Peter Shepherd & Jen Waldman

The Long and The Short Of It

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. E...

Author

Peter Shepherd & Jen Waldman

Category

Education

Latest episode

Jul 7, 2026

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Episodes

382. What To Do? 20.01.2026

As Jen confronts an upcoming change, she asks Pete for advice and questions to help shift the framework of her status quo. Specifically, in this episode Jen and Pete talk about: What does success look like? How might we reframe a problem as the best possible thing that could happen? Where might we be able to challenge our own assumptions and rules? To hear all episodes and read full transcripts, v...

381. Books 13.01.2026

Looking at his reading list for the year ahead, Pete asks Jen about her processes for selecting and reading books. Specifically, in this episode Jen and Pete talk about: How might we enable ourselves to quit reading a book that isn't exciting to us? Where might we look for the next book to read? How might we examine the list of books we've already read, and use that to guide the future of our read...

380. 2026 08.01.2026

This week, Jen and Pete go through their intentions, phrases, and things they are thinking about in preparing for the year ahead. Specifically, in this episode Jen and Pete talk about: How do Jen and Pete reflect on the past year, in order to look ahead? How is an unexpected unknown shaping Jen's year? What intention is Pete going to set for his upcoming year? To hear all episodes and read full tr...

379. Have a Goal 30.12.2025

In the final days of 2025, Jen and Pete noodle on what should be the top priority to have prepared as we move in to 2026. Specifically, in this episode Jen and Pete talk about: Why is it important to have an idea of what success looks like for you? What is an outcome goal? What is a process goal? How might we measure and take an audit of our existing assets? To hear all episodes and read full tran...

378. Favo(u)rite Things: 2025 23.12.2025

In their annual tradition, Jen and Pete list their very favo(u)rite things of 2025. Specifically, in this episode Jen and Pete talk about their favo(u)rite: Fiction book. Non-fiction book. Podcast. TLATSOI episode. Thing they watched. Motto. Thing they discovered about themselves. To hear all episodes and read full transcripts, visit The Long and The Short Of It website: https://thelongandtheshort...

377. Relative Effort 16.12.2025

Coining a new term, Jen introduces Pete to the idea of, while working on a project, considering the relative effort of both the creator and the receiver. Specifically, in this episode Jen and Pete talk about: What is relative effort? What is relative risk? How might we ship things without the pressure of absolute perfection? Why might we think about the worst case scenario or fear, in order to mov...

376. Cadence 09.12.2025

In Pete's version of an episode about running, he noodles with Jen about the idea of cadence, and how to break our routines projects into smaller steps. Specifically, in this episode Jen and Pete talk about: What does "cadence" mean, and how might we apply the idea to our everyday lives? Why is it better to not rush to the finish line, either while running or working?  How might we return to the b...

375. The Perspectives Wheel 02.12.2025

Jen shares a framework with Pete for thinking about many different perspectives at once, as opposed to sticking with the first perspective you might think up. Specifically, in this episode Jen and Pete talk about: How might you choose to believe in a perspective that is most beneficial to yourself? Why is considering many different perspectives a version of sonder? How might we broaden our idea of...

374. Competent or Complacent? 25.11.2025

After a small existential crisis, Pete asks Jen how he might tell the difference between being competent or complacent. Specifically, in this episode Jen and Pete talk about: What is the relationship between boredom, competency, and complacency? How might the repetition of a workshop, keynote, or show create an illusion of complacency? Why is having a coach, mentor, or trusted friend important in...

373. The Six Points of Focus 18.11.2025

This week, Jen teaches Pete her framework of six points of focus, to help grow your career towards your goals. Specifically, in this episode Jen and Pete talk about focus in relationship to: Artistry and Inspiration. Industry Knowledge. Marketing. Mindset. Network Building. Skill and Craft. To hear all episodes and read full transcripts, visit The Long and The Short Of It website: https://thelonga...

372. Lessons from a Triathlon 11.11.2025

After completing his first triathlon, Pete shares with Jen some learning that he found in training, and while swimming, biking, and running. Specifically, in this episode Jen and Pete talk about: Why is there power in acting as if? How might we more actively encourage and appreciate each other? What does it mean to taper? To hear all episodes and read full transcripts, visit The Long and The Short...

371. Shark Week 04.11.2025

This week, Jen and Pete noodle on the question, what if every week was Shark Week (i.e. what if we stopped tying conventional constraints to enjoying the things we love or want to accomplish)? Specifically, in this episode Jen and Pete talk about: Why might we link certain constraints to tasks we want to accomplish? How might we commit to our goals in non-traditional ways? What is Jen going to do...

