Invent your new story– we are all carrying baggage with us that does not serve us. Most of us have some lesson from our past that is preventing us from getting to our future. The key is to take those experiences that were anchors holding you back and transform them into rocket fuel for your future. Do this by rewriting the story. Ask better and more empowering questions until you can come up with an unforeseen positive event that occurred, or someone you met or a valuable lesson you learned from the experience, then take that lesson and leave behind the pain.


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 Rob Dubin.

Rob Dubin is a serial entrepreneur who built multiple 7 figure businesses. He has captained his own sailboat around the world, climbed Denali the highest peak in North America, set an aviation record in an experimental aircraft, kayaked unexplored jungle rivers, driven 9,000 miles of backroads through Africa and faced fear of failure frequently.



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 was a professional filmmaker who started my own film production company at age 22 when I did not know enough to be fearful of failure. Later at age 42 my wife and I retired, sold our home and spent the next 17 years living on our sailboat and circumnavigating the world. As we were living out our dream of sailing around the world I came to realize how few people actually do live out their dreams and why- FEAR.

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

I grew up in the Colorado mountains and got used to being very adventurous so fear of physical risks was never much of a challenge for me. But one of the first big film opportunities I had was making a film about Buckminster Fuller. Younger readers may know “Bucky” as the inventor of the geodesic dome but he was also one of the greatest thinkers of the 20th century. For me as an inexperienced 25 year old facing the responsibility of interpreting for history this brilliant and great man was nearly a paralyzing fear. It was Bucky himself who allayed my fear and he did so by turning the tables on me. He had me put down the camera and stop recording his brilliance while he asked my opinions and thoughts on things. He showed me my own value that I had not been able to see in myself. I’ve often used this same technique to help others see the value in themselves.

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?

By far the most important trait for any leader is to surround yourself with people who can do what you cannot, then trust them, support them, inspire them and help them do their job.

An example is this silly sounding response I learned from my mentor Tony Robbins. I had several employees with whom this worked EVERY time. I would say, “I know you don’t know how to do this, but if you did, how would you do it?” I had employees who would hear that, not see the irony in it and immediately step up to the plate and solve the problem. They just needed the same boost Bucky Fuller had provided me- to be valued

I’ve been lucky in my career to meet some truly great people-several US Presidents, Fortune 500 CEO’s, successful businesspeople and sports stars. I have adopted a trait I have seen in most all of them- the ability to learn from their failures and mistakes- take the lesson from the experience and move on without being fearful or stifled by the failure.

I served several terms as President of the Colorado Film and Video Association and often spoke to film students and was asked what led to my success. I told them, “in every industry there is someone who will get up just a bit earlier in the morning, work just a bit harder, give the clients a bit more value and always deliver 110%. In the film industry that guy won’t get the job- I will- because I will be giving 120%.”

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?

First off I think we need to recognize there are two different fears of failure involved. The first is the fear of “what will other people think if we fail.” The second is the consequences of the failure. A common goal for many people is they want to start their own business. Consequences of failure could mean loss of your investment, having to go back and find a job, etc. In reality though most people give up on the dream before they even start because they worry what others will think.

I read a study that said most people don’t stop worrying about what others think of them until around age 46. So the exact years when we should be out learning and trying and risking failure from ages 20–45 we don’t because we worry what others will think IF we fail. Then by age 46 we are settled and comfortable and the consequences are bigger-how will we make the mortgage payment, keep the kids in college, etc.

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

The downside can be seen all around us- people living small, playing safe, getting to the end of their lives and realizing they never lived. Almost everything that brings joy and purpose to our lives lies on the other side of fear. Truly all the magic lies outside your comfort zone.

We have all burned our hands on the stove. One lesson you could take away from that is to never eat hot food again in your life. When I use that analogy in my speeches people always laugh. But most of us have some other area of our life where we have closed down in the same way. We get our heart broken and enter our next relationship with one foot out the door. Or we fail at something and say, “well I’ll never try that again.”

Failure is part of life- if every failure makes you afraid to try again your world gets smaller and smaller the longer you live. For those willing to risk failure the world gets larger and larger. That’s why I’ve built 4 different businesses, visited over 100 countries, met interesting people all over the world and had magical experience after magical experience- I’m always willing to fail.

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

Many years ago my wife and I were lost for 5 days in a winter storm in the rockies and given up for dead. The sheriff announced our frozen bodies would be recovered the following spring. Our story had gone viral and when we did survive the first call I received was from the President of the United States congratulating us on our survival.

In the next days I appeared on the Today Show, Good Morning America, CBS This Morning and many others. The interviewers all asked the same question, “are you going to be more careful and conservative in the future?” The lesson they wanted was be more careful, live smaller, don’t risk danger. The lesson we took instead was ..”we survived this, look how much we can accomplish.” Two years later we sold our home and set off to sail around the world.

In another instance I took action on a crazy idea I had — an idea with a 90% chance of failure- it led to meeting Tony Robbins and being invited as his guest to all his programs. What I learned from Tony changed EVERY part of my life.

In my late 60’s I started a new career as a motivational speaker and happiness expert. I did not need a new career, did not need it financially and it has a high risk of failure. Yet it has opened up doors I never knew existed. And every door this career opens improves and enriches my life and the lives of others.

