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

332. Tolerance of Uncertainty 04.02.2025

After facilitating the Real Skills Conference, Pete brings Jen the most valued real skill from a poll of leaders, and together they dissect what it means to be tolerant of uncertainty (and what other words might fit into that phrase). Specifically, in this episode Jen and Pete talk about: What is a real skill? What might it mean to be tolerant of uncertainty? How can we be more active, than to jus...

331. The Year of Experiments 28.01.2025

Entering into a year full of experiments, Jen asks for Pete's coaching and guidance about what it means to experiment and how to implement the idea in her studio and day-to-day life. Specifically, in this episode Jen and Pete talk about: How might you make rules around creating experiments? What role does the audience take in the formation and implementation of an experiment? Why might it be impor...

330. Pete's Solo Off-Site #2 21.01.2025

In a new annual tradition, Pete describes his solo off-site, and Jen interviews him about it, to get to the core of the learnings from the two-day journey. Specifically, in this episode Jen and Pete talk about: What is a solo off-site, and why is it a catalyst for reflection and learning? What are the questions Pete used to set up the experience for himself? What were the aha moments (big and smal...

329. 2025 14.01.2025

At the start of the new year, Jen and Pete share their catchy catchphrases, which incorporate the ideas they'll be thinking about and working on this year. Specifically, in this episode Jen and Pete talk about: What are some tools and strategies to utilize when creating goals and resolutions? Why does specificity of language matter? How might AI be useful in reflecting and planning? To hear all ep...

328. Relative Tanking 07.01.2025

After coining yet another phrase, Jen unpacks the idea of relative tanking with Pete, and together they ask the question of why small failures can feel so huge, and how to help with that. Specifically, in this episode Jen and Pete talk about: What does relative tanking mean? Why might we have a tendency to over-examine and inflate our mistakes? When might it be a good thing to aim for just good en...

327. Favo(u)rite Things: 2024 31.12.2024

In their annual tradition, Jen and Pete ping-pong back and forth, going through all of their favorite things of 2024. Specifically, in this episode Jen and Pete talk about their favorite... fiction book. non-fiction book. podcast. The Long and The Short of It episode. documentary / film / TV show. aha moment. thing Jen and Pete changed their mind about. theatrical experience. question. To hear all...

326. Bite-Sized 24.12.2024

This week, Jen and Pete noodle on the idea of breaking plans and goals up in to smaller pieces, and wonder what that strategy might help accomplish. Specifically, in this episode Jen and Pete talk about: How might we turn our dreams in to goals? How can constraints help with efficiency? What are some tactics in which to practice making things bite-sized? To hear all episodes and read full transcri...

325. Curiosity 17.12.2024

Isn't it amazing that a podcast meant for curious people has never had an episode based solely on curiosity? This week, Pete and Jen change all that, and noodle together on the subject that is the basis for the creation of this podcast. Specifically, in this episode Jen and Pete talk about: What does being curious mean? What is curiosity in action? How does approaching something with curiosity cha...

324. Small Fish Mindset 10.12.2024

This week, Jen and Pete noodle on what it means to be a small fish in a big pond, and how they might create more opportunities for themselves to be the small fish. Specifically, in this episode Jen and Pete talk about: What does being a small fish in a big pond mean, and what are some real-world examples? What strategies might we use to become the small fish in a big pond? How might we continue to...

323. 13 Lessons 03.12.2024

Inspired by Jen's ten lessons, this week, Pete goes through thirteen lessons around how to become a better communicator. Specifically, in this episode Jen and Pete talk about: Ask yourself, who's it for and what's it for? Concise is nice. Find your allies. You are not a news reader. (Translation: You are not a news anchor.) Fix your umm. Be where your feet are. Slides are not teleprompters. Have a...

322. Graction 26.11.2024

This week, in the spirit of modern-day Thanksgiving, Jen and Pete noodle on how they might turn their gratitude in to action. Specifically, in this episode Jen and Pete talk about: What does "graction" even mean? How might we honor what we are grateful for with positive action? What are some words we can use as jumping off points, to start practicing graction? To hear all episodes and read full tr...

321. Uncoachable? 19.11.2024

This week, Pete and Jen noodle on the provocative question of: What might not be coachable? Specifically, in this episode Jen and Pete talk about: What are the differences between coaching and teaching? How might being coached require a base knowledge? What are some things that Jen thinks are not coachable? And Pete? To hear all episodes and read full transcripts, visit The Long and The Short Of I...

