Most fear is not actually based on anything with merit. So, when you think about things you’re scared of, ask yourself if it’s based on an experience or just the idea that it’s scary. I went skydiving one time and I was thinking, why would I do this? It’s scary to jump out of a plane! It wasn’t based on anything I’d actually done, just the thought. Obviously, it’s scary to skydive, but all the safety measures were in place to protect me. My fear was only imagined. It turned out to be one of the best experiences of my life.

The Fear of Failure is one of the most common restraints that holds people back from pursuing great ideas. Imagine if we could become totally free from the fear of failure. Imagine what we could then manifest and create. In this interview series, we are talking to leaders who can share stories and insights from their experience about “Becoming Free From the Fear of Failure.” As a part of this series, I had the distinct pleasure of interviewing Brandon Brittingham.

Realtor Brandon Brittingham is the CEO and team leader at the Maryland & Delaware Group of Long & Foster Real Estate based in Salisbury, Maryland. His real estate team is one of the best and busiest in the country. In April 2021, his group was named the №1 team for the number of homes sold in all of Long & Foster Real Estate with 749 homes in 2020. Brandon’s team was also ranked #1 in Maryland and #5 in the nation by Real Trends for the number of homes sold in 2020–749 properties worth $186 million. He is a past leadership panelist with Inman Connect and best-selling author of his recently published book, Converting Units to Dollars: Elite Ops Property Management.

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

I’ve always had an affinity for real estate. My family didn’t come from money and I was curious about how to create wealth and began studying it. I discovered that many affluent people invested in real estate. My grandfather and my dad built houses growing up, so it seemed like the perfect combination of what was familiar and what I was learning. I didn’t go to college, but straight into real estate. I got my license when I was 24 and represented myself on investment deals. I soaked up as much training as I could and sought out multiple mentors because I knew I’d need both information and guidance to become the very best in every aspect of my profession. I’ve been able to build one of the top real estate agencies in the U.S. and top investment portfolios in the country.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘takeaways’ you learned from that?

I received a call to potentially list a very expensive house. When I arrived, I found out it belonged to an NFL quarterback. We sat down at a table and he explained that he wasn’t as concerned about selling the house as he was about actually packing up and moving. He was going to choose the agent who could quickly get him from one part of the country to another. I told him I could do it. I didn’t know how I would, but I didn’t let that stop me. The moment I walked out of his house, I sat in his driveway, made some calls and started my own moving company. I got the listing and am still running a moving company today. The major lesson is to always look for ways to solve consumer problems and don’t underestimate your ability to do so when they’re presented. If you can imagine it, you can take the steps to make it happen.

You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. You have to master one skill at a time. Entrepreneurs tend to chase shiny objects and too many ideas without homing in on one skill at a time. First, I focused only on sales until I became an expert. Next, I moved on to marketing and then leadership. I was able to build and expand companies by practicing tunnel vision and focusing on one thing at a time.
  2. Commit to your own personal development and self-reflection. You have to be consistently investing in yourself by going to trainings, reading books, getting a coach and being mentored on leadership. Being an entrepreneur is hard enough. If you don’t regularly reflect upon your own roadblocks and learn how to get past them, leadership will be really tough for you and you’ll probably fail at it.
  3. If you want to grow or scale any business, you have to learn to successfully manage people. This one thing is so often overlooked. You’re never taught about leadership in school, not even when getting a Master of Business Administration. Everything in leadership lives and dies by it. It doesn’t matter how you spend money; if you don’t invest in good leadership, everything will fall down. Some people may be natural-born leaders, but you need to educate yourself on how to lead human beings. This involves going deep into your own personal development. If you don’t, you’ll hit a ceiling of problems that you won’t be able to break through no matter what you do.

Ok, thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the concept of becoming free from failure. Let’s zoom in a bit. From your experience, why exactly are people so afraid of failure? Why is failure so frightening to us?

If you want to go really deep, it’s all about our fight or flight response. A long time ago, when we had to hunt and kill animals to feed our families, our fight response was so dialed in because that was how we survived. Over time, the world has conditioned us to live in a flight response. Today, if you don’t want to do something, you don’t have to.

