A Conversation with Mike Posner on Gaining Success, Dealing with Jealousy, and More

Mike Posner is a Grammy nominated singer-songwriter, poet, rapper, and music producer.

I met Mike recently on Instagram after he heard me on Tim Ferriss’ podcast.

He joined my Noah Kagan Presents podcast to share his incredible journey from growing up in Southfield, Michigan to becoming a world-famous artist (and all the lessons for success he learned in-between).

Even uber-successful people run into problems, have fears, and deal with frustrations. Mike shared fascinating insights on what he still struggles with, and how he maintains perspective and priorities alongside his growing fame and fortune.

This episode is jam-packed full of insights and lessons for budding creatives and artists, seasoned entrepreneurs, or anyone trying to find their passion.

Listen as Mike drops some #knowledge from his journey, including the importance of change (and why you should embrace it), the vast difference between success and popularity, what it’s like to meet Jay Z, and how to combat jealousy and live your own life.

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Mike just released a new album called Mansionz, plus a new poetry book called Tear Drops and Balloons, so this is the perfect time to hear about Mike’s creative process, how he’s dealing with success, and tons more.

In this episode, you’ll learn:

• What Mike Posner’s creative process looks like
• How Mike got a record deal — while studying full-time at college
• Why Mike is constantly reinventing himself (and the importance of change in life)
• How to create what you really want vs. what others expect of you
• What it’s like to meet Jay Z
• How to find inspiration (and unlock your max productivity)
• Why he schedules time to learn — and blocks out time to explore new ideas
• How to fight jealousy
• The vast difference between success and popularity
• Why he decided to distribute his music for free in his early days
• Plus much more…

Throughout this episode, there were a few key themes that really stood out to me and I’d love to highlight a few of these below:

1. Mike Posner’s Long Road to Success
2. The “More is Better” Fallacy
3. The Importance of Empathy
4. Being Happy When You Have Nothing

BONUS: Success tips from 53+ other famous celebrities, entrepreneurs, and more

Mike Posner’s Long Road to Success

“I remember having these delusions of grandeur and becoming the white Lil’ Bow Wow.” (Click to Tweet)

Seeing young artists skyrocket to insane levels of popularity and success early in their careers led Mike to envisioning his own instant success.

But success doesn’t usually happen overnight.

Mike’s journey to his first record deal and hit song took more than 10 years of dedication:

• At 8 years old Mike began writing raps
• When he was 13, he started making beats at his Mom’s computer
• In his senior year at high school, he released his first CD “Reflections of a Lost Teen” and sold it out the trunk of his car

Just before Mike started at Duke University as an 18-year-old, his close friend Big Sean was signed to Kanye West’s GOOD Music record label. Mike was a bit jealous… but if Sean could do it, Mike thought he could too. Success seemed more realistic.

Motivated and focused, Mike would spend college weekends and nights making beats, recording verses, and perfecting his flow.

In 2010, at age 22, Mike had his first hit. “Cooler Than Me,” a single from his first album jumped to number 10 on the Billboard Hot 100 chart.

Too often, people fall into believing the “overnight success” trap. People expect:

• Their startup to be successful in weeks or months (instead of the years of failures it usually takes)
• A Director-level promotion in their early 20s
• Fame, fortune, and recognition immediately

Here’s the truth: What’s valuable never comes easy.

As an early employee at Facebook, I saw behind-the-scenes what success is like (and then I saw it again as employee #4 at Mint.com). The outside world has the illusion we just “made” it at both companies one day — but in truth, we were grinding in the background for years.

We faced a lot of failures, ran a lot of experiments, and had a little luck. This is the real reason for success.

When you have an idea or passion you want to pursue, you have to commit for the long term to achieve it. For example, I’ve been blogging here on OkDork since 2005 — and here’s one of my very first posts to show you how long it can take.

What are you passionate enough to commit to for the next 10 years?

The “More is Better” Fallacy

Being close friends with one of the world’s hottest rappers, Big Sean, doesn’t come without its challenges. And during our conversation Mike touched on fighting jealousy.

At age 18, as Mike was heading to Duke University, Sean got signed to Kanye West’s GOOD Music label. This provided Mike with one of life’s most important lessons on how to combat jealousy.

