Vulnerability — how open and honest do you get to be on a daily basis? Authenticity — how much do you get to be yourself on a daily basis? Balance — how well do you balance physical, personal, and professional development (the “3 Ps”) Joy — how much joy do you experience on a daily basis? Energy — how energized do you feel by what you do every day?

Have you ever noticed how often we equate success with more? Whether that’s more products, more profits, more activities or more accomplishments, we buy into the belief that we have to do more to have more to be more. And that will sum up to success. And then along comes The Great Resignation. Where employees are signaling that the “more” that’s being offered — even more pay, more perks, and more PTO — isn’t summing up to success for them. We visited with leaders who are redefining what success means now. Their answers might surprise you.

As a part of this series, I had the distinct pleasure of interviewing Jeff Lerner.

Prior to “The Great Resignation” there was perhaps no one person who inspired more soon-to-be entrepreneurs get control of their future and reshape their life than Jeff Lerner. From humble beginnings as a jazz pianist with half a million in debt to becoming a serial entrepreneur building multiple businesses to over 8 figures and landing multiples times in the Inc 5000, Lerner now leads ENTRE Institute, the fastest growing online education company in the world that is teaching more than 200,000 aspiring entrepreneurs how to start and build their own business.

Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today?

I’ll pick one that explains a lot about who I am today and, in particular, my crusade (axe-to-grind?) around disrupting education.

My sophomore year of high school I got accepted into a program called School Year Abroad (SYA) and was going to spend my junior year in Barcelona, Spain. I had spent hours filling out the application, writing essays and collecting teacher recommendations, and felt really good about being accepted. I had worked hard and believed the change-of-scenery would be good medicine after struggling with typical teenage issues — what you might call angst or even mild depression. Well, I never made it to Spain and in fact I never even finished my junior year thanks to a bizarre sequence of events that forever changed how I see the world.

Not long after being accepted to SYA I was transitioning between classes one morning. We had 10-minute breaks between classes and I had a math test coming up so was really trying to be on time, but also knew that teacher was pretty relaxed and if I was a minute or two late it’d be okay. Even though it was 26 years ago, I remember the events of that 10-minute break as if it happened yesterday because I ended up having to recount them dozens of times. The break went like this — I went by the Dean of Student’s office to ask him a question about a project I was doing, then I went to the restroom, then I bumped into my old 6th grade math teacher in the hall and chatted with her for a minute, and by the time I got to class I was at least 5 minutes late. The teacher wasn’t there though, he had handed out the test and left the room, trusting the students to self-police and not cheat, so seeing the stack of blank tests on the teacher’s desk I took one and sat down to take the test. Even with my late start I finished in plenty of time and upon turning in my test the teacher, who was back in the room now, asked me why I had been late. I told him “I had to stop by the Dean’s office during the break and got running behind.” All seemed well. Then the next day I got called into the Dean’s office during morning announcements. The Dean explained that the math teacher had come by his office the previous afternoon to confirm that I had in fact gone by his office before class and that that’s why I was late. The Dean was concerned that I had left his office with enough time to be on time to class so he wanted to know why I had actually been late and why I had blamed it on visiting his office. I explained that visiting his office had used up the first few minutes of the break which then made me late because I had to use the restroom, which took a few extra minutes and then I unexpectedly ran into my old teacher who struck up a conversation which I did my best to end quickly without being rude. When asked I had only reference my visit to his office and left out the full story because he didn’t seem that concerned plus I had been a bit shy with details because the majority of the break was actually me using the restroom. I certainly had nothing to hide about my trip to the restroom or a visit with my old teacher which was easy to substantiate, I had just given a flippant answer that left out some details. Well. what happened from there was straight out of a Franz Kafka novel. I was written up for an “honor code violation” for lying about my whereabouts, cheating (though it was never explained how being a few minutes late to a test gave me any sort of advantage or opportunity to cheat), submitted to a “trial” by a “jury” of my fellow students in a surreal proceeding where several faculty members (none of whom knew me and had never had me in a class) urged the students to “convict” me, which ultimately happened. I was suspended for 3 days and to top it off they notified the School Year Abroad program that I had been found guilty of breaking the school’s honor code, at which point my year abroad offer was revoked.

You can imagine how livid both my parents and I were but there was no un-ringing the bell, the door was closed. Fast forward to that summer and after having finished out the school year with a sour disposition (though still good grades) the school let my parents know in July that I was not invited to come back for my junior year. I was forced to transfer to a new school where I knew no one and halfway through my junior year, in total disgust with the educational system, I dropped out of high school altogether to become a musician.

