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

208. Different Processes 20.09.2022

Fresh off of an exhilarating experience with two of her clients, Jen tells the full story to Pete and together they noodle on how many different approaches there are to a process, and how we might navigate that in artistic and workplace environments. Specifically, in this episode Jen and Pete talk about: How might we notice and learn from other people's processes? What are strategies leaders can u...

207. Practice What You Preach 13.09.2022

Dancing with a topic that drives Jen crazy, she and Pete break down the phrase "practice what you preach" and investigate how we might instead preach what we practice. Specifically, in this episode Jen and Pete talk about: What are some tools to developing a good practice, and then sharing what you've learned from that? What is the difference between a mentor and a coach? Why is humility so import...

206. Advice 06.09.2022

This week, Jen and Pete discuss the differences between advice, feedback, and questions, and noodle on how they might think about and ask for which of those they need. Specifically, in this episode Jen and Pete talk about: How might "advice" be defined? How might a coach know when to give advice, ask a question, or propose their opinion? How might we turn someone's opinion into advice? To hear all...

205. Give More F*cks 30.08.2022

Jen catches Pete by surprise by cursing to start off this week’s episode, and the fun (and swearing) just continues from there. Specifically, in this episode Jen and Pete talk about: What are the benefits of using swear words as part of your writing or creative practice? And how might using these words actually bring more humanity to your writing? What are some helpful, sometimes curse-filled writ...

204. 137 Reach Outs 23.08.2022

With a renewed reach out practice since returning from his wedding/honeymoon, Pete gets interviewed by Jen to find out all about his reinvestment in new connection. Specifically, in this episode Jen and Pete talk about: What are some different kinds of reach outs? Why might come from reaching out to the edges of your existing networks, and beyond? Did Pete receive any negative feedback from any 1...

203. Serendipity 16.08.2022

After experiencing an incredible and serendipitous moment, Jen shares what she learned with Pete, and together they noodle on taking the unexpected or the unplanned path. Specifically, in this episode Jen and Pete talk about: How can a person increase the serendipity in their schedules and to-do lists? How might we prepare and/or plan for the unexpected? How might serendipitous moments influence t...

202. Running 2022 09.08.2022

In the latest Running episode of The Long and The Short Of It, Jen shares some learnings from her practice of running, and she and Pete noodle on their larger implications in every day life. Specifically, in this episode Jen and Pete talk about: What might happen if you don't give yourself the break you've become accustomed to? What are different ways we might be able to push ourselves farther tha...

201. Finding a Groove 02.08.2022

After returning from his three-week holiday, Pete has been struggling to find his groove, and together, he and Jen unpack why that may be and how to get in to a groove again. Specifically, in this episode Jen and Pete talk about: What is a groove? How might we create more flow states in our lives? Why is it important to look for a new groove, as opposed to getting back an old one? To hear all Epis...

200. Ask Us Anything 26.07.2022

To celebrate Episode 200, Jen and Pete answer brilliant questions from their brilliant listeners. Specifically, in this episode Jen and Pete answer questions like: When was the last time you changed one of your deeply held beliefs, perhaps even one you'd consider core to your identity? And what was it? If you could live anywhere in the world for one year, where would it be? Dropping the "um's", th...

199. Mistakes vs. Failures 19.07.2022

This week, Jen and Pete dive in to a discussion about mistakes and failures, and how we might encounter, approach, and learn from these instances within our lives.  Specifically, in this episode Jen and Pete talk about: What are some different frames through which to view failure? How might we add some levity into mistake making? How can we lead with grace, and allow those around us to make and le...

198. Second Drafts 12.07.2022

Jen and Pete broach a topic that they have never talked about before either on-air or off-air, and ask each other the question, how might we approach second drafts? Specifically, in this episode Jen and Pete talk about: How might we qualify a second draft, in relation to a shitty first draft? Who is the second draft for? Why is it important to know the audience you're creating for, when looking fo...

197. Self-Promotion 05.07.2022

This week, Jen brings up an idea that initially elicits a groan from Pete, but they both end up with some aha moments about the (dreaded) topic of self-promotion. Specifically, in this episode Jen and Pete talk about: How might self-promotion be reframed? How are self-promotion and idea sharing linked? What are some ways to start a practice of positive self-promotion? To hear all Episodes and read...

