take this exhaustion as further evidence that you don't measure up.

Research shows that up to 82% of entrepreneurs experience these feelings of inadequacy, proving that you're far from alone in this battle. In fact, impostor syndrome is most common among high-achievers and tends to intensify during periods of growth and new opportunity—exactly when you most need confidence in your abilities.

My journey with impostor syndrome began when I transitioned from military service to civilian life. After years in a structured environment where roles, expectations, and chains of command were crystal clear, I suddenly found myself in a world where the rules seemed unwritten and everyone else appeared to know something I didn't.

Since then, I've built multiple businesses—from a web design agency to a 7-figure cleaning franchise to tech platforms and apps—and I've wrestled with impostor syndrome at every stage of my entrepreneurial journey. Today, I want to share how I overcome it—and how you can too, whether you're a veteran, career professional, or entrepreneur.

I was extremely accomplished in the military- always excelled at everything, even becoming the youngest Staff Sergent in my entire brigade at 21. Taking charge and figuring out a solution came natural to me. I was super confident in my ability to make something happen.

I had lead platoons, trained soldiers , top recruiter, top this lead that. It was easy .. and i enjoyed being the best. I had even gotten selected to be the face of recruiting for the “Army Of One” campaign for my region Los Angeles. This meant not only recruiting but interviews, red carpet events, and a flood of “Thank You For Your Service” from politicians to celebrities at awards shows.

From there, I moved directly went from the Hollywood scene directly to the combat in Iraq. I was pulled from my plush assignment in Hollywood because 2 years prior to 9/11, I was part of the team that tested and taught the new technology that our artillery units would use on the battlefields of Iraq.

So facing the prospect of playing battlefield roulette on a 2nd tour, I decided to leave the Army and try my hand as a civilian. I blindly picked Atlanta as my home out of a hat in the middle of an active warzone because, well, I was John Thomas and I could do whatever I wanted.

I had been looking for a corporate job with no luck. After driving cross-country for a job interview only to arrive and find that they had filled the position while I was on the road, my confidence was shaky at best. I ended up sleeping in my truck to save money and showering at LA Fitness because I did not know how long this “no job -  drought was going to last and I was too cheap to pay for a hotel until my apartment was ready.

Not knowing much about Atlanta or their famous 285 highway that loops around the city, I found myself interviewing for a temp recruiting job at Coca-Cola 90 minutes away for Manpower (shoutout to Manpower for their veteran support initiatives post 9/11).

Long story short, I found myself in front of 3 accomplished senior recruiters interviewing for a recruiting assistant job. I thought things were going well until they started explaining the recruiting terminology and corporate jargon. Most of the terms and processes I had never heard of, much less understood. That's when the doubt set in.

Then I felt it, I remember thinking, “Well that’s different. Eww, What the hell am I feeling?” I felt I wasn't good enough. I felt I didn't know enough. I felt I didn't know the right people. My military experience felt disconnected from civilian business realities. “Weird” I thought. “Shake it off”

Then they asked me a few questions about my background. I told them about my experience as an Army recruiter in Los Angeles and my methods of sourcing, attracting, and onboarding recruits. I explained my passion for community building and volunteering at the alternative school in my neighborhood in Pasadena.

Then came time for the salary question. I felt I only had my military experience and tactics to draw from and no stellar resume like the interviewing panel. I knew I probably wasn't getting the job, so I decided to low-ball it to give myself a shot.

"Well, I already received an offer from another employer for $13.75, so that is what I want, but I'll take $12."

There was a long awkward pause as the interviewers looked at each other, then turned to me. I'll never forget—Susan Little sighed, shook her head, and quietly said:

"Sir, we are not allowed to pay you less than $15."

Oh crap... I thought, I don't even know the pay scale. "I'm definitely not getting the job now."

I buried my disappointment and decided to enjoy the moment and the fact that I made it to the interview at Coca-Cola. I spent the rest of my time telling Army stories.

And guess what? I got the job.

Susan explained that I had more than enough experience and that my creative recruiting tactics and willingness to work until the mission was accomplished was exactly what their team needed. I went on to become one of the top recruiters in my organization, leading talent acquisition for my whole region (Alabama, Mississippi, and Louisana).

Later, Susan explained to me what Impostor Syndrome was and told me that I already had everything I needed to do the job when I walked through the door. This taught me to recognize Impostor Syndrome and also to value my experience and hard work.

Although I was probably the lowest-paid person in recruiting, I performed like I was the highest, and I loved what I did. This gave me the confidence to pursue other opportunities and shake the feeling when I am presented with a promotion, a large contract, or just in the presence of accomplished people.

