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
Podcast website
Latest episode
Jul 7, 2026
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Episodes
406. Perfectionism Trap 07.07.2026 18:01
This week, Pete shares with Jen a perfectionism trap within an AI model, and together they noodle on how to get their work unstuck and shipped. Specifically, in this episode Jen and Pete talk about: What tools might we use to gauge when our work is good enough? What are the signs and symptoms of looking for perfection? How might we use AI to ship our work more frequently? More from us in your inbo...
405. Creative Process 30.06.2026 19:09
This week, Jen and Pete noodle on the creative process, and how we might build and iterate on our ideas. Specifically, in this episode Jen and Pete talk about: How does Jen think about the creative process? And Pete? What is the Ship of Theseus? What are some tactics and questions we can use to build and expand on existing ideas and frameworks? More from us in your inbox. Subscribe to Box O' Go...
404. Pete, The Student 23.06.2026 15:15
This week, Pete revisits what it's like to be a student, and he and Jen noodle on the mental frameworks this inspires in them. Specifically, in this episode Jen and Pete talk about: What is it like to be new in a learning environment? How might we learn from our peers, and their questions and learnings? How might we more often put ourselves into communities that are growth minded? More from us i...
403. Lessons from Jen's Coaching Retreat 16.06.2026 21:37
Energized from her coaching retreat, Jen shares with Pete five learnings from the three-day discourse between herself, the coaches, and their clients. Specifically, in this episode, the learnings that Jen and Pete talk about are: Know what hat you, as the coach, are wearing. Know what hat they, as the client, are wearing. Say less. Sort your thoughts into objective and subjective, before you say t...
402. Occam's Razor 09.06.2026 17:18
This week, Jen and Pete noodle on the idea that sometimes the simplest answer might really be the answer. Specifically, in this episode Jen and Pete talk about: What is Occam's Razor? How might we simplify our problem solving? What tactics can we utilize when we are stuck on something? More from us in your inbox. Subscribe to Box O' Goodies . A weekly email with the books, podcasts, quotes, and...
401. Subtraction 02.06.2026 17:50
This week, Pete and Jen noodle on the activity of a subtraction audit...one more thing to add to their plate, that will hopefully free up more space. Specifically, in this episode Jen and Pete talk about: What is a subtraction audit? How might we help ourselves filter the things we say yes to? What are some tactics protect the free time in our calendar? More from us in your inbox. Subscribe to B...
400. Episode 400 26.05.2026 20:22
This week, Pete and Jen are celebrating four hundred weeks of podcasting (with no breaks!). To honor the occasion, they answer questions that were sent in by you, the listeners. Specifically, in this episode Jen and Pete talk about: How have Pete and Jen sustained their momentum of recording, over four hundred episodes? What episodes are in The Long and The Short Of It's cutting room floor? What e...
399. How Do I Start? 19.05.2026 19:24
Almost four hundred episodes later, Jen and Pete throw it back, in a way, to Episode 1, asking: How do I start? Specifically, in this episode Jen and Pete talk about: Why can starting something become scary or overwhelming? What are many different tools and frameworks through which to experiment with starting? How are endings and beginnings related? More from us in your inbox. Subscribe to Box O'...
Bonus Episode: We Need Your Questions 14.05.2026 0:51
In anticipation of Episode 400 of The Long and The Short Of It, Jen and Pete are asking for questions from you, our listeners, to answer in an Ask Us Anything episode. Do you have a question that you'd like Jen and Pete to ponder, to noodle on, to think out loud about on Episode 400? Head on over to thelongandtheshortpodcast.com/400 , and submit your question. To hear all episodes and read full tr...
398. The Eisenhower Conundrum 12.05.2026 16:28
This week, Pete coaches Jen as she navigates the urgent and important curveballs and projects that have been thrown into her life recently. Specifically, in this episode Jen and Pete talk about: What is The Eisenhower Matrix? How might we prioritize the urgent and important? How might we move between periods of sprinting and periods of recovery? To hear all episodes and read full transcripts, visi...
397. Thought Leadership 05.05.2026 16:30
This week, Jen and Pete noodle on the questions: Is thought leadership a teachable skill? And if so, how might we teach it? Specifically, in this episode Jen and Pete talk about: What is thought leadership? What attributes does a thought leader possess? How might we turn our thoughts and ideas into implementable and practical actions? To hear all episodes and read full transcripts, visit The Long...
396. Spring Cleaning 28.04.2026 17:56
This week, Jen jumps in to spring cleaning and Pete jumps in to autumn cleaning, and together they noodle on questions that might help us to question, sort, and polish the things in our lives. Specifically, in this episode Jen and Pete talk about: What questions might we ask ourselves, to get intentional about the systems in our lives? How might we question, sort, and polish our marketing material...
