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416 episodes

411. Proposals
11/08/2026 | 19 mins.
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: hello@thelongandtheshortpodcast.com
Pete's work: humanperiscope.com · Jen's work: jenwaldman.com
410. Grown Up Sh*t
05/08/2026 | 16 mins.
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: hello@thelongandtheshortpodcast.com
Pete's work: humanperiscope.com · Jen's work: jenwaldman.com
409. Unpacking
28/07/2026 | 17 mins.
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: hello@thelongandtheshortpodcast.com
Pete's work: humanperiscope.com · Jen's work: jenwaldman.com
408. Strategy
21/07/2026 | 18 mins.
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: hello@thelongandtheshortpodcast.com
Pete's work: humanperiscope.com · Jen's work: jenwaldman.com
407. Packing
14/07/2026 | 18 mins.
As Jen prepares for her summer travel, she and Pete noodle on the activity of packing, and the sometimes difficult decisions of what to bring and what to leave behind.

Specifically, in this episode Jen and Pete talk about:

Why is making decisions so hard?

How might the usage of constraints and rules be beneficial when making choices?

What are some tactics to deliberately carry less around with us?

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: hello@thelongandtheshortpodcast.com
Pete's work: humanperiscope.com · Jen's work: jenwaldman.com

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About 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. 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.

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