I wish I would have known that there are so many paths to success and definitions of success. I pursued one type of success (corporate ladder climbing) primarily because it was the only one I knew. Once I started meeting other people with different definitions of success, I saw a broader and wider world of possibilities!
As part of my series about “authors who are making an important social impact”, I had the pleasure of interviewing Roger Osorio.
Roger Osorio is an author, reinvention expert, and founder of The School of Reinvention, a community-based coaching platform empowering people to launch and succeed in personal and career reinvention.
In September of 2022, he released his first book, The Journey to Reinvention: How to Build a Life Aligned with Your Values, Passion, and Purpose.
After graduating from Penn State University, Roger worked for a Fortune 500 company in marketing and sales. In 2008, after falling in love with a part-time job tutoring math, he quit his day job to reinvent his career. Since then, Roger has earned a masters degree in psychology and reinvented himself into a middle and high school math teacher, international speaker, executive coach at a major tech company, Ivy League educator, entrepreneur, and author.
When Roger isn’t working on his business, he teaches entrepreneurship at University of Pennsylvania and Sarah Lawrence College.
Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?
Well, my story starts in northern New Jersey, just outside of New York City. I grew up in a mostly Latino community where Spanish was the primary language spoken. I went to public schools and played soccer. Early on math was the subject that got most of my attention and who knew later in life I would serve as a classroom math teacher for four years.
Eventually, I left my hometown and went to middle of Pennsylvania to attend Penn State University. That was quite the adjustment but one that set me on a path to where I am today.
When you were younger, was there a book that you read that inspired you to take action or changed your life? Can you share a story about that?
While I was at Penn State University, I read a copy of How to Win Friends and Influence People by Dale Carnegie. This book was a game changer for me because it taught me how to work with others and unlock new levels of partnership, relationship, and leadership. I practiced the ideas right away while leading the largest student-run organization on campus. Then, years later when I made a pivot into teaching math, the book served me again by helping me reach students who were struggling with math to help them unlock their potential in the subject.
This book helped me along my journey to reinvention many more times and positioned me to get to the point where I could write my first book, The Journey to Reinvention: How to Build a Life Aligned with Your Values, Passion, and Purpose. Dale’s guidance is timeless!
In fact, this past September, I recommended Dale Carnegie’s book to someone in their early 20’s who asked me for help learning how to help people. I am confident this book will do for him what it did for me.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
One mistake that comes to mind definitely wasn’t funny in the moment, but I suppose I can laugh about it now. When I was working my first corporate job, I needed to work a part-time job parking cars in order to pay off my student loans a little faster. On Thursdays and Fridays, I worked from 8–5pm at the office and then drove to the restaurant where I parked cars from 6pm-1am. Needless to say, these were long days with little sleep in between.
One Friday night, I was so tired and I crashed a car into a lamp post while backing it into a parking spot. I made the scary decision to tell the owner of the car that I hit his car and would pay for the damage. Somehow, he was the last person to come out that night, making his car the last one left. After I showed him the damage, I promised to pay to fix it, even if it was going to cost me a few weeks of tips from parking cars. He didn’t say anything for what felt like a very long minute. Then he proceeded to take some money out of his pocket and tip me. I told him, “I can’t take your money, I hit your car, I promise to fix it.”
And then he said something that taught me a valuable lesson along my journey to reinvention. The man said, “I’m tipping you because you did the right thing by telling me the truth. I know it must have been difficult, but you did it anyway and honesty really is the best policy.”
I learned that day that the journey to reinvention isn’t worthwhile if we compromise our values and integrity to move along the path. Telling him the truth was my way of staying aligned with my values and he appreciated that. The craziest part happened after that when he went on to tell me not to worry about fixing the car because his wife wanted him to get a new car and I probably just did her a favor! I didn’t have to pay him for the damages and I could continue on my path to paying off my student loans.
I’ll never forget that lesson and today, I can laugh a little about it!
Can you describe how you aim to make a significant social impact with your book?
When I wrote, The Journey to Reinvention, I did it with the intention to make it the playbook for building your best life and becoming your best self. I believe that when people achieve those two things, they make the world a better place.
For me, early in my journey, I did my part to make the world a better place by teaching math to students who struggled the most. I wasn’t rich and famous as a result; I was just a guy living life on my terms. From that place, I was able to be at my best for my students. This is what I want for others.