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?

Most of us experience some failure that matters to us pretty early in life. Maybe in school or early in your career. I’ve found the moment that you confront your first big failure is critical- it has the power to define your entire life because you have an existential choice. You either make an excuse and dodge responsibility or you accept responsibility.

Making excuses tells your brain it was not your fault, it was circumstances beyond your control. Since it is not your fault then you need never do anything different in the future. And since there are always circumstances beyond your control any venture has a risk of failure. The way to fail less is to risk or try less. The fate of your life has now been decided. Your world will get smaller and smaller.

I firmly believe the only way to grow as a human is to make mistakes, admit your mistakes, learn the lesson from them so you don’t repeat the mistake, then move forward knowing more than you did before.

Early in my career I had the highest profile public humiliation possible. I had been invited to produce a multi-media slide presentation for a black tie awards evening honoring achievements in the Denver advertising industry. An Academy Awards sort of night. Every person in the audience was my potential client so the evening would literally make my career. At the same moment I started the presentation in the event space, the caterers arrived to the next room plugged in their hot trays to our dedicated electric circuits and blew all the circuits time after time. The entire evening was a bust- the amazing 40 minute show I had spent weeks preparing never played- all the award winners in their tuxedoes and evening gowns never even got their names announced, it was my fault and my career getting work from any Denver ad agency was over in that instant. I had humiliated myself spectacularly in front of every one of my clients, potential clients and my peers.

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?

The critical lesson I learned that night was to take responsibility for my failure. I owned it. The odds of the caterers showing up just then was maybe 100:1. So the lesson I took from the experience was cover every contingency and solve every problem in advance even if the odds of needing that solution were 100:1. This attitude led me to take action and exert more and more control over my projects. The more things I controlled the fewer circumstances beyond my control. Since I controlled the outcome more I could tackle bigger and bigger projects with bigger and bigger risks. This led to bigger and bigger success.

Because I was known for covering every contingency and tackling very complex projects pretty soon the Denver Advertising Industry were coming to us whenever they had their biggest most complicated film productions.

I also was forced to pivot to the filmmaking side of my business. I worked on making documentary films with ABC, NBC, CBS out of New York and ended up becoming the youngest person on many crews doing documentary films all over the world.

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.

I teach employee happiness workshops and a key part of my workshop is an exercise called “Dream Harvesting.” Early on I learned it did no good to help people create a list of meaningful dreams and goals if I could not also teach them a framework for breaking through fear because in so many cases fear lies between us and our dreams.

Step 1- Invent your new story– we are all carrying baggage with us that does not serve us. Most of us have some lesson from our past that is preventing us from getting to our future. The key is to take those experiences that were anchors holding you back and transform them into rocket fuel for your future. Do this by rewriting the story. Ask better and more empowering questions until you can come up with an unforeseen positive event that occurred, or someone you met or a valuable lesson you learned from the experience, then take that lesson and leave behind the pain.

Step 2. Don’t be ruled by others opinions. Your sense of self-worth comes from you and nobody else. Others may have wise advice to guide you but do not be derailed from your future by trying to please others.

Step 3. Stack your successes. List all the similar experiences you have had that you succeeded at. Each one is a building block for self confidence. List all the resources you have at your disposable. List all the other improbable goals you set and reached. See problems in advance but don’t focus on them instead focus on solutions. Visualize the goal already having come to pass. Visualize it in great detail.

Step 4. Chunk it down. When we tell people we sailed across oceans or around the world the usual response is, “I’d love to do that but I’d be afraid.” Well what specifically are you afraid of? Break that fear down into manageable chunks and come up with a solution for each one. If you are afraid of getting lost at sea- carry 2 or 3 extra GPS units. Afraid of sinking, get a really stout boat and carry extra bilge pumps. Afraid of sea sickness, find medications that work for you. When you break your BIG fear down into small bite size chunks and come up with a solution for each one it all becomes more manageable.

Step 5. Take action. The only real failure is failure to try. Everything else is a learning experience and an investment in your future. Courage is not the absence of fear- courage is feeling the fear and going forward anyway.

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?

I hate to disagree with one of the greatest thinkers of all time- but I think there are numerous ways to succeed. We probably have all had the experience of not getting to the destination we planned on and yet found the detour even more wonderful.

I prefer another of Aristotle’s quotes which I use often in my workshops, “Happiness is the meaning and purpose of life, the whole aim and end of human existence.”

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. 🙂

I am already on that mission to inspire a movement. I teach happiness. The pandemic caused millions of people to reexamine their lives and ask questions they may have never asked before- am I happy? Am I living the life I had hoped for? Too many answered no they were not living the life they want. I think the silver lining in the pandemic is millions of people are now looking for more happiness and I want to help as many as possible find it. For businesses it is the solution to the Great Resignation and for employees it is the key to an engaging career and fulfilling life.

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 🙂

Mark Cuban. Like many people I love watching Shark Tank. All the investors are brilliant at seeing new products they can apply their proven strategies to, but Mark Cuban sees something else. He has a genius for seeing things that are not there and creating a new future.

How can our readers further follow your work online?

They can reach me through my Linkedin Profile at:

https://www.linkedin.com/in/robdubin/

Or my website at https:///www.robdubin.com

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

Author(s)

  • 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.