Three Times Rappers Taught Us Lessons in Leadership

Important Takeaways from 50 Cent, Jay Z, and Kanye West


“My momma gave birth to a winner, I gotta win.” -50 Cent

Confidence is like wealth. It’s typically unevenly distributed, and famous rappers have a lot more than the average person. But I think it’s important to point out what 50 Cent acknowledges here: he had confidence before he was a famous rapper. He felt he was born a winner, and that he shouldn’t be doing anything but winning.

He didn’t say, “My momma gave birth to someone with average skills, and if used properly, I could get a mediocre job with them.” He didn’t say, “My momma gave birth to a superstar, and that’s why my brother is so famous.” (See what I did there?)

50 Cent embraces the skills that he has and is confident in his abilities to use them.

I second-guess myself all the time, and I hear when other people do it too. In general, people spend way too much time doubting themselves and not enough time reminding themselves why they should win…and everyone deserves to win at some point.

Believe that you have the capacity to make it happen and you will be much closer to getting the victory you deserve.


“I will not lose, for even in defeat, there’s a valuable lesson learned so it evens it up for me.” -Jay Z

While you may read this and think it is another quote about winning, this is actually a quote about improving. Jay Z isn’t saying that things always go his way. He isn’t stating that he always wins (T-Pain and Ludacris said that…or was it Howard Wolowitz?). What he is saying is that if things don’t go his way, he’s going to take the knowledge he gained to do better next time.

The implications of this quote are that Jay Z reflects on his experiences and looks to grow from them, something that all of us should be doing on a regular basis.

Real improvement happens from setbacks, and setbacks come when you are passionately pursuing something. If you experience a setback, ask yourself what lesson can be learned from the experience. By doing this, you’re working to save yourself from experiencing the same setbacks in the future…and if it does save you from that future setback, was it really a loss?


“When it feels like living’s harder than dying, for me giving up’s way harder than trying.” -Kanye West

If you haven’t figured it out. Here is the storyline of this blog. First, believe you can win. Second, improve over time. Third, don’t ever give up.

Kanye’s quote suggests that trying your best and sticking to it need to become so second nature that giving up is no longer an option. So when you experience setbacks, you’re not just learning from them; you’re also overcoming them and refusing to let those setbacks keep you from whatever dreams you’re chasing.

Life gets difficult. It is not easy being a human being (Does Kanye still think he’s a human being?). But by believing in yourself, constantly improving, and refusing to give up, things are going to be okay (and if it’s not okay, it’s not the end).

So the next time you experience setbacks that make you feel like all hope is lost or that your dreams don’t matter, refuse to let yourself give up. Push through it. Your breakthrough might be just around the corner.


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