Of my many takeaways from the whole experience the most impactful was seeing how easily my fellow students had been pressured into “convicting me” by teachers and school administrators even though there clearly was no “crime” or malicious intent. Although the “jurors” were prohibited from discussing the matter with me directly I heard from mutual friends that some of them had shared the ridiculousness of the proceedings and admitted they had “convicted” me to keep themselves out of disfavor with the administration and teachers. I haven’t told this story in a decade but as I’m telling it I can feel the indignation welling up inside me and I suspect a lot of my fervor for setting people free financially is about eradicating the moral compromises that happen when people depend on institutional authorities (schools, employers, banks & lenders, the government, etc.) for their survival.

We all have myths and misconceptions about success. What are some myths or misconceptions that you used to believe?

That it would have lots of build-up and then happen really fast — like a dam breaking. Instead, it’s more like getting in shape — always hard work and results come in the form of small incremental gains that seem to take longer than they should. Also, I have been surprised by how little success has had to do with specialized skills or technical ability. Of course it’s important to be “good” at whatever we do but that by itself doesn’t close deals or win jobs. The softer and more general skills were what I lacked for a long time — knowing how to listen, how to validate and encourage, how to set people at ease, how to spread contagious enthusiasm, etc. — those were the breakthrough skills for me.

How has your definition of success changed?

Success used to be about net worth. I thought once I was financially free and had (forgive the term but it sums it up pretty well) “FU money” that I would be successful. Now I measure success by 3 things in this order: how I feel physically, the time I get to spend with people close to me, and the impact my work has on the world.

The pandemic, in many ways, was a time of collective self-reflection. What changes do you believe we need to make as a society to access success post pandemic?

The pandemic shined a light on an issue that’s been burgeoning under the surface in society for a generation — our declining self-reliance. We are so dependent on others now for not only our incomes but our physical, emotional, and mental well-being that it’s weakened us as a society. When things got tough, who did we look to? In tough times past we looked to ourselves or those around us but nowadays we look to the government or the medical establishment. This is a chilling sign of where we’re headed — dependency always breeds hostility.

What do you see as the unexpected positives in the pandemic? We would love to hear a few of your stories or examples.

There has probably never been so much economic “creative destruction” in one year ever. Much that was outdated got upgraded. Businesses that drive progress got rewarded, and legacy businesses got deprecated faster than they would have otherwise. But this is good news. To fix the fundamental challenges our society is facing right now we have to get better at tolerating discomfort — our obsession with being comfortable is a root cause of much that ails us. As it is said: hard times create strong people, strong people create good times, good times create weak people, and weak people create hard times. During the pandemic we were forced to accept some discomfort and in general we’ll be better for it. We needed to toughen up a bit.

We’re all looking for answers about how to be successful now. Could you please share “5 Ways To Redefine Success Now?” (Please share a story or example for each.)

5 modern KPIs to measure success:

Vulnerability — how open and honest do you get to be on a daily basis?
Authenticity — how much do you get to be yourself on a daily basis?
Balance — how well do you balance physical, personal, and professional development (the “3 Ps”)
Joy — how much joy do you experience on a daily basis?
Energy — how energized do you feel by what you do every day?

How would our lives improve if we changed our definition of success?

Less than 10% of people self-report as “very happy”. This number would change dramatically because we would be living according to our design. We were endowed with higher faculties so we could dwell in them not numb them.

What’s the biggest obstacle that stands in the way of our redefined success? And what advice would you offer about overcoming those obstacles?

Fear that we aren’t enough. In the modern world it’s become unfashionable to believe that we as individuals are great and capable of great things. We are taught to lean on the collective and depend on the tribe (or school or employer or government or other institution). We could all be so happy and fulfilled if we just prioritized the things we actually care about instead of the things we were taught to care about by others who were as scared then as we are now.

Where do you go to look for information and information about how to redefine success?

I agree with Stephen Covey that after World War I society shifted toward a personality ethic of success rather than a character ethic of success. The game became all about the player rather than the values of the game itself. I like “old wisdom” — sources that are grounded in principles that have endured hundreds of years. Take a book like “Start With Why” by Simon Sinek. It’s great not just because it’s true but because it’s always been true. It doesn’t just tell us how to be it helps us understand who we are. Those are the sources I try to find.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment 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, she or they might just see this if we tag them.

Elon Musk. I don’t see him as a God or an icon like so many of his hero-worshippers, nor do I presume to know him at all based on what we see in the media. I only really know one thing about him for sure — he takes large risks that he mitigates by betting on himself — pretty much the opposite of what I see most in society doing. I’d like to ask his advice on how to help spread the ideas of self-reliance and asymmetrical risk to a population that is veering hard the other direction.

How can our readers further follow your work online?

@jefflernerofficial on all the major platforms

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. We wish you continued success and good health.