This episode of The Unobstructed Podcast is about “leveling up” in life by collecting skills and experiences.

In this conversation, Caleb framed skill-building like role-playing. Once upon a time, he was a football player. Then he found theater. He still carries lessons he learned from both, but says he’s come to look at the chapters of his life as time invested in playing a role. That’s also the lens through which he decides what to do next—the role(s) to audition for so to speak.

To me, that’s like stacking transferable skills.

I didn’t really expect us to get into social masking or code switching, but I’m psyched we did. A lot of how we learn to navigate the world comes from stuff that shaped us during childhood. It seems like that’s when we experience being beginners the most. Then, somewhere along the way, we tend to stop trying new things. Caleb brought up the concept of being a “jack of all trades,” which is how we got to talking about the role of observation, impersonation, and leveling up… a powerful equation, so long as you also remember to get rid of what no longer serves you.

Auditioning for the wrong roles in life is how you get good enough to actually land the ones you want.

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The Unobstructed Podcast: Listen in on big thoughts and small steps for navigating agency, grief, and creativity in daily life. New episodes every month.

About the hosts:

Derek MacDonald — writer and systems consultant who likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his live storytelling at derekmacdonald.com.

Caleb Walker — digital marketer by trade, outdoorsman, hobbyist chef, and avid reader who just likes hanging out with his family and spending time outside.

Read the latest from Derek and Caleb at theunobstructed.com

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