Author David Rey on Becoming Free From the Fear of Failure

An Interview with Savio P. Clemente

Savio P. Clemente
Authority Magazine
17 min readAug 2, 2022

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Trust Your Ability to Make a Solid Decision — I learned a lot of important lessons managing in renowned flagship luxury retail locations in NYC. One of those lessons is that your decisions will be questioned, challenged and criticized by your business partners on a regular basis. It is a cutthroat world within luxury retail and if you are not ready to stand by your decisions, you will not be respected. People can smell fear from a mile away, especially in my line of work. Your non-verbal clues will be on full display for everyone to notice. Stand strong and trust in every decision you make as if it is the best idea you ever had.

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 David Rey.

David Rey is currently pursuing his graduate degree in Government from Harvard Extension School and has spent seventeen years overseeing the security operations at several internationally renowned flagship retail locations in New York City, including Tiffany & Co., Louis Vuitton, Bloomingdale’s, and Brooks Brothers. It is however, from his tenure at Macy’s Herald Square, that he has decided to chronicle his experiences in a memoir titled “Larceny on 34th Street: An In-Depth Look at Professional Shoplifting in One of the World’s Largest Stores.” By running the security operations in one of the world’s most extraordinary retail establishments, David Rey has experienced a realm of Organized Retail Crime, most of which the general public knows little about.

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’?

After achieving my undergraduate degree, I had my sights set on a career in law enforcement, following the footsteps of my father. While on stand-by as I waited to hear from several local and federal agencies, I decided to test the waters in luxury retail security. What I had expected to be a pit-stop, turned into an unexpected career leading the security operations at several internationally renowned retail organizations in New York City such as Tiffany & Co.’s iconic 57th Street flagship, Macy’s Herald Square, Louis Vuitton’s Maison 57th Street location, Bloomingdale’s 59th Street flagship and Brooks Brothers’ Madison Avenue flagship. By leading security teams in such remarkable yet intimidating landscapes, I was immersed into a world of Organized Crime which included but was not limited to professional shoplifting, credit card fraud and identify theft.

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

My career is certainly not devoid of interesting stories but when considering the theme of being free from the fear of failure, one particular story stands out to me.

One of my most successful investigations involved claims of misconduct against an employee. When sharing the details of these allegations with my business partners, the consensus feeling throughout the team was that this investigation was destined to fail due to the employee being a senior figure within the company. The politics that would ensue as a result of this case was deemed too much of an obstacle to overcome and I was deterred from pursuing it. Many people in this situation would have cut their losses and moved on but I couldn’t bring myself to it. As Einstein once said, “The world will not be destroyed by those who do evil but by those who watch them without doing anything.” I felt a duty to continue the investigation and in doing so, uncovered enough misconduct that could not be ignored. Confronted with the evidence, the team had no choice but to join my efforts in pursuing the case.

The key takeaway from this story is that at some point, whether it is in your professional or personal life, your stance on a particular topic will be in the minority — perhaps you might even be the lone dissenter in a room of opposing viewpoints. If and when this happens, remember this — “the truth will not be diminished based on the number of people who believe it.” Just because everyone in the room disagrees with you, might not necessarily mean you are wrong. Successful people embrace these situations, taking advantage of every opportunity they can to prove the majority wrong. Stand by your beliefs and do not let a room full of doubters discourage you from having an opinion that may be different than theirs.

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?

Persistence — this term is defined as “continuing firmly or obstinately in a course of action in spite of difficulty or opposition.” Staying the course in spite of difficulty or opposition is what makes this character trait so invaluable. Many of us have heard the story about how J.K. Rowling’s Harry Potter novel was rejected 12 times before a publisher finally accepted it. This kind of persistence is certainly relatable to published authors such as myself. Though we are passionate about the topics we write about, it is extremely difficult to find a literary agent or publisher to share that same passion and interest. I lost count of how many pitch letter rejections I received from literary agents. I also lost count of how many literary agents didn’t even bother to respond to my pitch letters. As frustrating as this was, I was willing to stay the course for however long it took because I believed in what I was trying to accomplish. Eventually this persistence paid off as Dorrance Publishing eventually approved my manuscript and offered me my first contract.