395. Trojan Horsing 21.04.2026 17:15
This week, Pete brings a Trojan Horse to Jen, and sneaks in ideas around leadership, empathy, curiosity, and humility along the way. Specifically, in this episode Jen and Pete talk about: How might we utilize the idea of a Trojan Horse in leadership and coaching? How might we set up our teams to feel they can fully contribute? When might we Trojan Horse something, versus being more straightforward...
394. Sports Teams 14.04.2026 18:00
The question of how we might utilize sports team models within corporate or theatrical organizations has Pete and Jen scratching their imaginary beards this week. Specifically, in this episode Jen and Pete talk about: How do sports teams differ from corporate and theatrical structures? And how are they similar? How might we utilize feedback, clarity, and communication within our teams? How can we...
393. BHAGs 07.04.2026 16:42
This week, Jen gets excited about the idea of risk progression, and she and Pete use the idea of BHAGs to think about steady risk implementation. Specifically, in this episode Jen and Pete talk about: What is the definition of a BHAG? How might we utilize progressive risk taking in our work and reach outs? What might a hairy risk or goal look like? To hear all episodes and read full transcripts, v...
392. Breakfast 31.03.2026 16:10
This week, Pete and Jen noodle on the importance of storytelling, starting with the story of what they each had for breakfast (or how they might approach a charcuterie board). Specifically, in this episode Jen and Pete talk about: Why is storytelling within the workplace and as leaders so important? How might you prompt someone else to tell you a story, and how might that help you learn about them...
391. Replaced by AI? 24.03.2026 16:44
This week, Jen and Pete noodle on the ways that AI cannot replace humans...yet. Specifically, in this episode Jen and Pete talk about: What role do love and care play in the workplace? Why is having a coach important for skill development and growth? How might we incorporate AI into our work, without relying on it? To hear all episodes and read full transcripts, visit The Long and The Short Of It...
390. Normal 17.03.2026 16:35
This week, Jen and Pete define (and redefine, and redefine, and redefine) the concept of what it means to be normal. Specifically, in this episode Jen and Pete talk about: What is the relationship between normal and average? When might it be a good thing to be normal? When might it be a good thing to not be normal? How might we push back against normalcy, where we want to be extraordinary? To hear...
389. Aspirational Prototyping 10.03.2026 17:35
This week, Jen shares with Pete a new phrase she's coined, in order to turn dreams into aspirational prototypes. Specifically, in this episode Jen and Pete talk about: How might we move inch by inch towards our goal? In what ways might defining the perfect day or week or schedule or calendar be useful to us? What are some different ways to think about the relationships in our lives, our goals for...
388. Zone 2 04.03.2026 17:48
Inspired by another learning from his triathlon, Pete shares with Jen a training technique, and both of them noodle on what it might look like to work within Zone 2 (and not constantly overexerting in Zone 5). Specifically, in this episode Jen and Pete talk about: What are the five zones of energy and effort? Why is it important to take periods of rest? How might a more continuous method of traini...
387. Revising Goals 24.02.2026 16:54
This week, Jen and Pete noodle on a mental framework in which they revisit and recommit, or revise, or replace, or remove the goals they've set for themselves this year (which leaves them feeling re-invigorated, re-energized, and re-inspired). Specifically, in this episode Jen and Pete talk about: How might we add and consider the context surrounding our goals? How might we reframe a pivot away f...
386. Physio 17.02.2026 17:21
This week, Pete shares with Jen some wisdom from his physio, and together, they noodle on how their leadership may be more simple, practical, and elegant. Specifically, in this episode Jen and Pete talk about: When might it be best to give direction versus ask a question? What are some practical ways to simplify the learnings we are trying to give to our clients or colleagues? In what ways can we...
385. Fear Reminder 11.02.2026 17:07
Throwing back to an idea from Episode One, Jen reminds Pete of the question: Is your fear keeping you safe, or is it keeping you stuck? Specifically, in this episode Jen and Pete talk about: How might we notice and call out our own fears? Why might it be helpful to hear about other people's fears? What are some tactics we can use to confront and push through the fear that is keeping us stuck? To h...
384. Writing 04.02.2026 19:45
After listening to James Clear talk on the habit of writing, Pete talks with Jen about their writing practices, and how he might investigate new and old ways of writing and thinking. Specifically, in this episode Jen and Pete talk about: How might the act of writing help us change up our patterns of thinking? How might we give up the idea of having to be perfect on our first try? What is Pete's wr...
383. Reframing Tonsilitis 27.01.2026 16:50
As Pete prepares to have his tonsils removed, he asks Jen for mental frameworks he can use during his two-week recovery. Specifically, in this episode Jen and Pete talk about: How might we use our internal google translator to switch negative language into positive action? How might we switch the words "have to" to "get to"? When life throws us a curveball, how might we embrace this unexpected pat...
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