Lessons in Leadership

Written by Jeremy Inglesi Jr.

Leadership means different things to different people, and I think it’s important to start there. Some see it in titles or positions. Others in strategy or influence. I tend to think in terms of fundamentals. To me, leadership is the ability to take action — especially when no one’s telling you to.

I wasn’t born into wealth or privilege. I was raised by a single mom who worked hard, but money was tight. I didn’t get an allowance. When I wanted something — like a little spending money — my options were limited. I remember one day having the idea to take my mom’s lawn mower and start knocking on neighbors' doors, offering to mow their lawns for a few bucks. I quickly learned the value of stepping out on my own. Adults were happily putting cash directly

into my hands. That feeling — of creating opportunity for myself and being rewarded for it — stuck with me.

Lesson #1: Leadership starts when you stop waiting and start acting.

No one told me to knock on doors. No one gave me permission. I saw a need and filled it. That simple decision taught me more about leadership than any classroom ever could. Apparently, this mindset was so deeply embedded in me that sometime between sixth and eighth grade, I told my mom she didn’t need to worry about paying for my college tuition — I was going to work hard enough for a college to pay me to play for them. In 2010, about five years later, I earned a full athletic scholarship to Elon University in North Carolina.

But my path didn’t follow a straight line. In 2012, I dropped out of college and hitchhiked across the country — from Tennessee to Florida to California, then on to Mexico and Guatemala.

That chapter of my life changed everything. I did things I never thought I’d do — psychedelics, looking for food in dumpsters, and sleeping in public parks. At the end of that journey, I met a truck driver who shared the Gospel of Jesus Christ with me. That encounter led to a relationship with God that truly changed my life.

Looking back, it’s clear how much stepping into the unknown shaped me. I often think about something Steve Jobs said in his 2005 Stanford commencement speech — that you can’t connect the dots looking forward, only looking back. That idea stuck with me.

Lesson #2: Leadership requires courage to step into the unknown.

When I dropped out, I wasn’t fearless. I was uncertain and uncomfortable. There was a good chance that this could be the biggest regret of my life. But action doesn’t require the absence of fear — it requires moving forward anyway.

In 2017, I made another leap. I quit my job at Chipotle to start a business. I had no formal training, no “network,” and no backup plan. What I did have was conviction and the courage to take action. Nearly a decade later, that business is still running and has moved with me across multiple states, from Charlotte, North Carolina to South Texas.

This didn’t happen because I had everything figured out from the start. It happened because I kept showing up — learning, adjusting, and taking massive, imperfect action.

Lesson #3: Leaders don’t wait to be ready. They act, learn, and adjust along the way.

I didn’t know how to run a business when I started. But I knew how to take the next step, and that’s what matters most.

Over time, I’ve come to reject the polished, curated versions of leadership that social media tends to glorify. Ideals are nice, but they don’t help much in everyday life. Real leadership is messy. It’s instinct blended with effort, faith mixed with failure. It’s forging a path where there isn’t one. It’s humbling yourself when you’re wrong — and realizing that someone “less qualified” may have the right answer.

It’s also about resilience. When your first plan fails, you get up and try again. When an easy option presents itself but goes against your values, you choose the harder route.

That’s why I believe this:

Leadership rarely arrives with ceremony.

More often, it happens quietly — in a split second, in a private moment when

someone decides:

I won’t wait for someone else to fix this.

I won’t leave this to chance.

I’ll go first.

That decision is where leaders are made. Not through position or power, but

through the simple, courageous choice to move.

Lesson #4: Leadership is a decision, not a title.

In one instant — in that private decision to take responsibility — a leader emerges.

But making that choice doesn’t mean doing it alone.

It simply means being willing to go first — to take responsibility before it’s assigned, to step forward when others hesitate. Support often follows action. In my case, I’ve been fortunate to have incredible people in my corner — family, mentors, and friends — who stood with me after I stepped up. Leadership may start with you, but it’s sustained by those who walk beside you once you move. I’m not offering my path as a blueprint. I’m simply sharing what I’ve learned: If there’s something inside you — a drive, an idea, a calling — follow it. Even if the path isn’t clear. Even if you’re

scared. Even if you don’t feel ready. Especially then.

Because leadership isn’t about being certain.

It’s about being willing.

And it begins the moment you decide to move.

Jeremy Inglesi Jr.

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