I learned that I "deserved to be in the room.". It also taught me to know your value

Impostor syndrome doesn't just go away with success—it evolves. My RedBag story proves this.

When launching RedBag, my on-demand gifting platform, I had all the ingredients for success: technical skills, customers, and product-market fit. But impostor syndrome had me in its grip. I spent almost two years obsessing over the smallest details and rewriting code and redesigning the website before launching.

When investor meetings came up, I'd spend days preparing for questions I feared I couldn't answer. I canceled so many meetings and pitches. I hardly told anyone about this amazing thing I had built.

I remember getting a coaching session from one of the founders of Barefoot Wines. I apologized so many times for "not being technical enough" or savvy enough that he finally stopped me and said:

"Your idea is genius. You just need to stop building and go show it."

Although we were currently doing about 15k monthly in transactions, selected as Google for Startups highlight, and had a few press articles, I felt it wasn’t moving fast enough compared to other startups. I began to shy away from pitch competitions and stopped traveling to investor meetings. I was in my own head.

I still didn't get it until later, after I sold the platform as COVID began to ravage the world in 2020. The company would go on to make insane profits because everyone was stuck in their homes and gift delivery was the only way to go! That company would turn around 7 months later and sell my platform to a larger corporate gifting company for - wait for it, $6,387,518.00.

Talk about a punch in the stomach

That's when the painful realization hit me: I had been undervaluing my actual expertise while overemphasizing my perceived weaknesses. I was ahead of my time—I just didn't believe in myself enough.

This is the true danger of impostor syndrome for entrepreneurs. It's not just about feeling uncomfortable in rooms—it's about holding back your brilliance from the world.

You are not alone in this battle. Some of the most successful entrepreneurs have openly discussed their struggles with impostor syndrome:

Sara Blakely, founder of Spanx and self-made billionaire, has said: "I have not let fear of failure stop me... I knew that if I failed, I wouldn't regret that, but I knew the one thing I might regret is not trying." Learn more about Sara's journey

Richard Branson, despite building the Virgin empire, has admitted: "I have had to deal with countless challenges and sometimes felt like a fraud... like I was about to be 'found out.'" Read Richard's thoughts on leadership

Howard Schultz, who grew Starbucks from a small coffee shop to a global brand, confessed: "Very few people, whether you've been in that job before or not, get into the seat and believe today that they are now qualified to be the CEO. They're not going to tell you that, but it's true." Explore Howard's leadership philosophy

The universal nature of impostor syndrome across even the highest levels of success proves an important point: these feelings don't disappear with achievement—you simply learn to act despite them.

When I mentor aspiring entrepreneurs, I tell them the first step in doing something is doing something.

You have to understand that everyone else was just like you—figuring things out as they went along, relying on their own experiences. The "experts" I had put on pedestals were often only a few steps ahead of where I was.

You don't have to know everything—you just need to own what you do know.

Studies from the International Journal of Behavioral Science show that impostor feelings are often highest among high-achievers—it's actually a sign that you're pushing boundaries and growing. The research reveals that those who manage to act despite these feelings are those who achieve the greatest success.

1. Recognize Your Fixed Mindset

Negative self-talk sounds like:

• "I'm not good enough."

• "I always mess up."

• "My background isn't impressive enough."

These aren't facts—they're negative thoughts. Recognizing them is the first step to disarming them.

Exercise: Keep an "impostor thought log" for one week. Each time you have a thought that makes you feel like a fraud, write it down. At the end of the week, look for patterns and ask yourself: "What evidence actually contradicts these thoughts?"

2. Get Comfortable Being Uncomfortable

Growth lives outside your comfort zone. The most successful entrepreneurs I know deliberately put themselves in situations where they don't feel like experts.

• Want to improve public speaking? Say yes to that industry panel.

• Want to become a better leader? Hire people smarter than you.

• Want to create content? Start posting 3x a week even if it feels awkward.

The more you stretch, the more you grow.

Exercise: Identify one uncomfortable action that would move your business forward. Schedule it on your calendar for this week, and commit to doing it even if you feel unprepared.

3. Seek Meaningful Feedback

Feedback starts with you:

• Do a weekly retro: What worked? What didn't? What's next?

• Ask clients or team members: What should I do more of? Less of?

Feedback is a gift for growth, not a weapon for self-criticism.

Exercise: Create a simple 3-question survey to send to your top clients or team members: "What am I doing well? What could I improve? What should I start doing that I'm not?" Their answers might surprise you

4. Detach Your Self-Worth From Your Business

You are more than your company's valuation or monthly revenue. Some of the most successful entrepreneurs I know are disciplined about separating identity from business outcomes.

