11 Conversations That Changed My Life

By Jesse J Rogers

Life can become routine. It might be pleasant from moment to moment, but we feel caught. Trapped in a loop. Our life’s sand slowly but surely draining from the hourglass.

Over the long run, it becomes unbearably unfulfilling if we don’t grow. As a snake sheds its skin, we have to shed our previous smaller self. Life is so much richer as an adventurer creating our own story. Here’s mine so far, by the way.

To break a rut and transform your life, a conversation is a powerful catalyst. Conversation offers an inflection point towards something greater, or even just different. This is why leaders and high performers people pay consultants and coaches enormous sums of money. Because it works.

If you feel stuck, what you need is a conversation.

Sometimes what I’ll talk about in this article was a one-way conversation, in the form of a lecture or a book. Sometimes I was involved in the conversation, sometimes I was merely in the audience.

At any rate, I’m going to walk you through 11 of the most crucial conversations and how and why they altered my path.

“My Name is Smeeeagoool”

When I was a kid, my mom and dad used to read a lot of books to me. The one that really stuck out was The Hobbit. This was in the ’80s, long before any of the movies had come out. Still my dad’s voice acting was right there in quality with the sort of work Andy Serkis would later do. He performed for an audience of one. But it mattered.

My dad is such a talented, brilliant guy. But he spent his whole career in a safe, stable engineering job making other people rich. Everything about him was self-taught, he even learned how to design trusses and get them approved. He built an addition to our house with his own hands.

By my early teens, I understood the world well enough to realize that my dad is a person of pretty unusual skill, integrity, and quality. Active in the church, he would routinely speak with ease and confidence in front of thousands.

I’d see Steve Jobs and other visionaries change the world, and although I’m biased, my dad seemed to me like he’s of the same caliber. I once asked him “dad, with all this ability why didn’t you make something really important?”

“I did,” he replied. “I created you.”

“You’re Going to College. Period.”

You might think that this pro-education messaging was coming from my parents, who wanted me to be wealthy and successful. Not so. My dad didn’t get a college degree. As I said, he’s a self-taught engineer. To this day, my parents are still anti-materialistic, pacifist, Bible fundamentalists. College was viewed more as a threat than as an opportunity. It was Satan’s trap, a place that could tear me away from God’s Truth and lead me down the road to sin and fornication.

Little did they know. Unique in Florida State University’s long and storied history as a party school, their son would later go on to be the only person shy and nerdy enough to graduate a virgin. Or at least to publicly admit it.

At any rate, no, it was my 8th-grade algebra teacher Mrs. Drucker who insisted I must go to college.

She was a round, tan, Jewish woman with dark short hair that looked like a helmet. Every day she wore a uniform of sandals, sunglasses, and jogging suits which she clearly never jogged in. Her long fingernails nails were always decorated to match each upcoming holiday. She might sound like an odd-looking character to you, but no one made fun of her. Not about anything. We wouldn’t dare.

This woman had taught in Brooklyn’s juvenile detention centers, and she was tough as nails. She scared the hell out of us. I remember one time when she was announcing the answers to last night’s homework and I was nodding along theatrically while looking down at my blank page. “Jesse. Come show me your paper.”

I didn’t know 13-year-olds could have heart attacks. It’s a miracle I didn’t pass out as I walked to the front of the class.

“I see. From now on you’re going to show me your completed homework every morning, Jesse.” I was the only kid in the class that had to that. But it didn’t matter. I finished it every night and showed her the next morning. I wasn’t going to turn up empty-handed the next day. I would cry over the endless hours of homework because I hated algebra so much. But I did it.

Mrs. Drucker was intimidating. But my goodness did she ever love us. She said she wore sunglasses all the time because “her students are so bright”. I think on the last day of middle school that the sunglasses hid her tears as she wished us goodbye. We kids hadn’t known to wear sunglasses that day.

She said I had to go to college. So I did.

