“Study the greats and become greater.”

- Michael Jackson

Last week I saw the biopic Michael, and I couldn’t stop thinking about the role courage played in his massive success.

And when I say massive, I mean, massive.

To be clear: Michael Jackson is the biggest entertainer of all time, and it’s not even close.

Don’t believe me?

Let’s look at some of the facts:

It's easy to look back at Michael Jackson and assume his greatness was inevitable.

But that's not true.

At almost every meaningful crossroads of his life, fear had a chance of stopping him, and he chose to act anyway.

Greatness wasn't a gift handed to him; it was a series of courageous decisions he kept making.

Scene after scene, there was a moment where, if Michael had let fear win, none of the rest would have happened.

No moonwalk, no Thriller, no global icon, no reason for anyone to be making a film about him 40 years later.

And it all started with the courage to believe.

One of my biggest critiques of the movie is it left out the letter that he wrote to himself, in November 1979, while on the Destiny Tour.

"I want a whole new character, a whole new look. I should be a totally different person. People should never think of me as the kid who sang 'ABC' or 'I Want You Back.' I should be a new, incredible actor/singer/dancer that will shock the world. I will be magic. I will study and look back on the whole world of entertainment and perfect it, take it steps further from where the greats left off. I will be a perfectionist, a researcher, a trainer, a master."

Sit with the context for a moment.

He was just 21 years old.

Notice he didn't write I hope to become, or I'd like to be.

He wrote, "I will be.”

“I will be magic.”

That sentence is the foundation of everything that followed.

He fully understood the magic of believing.

He knew that our levels of achievement will never exceed our levels of believement.

He had the courage to believe.

Here are 5 more ways courage played a role in him becoming the G.O.A.T.

1. The courage to go solo against Joe.

Joe Jackson, Michael’s Dad, was the visionary, the manager, the disciplinarian, the engine that took five kids out of Gary, Indiana, and put them on the stage of the Apollo. So going solo wasn't just a career move; it was a betrayal of the man who built him. When Michael chose Quincy Jones to produce Off the Wall over his father's preferred team, he was choosing his own ear over Joe's authority, and when he kept choosing Quincy for Thriller, that choice became a pattern. The fear of disappointing the parent who shaped you, walking out on the deal that made you possible. That’s real. That requires courage.

2. The courage to make Beat It.

In 1982, Black artists weren't supposed to make rock songs. Rock was reserved for white artists and gatekept by executives at radio stations and MTV that had rigid opinions about musical categories and who got to play what. Michael told Quincy Jones he wanted to write "the type of song I would buy if I were to buy a rock song," and the two of them called Eddie Van Halen, the most famous rock guitarist in America, and asked him to play the solo on a song for a pop record. Eddie thought it was a prank call. Both had to face real fears. The fear at that your fans won't follow you. The fear the rock crowd won't accept you. The fear you'll fall through the cracks and lose both. The safe play was always to stay in the lane that was already working. He didn't take the safe play, and Beat It won Record of the Year and Best Male Rock Vocal at the 1984 Grammys, the first time a Black artist had ever won in a rock category.

3. The courage to do the moonwalk LIVE in front of 47 million people.

In March 1983, Motown was filming its 25th anniversary television special, and Michael was invited to reunite with his brothers. He initially said no, until Berry Gordy himself came to him personally and asked. Michael said yes on one condition: he would do a solo spot, and he would perform "Billie Jean." The producers lost their minds. Billie Jean wasn't a Motown song, and the whole point of the special was the label's old hits — Marvin Gaye, Stevie Wonder, and Diana Ross had all been told no new material. Michael was a 24-year-old asking for an exception nobody else was getting. He kept asking, until they said yes.

He’d been practicing the moonwalk in his kitchen for weeks, and had never done it in public. He debuted it that night, live, in front of 47 million viewers — including every artist he'd grown up idolizing, sitting in the front rows. The fear is obvious: you miss, you bomb in front of the room that made you, you cement the wrong story for the rest of your career. He landed it, and the world's relationship to dance shifted in the span of two and a half seconds. He cried backstage afterward. Not from joy, but because he'd wanted to hold the toe stand longer. The cost of being the person from the 1979 manifesto is that even the breakthroughs are never enough.

4. The courage to ask for the MTV phone call.

That same year, MTV wasn't playing Black artists. The "Billie Jean" video was finished, the song was #1 on the radio, and MTV still wouldn't put it in rotation. Michael walked into the office of Walter Yetnikoff, the president of CBS Records, with his lawyer John Branca, and asked for one thing: get my video on MTV. Yetnikoff told him it wasn't possible. Michael said, "Please try harder."

That sentence is the whole thing. A 24-year-old Black artist, in 1983, sitting across from one of the most powerful executives in the music industry, simply refusing to accept the answer. Not yelling, not begging, just asking again, more directly, until the man across the desk picked up the phone. Yetnikoff told MTV that if they didn't put the video into heavy rotation within ten minutes, he would pull every CBS artist off the network and go public about why. The video aired. Then Beat It. Then Thriller. The color barrier didn't break by itself.

5. The courage to end it on stage in front of his family.

On December 9, 1984, the Victory Tour, reunited all the brothers on stage. Michael joined the tour reluctantly because his brothers needed the money. It was his last consolation to his father and brothers. At the end of the show, he stepped to the mic and announced that this would be the last time they would perform together. The European and Australian legs of the tour were cancelled in real time.

His family found out the same way the crowd did.

Boom. Metaphorical mic drop.

In honor of Mother’s Day I want to wish a Happy Mother’s Day to all the moms and give a special thank you to my mom, for her sacrifice, love, support and dedication.

Love you, Mom! Happy Mother's Day 😘

Here's your reflection for the week:

Reflect on this quote.

“Our levels of achievement will never exceed our levels of believement.”

Sit with it and pay attention to what immediately comes to mind. There’s something there.

Here's your challenge for the week: Write your own manifesto

Between now and next week find some time to draft a one-page manifesto for the version of you that doesn't exist yet. First-person. Present tense. Specific. Put it somewhere you'll see it daily. Have the courage to dream and believe.

With courage,

Jonathan