People Processes Interviews: How to Prevent Bad Moments from Turning Into a Bad Day with Michael O’Brien

Everything that happens in life is neutral until you put a label on them. Listen in as today’s guest shares how he was able to turn a near-death experience into a catalyst that shaped his life’s purpose: to help corporate leaders and their people build resiliency.

We have interviewed Michael O’Brien, executive business coach, TEDx speaker, author, and Chief Shift Officer at Peloton Executive Coaching. His mission? To help leaders prevent bad moments from turning into a bad day.

1) Can you recall your worst day as a leader and entrepreneur?

A couple of stories come to mind. My “last bad day” was when I got hit head-on by an SUV when I was out on a bike training ride. Another one was early on in my entrepreneurial life.

I spent 22 years in corporate America. The last job I held was General Manager for sales and marketing operations for a global pharmaceuticals company. I was doing pretty well, but I decided to follow my purpose and passion by starting my executive coaching career. In 2016 I was a year and a half into it. I was preparing a talk one day but didn’t have a lot of prep time due to family reasons. The talk was an absolute disaster. 15 minutes into it, I just lost my way, and for the first time in my professional life, I had to say, “Can we stop?” I just wanted the whole day to be over. Later, I was in my car and called my wife to tell her that I stunk up the joint. She told me that I was probably making a bigger deal out of it than it really was. I thought that my whole career as an entrepreneur was over. When I got home, I wrote a blog post and recorded a podcast in order to turn my experience into a teaching moment that I could share with others.

That day taught me about resilience and using lessons from my setbacks to lead me down a better direction. By the way, that company stayed as one of my clients because it was such an authentic moment for them.

2) You talk about another story on your website that really set the stage for how you view resiliency today. Can you tell me about that?

This is my origin story. It was July 11, 2001. I was out for a company offsite in New Mexico. I decided to bring my bike since I had a goal to cycle through all 50 states. That morning, I came around a bend, and a Ford Explorer was fully in my lane, traveling around 40 miles an hour. I didn’t have enough time to avoid him. I remember hitting his grill, into the windshield I went and came to the asphalt below as he came to a halting stop.

I regained consciousness surrounded by EMTs, and I knew that my life was in the balance. Throughout my whole life, I thought I was following the script, adhering to the letter of the law. In reality, I was chasing happiness by comparing myself to others and keeping up with the Joneses. And now, here I was, on the cold, desert asphalt of New Mexico fighting for my life. As they brought me to Albuquerque, I told myself that, if I got through this, I would change how I lived my life. When my doctor told me that my future was uncertain, I thought I’d never been happy again.

I stayed in that funk until a mentor told me that everything in my life is neutral until I label them. Nothing has meaning unless I give it meaning. I could stay a victim, or decide to rise up. That, to me, was a big “ah-ha” moment. I believe that an accident happened to me, not to me. It helped me lead in a different way that allowed me to get into the executive suite at a very young age. I credit my recovery as a big driver in helping me reshape my life—shifting my life if you will.

3) What exactly were those new paradigms that helped you climb the ladder in the corporate world?

One of the big ones was spending some time each day just being quiet and being present. Some people can call it “meditation” or “mindfulness”. I didn’t think of it that way. I grew up doing sports and knew that the mind was very important; so I knew that if I could get my mind right, I could get my body right.

Every morning, I get quiet and set my intentions for the day by asking myself three questions: 1) How do I wish to be today; 2) What do I wish to do (i.e. priorities); 3) What do I want to have more of at the end of the day?

4) If someone who is in charge of the scaling, growth, and efficiency of staff sits down with you, what advice would you give them to begin improving the resiliency of the company’s employees on a corporate level?

We should consider the health crisis brought about by COVID-19, as well as its impact on the economy. We’re now working through equity and equality issues. We have a lot to face as HR professionals and corporate leaders.

At a corporate level, if leaders can role model the right behaviors and show up with a more resilient mindset, it allows the company to become more agile. My definition of resilience is: “Fall down seven times, get back up eight times.” This will help us to adapt to future challenges. Who’s to say what the future holds? All we know is that things will continue to move faster as time goes on.

To reframe tough situations, I do what I call “grabbing a PBR”, which I developed when I was in the hospital. PBR stands for “Pause, Breathe, and Reflect”. We slow it down so that we can go faster and be better, taking breaths so that we can think things through before replying or reacting too soon.

Another thing is to work on our relationships. Resilient people have a “strong peloton”, which is a group of cyclists in a bike race like the Tour de France: They’re all on different teams and they all come from different departments, but they all need each other to go down the road as fast as possible. We all need strong peloton. It’s my metaphor for a tribe at work.

