The Long and The Short Of It
Peter Shepherd & Jen Waldman
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.
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.
Episodes
Mentioned books
Sep 22, 2026 • 19min
417. FOBA
Pete and Jen unpack FOBA, the fear that overreliance on AI could atrophy creativity, judgment, and problem-solving. They explore practical limits for using AI, why thinking first matters, and how helpful tools can sometimes create more friction. The conversation also champions human coaches, peers, authentic communication, and the joy of doing the thinking yourself.
Sep 15, 2026 • 17min
416. FOYF
Jen’s vacation takes an unexpected dive while learning to hydrofoil, sparking a lively conversation about falling, persistence, and the courage to try again. They explore how encouragement makes failure feel safer, how to replace “can’t because” with “can if,” and why deliberately chasing more low-stakes face-plants can open the door to bigger possibilities.
Sep 8, 2026 • 17min
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: [email protected]'s work: humanperiscope.com · Jen's work: jenwaldman.com
Sep 1, 2026 • 19min
414. Disney Map
Taking inspiration from the Disney Map, Jen and Pete noodle on what their own mind maps might look like, and how they might be created in the first place.
Specifically, in this episode Jen and Pete talk about:
What is the Disney Map?
How might seemingly disparate projects actually be related?
What does the 30,000 foot map look like for Pete and Jen? And what about the sea level map?
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: [email protected]'s work: humanperiscope.com · Jen's work: jenwaldman.com
Aug 25, 2026 • 18min
413. Looking Back
After a trip down memory lane this week, Jen noodles with Pete on the ways in which we reflect, and how we might learn from our past self.
Specifically, in this episode Jen and Pete talk about:
What are different tactics for reflecting on the past?
Why is it important to notice the repetitions in the problems we face?
How might we look to the past for evidence or help with where we are now?
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: [email protected]'s work: humanperiscope.com · Jen's work: jenwaldman.com
Aug 18, 2026 • 17min
412. Counting Strokes
This week, Pete shares with Jen some lessons he has learned from his swimming coach, on how to measure progress...by stopping the measuring.
Specifically, in this episode Jen and Pete talk about:
Why might our existing tools actually hinder our forward momentum?
Where might we be able to rely on ourselves more, rather than searching for external validation?
Why is it important to go slow, in order to go fast?
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: [email protected]'s work: humanperiscope.com · Jen's work: jenwaldman.com
Aug 11, 2026 • 20min
411. Proposals
After submitting many proposals between the two of them, Pete and Jen noodle on their proposal writing process, and how they might help their clients to write their own.
Specifically, in this episode Jen and Pete talk about:
What are the three key questions to answer when writing a proposal?
How might you identify the core problem that your proposal is meant to solve?
Why is it important to consider who will be reading the proposal you submit?
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: [email protected]'s work: humanperiscope.com · Jen's work: jenwaldman.com
Aug 5, 2026 • 16min
410. Grown Up Sh*t
This week, Pete brings his sighs and his aha moments around grown up sh*t to Jen, and they unpack it all together.
Specifically, in this episode Jen and Pete talk about:
Why is adulting so hard sometimes?
What tactics might we utilize to navigate difficult situations and conversations?
How might we think about finding solutions and take ownership of the problems we encounter?
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: [email protected]'s work: humanperiscope.com · Jen's work: jenwaldman.com
Jul 28, 2026 • 17min
409. Unpacking
After a recent episode on packing, Jen and Pete spend this week mulling over the idea of its opposite: unpacking.
Specifically, in this episode Jen and Pete talk about:
What are some tactics we might use to make it easier to manage change?
How might we assess what everyone on our team needs before making a plan?
What surprises might we find when we take a different path than planned?
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: [email protected]'s work: humanperiscope.com · Jen's work: jenwaldman.com
Jul 21, 2026 • 18min
408. Strategy
After thinking over and over about the concept of strategy, Pete turns to Jen to help him unravel what strategy actually is and how it can be best utilized by individuals and companies.
Specifically, in this episode Jen and Pete talk about:
What even is strategy?
How might we move from our goals to a clear strategy?
What are some tactics to stay focused on the things we actually have control over?
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: [email protected]'s work: humanperiscope.com · Jen's work: jenwaldman.com
