Drake Turns 40: 40 Things I’ve Learned From Drake

Drake is 40. Let that sink in.

It seems like yesterday that this young Canadian actor-turned-rapper was making his way into the rough-n-tumble world of Hip-Hop. He was singing and rapping about relationships, ambition, insecurity and everything in between. Some dismissed him. Others saw the future. But very few could have predicted that Aubrey Drake Graham would become one of the most successful, polarizing artists in music history.

I actually interviewed Drake in June 2010, when his debut album, Thank Me Later, was taking off. What struck me was his ambition, self-awareness and refusal to accept that commercial success somehow made him less Hip-Hop. I remember defending his lyricism during our conversation. He was already talking about longevity, improving his craft and challenging expectations. I even got to tell him Rihanna had expressed interest in working with him. His reaction was priceless, especially considering what happened later. (He infamously placed Leonardo DiCaprio in his Top 5 Dead or Alive.)

Sixteen years later, that conversation remains revealing.

Drake has experienced extraordinary victories, public defeats, rivalries, criticism and the relentless scrutiny that accompanies superstardom. He’s also helped redefine what a rapper can look and sound like.

In 2013, I wrote “40 Things I’ve Learned From Nas” when the Queensbridge legend reached this same milestone. Thirteen years later, Drake deserves his own…Octobers Very Own, if you will.

This isn’t about beef, Billboard rankings or determining who’s the greatest. We’ve had enough of those arguments. This is about the lessons.

Here are 40 things I’ve learned from Drake.

40 Things I’ve Learned From Drake

40. BE YOURSELF. Drake didn’t fit the traditional rapper stereotype. He succeeded by embracing his differences.

39. EMOTIONS ARE STRENGTH. Men have feelings, too. Drake made vulnerability commercially viable in Hip-Hop.

38. REPRESENT YOUR CITY. Toronto wasn’t a Hip-Hop capital. Drake helped change that.

37. CONSISTENCY WINS. Talent opens doors. Consistent work keeps them open.

36. NEVER GET COMFORTABLE. In 2010, Drake told me he was already thinking about his next victory. Success wasn’t enough.

35. BE YOUR TOUGHEST CRITIC. Drake admitted he could write better verses and hooks. Growth requires self-assessment.

34. SING YOUR SONG. Who said rappers couldn’t sing? Drake helped erase that boundary even if he did not invent it.

33. BUILD YOUR TEAM. OVO became bigger than music. Build something that extends beyond yourself.

32. LOYALTY MATTERS. His longstanding partnership with producer Noah “40” Shebib demonstrates the value of trusted collaborators.

31. THINK GLOBAL. Great music travels. Drake embraced international sounds and audiences.

30. LOVE YOUR MOTHER. Sandra Graham remains central to his story. Never forget who raised you.

29. FATHERHOOD CHANGES THINGS. Becoming a parent adds another dimension to life. Priorities evolve.

28. EMBRACE YOUR ROOTS. Your background isn’t a liability. It’s part of your power. He’s floated between his Canadian Homelife to his father’s background as well.

27. DEFINE YOUR OWN AUTHENTICITY. Drake challenged the notion that commercial success diminished his Hip-Hop credibility. I agreed.

26. TAKE RISKS. Honestly, Nevermind challenged expectations. Artistic exploration requires courage.

25. KNOW YOUR AUDIENCE. Drake understands what connects with listeners. That’s a powerful skill that other’s ignore.

24. BE MEMORABLE. From “Started From the Bottom” to “Worst Behavior” to “God’s Plan,” memorable messages endure. They aren’t all positive or perfect, but we’re not forgetting them.

23. HAVE FUN. Sometimes music should simply make people dance, laugh and enjoy themselves. We have enough stress.

22. SUCCESS REQUIRES SACRIFICE. Extraordinary achievement demands extraordinary commitment and vision.

21. STAY READY. Lil Wayne’s unexpected phone call changed Drake’s trajectory. Opportunity rarely waits and one must be ready.

20. COLLABORATE. Great partnerships create opportunities for everybody involved.

19. GIVE BACK. The “God’s Plan” video demonstrated how generosity can become a cultural moment.

18. STYLE EVOLVES. Fashion is another form of self-expression. Wear your confidence.

17. BE VERSATILE. Rap, R&B, dancehall and house music can coexist. Creativity has no borders.

16. HUMOR HELPS. Drake understands the power of laughing at himself. Sometimes that’s the best response.

15. CELEBRATE SUCCESS. There’s nothing wrong with enjoying the fruits of your labor.

14. STUDY THE GREATS. Drake has acknowledged artists who influenced him. Respect your predecessors.

13. UNDERSTAND THE MOMENT. Drake told me listeners sometimes confuse nostalgia with musical quality. Timing matters.

12. INVEST IN YOURSELF. Your greatest asset might be your own creativity.

11. STUDY YOUR CRAFT. Drake once described researching words and writing rhymes on his BlackBerry. Preparation matters.

10. BUILD A BRAND. OVO’s owl became globally recognizable. Identity has value beyond music.

9. OPEN DOORS. Drake’s collaborations introduced numerous artists to wider audiences.

8. ACCEPT CHANGE. Audiences, technology and culture evolve. Adaptation is survival.

7. BE AMBITIOUS. There’s no shame in wanting to be number one. Dream enormously.

6. DOCUMENT YOUR JOURNEY. Drake’s catalog chronicles his evolution. Your story matters.

5. TAKE THE HITS & KEEP BANGING. Every career encounters setbacks. The challenge is continuing forward. The Kendrick Lamar beef could have ended his career. Some how, some way, he made a remarkable comeback.

4. OWN YOUR SENSITIVITY. Emotional expression doesn’t diminish masculinity. It expands it.

3. CREATE YOUR LEGACY. Hits are wonderful. Cultural impact lasts longer.

2. PLAY THE LONG GAME. Drake discussed longevity with me in 2010. Sixteen years later, he’s still here.

1. BELIEVE IN YOURSELF. Before the records, awards and stadiums, there was a young man with a dream. Believe before the world does.

Happy 40th birthday, Drake.