320. 10 Lessons 12.11.2024

This week, Jen and Pete go through ten lessons that Jen has learned over her twenty years of coaching actors. (Which are the possible table of contents for her book!) Specifically, in this episode Jen and Pete talk about (in no particular order): If you don't know where you're going, any road will take you there. Your marketing tells a story...whether you know it or not, whether you like it or not...

319. The Trust Equation 05.11.2024

This week, Pete and Jen noodle on the following equation: Credibility + Reliability + Intimacy ÷ Self-Orientation = Trustworthiness. Specifically, in this episode Jen and Pete talk about: How might the equation for trust change, based on the context you're in? What is the difference between an equation and a recipe? How might you jumpstart the trust-making process? To hear all episodes and read fu...

318. Games 29.10.2024

This week, Jen and Pete noodle on how they might create games for the daily processes in their lives. Specifically, in this episode Jen and Pete talk about: What factors might we consider while creating a game for ourselves or for others? Why might a game or a challenge be motivating? How might we celebrate the process, as opposed to the outcome we are seeking? To hear all episodes and read full t...

317. Go Slow To Go Fast 22.10.2024

This week, Jen (a planner) and Pete (not really a planner) go back and forth on what it means to go slow in order to go fast. Specifically, in this episode Jen and Pete talk about: In what ways might we spend more time preparing for the goals we want to achieve? How might we craft our reach outs with gratitude? Why might it be helpful to set a timeline for ourselves, before we start a project? To...

316. Partnering 15.10.2024

This week, Pete and Jen dive into a topic that they are very familiar with, both with each other and with their clients: partnering. Specifically, in this episode Jen and Pete talk about: Why is tension important to a partnership? How might we learn from dancing partners, when thinking about partnerships in our lives? What are some characteristics of successful partnerships? And unsuccessful ones?...

315. Six Years 08.10.2024

To celebrate six years of recording the podcast together, Pete and Jen noodle on six ideas (plus a bonus) that they wish they had known at the start. Specifically, in this episode Jen and Pete talk about: How might we better trust in our own ideas? What were the outcomes that Pete was hoping for, for the podcast? And Jen? Why is it so important to get things on the calendar? How might we more deep...

314. Role Play 01.10.2024

This week, Jen and Pete noodle on the tool of role playing as a way to safely play out what might happen if what you fear were to actually come true. Specifically, in this episode Jen and Pete talk about: What does it mean to role play? What is a pre-mortem? What kinds of questions can we ask ourselves and each other, to think about and unpack fear and possibility? To hear all episodes and read fu...

313. Others in Action 24.09.2024

Feeling inspired, Pete shares with Jen an experience of a recent workshop he attended, and together they noodle on what they might learn by watching others in action. Specifically, in this episode Jen and Pete talk about: Why is it important to seek out other people in your industry and watch them work? How might we ask other people about their process? How might we find courage to share our own w...

312. Rejection 17.09.2024

This week, Jen and Pete start to scratch the surface on how they think about rejection, and what helps them move through that feeling. Specifically, in this episode Jen and Pete talk about: How might we reframe rejection as context? How does the addition of information allow for rejection to be less prevelant? What four words does Pete use to help himself reframe rejection, especially when there i...

311. Assumed Knowledge 10.09.2024

This week, Pete and Jen noodle on the assumption that everyone knows the same things that they know, and how they might work in the reverse of that notion. Specifically, in this episode Jen and Pete talk about: How might leaders run workshops where the knowledge and vocabulary used are built from the ground up? In what ways is it brave to ask a question that you assume everyone else knows the answ...

310. Under Your Nose 03.09.2024

This week, Jen uncovered something that has been hiding just under her nose for a long time, and she and Pete discuss that discovery process. Specifically, in this episode Jen and Pete talk about: In what ways might we seek to problem solve in non-obvious ways? How might we think about the assets, boundaries, and narratives in our lives? What else might be hiding just under Jen's nose? And Pete's?...

309. Indifference 27.08.2024

Feeling somewhat indifferent about the idea of indifference, Pete brings the topic to Jen this week for the two of them to noodle on. Specifically, in this episode Jen and Pete talk about: How can indifference be a positive thing? And a negative thing? How might indifference allow us to relinquish some control? Where might indifference show up in our day to day lives? To hear all episodes and read...

308. Running 2024 20.08.2024

In their annual episode themed around running, Jen and Pete noodle on the ideas of giving yourself a break, and how that might actually help you move ahead. Specifically, in this episode Jen and Pete talk about: How might you add more randomness in to your routine? How can a variety of tasks help you to accomplish the same goal? What are some tools to allow yourself to take more breaks? To hear al...

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