5 of My Favorite Recent Podcast Listens

On the hunt for great podcast content? Sometimes it helps to know not just which shows are good – but which interviews and episodes are the best places to start.

I’m subscribed to dozens of podcasts on my Pocket Cast app, but some shows stand out in my recent listening.

1. The Voluntary Life – “Designing a Life Without Regrets” 

I must have started listening to The Voluntary Life back in 2012 or 2013, but I took a long break until recently. This podcast delves into a wide range of topics ranging from personal finance to psychology to business and political philosophy. It’s great for people who care about “living freely in an unfree world.”

This particular episode from 2017 delves into some really interesting self-reflection questions/journaling practices based on the popular findings in the book The Top 5 Regrets of the Dying. Give it a listen!

2. The Tim Ferriss Show – Joe Gebbia – Co-Founder of Airbnb 

The Tim Ferriss show is one of my regular favorites. It features some of the best interviews I have ever heard, collected by one of the best interviewers out there. In this one, Tim interviews Airbnb Joe Gebbia about his colorful career. Gebbia is an incredible storyteller. I was riveted as he explained how he executed a legendary high school prank, proved a notoriously difficult professor wrong, brought an artist seat-cushion to market, and founded what is probably now the world’s fastest-growing home-sharing service.

If you want to observe how Joe created such an interesting life (and take notes on how to tell the story of that life), give it a listen!

3. The Jordan Harbinger Show – Jocko Willink | Why Discipline Beats Motivation Every Time

Former Art of Charm podcast host Jordan Harbinger is a great interview and curator of interviews with people who have interesting things to say about personal development. Former Navy SEAL Jocko Willink is one of those people. This guy is tough, and he has a tough philosophy of discipline which (despite it all) is appealing. This podcast drops some great resources and ideas on living a more disciplined life, including a recent favorite – Jocko’s spoken word “motivational” album Psychological Warfare.

Give the interview a listen!

4. The Joe Rogan Experience – Jordan Peterson and Bret Weinstein

Joe Rogan has just about mastered the art of long-form interviews/conversations with podcasts. He has a gift for making guests comfortable and (passive, non-critically-thinking) listeners uncomfortable. Rogan is an independent thinker who doesn’t fall into easy ideological categorization, which means that when he dips his toes into political controversies, you can at least rely on him to say something interesting.

In this episode Rogan talks with professors Jordan Peterson and Bret Weinstein, who have both recently (in the last couple of years) been targets of extreme behavior and accusations by campus protestors representing left-wing identitarian political philosophies. They have interesting things to say about psychology, biology, totalitarianism, political polarization, identity politics, and many hot-button issues.

You can actually watch this one on YouTube (and get it on a podcast app).

5. The Good Life Project – Finding Grace in the Face of Unrelenting Pain: Ruthie Lindsey

This interview goes deep into how interior designer Ruthie Lindsey has worked to transcend the suffering which started with a car crash in her teens and led her through divorce, depression, and tragedy. Lindsey is an inspiring person with a good heart, and this is a seriously good story relevant for anyone expects to experience debilitating illness or other suffering (it’s likely). Probably most impactful for me was Lindsey’s description of her father and the impact of his life.

Give it a listen!

I listen to a ton of other podcasts, too! If you have any you think I’d like, let me know in the comments.


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James Walpole

James Walpole is a writer, startup marketer, and perpetual apprentice. You're reading his blog right now, and he really appreciates it. Don't let it go to his head, though.

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