113: Great Writers Are Risk Takers

Playing it safe is comfortable. It makes you feel in control. It gives you a sense of security. But it may be killing you slowly.

It’s like driving a car with a slow leak in your tires. It might work for a while, but sooner or later, you will get stuck, fall behind, and need to make changes to get back on track.

I played it safe for years in my 20s. I had a job that was comfortable enough, and so I kept my dream in the “someday” pile. I wasn’t ready to take a risk and call myself a writer, and as a result, I wasn’t one.

It’s been a few years since I decided to start building a bridge toward my calling, and what I’ve learned on the journey is that the fear of taking risks never goes away. It doesn’t get easier to try something new, but it does get more comfortable than standing still can ever be. It’s certainly more comfortable than driving with deflated tires.

I’m not saying you need to risk everything in blind pursuit of a dream. Far from it. There are healthy and unhealthy ways to move from where you are now to where you want to be.

But I am saying that all writers are risk takers. They just are. Taking risks is how we become better at what we are called to do. It might be the only way, in fact. We must do the uncomfortable things if we want to create interesting and enduring work, and if we want to make a difference in the lives of others.

This week on The Portfolio Life, Andy Traub and I discuss wrestling with the tension of playing it safe and taking risks, and why taking risks is necessary to improve yourself as a writer.

Listen in as we talk about how I’m pushing myself with my latest book, and the risks we’re taking with this blog and Tribe Writers in the future.

Listen to the podcast

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

Show highlights

In this episode, Andy and I discuss:

  • Where I need to take more risks and make changes.
  • The downside to living the Portfolio Life.
  • Why you need to be good at a few things if you want to succeed as a writer.
  • Why I want to provide community and connections for writers.
  • Focusing on getting better as a writer.
  • How I’m pushing myself as a writer with my latest book.
  • What risks we’re taking with this blog and Tribe Writers in the future.
  • Creating meaningful work that will stand the test of time.
  • How taking risks is good for you and your work.

Quotes and takeaways

  • Focus your life and work to continually improve yourself as a writer.
  • Community creates opportunity.
  • Identify your core skill, build it, and then develop complementary skills.
  • You will do more interesting work when you aren’t afraid to lose what you have. And you will do more boring work when you’re afraid to lose.


Where are you taking risks in your life? Where do you need to seek out risks? Share in the comments.