“I Know You’re Not In the Class. Just Come Anyway.”

It wasn’t easy for me to make friends in high school. Probably a weird side effect of playing computer games 7 hours a day, or something.

But on the bus, I did make one friend named Manny. We bonded over my magnetic chess set and trying to ignore the fact that we had faces covered in acne.

Eventually, I moved schools, but Manny and I stayed in touch. One day in Junior year, he invited me to a study group to work on a project for Mr. Lott’s history class. I thought that was kinda weird because I wasn’t in the class.

“Yeah, I know you’re not in the class. Just come anyway. You like history, and I think you’d get along with the group,” Manny said.

It’s not like I was doing much of anything else.

I guess I was helpful on the project because Manny was right. I did click with that group. Saying “yes” to that conversation changed my life.

We ended up becoming inseparable for the rest of high school. 23 years later, I’m still friends with all these guys and we still talk regularly except Jose. If you’re out there reading this Jose, I miss you bud. Let’s catch up.

“You Seem to Like Math, Why Not Check if They Need Tutors”

After high school, I went to Palm Beach Community College (now a state college) before heading off to FSU. The friend group that I had finally made went their separate directions to other schools. I was back to heavy gaming.

I knew I needed a change and figured math is something I’m pretty good at now, so maybe I should join the math club that my teacher Mrs. Rosenthal mentioned. It could be a great way to meet people.

I ended up not only checking it out but becoming the president of the club. Calm down. That year, the math club was just me. No one else came to the meetings.

Still, “Math Club President” got me the job that would come to change everything and define my career. I became a tutor for the math area at the Student Learning Center, which I now run.

“Here’s the List”

As a young tutor, it was gratifying to have people twice my age learning from me. But I knew I had a lot to learn from them too.

Because I was receptive and coachable, I got into a conversation with a middle-aged student who had been serious about self-improvement and had first built a successful career first before coming back to college to complete his degree.

At the end of our conversation, he handed me a list of books that I needed to read. I don’t remember what most of them were, but I remember some of the authors: Robert Kiyosaki, Dan Baker, and Tony Robbins.

The practice of self-improvement and the influence of these and many more authors have revolutionized the quality of my life over time. I rarely saw the benefits immediately, but the slow bending towards daily incremental improvement has yielded undeniable results. Including the fact that I’ve become a writer who can force myself to sit down and write stories like this one as part of a daily habit!

I hope to do the same that the student did for me by sharing books, conversations, and lectures from authors that I know can help you.

That’s essentially what this article is intended to be — me in turn handing a list to you. After decades of looking for excellence in leadership and self-improvement, here are some of the best virtual mentors that I can fully recommend.

“Hi, I’m Calling About an Internship Opportunity.”

Brian Harbin has a slight southern accent and a friendly voice. When he called me asking if I had already secured an internship yet, I realized that it was a problem for my answer to be “no”. The job market is competitive. I need an edge.

In sales-speak, he identified a pain point and helped me to see that I had a problem. He had a solution.

He sent me to the sales presentation of another Brian — Brian Ross. Somehow I knew right away that B. Ross was the guy I needed to follow. He spoke confidently, and what he was saying made a lot of sense. I ended up selling educational books and software door to door in Ohio.

It was hell. I worked 70–80 hour weeks and ultimately earned the equivalent of about $1.5 an hour.

So naturally, I went back to do it again the next summer as a manager.

Look, I know that sounds odd to voluntarily and knowingly sign up for the discomfort. But the things that are worth doing tend not to be easy. I am so grateful for having had the experience of this “business boot camp”. I wasn’t the same person going into it that I was coming out. The first full-time job that I got at an unusually young age (for that position) of 25 — the dream job that I am still in — I owe to the transformation that this internship provided me.

I should also mention that Brian Ross was the first real fan of my writing. At our end of summer debrief, he took from his pocket the long, meandering weekly journals I had written to him, unfolded them, and repeated a few of his favorite lines that he had highlighted. He told me, “Jesse, you have a special talent. You’ve got to keep writing.”