Seeing those closest to you succeed can put you in a tough spot. “I get jealous of friends all the time,” Mike told me. “It’s the first emotion that comes up a lot of times.”

It seems that no matter what level you reach in life, jealousy can always appear.

So how do you counter jealousy?

Mike believes almost all jealous feelings are related to the fallacy that “more is better”:

• You see a friend with a nice new car and you want one
• Your sister buys a big house and you want a bigger one
• Your friend (who definitely isn’t as smart as you) is making more money

The reality is: more isn’t always better.

When someone close to us achieves something, even if our gut reaction is to be jealous, it’s probably a good for us in the long run.

Take Mike and Big Sean for example: when Sean blew up, a song feature or shoutout could elevate Mike to new levels of success.

To get over feelings of jealousy, flip the situation and see how it can help you.

The Importance of Empathy

At 22, with his first hit single “Cooler Than Me” under his belt, Mike had a revelation about fame: We don’t actually see famous people for who they are. Instead, we idolize these people to become who we want them to be.

For example, Mike shared a story about attending an NBA game to see his Detroit Pistons take on the Cleveland Cavaliers:

I remember this one player, Drew Gooden, he was very antagonistic. He’d rile up the crowd and I remember sitting there and saying: “I fucking hate Drew Gooden.” Right when I said it, I felt terrible. I’d just started to be known for my music at that time and I realized that he was a real person.

Empathy has become more important to Mike as his career grows. Once you become known for something, people assume you’re the same exact person you are on stage. Or in the interviews. Or at your office. But we ALL have different hobbies and interests.

Who we are at work or in our business is only one flavor in a whole dish. There’s plenty more depth to people than what we see online.

I think the same is true of my podcast and OkDork. I try to be vulnerable in as much as I can, but you still only get to see a small percentage of who I really am through my podcasts, videos, and posts.

Empathy is an often overlooked factor in success.

Many entrepreneurs look for a quick fix to solve problems. But, with true empathy you can:

• Step into your customer’s shoes and build better solutions than your competitors
• Build stronger, lasting relationships with people in your network
• Feel happier and more peaceful knowing we all share similar issues, problems, and fears

The next time you’re writing a cold email or responding to an angry customer, embrace empathy and put yourself in the other person’s position. It’ll make a world of difference to how you deal with the challenge.

Being Happy When You Have Nothing

“When you’ve experienced real highs, even the normal can feel low.” (Click to Tweet)

Between his two waves of popularity, first in 2010 with his hit song “Cooler Than Me” and now with “I Took a Pill in Ibiza,” Mike found it really tough to adjust to life without being somewhat famous.

After “Cooler than Me,” Mike confessed his self-identity was wrapped up in being popular.

Every day, Mike had to see how many Facebook Likes his posts were getting, how many Twitter followers he had. He was used to free clothes, complimentary drinks at bars, being lauded when out in public…

But fame comes and goes for everyone. Eventually, even the most famous people are forgotten.

Gradually, as Mike’s popularity waned, he was receiving less social media notifications, no free meals, no free clothes. Everything dried up.

This was a difficult time for Mike:

Instead of my shimmying out of a snakeskin and into a fresh one, it felt like someone was ripping the skin off me and everything was out of my control. When I look back on it, though, this was one of the best things to ever happen to me. It forced me to realize who I am without all these things.

Mike learned to embrace these changes and his “new” self. He took all his expensive toys, and got rid of them. He sold his:

• Porsche
• Million dollar house in the Hollywood Hills
• Limited-edition Jordan sneakers

He then took his 1993 Dodge van, put a bed and his recording equipment in the back, packed a few clothes and hit the road. “I wanted to turn the volume up on losing stuff and see if I could still be happy.”

Through the ups-and-downs, Mike realized he isn’t defined by the things he owns or what others see.

It’s easy to fall into the trap of defining ourselves by how much money we have, what company we work for, the friends we hang out with.

Honestly, I’m guilty of this, too. But Mike’s story is a reminder we shouldn’t define ourselves by external factors of success.

After all, like Mike realized, it comes and goes.

Want to listen to my whole conversation with Mike Posner? Check out the recording below:

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Challenge: If you had a rap name, what would it be? Mine’s “Rabbi Can’t Lose.”

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