When I was 23 or 24, I had a near-death experience. The doctors told me that if I would’ve waited 30–45 minutes to get to the hospital, I wouldn’t be alive. I was diagnosed with Lyme disease that causes liver and kidney failure. They said I couldn’t maintain the pace at which I was working, had to quit working out and was given strict parameters around my life. I was terrified, frozen in fear. Then, I realized that the diagnosis was simply one of many stories I could believe about my future, and everything I wanted was on the other side of my fear.

I went against the doctor’s orders and ended up in and out of the hospital several times. Over time, I was able to conquer the disease. I moved through the fear to get to what I wanted on the opposite side. Once I stopped thinking in terms of limitations, I became fearless.

Most people run away from things they’re scared of. We are physiologically and psychologically wired to run from what’s uncomfortable. When I coach others who tell me they’re scared to do something new, I explain to them that the fear is coming from the discomfort of not having done it before and they’ve been conditioned to retreat to safety. That’s where most people stay. I teach people to condition the mind and body to go the opposite way, to go toward what makes them afraid because everything they want is on the other side of that fear. When you grow people and businesses, you have to take significant risks. Anyone who has built a company hasn’t taken the safe route. If you don’t understand that, then it’s keeping you from going to the next level.

What are the downsides of being afraid of failure? How can it limit people?

The biggest mistake we all make, and the biggest misconception of this world is believing that we have more time. I see it differently because I almost died. When that happened, I replayed all the things in my life and a lot of what I saw was how much time I wasted on what I was scared of or indecisive about. If someone said you had one shot at a redo in your life, you’d probably look back at something you didn’t do because you were afraid or indecisive. My near-death experience took that fear away because I had no time left. I want to say that I am using every second stepping into the person I am meant to be rather than into fear and indecision.

In contrast, can you help articulate a few ways how becoming free from the free of failure can help improve our lives?

The highest level of self-actualization is living to your full potential. Step into it. The worst feeling is regret, and many things we regret are just decisions we were too scared to make. If you’re faced with the reality that time is finite, you’ll make decisions differently. Procrastination is a form of depression and when you stand against the wall with fear, it can affect your mental health and seriously affect your life. In contrast, acting upon your goals now will grow your confidence so you can walk in the highest expression of yourself.

We would love to hear your story about your experience dealing with failure. Would you be able to share a story about that with us?

I fail every day. It’s part of the process. In my first year in real estate, I made $18,000. It wasn’t enough to pay my bills and was a failure by industry standards. Most people would’ve quit. I’ve started multiple businesses that have failed. Now, my company is #2 in the U.S. and #1 in Maryland for homes sold.

We fail at everything we do at some point because, as we grow, we’ll hit a ceiling. The person who consistently tries and fails, but tries every time, is going to beat the person who stops short of the goal because they have to have things perfect. Imperfect action will win every time. I’ve trained people with degrees who fail because they’re so focused on perfection and people off the street who thrive because of their mindset and insatiable hunger. You can’t let it shut you down. If you take action and build businesses, failure is inevitable. The people who move forward from that will always win.

How did you rebound and recover after that? What did you learn from this whole episode? What advice would you give to others based on that story?

People measure success in time and think you have to do everything overnight. I thought the same. Success is also tied to a monetary value or prize. After the first year, I decided I wasn’t going to worry about how much money I made or the outcome, but I’d get really good at the process. Focusing on the process is difficult and takes time, but as you get better at it, the money will work itself out. That’s what happened to me.

Fantastic. Here is the main question of our interview. In your opinion, what are 5 steps that everyone can take to become free from the fear of failure”? Please share a story or an example for each.