For some, this book will give them permission to leave behind some part of their life that isn’t aligned with their purpose. Then they can begin moving towards what drives them to be at their best.
Solving the world’s toughest problems requires us to perform at our best and that happens when we live a life aligned with who we really are and what matters most to us.
Can you share with us the most interesting story that you shared in your book?
Fortunately, there are many great stories, but one of the most interesting has to do with Leonardo da Vinci’s reinvention at 30 years old. After a few years of feeling down about his life and career, he decided it was time to start up his career again in a new city. He moved from Florence to Milan, Italy and started looking for new jobs. To get the freshest start, he decided to reinvent his career and move away from painting. At the time, the Duke of Milan was hiring military engineers and da Vinci decided to apply for that job!
He had never been one before, but he knew he could do the job if they gave him a chance. He got to work on the job application and wrote what is probably the boldest cover letter ever written. In that letter, he stated about ten specific innovative military projects he could execute and even offered to build one of them if so challenged!
What made his cover letter even more incredible was the fact that in those ten ideas, he didn’t say anything about painting. It was only at the end of the letter that he essentially said, “oh and by the way, I can paint better than anyone you can find.”
In my book, The Journey to Reinvention, I use that story to teach powerful strategies anyone can leverage today to be as bold as da Vinci.
What was the “aha moment” or series of events that made you decide to bring your message to the greater world? Can you share a story about that?
In May of 2020, during global pandemic lockdown, I was laid off by my company. I had thirty days to hand off my work before I would be kicked to the street.
Unfortunately, over 10,000 others were laid off with me and many were older than I was and had been working for the company most, if not all their career.
A dear mentor of mine inspired me to serve these people and prepare them to begin writing the next chapter of their lives and navigating this massive change. I had an idea to launch a mastermind for our remaining weeks at the company and called it the Reinvention Mastermind. Over 700 people joined and attended the calls every other day.
To prepare for those reinvention mastermind sessions, I wrote down a lot of my own journey and the strategies that helped me along the way and the lessons I learned. I also looked for inspiration in other people’s reinvention stories, including my father.
Along the way, I realized, there’s a book here that could serve many more people if I write it and so I began the journey to becoming an author.
Without sharing specific names, can you tell us a story about a particular individual who was impacted or helped by your cause?
I had a client not too long ago that was in a job that he wasn’t fully satisfied in, in fact, he was quite bored and unfulfilled in it. In addition, that job was on the other side of the country from his fiancé. These two major areas of his life that were not aligned with his values, passion, and purpose. He hired me to be his reinvention coach and we got to work on implementing various strategies including getting hyper focused on the most important area of his life that required alignment — his relationship.
Often, what happens is we want to fix everything at once and we end up overwhelmed and don’t fix anything. Getting focused on the most important thing is the equivalent of pushing the first domino that begins knocking down the rest. For him, that domino was his relationship — reuniting with his fiancé and beginning their life together.
With his focus set on that, it only took him about a couple of months to create an opportunity to move across the country and reunite with her. Now, living with his partner, he’s ready to take on the challenge of aligning his career with his passion and purpose. From this place, that challenge is significantly easier, even if still challenging.
The work he does is in education and that of course connects with me deeply because of my experience as a math educator. As he builds his best life and becomes his best self, the students he serves will be better off.
Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?
I think there are few things that can get to the root cause of living a life that isn’t aligned with your values, passion, and purpose.
First is to embrace people’s unique and interesting view of the world. When someone has a response that sounds different or doesn’t match the usual response, we tend to “correct” them. When I taught math, I always invited my students to explain their ideas before I said anything. Often, they had beautifully unique and creative logic that you could never find in a math book. When we embrace those ideas, we all learn and that person starts to move closer to becoming who they really are.
Another thing that can be done is to erase the stigma attached to not attending university or having a university degree. University is not for everyone, especially at the same age in life. Sometimes it’s better saved for later, other times, it’s not necessary at all. By the way, this is coming from someone who teaches at two universities.
Especially given the cost of a university degree, we really need to reconsider all the other unique and beautiful paths there are to success. A degree is not the only way. I became a math teacher without a degree in math or teaching. It can be done.
