056: Courage and the Creative Pursuit

It’s present every time you sit down to create. No matter how often you face it, it never gets easier. And as you make daily decisions to do your work, this enemy is constantly trying to stop you.


Fear. We all have it. It manifests in a variety of forms: fear of success, fear of failure, fear of insignificance. But we all deal with it at some point. We who dare to create are not strangers to this thing called fear.

Here’s the thing, though: the way you and I have been conditioned to face this adversary is wrong. Motivational speakers and inspirational memes would have us believe that boxing fear into submission is the path to bravery. It’s not. 1In my experience, true courage is not so much about beating fear as it is about outrunning it — doing your work in spite of feeling afraid.

In this week’s episode of The Portfolio Life, Andy Traub and I talk about the defiant nature of creative pursuits, the power of habit, and the quiet courage you need to do your best work. Listen in as we discuss why fear never really goes away but how you can still escape its grasp.

Listen to the podcast

To listen to the show, click the player below (If you are reading this via email, please click here).

You can also listen via iTunes or on Stitcher.

Fighting fear is a losing battle

Any time someone tweets or posts an Instagram graphic about beating fear, I cringe a little. When we think of it as a conquerable enemy, we miss the mark.

Fear is more akin to a shadow lurking at our heels. You can’t fight it, no matter how hard you try. And if you stand still, it will catch you. So what do you do? You outrun it.

Courage, especially for the creative person, is found in daily decisions to pursue momentum. To keep moving. To do the thing only you can do, regardless of the fear you feel. You must make things.

You can only control what is in your control, and sometimes that means doing your work afraid. Which is a whole lot better than not doing it at all.

Show highlights

In this episode, Andy and I talk about:

  • The true nature of creative courage
  • Why punching fear in the face is a bad idea
  • What it takes to outrun fear
  • Defiance as a key attribute of the creative pursuit
  • How the internet is the best and worst thing for a creative
  • What I consider quitting about twice a week
  • The secret to connecting with your audience
  • How private courage leads to public impact
  • What bravery looks like
  • Why people react when we challenge the norm
  • Practical steps writers can take to be courageous
  • Ernest Hemingway’s “secret” vanity published titles
  • How book publishing is not dead and what innovations to watch for

Quotes and Takeaways

  • “Courage is doing the thing only you can do.”
  • “Our responsibility as creators is to sit down and create again and again.”
  • “The only things that matter are the things that only we can measure.”
  • “…the only way to find your voice is to use it.” —Austin Kleon
  • Quantity X Time = Quality
  • “The only decision you control is the decision to make something.”
  • “You don’t find your voice and then write. You write to find your voice.”


Note: Be sure to check out my brand-new podcast, The Art of Work Conversations, in which Andy and I do a limited series of episodes exploring the seven stages of discovering meaningful work. I think you’ll dig it.

What does courage look like in your life? Share in the comments.