Grow in areas that align with your values:

• Nurture relationships outside your industry.

• Pursue passion projects unrelated to your business.

• Volunteer or give back to your community.

• Prioritize hobbies that bring joy and refresh your mind.

Exercise: Block off two hours this week for something entirely unrelated to your business that energizes you. Protect this time as strictly as you would an important client meeting.

5. Add "...Yet" to Reframe

Turn self-doubt into self-belief with one word: "Yet."

• "I'm not a great leader...yet."

• "I don't have a successful business...yet."

• "I'm not a skilled networker...yet."

This simple reframing acknowledges where you are while committing to growth.

Exercise: Make a list of your three biggest "I'm not good enough" statements. Add "...yet" to each one, then write down one small action you can take to move closer to that goal.

In my experience working across different sectors, I've noticed that impostor syndrome manifests differently depending on your field:

For Entrepreneurs: It often centers around technical skills and innovation. "Am I technical enough?" "Is my product truly innovative?" The fast pace of technological change makes many feel perpetually behind.

For Service Business Owners: The focus shifts to expertise and client delivery. "Do I really have enough expertise to charge these rates?" "What if my client realizes I'm figuring things out as I go?"

For Veterans: Many struggle with translating military skills to business contexts. "Do my leadership experiences actually matter here?" "Will civilians take me seriously?" For more on veteran transitions, check out American Corporate Partners, which offers mentoring programs for veterans entering the business world.

For Career Changers: The challenge is often around legitimacy. "Do I belong in this new field?" "How can I compete with people who've been doing this for years?"

No matter your sector, recognize that your particular flavor of impostor syndrome is common in your industry—and can be overcome.

In my experience building and scaling businesses from scratch, I've learned that impostor syndrome never completely disappears—even after a few successes. The difference is learning to act despite the fear.

For me, conquering impostor syndrome comes from just getting out and doing it, knowing that it's okay if you fail. Go into situations accepting you may not know all the answers, but you know what you know. You're an expert at what you know, and you have to take that and run with it.

In business, I learned not to take blow-offs or dismissals personally. People just may not know or understand your story. It's more about your mindset and your view of things.

When I talk to my team at my service business 360clean, I like to tell the story of the space race when the world rushed to put a man on the moon. The president walks in and asks different people about their job. Most people gave their titles or their job descriptions. He got to the janitor and asked him what he did there.

The janitor replied: "I'm helping put a man on the moon."

Although he was a janitor in a room full of rocket scientists, he understood his purpose. And that is how you approach who you are and why you are here.

Your Impostor-Busting Action Plan

This Week: Choose one action from the exercises above that resonates most with you. Commit to completing it before our next newsletter.

This Month: Start documenting your wins, no matter how small. Research shows that keeping a "success journal" can significantly reduce impostor feelings over time. Try apps like Day One or Journey to make this practice easier.

Share Your Experience: I'd love to hear about your journey with impostor syndrome. What triggers it for you? What strategies have helped you overcome it? Email me your story, and you might be featured in a future newsletter.

Next week, we'll explore how the lessons from overcoming impostor syndrome can fuel innovation and creative problem-solving in your business. We'll look at how the willingness to step outside your comfort zone—a skill you're developing now—is the same muscle that drives breakthrough business ideas.

Until then, remember: Everyone you admire has felt exactly the way you do. The only difference is they took action anyway.

What's ONE step you can take today to move past impostor syndrome and closer to your vision? Reply to this email and let me know

Want to dive deeper into conquering impostor syndrome? Here are some resources I've found invaluable:

• The Impostor Cure by Dr. Jessamy Hibberd - My go-to recommendation for understanding the psychological roots of impostor syndrome

• Mindset: The New Psychology of Success by Carol Dweck - Groundbreaking research on fixed vs. growth mindset

• American Corporate Partners - Free mentoring program specifically for veterans transitioning to business careers

• Adam Grant's WorkLife Podcast - Outstanding episodes on impostor syndrome in various professions

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This article is part of the Alternative Programming newsletter, where we help entrepreneurs and professionals break barriers and build success. Subscribe here for more insights on leadership, technology, and growth.

About the Author:

John Thomas is a veteran entrepreneur and advocate for community-powered success. Through Alternative Programming, he helps veterans and entrepreneurs transform challenges into opportunities. His insights come from two decades of experience building multi-million dollar businesses and supporting veteran entrepreneurship.

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