Finally, regarding the price of a university degree, I think our government can set the standards for what universities should charge for education. It’s hard to pursue your passions and purpose when the opportunities to learn the necessary skills are priced so far out of reach.
Today, public and non-profit higher ed institutions operate like a business, adding as many streams of revenue as possible and pay high salaries to its leaders, however, they ask for donations like a religious institution. You can’t have it both ways. We need government to step in and let them decide, do they want to be a for-profit business or a non-profit and to start getting focused on what really matters — students. It’s time to stop spending money on building new buildings for show and start investing in the faculty that spends time with students.
How do you define “Leadership”? Can you explain what you mean or give an example?
I define it as empowering, coaching, and unleashing talent in pursuit of a clearly defined vision. What I mean is that leaders have an opportunity to unleash the potential of a company by empowering its people to run towards a vision that inspires and makes an impact.
What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.
- I wish I would have known that there are so many paths to success and definitions of success. I pursued one type of success (corporate ladder climbing) primarily because it was the only one I knew. Once I started meeting other people with different definitions of success, I saw a broader and wider world of possibilities!
- I wish I would have known that starting and failing was better than waiting to start until I was ready. I eventually learned this but there are so many things I really could have tried earlier in life like building my own courses, writing blog articles, starting a business, etc. I learned these things later in life by connecting with others who did them and inspired me to do so as well. Today, I work hard to inspire people at any age to try first and figure it out later.
- I wish I would have known that I had limiting beliefs quietly holding me back. It wasn’t until my 30s that I started to become aware of the beliefs that were guiding my decisions and behaviors, often keeping me from pursuing a life aligned with my values, passion, and purpose. There were limiting beliefs I had about success, finances, relationships all pulling the strings in the background. As I started to become aware of them, I was able to intentionally replace them with empowering beliefs. I often wish I knew this earlier.
- I wish I would have known to accept help from the amazing people around me who wanted to help me. I recall one speaker who always offered to support and mentor me. At that point, I partly felt like I wasn’t good enough to follow his advice or maybe not ready enough to do the things he suggested. Ultimately, that relationship slowed evaporated and when I wanted his help, he wasn’t as willing. In another case, I had the support of a CEO who met with me monthly and I didn’t know how to make the most of his support. I didn’t have much prepared and I looked back and regretted not accepting the help I was offered. We are often surrounded by amazing humans who want to help, we must be willing to see it and feel worthy to accept it.
- I wish I would have known earlier in my life to hire a coach. After I finally hired one, I learned first-hand how important a coach is to unleash our best performance. While coaching can seem expensive, there are always coaches that are just getting started and charge less. I used to think coaches were for people better than me and that I had to work to the level that I deserved a coach. I had it wrong because coaches help us get to that level in the first place.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
There’s a quote that was born out of the interviews I did for the book. It goes like this, “reinvention has nothing to do with becoming someone else and everything to do with becoming who you really are.”
This quote has been so relevant to my life because as I walked my journey to reinvention, I was slowly but surely becoming who I really am. Every year my best-self shines a little brighter as I continue walking the journey.
Thanks to this knowledge, I can walk the journey more confidently, knowing that each step of the way I am getting closer to the real me.
Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂
For me, this person would be Cristiano Ronaldo, the professional soccer player. Cristiano has been such a positive influence in my life over the last 5 or so years. His values, ideals, and beliefs are so empowering, and it is by design. He programs his mind with beliefs that empower him to be at his best and this doesn’t just apply to his work as a footballer. He reinvents all areas of his life to create the most fulfilling life he can for him and his family.
Currently, he is going through a reinvention in his career as he moves into the latter stage of his playing career, and I am watching very closely to see what I can learn from him in this moment. If I could have a private breakfast or lunch with him, I would ask him about his journey, his decisions, his habits and offer to help him navigate this next part of his journey to reinvention.
How can our readers further follow your work online?
People can follow me on Instagram and Twitter using my handle, @rogerosorio
I’m also on Linkedin where I share a lot of content on reinvention, www.linkedin.com/in/rogerosorio
You can learn more about me, my ideas, and my business at www.rogerosorio.com
Finally, you can learn about and purchase the book at www.rogerosorio.com/book
This was very meaningful, thank you so much. We wish you only continued success on your great work!
Social Impact Authors: How & Why Author Roger Osorio Is Helping To Change Our World was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.