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Michael O’Brien of Peloton Executive Coaching: “How I Was Able To Thrive Despite First Experiencing Impostor Syndrome” With Candice Georgiadis

Accomplishments List — Develop a list of life and career accomplishments and mantras that will help you counter-balance your self-narrative when it gets negative or anxious. You can develop your list in private and then ask others what strengths they see in you. I had the pleasure of interviewing Michael O’Brien. Michael is the Chief Shift […]

Accomplishments List — Develop a list of life and career accomplishments and mantras that will help you counter-balance your self-narrative when it gets negative or anxious. You can develop your list in private and then ask others what strengths they see in you.


I had the pleasure of interviewing Michael O’Brien. Michael is the Chief Shift Officer at Peloton Executive Coaching. He elevates successful corporate leaders by preventing bad moments from turning into bad days, as he illustrates in his current book, My Last Bad Day Shift. His award-winning, best-selling memoir Shift: Creating Better Tomorrows chronicles his Last Bad Day and near-death cycling accident recovery journey. He has shared his inspirational story and leadership expertise on the TEDx stage and with multiple Fortune 500 companies,Entrepreneur, Fast Company, ABC, Real Simple, and Authority Magazine.


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

Thanks for having me. I’ll start with the promise I made when they put me on the medivac. I made the commitment that if I lived, then I would stop chasing happiness. I made that promise on July 11, 2001, after being hit head-on by a speeding SUV during a bike training ride. I consider it My Last Bad Day. Over time it has become one of my best because it has helped me shift my perspective on almost every aspect of my life and reach the executive suite on my terms.

During my recovery, I knew that I would eventually help others write a different life and career scripts so they can achieve more happiness and success. I see my work today as one of the reasons I survived my Last Bad Day.

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?

When I was a few years into my sales career, I lost my position in a company-wide downsizing. It was my first experience with job loss and I started to become angry and worried about my future.

A few months later, something interesting happened. The recruiting firm that they provided called with a new “ground-floor” opportunity that was too good to pass up. That company became my home for eighteen years, but, most importantly, I gained the type of experience my clients need today. It helped me see that often things happen for a reason or when one door closes; another opens. Now I look back at my downsizing with gratitude because it was a gift that led to many wonderful career experiences.

What do you think makes your company stand out? Can you share a story?

It comes down to the results that my clients achieve. Over 87% have gone on to positions with more influence or compensation after they discovered how to lead differently. But the most meaningful results are when my clients tell me that their husband or wife now sees that they are happier, which makes a significant difference at home. They become better partners and parents and become wealthier, starting from the inside-out.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

When I was in the ICU from my Last Bad Day accident, I told my wife to find David. I shared that “he will show us the way.” When I moved from the ICU and my wife asked me about David, I was surprised because I never talked about work at home. She had no idea who he was until I said something in the ICU.

David was the first executive coach in my life. My team hired him about six months before my accident, and he was starting to help me discover different leadership approaches. When my wife shared that I referenced him, I knew it was a sign that I would follow in his footsteps and he’s been a mentor to me ever since.

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 experience of Impostor Syndrome. How would you define Impostor Syndrome? What do people with Imposter Syndrome feel?

Impostor Syndrome has impacted seventy percent of the US population and involves feeling like a fake or fraud because you don’t feel like you have the proper skills, training, or experience. What’s interesting about imposter experience is that feelings of loneliness, worry, and anxiety often occur after an accomplishment because you begin to believe that your success isn’t warranted, and others will see it as well.

What are the downsides of Impostor Syndrome? How can it limit people?

The challenges with impostor syndrome are significant because when present, your feelings can restrict you from moving forward with confidence and lose confidence in your ability to perform.

How can the experience of Impostor Syndrome impact how one treats others?

Having dealt with Imposter Syndrome, I can attest that when it’s present, it impacts our relationships. It’s common for us to feel alone, cynical or skeptical. As a result, it’s harder to partner with colleagues and trust and productivity starts to wane.

We would love to hear your story about your experience with Impostor Syndrome. Would you be able to share that with us?

My first experience with imposter syndrome came after I was promoted to National Sales Director. I started to believe that the only reason I got the job was that I was the only candidate willing to move to New Jersey. I also thought I had to lead like all the National Sales Directors in my industry, but that wasn’t my style. As a result, I lost my identity for a few months. It was an extremely stressful period and I wondered if I was the right person for the job. These feelings stayed with me until I shifted my thinking and regained my confidence.

Did you ever shake the feeling off? If yes, what have you done to mitigate it or eliminate it?

Yes, I was able to shake off my imposter syndrome by shifting the conversation I was having with myself by developing an accomplishments list and a few mantras that helped me see why I was promotion. I also started looking for small wins, which I knew would lead to bigger ones down the road, which they did.

In your opinion, what are five steps that someone who is experiencing Impostor Syndrome can take to move forward despite feeling like an “Impostor”? Please share a story or an example for each.

Here’s what I do when I feel like an imposter and recommend to my clients today:

1: Breathe — When imposter syndrome is present, it’s common for your head to be spinning and be filled with emotion. It makes it hard to know what to do next. Focusing on your breath slows you down, shifts your perspective, and sparks a healthier self-narrative.

2: Accomplishments List — Develop a list of life and career accomplishments and mantras that will help you counter-balance your self-narrative when it gets negative or anxious. You can develop your list in private and then ask others what strengths they see in you.

3: Develop Your Network — Since life and career are not solo projects, it’s essential to have a strong network. They can help you see attributes you might not realize — especially when can’t.

4: Small Wins — Look for small victories to gain the type of momentum that will lead to big wins down the road and reframe your situation.

5: Gratitude — Develop a gratitude practice to help you see what’s working in your life. You can even be grateful for your moments of self-doubt or feeling like a fraud because they are a natural part of being alive and an opportunity to show yourself and the world that you are gritty.

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. 🙂

My recovery from my near-death cycling accident has been a miracle. I now believe that one of the reasons I lived is to help over 1,000,000 people have their Last Bad Day and live life and build their career with awareness, purpose, gratitude, and community. I know my Last Bad Day can help others live their best days.

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 🙂

There are so many I wish I could name. If I could only choose one, it would be Sir Richard Branson because he has written his script, achieved great success, rebounded from setbacks, and seems to be wealthy from the inside-out.

How can our readers follow you on social media?

Yes, they can follow me on LinkedIn, Facebook, and Instagram.

Thank you for all of these great insights!

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