The Long and The Short Of It

Hosted by Peter Shepherd & Jen Waldman

Business Management Education Arts

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Episodes

429

Latest episode

Nov 2026

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About the show

What do two coaches on opposite sides of the world actually talk about when they think out loud together? For eight years and 400-plus episodes, that has been the whole of The Long and The Short Of It: a weekly conversation for thoughtful leaders, coaches, and creatives who would rather be useful than loud. Pete Shepherd is an Australian leadership coach and the former Head Coach of Seth Godin's altMBA, who has worked with leaders at Google, Toyota, Woolworths, Kraft Heinz and the Australian Navy. Jen Waldman runs her own studio in New York and has coached performers across much of Broadway. Every Tuesday they take one small, real moment, a difficult conversation, a 3am worry, a question from a client, and turn it into a question or a reframe you can use today. The show is about leadership, coaching, creativity, fear, feedback, imposter syndrome, habits, and what it actually means to be human at work. Under twenty minutes. No guests. No ads. No script. If a friend sent you here, start anywhere. And come find the Box O' Goodies, our weekly email, at thelongandtheshortpodcast.com.

Listen to episodes

60 recent

November 10, 202618 min

424. FOBA 2.0

This week, Pete and Jen revisit (for the first time of many) their fear of brain atrophy while interacting with AI. Specifically, in this episode Jen and Pete talk about: What work is best to not outsource? Why might all of the capabilities of AI actually be a hindrance to our work and communication? Why is the human act of creation (and error) so important? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

November 3, 202620 min

423. Reach Up

This week, Jen and Pete dig in to a new reach out practice, with the question - what does it look like to reach out without an ask, to the people you really admire? Specifically, in this episode Jen and Pete talk about: What is a reach up, versus a reach out? How might we think about connecting with the people inside of and outside of our industry? How might you build a sustainable reach up practice? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

October 27, 202618 min

422. Five Minute Rule

In this week's episode, Pete shares with Jen a recent lesson from James Clear, and together they noodle on how it can just take five minutes to break the cycle. Specifically, in this episode Jen and Pete talk about: What is the five minute rule? What is the five second rule? How might we use five minutes or seconds to nudge something forward, as opposed to taking on an entire project at once? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

October 20, 202619 min

421. Leading People Who Don't Want To Be Led

This week, after moving beyond the obvious answer to the question, Pete and Jen brainstorm on possible tactics for attempting to lead those who don't wish to be led. Specifically, in this episode Jen and Pete talk about: What does covert leadership look like? Why is it important to ask someone if they are okay, if you notice their behavior shifting? How can you get used to the fact that not everyone can be enrolled in the collective vision? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

October 13, 202619 min

420. Jen's Big Oopsie

After a big mistake, Jen confides in Pete, and together they brainstorm (with some wise advice from Jen's daughter) on how to confront mistakes when they happen, and how to move on from them. Specifically, in this episode Jen and Pete talk about: What are some tactics for moving on from a big mistake? How might we assume best intentions of those around us? How might we be more quick to forgive ourselves and others? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

October 6, 202618 min

419. Thinking Out Loud

This week, Jen and Pete noodle on an activity that they do together every week: thinking out loud. Specifically, in this episode Jen and Pete talk about: What might be some fears and hesitancy around thinking out loud? How might leaders encourage more thinking out loud on their teams? What are some tools and tactics to starting thinking out loud more frequently? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

September 29, 202617 min

418. The Witch

After visiting a witch, Jen shares her experience with Pete, and together, they noodle on the power of a reframe. Specifically, in this episode Jen and Pete talk about: What is the gift to be found out of some of our hardships? When is a gentler approach important to solve a problem? And a more firm approach? Why is important to seek help or feedback from a trusted mentor or colleague? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

September 22, 202619 min

417. FOBA

Another week, another acronym, as Pete and Jen noodle on the fear of the atrophy of the brain, due to reliance on AI. Specifically, in this episode Jen and Pete talk about: How might we limit and monitor our usage of AI? How might we find more joy in the usage of our brain? What is the importance of having a human coach, and relying on peers rather than a robot? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

September 15, 202617 min

416. FOYF

After a recent vacation adventure, Jen shares with Pete an experience of falling on her face, and together they noodle on the advantages of failures. Specifically, in this episode Jen and Pete talk about: What makes us return to an activity, after we have failed? How can we set others up for success, even in difficult environments? How might we actually seek out more things to fail at? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

September 8, 202617 min

415. Lessons From Pete's Mum

Inspired by Pete's mum, Pete and Jen noodle on the qualities of leadership that allow everyone in the room to succeed, whether in the back of a car, on a stage, or in an office. Specifically, in this episode Jen and Pete talk about: What are the correlations between parenting and leadership? How might you lead by example, as opposed to with words? In what way is behavior and energy contagious to a full team? And how might we consider that in the approach to our work? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and other noodles Jen and Pete are mulling over. Listen to all episodes and read full transcripts at thelongandtheshortpodcast.com . Reach us: hello@thelongandtheshortpodcast.com Pete's work: humanperiscope.com · Jen's work: jenwaldman.com