196. Vujà Dé 28.06.2022

Jen introduces Pete to the idea of vujà dé, and together they dive into what the topic might mean and how we might employ it in our lives. Specifically, in this episode Jen and Pete talk about: What is vujà dé? What are the benefits of doing something as if for the first time? What are some strategies with which to start practicing vujà dé? To hear all Episodes and read full transcripts visit The...

195. Forks in the Road 21.06.2022

This week, Jen and Pete thrash about strategies a person might utilize when they are unsure of which strategy to utilize. Specifically, in this episode Jen and Pete talk about: What can a person keep in mind when they encounter a fork in the road? Why might making a decision and leaving the fork in the road feel scary? How might a person navigate a decision when both options (or more) are in align...

194. Attitude 14.06.2022

After receiving positive feedback to the idea, Pete and Jen dive in to why, "Attitude is a skill," is such a mic-drop statement. Specifically, in this episode Jen and Pete talk about: How might attitude be a skill that can be practiced? Why might it feel scary for a person to make changes to or work on their attitude? What are some strategies for cultivating a positive attitude? To hear all Episod...

193. Humility 07.06.2022

An often discussed topic on the podcast, Pete and Jen dive even further into noodling on why humility is a superpower. Specifically, in this episode Jen and Pete talk about: Why is having humility so important? How might leaders use humility to better lead? What are some ways to cultivate humility? To hear all Episodes and read full transcripts visit The Long and The Short Of It website: https://t...

192. More Than You Can Chew 31.05.2022

Jen and Pete dive in to what happens when you bite off more than you can chew and develop strategies to help while in that situation, as well as how to avoid taking on too much in the first place. Specifically, in this episode Jen and Pete talk about: How might a person deflate tension when they have too much to do? Why are we our own worst boss? Why might we be afraid of saying no to an opportuni...

191. 1% 24.05.2022

After (re)reading James Clear's Atomic Habits, Pete shares with Jen what he's learned from that book, and together they dive deeper into the idea of getting 1% better at something every single day. Specifically, in this episode Jen and Pete talk about: How does compound improvement work? What are the benefits of building skill slowly, as opposed to all at once? What are some strategies to build th...

190. Bad Reviews 17.05.2022

Speaking from personal experience, Jen and Pete noodle on how to find some levity and insight if you're on the receiving end of bad reviews. Specifically, in this episode Jen and Pete talk about: What might a person learn from a bad review of their work or performance? What strategies might one use to look at and interpret a bad review? When looking at your own work, what are the important questio...

189. Review the Tape 10.05.2022

Speaking in sports terms, Jen speaks with Pete about what it means to "review the tape," and how we might use this strategy to learn more about our own behavior and to grow our skills. Specifically, in this episode Jen and Pete talk about: In what instances in our lives might we be able to review the tape? Why is it important to review tape with a certain goal or aim in mind? How might a leader us...

188. Ask Better Questions 03.05.2022

In this very meta episode, Jen and Pete ask each other how they might ask better questions, and how to develop/discover questions to help them get unstuck. Specifically, in this episode Jen and Pete talk about: Why is asking quality questions an important skill for a leader? How might a leader listen to their team and develop their own questions in response, as opposed to just following a script?...

187. Crossroads 26.04.2022

This week, Jen and Pete dive in to goal-setting, fear-setting, and strategies for how to get to where you're going. Specifically, in this episode Jen and Pete talk about: What does success look like? Why is it important for a team to be able to disagree but still commit? How might a person discover different paths that lead to the completion of their goals? To hear all Episodes and read full trans...

186. Bad Ideas 19.04.2022

Jen and Pete dive into one of their brainstorming tactics, which is to tell each other, "This might be the worst idea ever uttered by man." Specifically, in this episode Jen and Pete talk about: Why is it important to share bad ideas? What is the effect of framing something as a bad idea? How might bad ideas lead to good ideas? To hear all Episodes and read full transcripts visit The Long and The...

185. KYA Questions 12.04.2022

Pete and Jen spend this week's episode listing questions that kick their ass and send them straight to the groan zone. Specifically, in this episode Jen and Pete talk about the following questions: What are you tolerating? What are you afraid of? How might you raise the stakes? What are you excited about? What would an older version of yourself do? What would your role model do? How are you compli...

184. Rest 05.04.2022

This week, Jen and Pete dig in to the ritual of resting, and how we might create more of it in our lives. Specifically, in this episode Jen and Pete talk about: What does "rest" even mean? What are different strategies for the action of resting? How might a person cultivate a habit of rest? To hear all Episodes and read full transcripts visit The Long and The Short Of It website: https://thelongan...

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