370. Collegial 28.10.2025

This week, Jen and Pete noodle on the negative aspects of being collegial, and how they might favor challenge instead. Specifically, in this episode Jen and Pete talk about: How might teams align on their why and their goals? What tools might we utilize to introduce more coaching into our work environments? How might feedback be utilized as a way to challenge and brainstorm and fight against FOPO?...

369. The OK Plateau 21.10.2025

This week, Jen and Pete noodle on the plateaus we might reach within certain skill sets, and how we might nudge ourselves forward. Specifically, in this episode Jen and Pete talk about: What is the OK Plateau? How might we push ourselves into situations that might make us afraid or uncomfortable, in order to build skill? What are some tools or tactics that might provide incremental increases of im...

368. Kicking Cans 14.10.2025

This week, Jen confronts a metaphorical can that she's been kicking down the road for several months, and she and Pete noodle on where else these cans might show up in our lives. Specifically, in this episode Jen and Pete talk about: How might we name and tackle certain decisions or projects that we've been delaying? What effect does fear of other people's opinions have on our actions? Why might l...

367. Tool Kits 07.10.2025

This week, Pete and Jen dive in to the idea of auditing your leadership tool kit, to help you solve problems and become more efficient. Specifically, in this episode Jen and Pete talk about: What are some tactics you might use to evaluate and assess your various skill sets? Why is it important to borrow ideas, questions, and tools from other leaders? How might we become more aware of our tool kits...

366. Momentum Mindset 30.09.2025

This week, Jen and Pete noodle on a topic that they were both surprised to have never recorded an episode on: momentum. Specifically, in this episode Jen and Pete talk about: What is momentum mindset? How might we turn an ending into a beginning? Why is it important to not sit around and wait for motivation or inspiration? To hear all episodes and read full transcripts, visit The Long and The Shor...

365. Value Add AI 23.09.2025

With AI being a pervasive topic in 2025, Jen and Pete discuss how they use the tool, and how they might utilize it to help their clients. Specifically, in this episode Jen and Pete talk about: How might we use AI to help other people, not just ourselves? Why is trust so important, in the building of skills and of organizations? What are several use cases for how Jen and Pete use AI? To hear all ep...

364. Into the Woods 16.09.2025

After a week in the woods working on a creative project, Jen brings Pete the lessons she brought back around building something new. Specifically, in this episode Jen and Pete talk about: Why is it important to have an agenda, and other constraints, when working on a project? What role do collaborators place in the creation of something new? What tactics might we utilize in sharing a work-in-progr...

363. Curious Leader 09.09.2025

After being taken by surprise by a question in a workshop, Pete noodles with Jen on what it looks like to show up as the opposite of a curious leader, and how we might return to a more curious state. Specifically, in this episode Jen and Pete talk about: What does it mean to be curious?  What tactics might we utilize to spur curiosity? How might you rely on your team, to give you feedback about wh...

362. Running 2025 02.09.2025

In their annual tradition, Jen talks to Pete about ways in which running (or not running) has taught her about life. Specifically, in this episode Jen and Pete talk about: How might we decide whether or not to take action on something that is hard or painful? What opportunities might arise from saying no to something? Why is it important to revisit the reasons behind our practices and routines? To...

361. Making Friends 26.08.2025

This week, Jen and Pete dive into a topic that seems to get harder as we get older: making new friends. Specifically, in this episode Jen and Pete talk about: What might be some tactics for making new friends, as an adult? Why do we have friends, and do we need more of them? How might we dedicate time and effort to the task of making friends? To hear all episodes and read full transcripts, visit T...

360. Lower Back Pain 19.08.2025

For the first time in three years, Pete is free of lower back pain, and he shares with Jen his journey and learnings on his way to healing. Specifically, in this episode Jen and Pete talk about: Why might we hide from our problems by creating a self-diagnosis? How can we work on discovering what our problems actually are? Who are the people in our lives who might serve as mentors and coaches? To h...

359. Building Skills 12.08.2025

This week, Pete and Jen return to basics, and ask the questions: How is it that we build skills? Specifically, in this episode Jen and Pete talk about: Are there finite and infinite skills? How might we coach and lead groups of people to build skills? How might we return to basics and question the methods we use every day? To hear all episodes and read full transcripts, visit The Long and The Shor...

358. Caramelized Onions 05.08.2025

This week, Jen shares an aha moment with Pete that she learned during the intensive process of caramelizing onions. Specifically, in this episode Jen and Pete talk about: Why might efficiency not always be the best route to an end goal? What can we learn by practicing patience, and not rushing? What are some tactics for continuing with a project when it seems uncertain? To hear all episodes and re...

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