But I didn’t. Not until the pandemic. For a long time, I let my talents lie fallow.

“Does God Exist?”

I had only been exposed to one perspective in the Bible fundamentalist religion that I was raised in after rejecting that perspective, it was very difficult to construct my own.

An inflection point in my development was a debate between atheist Sam Harris and Christian apologist William Lane Craig.

View it here.

I would later come to realize that this debate wasn’t actually that great. The participants mostly talked past one another. But back then, it did give me quite a bit more perspectives on how to view reality and God than what I was raised with.

Even more helpful to me has been a philosopher and scholar of comparative religion named Alan Watts.

Interestingly, Watts is also admired enough by the creators of the popular Comedy Central show South Park that they paid this tribute to him.

“Yes”

After about 8 months of dating, I asked my best friend if she wanted to spend the rest of her life as my wife. Said “yes”. The years that followed have been the happiest in either of our lives.

Our adventure deserves its own set of stories so I won’t elaborate much here.

I’ll simply give the advice to not wait until your life passes you by to tell someone how important they are to you.

“It’s Gotta Go.”

Sam Ovens is a polarizing figure who some people view as a “fake guru” and others view as a guide who is responsible for leading them out of the wilderness and into a life they never imagined. I don’t think either perspective is close to the full truth, but my experiences put me closer to the second category.

That’s because for so long I’ve been a “smart” person living an extremely irrational life. The ability to persuade people towards living better is priceless, even if the knowledge being conveyed isn’t necessarily “new”. Motivation doesn’t always require telling someone something they didn’t already know.

See, even though I knew better, once I got married I still regularly spent at least 5 hours per night gaming along with almost the entire weekend. How does that make sense? How does that help me? But that was my reality.

This ad shamed me out of gaming and reminded me in a powerful way that I’m capable of doing more. Yes, as weird as that sounds, it’s the truth. An ad turned out to be the catalyst that changed the course of my life. I uninstalled all my games and got back to work on reading, learning, and studying successful people after a very long hiatus.

None of the people that I want to emulate spend 5 hours a night playing computer games. To get the results of your heroes, you have to do the things they do.

(note: I am not affiliated with Sam Ovens and I did not buy his course which was out of my price range, so I am unable to review it).

“There’s a War on Normal People”

I don’t think of myself as a very political person, but the polarization of this era has become unavoidable and all-consuming.

Around 2019 one of my friends turned me on to a possibility, however faint, of moving beyond the trench warfare and acrimonious name-calling of partisanship and towards a more solution-oriented approach.

I had a listen and was fascinated by this conversation between Andrew Yang and Ben Shapiro. People with opposing views usually tear each other down and attack each other, but here was a leading conservative pundit sitting down with a serious Democratic contender (who got much further than most had expected).

After reading Andrew Yang’s case for his platform, I became a vocal member of Yang Gang. As heartbreaking as it was for me when Andrew Yang dropped out, I can now see a way forward for America towards coming together and overcoming our divisions. I believe it starts with a Biden presidency, but that is only the beginning. It will be up to each American to make our country better through how we treat each other in our daily lives.

“Mr. Rogers, this is Candy Magic!”

One of the transformations that my Yang Gang conversion brought about was exposure to lots of new and interesting people. Included among too many people to name are Fred Eder of Fred’s Front Porch, and Jenner Zeno of the Mind Wave Podcast. We each formed Facebook groups and podcasts to broadcast our message of hope and inclusion. Through that, I made a friend named Nick Argall and eventually found Medium. The great work being done by ILLUMINATION eclipses my own humble attempts, so instead of recreating the wheel, I’ve become a regular contributor.

I look forward to interviewing some of Medium’s authors and editors for conversations about writing, personal growth, education, and as of recently, business and real estate.

If you’d like to be included in my interview queue, drop me a line at [email protected]

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