Confidence — part of what drove my persistence in getting my book published was the confidence I had in my memoir and how well I felt the topic of the book would be received by the general public. I mentioned in the prologue of my book that I developed this confidence from the consistent positive feedback I received from people about my line of work and how intriguing they thought it was. Armed with this confidence, I was able to withstand any and all rejections from literary agents and publishers that felt my memoir was not good enough for them. To me, the people had spoken and made it clear that this was a path worth taking. Though I was entering uncharted waters into the world of creative writing, my confidence in this memoir shielded me from any bouts of discouragement and self-doubt. A confident person does not know what will happen but whatever does happen, a confident person will be able to handle it.

Ambition — this is one of those character traits that you cannot teach. You cannot train or push someone to have ambition, either they have it or they do not. The desire to become successful has to come from within. At one point or another many of us have come across that one person who is uber-talented in a particular set of skills or who demonstrates such superior knowledge that you may feel they could give Ken Jennings a run for his money on Jeopardy. You may suggest to them to try out for a gameshow or encourage them to write a book or do anything that helps market their skills but all you get in response is a shoulder shrug or an eye-roll or a big sigh followed by countless excuses why they “can’t” do it. In reality, the thing holding them back is a lack of ambition. Though armed with remarkable talent, their personality is devoid of any kind of drive or initiative. So many talented people in the world will never achieve greatness because they simply have no desire to be great. Determination and willpower are very difficult traits to instill in a person. From what I’ve seen, the type of ambition that leads to success is usually deep-rooted.

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?

From my perspective, the two main reasons people fear failure are due to rejection and a lack of confidence.

Rejection — “A man who fears suffering is already suffering from what he fears.” — Michel de Montaigne

One of the many things I’ve learned throughout my adult life is that people do not want to hear the truth about themselves. They rather have someone tell them what they want to hear than actually have that person be honest with them about their shortcomings. Some people do not possess the maturity or ego necessary to handle being told that they do not meet a certain standard. For many years of my young adult life, I was one of those people. I would do whatever it took to avoid putting myself in a position to have my abilities or character critiqued. I could not stomach the idea of being told I was not good enough. After facing rejection enough times, I eventually developed the epiphany I needed to identify and address my limitations.

Lack of Confidence — The Wolf of Wall Street Jordan Belfort once said “Act as if you have unmatched confidence and people will have confidence in you.” This may be easier said than done for many people because having confidence is sometimes frowned upon. There’s a fine line between confidence and conceit and because of this, many people sometimes misinterpret a person’s confidence for conceit. People with a lack of confidence in themselves tend to shun and disparage those who display the kind of confidence they wish they had. People with confidence tend to get labeled as arrogant or egotistical and as a result, find it harder to make friends and be accepted within the general public. They say it is lonely at the top and this is certainly the case for those who have achieved success while maintaining their confidence through all the noise. Do not let anyone force their insecurities on to you. I would rather be successful and labeled as a conceited a-hole than unsuccessful and labeled as an underachiever or a disappointment.

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

One of the most mentally torturous things you can do to yourself is to live a life where you are constantly asking yourself “what if?” What if I tried writing that book? What if I went back to school and got my degree? What if I tried out for that casting call? Stepping out of your comfort zone will help train your brain to change what it normally perceives as dangerous. Being afraid of failure limits people because the part of the brain that associates failure with pain will always be the dominate force driving a person’s decision making. Mark Manson’s “The Subtle Art of Not Giving A F*ck” said it the best, “If you think about a young child trying to learn to walk, that child will fall down and hurt itself hundreds of times. But at no point does the child ever stop to think, ‘Oh I guess walking just isn’t for me, I’m not good at it.’” You have to be willing to fail. If you are unwilling to fail you are unwilling to succeed.

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

Being fearful of failure gives us the false perception that our mind is trying to protect ourselves. By being free from failure, we can improve our lives by training our mind to focus on what can go right instead of overthinking about what could go wrong. Due to being stuck in a nervous loop, we are not leaving any room in our minds for inventive solutions. Though it is important to have a plan just in case something goes wrong, we should be more focused on the possibilities of achieving the goal than the possibilities of not achieving the goal. The idea is to train our brains to believe that we trust ourselves to make a solid decision. Being fearful of failure forces us to be stuck in an overthinking loop where we are constantly second guessing ourselves over even the smallest decisions. Being free from failure can help us overcome the painful world of anxiousness and chronic overthinking. “The first and greatest victory is to conquer yourself; to be conquered by yourself is of all things most shameful and vile.” — Plato

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?