  1. Most fear is not actually based on anything with merit. So, when you think about things you’re scared of, ask yourself if it’s based on an experience or just the idea that it’s scary. I went skydiving one time and I was thinking, why would I do this? It’s scary to jump out of a plane! It wasn’t based on anything I’d actually done, just the thought. Obviously, it’s scary to skydive, but all the safety measures were in place to protect me. My fear was only imagined. It turned out to be one of the best experiences of my life.
  2. Question everything. A lot of what we base fear on is someone else’s story or experience. When I was diagnosed with an autoimmune disease, the doctors put fear in me by telling me a story that they believed would be the best plan for my survival. I questioned it and challenged it. I’ve done the same in my career. I’ve asked: Why can’t we be the top agency in the state? Getting over fear means questioning reality and everything in front of you. When you dig deeper, you’ll often find that fear is based on someone else’s story and not your own.
  3. Fear is an indication that you’re onto something. Your mind and body will only create it when you’re out of your comfort zone which means you’re doing something new. Look at it from this perspective: If it scares you, it’s evidence that you’re growing and going in the right direction. Everything you want in life is on the other side of what you’re scared of.
  4. Don’t live in fear because you don’t know how much time you have — if you knew you had only a certain amount of time, you’d do whatever it takes to succeed. Look at how all the political campaigns hype up just before the election. They pull out all the stops because time is almost up and there will be one winner and one loser. People who procrastinate and bury their heads in the sand think they have time, but they aren’t going to win. If you knew time was limited, you wouldn’t let fear grip you. You’d give it your all.
  5. Fill your environment with people who don’t live in fear. You are the sum of the five people most closely surrounding you. Their presence will naturally affect how you act and you’ll either rise or sink to their level.

The famous Greek philosopher Aristotle once said, “It is possible to fail in many ways…while to succeed is possible only in one way.” Based on your experience, have you found this quote to be true? What do you think Aristotle really meant?

No, I disagree. Success is a lens you look through and not only will it look different to everyone, but there are multiple ways to achieve your goals. My view of what success is and the path I take to accomplish it may be totally different from another’s, but we could both make it happen.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

For people to really step into who they’re meant to be and live as the best version of themselves in optimal health, relationships and business. It’s constant work, but we aren’t here to be mediocre. People may be great in business but their kids don’t know them and their relationships suffer. It’s not balance we need to achieve, but harmony. That involves stepping into the person you’re meant to be while inspiring others to do so. Do your actions inspire others to be in good relationships and in their best physical condition? When your mind, body and soul are in harmony and you’re inspiring others to live the best version of themselves, that’s when you’re living as your highest self.

Every day you have is a gift. If I give you a present and I’m in front of you and you walk into a corner and threw it into the trash, it would make me upset. Every day that you live in fear or not as your highest self, you’re taking the gift and throwing it in the trash.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them 🙂

Elon Musk. He’s created multiple companies that didn’t exist and a car that everyone said we didn’t have the technology for and wasn’t possible. He didn’t listen to that story. He figured out how to do it and now it’s the world’s best-selling, most profitable electronic car. That’s wild, to take something from inception and create a global empire. That talent and vision are insane.

How can our readers further follow your work online?

You can follow our team on Facebook @TheBrandonBrittinghamTeam or instagram on @themarylandgroup. If you’d like to connect with me, you can follow me on Facebook @Brandon Brittingham or Instagram @bbrittingham. If you’re interested in learning more about my leadership coaching program, visit my training website or watch market updates on our YouTube channel Brandon Brittingham.

This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.

Thank you so much!


  • Savio P. Clemente

    TEDx Speaker, Media Journalist, Board Certified Wellness Coach, Best-Selling Author & Cancer Survivor

    Savio P. Clemente, TEDx speaker and Stage 3 cancer survivor, infuses transformative insights into every article. His journey battling cancer fuels a mission to empower survivors and industry leaders towards living a truly healthy, wealthy, and wise lifestyle. As a Board-Certified Wellness Coach (NBC-HWC, ACC), Savio guides readers to embrace self-discovery and rewrite narratives by loving their inner stranger, as outlined in his acclaimed TEDx talk: "7 Minutes to Wellness: How to Love Your Inner Stranger." Through his best-selling book and impactful work as a media journalist — covering inspirational stories of resilience and exploring wellness trends — Savio has collaborated with notable celebrities and TV personalities, bringing his insights to diverse audiences and touching countless lives. His philosophy, "to know thyself is to heal thyself," resonates in every piece.