Big Sean on Dreams and Fear

It was recording artist Big Sean’s birthday and he was performing at WeDay, an event to honor the good work young people are doing in their communities and around the world and I had a chance to catch up with him and hear more about the work he’s doing.

Before performing, Big Sean talked to the audience about the importance of community service and volunteering. Growing up, he didn’t have much but his family always made sure they emphasized the importance of giving back. Regardless of where you are from, you have something to give. He talked about donating food and clothes to local shelters and how much those small acts stuck with him to this day.

After the event, I got a chance to talk to him about his upbringing he mentioned on stage and more. When he made his way over to me, I embraced him with a hug, happy birthday and hello and we talked about his fears, his life, his career and his grandma.

When I asked how he was at 14 or 15, he said he was ‘constantly worried’ and worried about the wrong things, he said he was worried about ‘having the right pair of shoes and things that would not matter later in life.

What changed?

One day, back in his hometown of Detroit he was out cashing a check for $200, what he made from his job at the time. He mentioned how much that check meant to him and how much it also pushed him to want to pursue something larger, ‘it was a lot of money to me at the time, but I knew there was more out there for me.’ ‘While he was out cashing the check his friend who was familiar with the the local radio station gave him a call. His friend told him record producer and fashion designer Kanye West was in town and suggested if Sean made his way over to the radio station he was at and rapped for Kanye, Kanye would sign him to his record label.

Big Sean was an aspiring MC at the time and had dreams of becoming a well-known rapper, but he still questioned his friends’ suggestion. He thought his friend was crazy and hung up the phone, but something in his gut kept biting at him. ‘Just go,’ a voice told him.

He picked up the phone, called his friend back and ran to the radio station.

He made his way through the door and tried to get to Kanye several times with fail. Then, the staff at the station let Big Sean know where Kanye would be leaving the station and he made sure he was positioned to see him once again before he left. He finally got to Kanye, tapped him on the shoulder and rapped for him. He said, ‘I’m an aspiring MC, can I rap for you?” After some hesitation, he agreed and the rest is sort of history and a great journey.

He was a teen at the time, 17 to be exact. Reminiscing he said, ‘I stuck to my gut. Something told me to try it.’ “Like I said, you never want to look back on your life and think you could’ve, would’ve, should’ve done anything,” he added.

His advice? Trust your gut.


If you want something, go after it.

And focus on the better things in life, things that matter, your career, your family, your ambitions.

If there is fear in your heart, he suggested:

“Never let fear hold you back, use it as motivation, use it as something to break through.”

It is better to have tried and failed then to look back and wonder how things would’ve been.

My takeaways?

Sometimes we wanna to break free from our jobs, and take a risk but we’re afraid to look silly. Maybe we fear what others may think of us, or maybe we fear our well being and security? But if something brings you to life, if there is still something in your heart you want to do, I urge you to do it because one day, the fear won’t matter. Looking back on your life, you will care more about the journey, no matter how scary or silly it may have been. The adventure will matter, no matter how embarrassing, hard or hurtful it may have been, it will matter that you were alive, because everyone dies but not everyone lives.

Take a leap and walk towards what brings you to life, do not worry about what will happen, for what is meant to happen will happen as it should.

Trust and believe and you will always be okay.


Check out the following song, One Man Can Change the World that is dedicated to Big Sean’s grandmother. And a huge Thank you to Microsoft, a proud sponsor of WeDay and Youth Movements around the world, for making this interview possible.


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