How I Really Got Started Podcasting

In the past five years, I’ve published 500 podcast episodes which have gotten over 10 million downloads. The show’s success has been unexpected and life-changing. I’m often asked how I got started.

I’ve never told the true story.

I usually say I started the podcast on a whim, and that is true. But maybe because “whim” shares roots with “whimsical”—the phrasing never quite sat right with me. 

That’s because I started my podcast the week my wife Khalilah was diagnosed with stage 3 breast cancer. While I’d been thinking about starting a podcast for a while, the bad news provided the motivation I needed to do it.

Khalilah and I had just returned from a trip to Australia. I spoke at a conference in Melbourne and we tacked on a week to explore the Great Ocean Road and make our way up to Sydney. 

Our time in the country was incredible, filled with some of our favorite activities—scenic drives, long hikes, great urban walks, and meeting locals and travelers. But by the time we made it home the mild discomfort that prompted an ultrasound right before our trip had become sharper, and she was scheduled for a biopsy immediately upon our return. 

When we got the news, I played what I thought my role was supposed to be. I would be strong for her and never let on that I was afraid too. In reality I was horrified at the thought of losing my best friend and partner of 20 years and I felt helpless to calm her fears, ease her pains, and get her through this experience.

My display of strength came at a cost. To cope I did what I’ve often done when confronted by emotions I’m not ready to face… I retreated into my work.

Within a week of the news I’d launched a new podcast and within two months had a new full-time consulting client. Before long I was too busy to grieve.

The level of activity and sense of urgency felt justified at the time. I’d been self-employed for five years and things were at a very turbulent place in my business. A business partnership that I invested more than a year developing had recently fallen apart, leaving me very frustrated and with limited visibility into how we’d pay our bills. That, plus the prospects of an avalanche of medical expenses, triggered a fight or flight response that launched me into action.

I’m not sure I could have done anything differently, but I do regret not making myself more emotionally available to Khalilah during what was an incredibly difficult and scary time. Rather than a stoic face, what she really needed was my tenderness and presence. What I thought was strength wasn’t strong at all.

That’s why I’ve never told this part of the story. In addition to being very personal, it’s also embarrassing because it forces me to confront my failure and the shaky foundations upon which I’ve built my beliefs about what it means to be a husband and friend. I’ve always prided myself on my maturity, but reflecting on this moment which put it to the crucial test makes plain how far short of my aspirations I’d fallen, and how much pain that caused for the person I love most in the world.

Five years on, Khalilah and I are much closer. Her fight against cancer brought me face to face with mortality and helped me to appreciate how much I love her.

The rupture in our lives gave us an opportunity to really dig into ourselves and our relationship, and we’ve emerged a much stronger couple. I’ve emerged a stronger husband too, with a definition of strength that permits vulnerability.

And that podcast that was formed from our pain five years before? It is now a catalyst for our continued growth as a couple. Khalilah started working with me at the beginning of last year, which has pushed us to face a whole different set of demons as we learn to work together, support, and appreciate one another in new and different ways.

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