Once the pandemic hit, retailers that were designated as “non-essential” were struggling to keep their businesses above water. With no storefront revenue coming in due to the shutdown, many organizations had to find alternative ways to maintain profitability. It was during this time that I was introduced to the dreadful world of “furlough” — when the company you work for decides who to keep on the payroll and who to remove.

Similar to the government deciding which businesses were essential and which ones weren’t, many companies were playing the same game with their employees — who’s important and who’s not. Needless to say, I was designated as a “non-essential” employee within my organization and as a result, was taken off the payroll indefinitely.

In a time of economic hardship, it would have been good to know the organization I worked for saw me as an asset and was willing to bring me along to fight the battle. Unfortunately, that wasn’t the case. Instead I was banished to the kids table, not worthy to sit with the grown-ups. I felt devalued and deflated with my ego punctured. I thought I had done enough to prove my worth to the company but instead I was relegated to sit on the bench in street clothes while the coaches played the players they felt gave them the best chance to win the game. It was certainly a tough pill to swallow.

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?

I used this shot to my ego as motivation to complete my memoir. Every time I got too comfortable and considered putting off completing another chapter of my manuscript, I quickly reminded myself of the emotional pain I associated with having the organization I work for tell me “you can’t sit with us” and then used that pain as inspiration to get my lazy ass off the couch or bed and sit right back down in that chair and type away. It was from this that I learned how powerful it can be to use the rejection or dismissal I have faced in my life as a driver that feeds my resolve to achieve a personal goal.

This is actually a common tactic many successful people use. In the ESPN documentary “The Captain” when discussing people who have doubted him in the past, Derek Jeter said, “I remember what you said, when you said it and what you were wearing when you said it.”

My advice to others would be to use the doubts and criticisms from your detractors as fuel to ignite your determination. It certainly is a satisfying feeling to look at the faces of those who did not want you or those who questioned you after you have achieved a goal they believed you were not good enough to accomplish.

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.

Stop Overthinking — when it came time to begin promoting the release of my first memoir I became a prisoner of my own mind. How will it be perceived? What if people don’t like it? What if people write negative comments about it on social media? What if people give it negative reviews on book seller websites? All these doom and gloom thoughts consumed me to the point where I delayed the initial promotion until I could motivate myself enough to go through with it. In hindsight, it was all a big delusion made up in my head. I went through with the initial promotion on LinkedIn and before I knew it, I had over 10,000 impressions of my post within the first week. So much for overthinking. I learned to trust myself a lot more after this experience.

Trust Your Ability to Make a Solid Decision — I learned a lot of important lessons managing in renowned flagship luxury retail locations in NYC. One of those lessons is that your decisions will be questioned, challenged and criticized by your business partners on a regular basis. It is a cutthroat world within luxury retail and if you are not ready to stand by your decisions, you will not be respected. People can smell fear from a mile away, especially in my line of work. Your non-verbal clues will be on full display for everyone to notice. Stand strong and trust in every decision you make as if it is the best idea you ever had.

Focus on What Can Go Right Instead of What Can Go Wrong — I feel it is quite common for people to dwell on the worst case scenarios instead of fantasizing about the best case scenarios. Even if you are a glass half full kind of person, there is always that one Debbie Downer around us who will be successful in projecting their negative energy on to us. As I said previously, those who are unwilling to fail are unwilling to succeed. Absolutely nothing good comes from focusing solely on what can go wrong. It is ok to be prepared for hardships but if you get in the habit of letting doom and gloom thoughts be the main driver in your decisions, you will always find yourself on the defensive, bracing for an impact that may never come. Instead, focus on the offensive, moving forward towards that goal regardless of what happens.

Don’t Assume Everyone Knows Better Than You — One thing our insecurities will have us doing is constantly asking everyone around us for advice. The problem with this is that you end up asking advice from people who never accomplished what you set out to accomplish or someone who doesn’t have the same ambition as you. Only seek out advice from those who have achieved what you are trying to achieve or from those who have accomplished their own personal goals. Those who have no ambition or have no experience in what you are doing will struggle to relate and might either force their own limitations on to you or give you bogus advice based on their own poor decision making. Be very selective on who you seek out for guidance.

Don’t Be Afraid to Say No or Walk Away — One thing I struggled with early on in my career was having the boldness to say no to bad offers or to a close business partner. To be free from failure, it helps to possess the courage to say “no” to people or organizations. Walking away is a powerful act and you must be courageous enough to use that ace up your sleeve when necessary. You must normalize saying “no” without feeling the need to over explain yourself. If someone is offended by your boundaries, you must see it as their problem not yours. You know that old saying, “The best weight you’ll ever lose is the weight of other people’s opinion of you.” After a while you’ll get used to being seen as the bad guy. With enough experience, you might even embrace it.

