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The American Dream starts over every December.

People get ready. “This is the year!’

We prepare by ceremoniously eating excessively, drinking more alcohol, sleeping less and seeing people who are guaranteed to traumatize us.

Nothin says, “I’m going to change my life” like a little bit of pre-self-sabotage.

But maybe that’s the down before the up.

People turn to the internet for advice.

This is when I update my “How to Quit Your Job The Right Way” article.

Two or three years ago, I got a video message from a woman who quit her job. And moved to South Korea. She smiled. And said, “Thank you.”

Sometimes I wish I did that.

We all have different ideas of what it looks like to (finally) choose yourself. And it can change yearly, monthly, daily.


Humble The Poet’s has changed from rapper to spoken word poet and philosopher to self-published author. To traditionally published author.

And the list keeps evolving.

Because he follows two simple ideas:

  1. Unlearn.
  2. Create Your Own Silver Linings

He can expand this list. And he has. But this is my take on it.

“We’re all wearing layers of other people’s judgments,” he said. “But we don’t have to.”

I wanted to dig into that concept. So I had him back on my podcast.In this episode, you’ll learn how Humble The Poet gave himself permission to step off of the approved life paths and create his own.

Here are the topics from today’s episode. And some of my favorite quotes:

  • “There’s no pot of gold at the end of this rainbow. I need be enjoying this journey while I’m on it.” — Humble The Poet
  • “The labor is the reward.” — Humble The Poet
  • “If you don’t have fun climbing the mountain then it doesn’t matter where it takes you.” — Humble The Poet
  • “Most people who criticize us are telling us their stories not ours.” — Humble The Poet
  • “We can create a silver lining in anything in our lives if we change out attitudes and perspectives.” — Humble The Poet


  • 0:40 | Episode Preview
  • 3:59 | Why I love self publishing. Humble The Poet is living proof that you can publish something totally amateur and use it to kick start your creative career.
  • 7:47 | How to get better at writing and storytelling. Including Humble’s “step one.” And advice Humble got from his editors.
  • 13:50 | Humble’s philosophy for dealing with anxiety, loss, jealousy, regret, insecurities, being heartbroken, etc.
  • 18:10 | Build human relationships. Not transactional relationships.
  • 22:02 | “There are so many sustainable ways to address loneliness,” Humble says. Hear the changes Humble personally made in his own life.
  • 23:00 | Should we expect people to love us unconditionally?
  • 25:30 | Change your metric of success from external to internal. Here’s how to stop keeping up with the Jones’s in today’s world
  • 29:17 | How to be lead by your passion. Insead of distraction
  • 37:02 | How to deal with toxic colleagues and bosses.
  • 38:19 | Stop following the trends. Don’t let social media distract you. Or dictate your direction.
  • 42:30 | Break out of mental prisons. How to block expectations from blocking you.
  • 50:22 | The joy of just creating… “The labor is the reward.” — Humble The Poet
  • 53:21 | How to continually reinvent as an artist.
  • 54:45 | There is no limit to content consumption. So how do you set standards. And how do you set boundaries?
  • 56:48 | How to protect your mental health. Diversify your happiness.
  • 1:00:12 | Book recommendation: “Steal Like an Artist” by Austin Kleon
  • 1:00:30 | The wrong goal leads to the wrong journey. That’s why Humble says make sure you’re having fun.
  • 1:02:55 | No matter your goals in life, some parts will suck.
  • 1:03:39 | How to handle criticism
  • 1:05:30 | “Double down on service.” = Humble’s advice for when you’re feeling your worst
  • 1:08:35 | We’re all wearing layers of other people’s judgements. But we don’t have to. Hear Humble’s thoughts
  • 1:10:44 | All humans have the need to feel significant. And there are lots of ways to feel this. We go over some ideas
  • 1:12:20 | I ask Humble how to become a rapper in 3 steps
  • 1:14:05 | The most sustainable way to continually be creative


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