Finally, take small steps and get back to the priorities that really matter. Have gratitude. As a corporate leader, you can weave in gratitude for the current moment. Highlight both the small and big wins. Negative news travels the fastest and we forget about our small victories. Leaders at the top should ask what the team is grateful for. “Grateful” doesn’t mean “satisfied”. It doesn’t mean that we’re done. It just means that we recognize that we’re making progress, and we can use those moments of progress or accomplishment to build into tomorrow and begin to gain momentum.

5) How do you communicate sensitive issues across your company?

Every company should have a good copy editor and a good corporate communications department. When a company statement is needed in particular moments, highlight how the moment is front-and-center for everyone. There is more awareness among the team. They can see more frames of this movie. They can be thankful for the awareness, but not necessarily joyful or excited about it. Instead, it’s an opportunity to address what should have been addressed long ago. When you look at the nation today with the issues of COVID-19 and inequity and inequality, we should look at it all as an opportunity to write a new script—a new story—if we want to make this a “last bad day” moment for our country. We can’t be satisfied with an external memo and a few social media posts. The real brass tax of it all is how we can change and do things within our company.

Businesses will continue to evolve their brand by asking themselves how they want the world around them to see their company. A tire-changing business doesn’t just “change tires”—they’re providing safety and security. The key is to define the purpose of your work, and the mission and branding of your company. It’s ultimately all about the soul of your business. What do you stand for? What kind of impact do you want to make? What kind of legacy do you want to leave behind?

6) What book would you recommend to those looking to better their outlook on life?

I often recommend The Alchemist by Paolo Coelho.

7) If you can go back and warn your past self against making a certain decision, what would that decision be?

I used to compare my beginning with other people’s middle. I wasted a lot of time playing the comparison game. Just do you. Be you. Speak to your people. Let them do them, and you’ll be very happy.

8) Is there anything taking place within the next six months that you’re most excited about?

In the next three weeks, on July 11, I’ll be celebrating 19 years since my last bad day. To celebrate life, I’ll be riding my bike inside for 19 hours for 19 charities supporting others during this moment in time. It’s going to be physically and mentally draining. Some people have called me crazy; but what’s really crazy is the racism, sexism, poverty, and hunger that is being felt all over the world right now. Riding for 19 hours doesn’t even begin to compare to that.

9) How can people reach you, and is there anyone who wouldn’t be a good fit to be your client?

Anyone can reach me through my website, which is There, they can grab my free A Better Life workbook which will help them build resilience and manage their energy.

As far as the fit, the people that I gravitate towards are those who want to create a better tomorrow. If you’re happy with how it’s always been, and you don’t see any way to grow and develop, you’re probably not a good fit. It doesn’t mean I’m judging you. I’d still be open to a conversation because I just like connecting with people. And anyway, those conversations can still lead to issues that you might have overlooked.

I’ve been given a second shot at all this. For me, I’m doing what I believe I’m meant to do. If I can help people shift their perspective on things to step fully into this wonderful life that we have, to change things from a corporate or business perspective, or even just from their own living rooms, I’m all about it. It brings me a lot of joy. It brings me a lot of happiness. I’m excited to do it.


2020 brought with it a plethora of world-shaking challenges. From the effects of COVID-19 to increased awareness around issues of racial equality, all manner of businesses is forced to adapt in more ways than one. It is the corporate leader’s responsibility to be a role model to their people in demonstrating how to navigate the many obstacles they currently face.

It all starts with displaying resiliency. By incorporating simple practices such as “grabbing a PBR” and highlighting what deserves gratitude, leaders allow the soul of their business to shine brighter, which will lead to stronger pelotons and team members who are able to move forward in the face of uncertainty with greater confidence.

Homework: Now that you know what makes for a company culture defined by resilience, what foundational priorities can you as a corporate leader highlight which you can then translate into bite-sized, actionable steps that you and your people can take to improve the company today?

Learn more about Michael O’Brien here:





About the author, Rhamy

Rhamy grew up watching and working with his mother and grandmother in the senior insurance market. This familiarity with the struggles faced by people trying to navigate the incredibly complicated and heavily regulated healthcare market led him to start Poplar Financial while working on his degree at the University of Memphis. After completing his MBA and Bachelors in Finance and Economics, Rhamy guided Poplar Financial through the disruptive opportunity that is the Affordable Care Act. Since then Poplar Financial has received numerous awards from major insurance carriers and has completed its fourth year in a row of doubling in size. Now his team focuses on the processes around human resources and specializes in providing companies with between 20 and 1000 employees with the payroll, benefits, and HR needs.

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