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?

Aristotle believed in the idea of a “meritocracy” in which he assessed an individual’s value to society based on their contributions to that society. With that being said, I believe Aristotle was advocating for the idea that you can only merit success by putting in the necessary effort needed to achieve that success. What contributions are you making to the society you live in? What social impact will your efforts have on society as a whole? “To succeed is possible only in one way” is his way of saying that someone’s contributions towards the goal will be the deciding factor in an individual’s success.

I agree with any system that is founded on the principle of rewarding those who contribute significantly to the well-being of a society and frowns upon those who benefit from inherited privilege. It is my hope that we can encourage our younger generations to strive to make great contributions for our society going forward. We must inspire Young Millennials and Gen Z’ers to be forward thinkers so that they can create the next impactful tools that will help make life better for everyone.

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. :-)

When doing these interviews, I try my best not to have my message come across as politically charged. We have enough talking heads on primetime news networks forcing their political viewpoints on their viewers each night. I certainly do not want to be seen as just another activist with a political agenda. However, if I could inspire a movement, it would be to encourage our Young Millennial and Gen Z generations to consider “personal responsibility” when striving for individual goals. The younger generations are always impressionable and sometimes it seems this current generation of youth are being influenced to believe that the government is responsible for their success. Though we have a long way to go to improve the equality issues in the United States, the path to the “American Dream” is still within reach for everyone, regardless of what families we are born into.

Coming from humble beginnings I can tell you that with hard work and dedication, anyone can achieve what I accomplished, even if they come from a disadvantaged upbringing. The thing that made me standout in a crowd of disadvantaged youth was the desire to be successful. Regardless of what socio-economic status you come from, the desire to be great, coupled with the ability to accept personal responsibility for whatever happens during your journey, will take you further than you ever imagined.

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 :-)

I once watched a quick video clip of Suze Orman which not only inspired me but convinced me that this is someone I would love to sit down with one day and just sponge up all the knowledge she can provide me. In this clip, it seems she is being interviewed on a podcast or some radio show. During this clip, Suze Orman shares a personal saying which is, “The elephant keeps walking as the dogs keep barking.” She goes on to explain that everyone wants you to be successful until you’re successful, then everyone wants to tear you down. Her message was clear, you have to be strong enough to handle the attacks from people who do not want to see you do better than them.

I certainly have experienced this firsthand — the cheers and congrats from those I thought were happy for me until I became a published author and was frequently interviewed by journalists, then the applause lessened significantly. Sometimes your pursuit of success can trigger the insecurities of those you thought were celebrating you. When this happens, keep walking towards your journey undisturbed, just like the elephant.

How can our readers further follow your work online?

Instagram — @larcenyon34thstreet

Twitter — @Larcenyon34thSt

LinkedIn — linkedin.com/in/davidrey819

Amazon — https://www.amazon.com/Larceny-34th-Street-Depth-Professional/dp/163867048X

Barnes and Noble — https://www.barnesandnoble.com/w/larceny-on-34th-street-david-rey/1141317257

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

About The Interviewer: Savio P. Clemente coaches cancer survivors to overcome the confusion and gain the clarity needed to get busy living in mind, body, and spirit. He inspires health and wellness seekers to find meaning in the “why” and to cultivate resilience in their mindset. Savio is a Board Certified wellness coach (NBC-HWC, ACC), stage 3 cancer survivor, podcaster, writer, and founder of The Human Resolve LLC.

Savio pens a weekly newsletter at thehumanresolve.com where he delves into secrets from living smarter to feeding your “three brains” — head 🧠, heart 💓, and gut 🤰 — in hopes of connecting the dots to those sticky parts in our nature that matter.

He has been featured on Fox News, and has collaborated with Authority Magazine, Thrive Global, Food Network, WW, and Bloomberg. His mission is to offer clients, listeners, and viewers alike tangible takeaways in living a truly healthy, wealthy, and wise lifestyle.

Savio lives in the suburbs of Westchester County, New York and continues to follow his boundless curiosity. He hopes to one day live out a childhood fantasy and explore outer space.

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Savio P. Clemente
Authority Magazine

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