Episode 80

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Published on:

2nd Oct 2025

80. Navigating Through an Uncertain World

In this episode we discuss: Navigating through an uncertain world. We are joined by Jillian Reilly, Author, Global change facilitator,  Keynote speaker, and International aid veteran. 

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  • We chat about the following with Jillian Reilly: 
  • What does it really take to be an effective facilitator of change within an organisation?
  • How can operators lead confidently in uncertainty without overpromising outcomes?
  • When should leaders rely on intuition over data—and how do they build that instinct?
  • Can resilience be intentionally developed, or is it only forged through hardship?
  • How do you balance empathy with accountability when leading teams through tough transitions?

References 

  • https://www.linkedin.com/in/jillianreilly/
  • https://jillreilly.substack.com/
  • www.tenpermissions.com

Biography 

Jillian Reilly is a founder, writer, keynote speaker, and consultant with 30 years’ experience in social, organisational, and personal change across Africa, Asia, and Central Europe. She helps people navigate change and accelerate growth, and is the author of The Ten Permissions (forthcoming), which challenges outdated approaches to adult life in the 21st century. Her memoir, Shame: Confessions of an Aid Worker in Africa, reflects on her early career in international development. Jillian’s work has been featured in the Washington Post, Newsweek, and the LA Times, and her TEDx talk Vain Aid offers insights from the aid industry. She also created the Courageous Conversations podcast, funded by the Ford Foundation, spotlighting African activists.  

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here

Summary

00:06:10 – Becoming a change facilitator

00:08:43 – Leading in uncertainty

00:10:46 – Trusting intuition

00:14:19 – Navigating profound change

00:18:29 – Leading without a grand vision

00:22:40 – Building resilience

00:28:15 – Reframing setbacks

00:35:50 – Holding onto purpose

00:42:10 – Empathy vs. accountability

00:44:05 – Final reflections



This podcast uses the following third-party services for analysis:

Podcorn - https://podcorn.com/privacy
Transcript
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Hello everyone and welcome to

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another episode of the operations

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room a podcast for COOs.

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I am Brandon Medsinga joined by my

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lovely co-host Bethany Ayers.

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How are things going Bethany?

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I'm really tired.

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It's Friday.

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It's been really hot.

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I know we're in London and this is

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basically what Londoners do as soon

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as it gets over 25 degrees,

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which is what 80 something in

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America.

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Yeah, yeah, I mean, legitimately,

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we've had a pretty hot run,

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I would say, you know, 30 degree

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plus weather for four

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days in a row.

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I mean it was pretty brutal.

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Like I think night number three,

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French doors are open in the master

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bedroom and it was as hot outside as

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it was inside and there was no

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breeze. So there was it was just

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boiling.

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It was horrible, there's

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no relief from it.

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So anyhow, exhausted,

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not sleeping.

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It's finally cooled down and

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then went to a

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COO round table dinner last night.

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It was a sass one.

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Oh, the SAS one.

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Oh, I missed out.

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Okay. I had my all-hands last night,

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so we had drinks after the all-hand,

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so that was my preoccupation.

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It was in a new restaurant.

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I mean, because normally we go to

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Zetter House or Zetter Townhouse

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in Farringdon.

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And this one was Art

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Yard and Bar,

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just south of Blackfriars

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in a brand new hotel, a brand-new

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Marriott.

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The food was excellent, because with

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a hotel you're never quite sure, but

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this was on the side of good food.

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And we did our introductions.

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So I went to a dinner two weeks

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ago. I haven't been to a diner in

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about six months, and then I've gone

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to two in two weeks.

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And so in that one, which was just a

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more general COO

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round table, we did introductions.

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And when it got to me, I just said,

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oh, and co-host

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of a podcast, I'm not sure if

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anybody here is a listener, and

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everybody raised their hands.

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And so I was like, okay, I

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don't need to introduce myself then.

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So I'll just go on to

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news. Anyhow, at this dinner,

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I kind of said the same thing and

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everybody stared at me blankly other

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than a couple listeners.

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Anyhow, that I did my intro, the

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next person, blah blah blah.

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And the person sitting next to me

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afterwards said, Oh, I've

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just discovered your podcast and

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really loving it.

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Okay.

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And then I didn't even think to

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ask this question.

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Somebody else did later on.

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It was like, how did you find the

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podcast chat?

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GPT really?

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Yeah. I know.

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How exciting is that?

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Ah, SCO going on here on

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Chachi BT.

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Yeah, but yeah, it's better than

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SEO, isn't it? So he put in,

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what podcast should I listen to as a

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COO and we

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This is actually really good when I

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think about it. I mean, just more

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broadly, obviously Google AdWords

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and keywords, all that's going to

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die, you know, pretty shortly,

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I think. So chat GPT discovery,

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if we're like the premier podcast

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being presented back to people,

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that's fabulous.

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We didn't even know how we did it!

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I suspect, but the fact that we

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did the custom GPT some time

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back, we loaded all of our content

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in there and they've obviously

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sucked that back into the vortex of

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OpenAI.

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So I suspect they're somehow knowing

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that we exist and therefore they're

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presenting it back to people.

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Any other action in the Bethany

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rule?

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So it was announced this week

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that I'm leaving peak because

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I'm living in two weeks in

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a day. So it's quite good to have

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that news out there.

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That's lovely. Yeah, that's great.

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The announcement is out.

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It's like something off your chest a

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little bit. You can now talk about

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it with people

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I can talk about it and I am

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immediately irrelevant.

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This is clearly how

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lame duck presidents feel.

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As soon as they know that you're not

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coming back, it just doesn't matter.

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I had a one-to-one with somebody

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where normally the one- to-one is

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jam-packed with so much content

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and trying to sort through stuff and

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we barely fit it all into an hour.

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I met on this Wednesday and

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15 minutes in, yeah,

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I'm done. I don't have anything

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else. We chatted a little more

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for another.

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10 minutes, and that was it.

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Yeah, so now my

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power is gone, my wisdom is

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gone.

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So it made me laugh, but then

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it gave me a bit of extra time back

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at the end of the day, so I wasn't

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complaining.

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I'm going up to Manchester next

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week and the week after, and

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then that'll be it, and whether or

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not I ever go to Manchester again.

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I wasn't t planning on leaving

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drinks, but somebody in my team

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insisted, so there might be leaving

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drinks with three or four people,

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and then hand in my computer on

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the Friday and I'm done.

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Okay, so you're giving back the

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laptop. I feel like somehow, I don't

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know how I've managed this, every

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company I've ever left, I always

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leave with a laptop.

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Not because I'm stealing it, but

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because somehow it's part of the

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package.

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I have the one from the last time

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I left Peak.

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I don't need yet another one.

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And then I'll get a new one very

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shortly. So I feel like

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I have one that will tide me over.

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Yeah, I cascade them down through

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the family. So my wife has, you

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know, one of my former laptops.

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So my husband cannot handle

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a Mac, just having

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the buttons on the other side.

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So he's actually like a PC user, is

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that what you're saying?

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I know isn't that incredible with

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somebody who chooses to use

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the Microsoft world.

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It really does date people, like all

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sorts of things to date people these

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days. You know, like the latest one

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that we had spoken with some time

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back, but like, if you're not on

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Notion, knowing Notion using Notion

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you're yesterday's news, you know?

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Yeah, I mean, I think it either

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dates people or just is corporate

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people because corporates

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only use.

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Team.

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Fucking teams.

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Yeah. And they all,

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yeah, they're all in this Microsoft

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world.

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Yeah, yeah.

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Somebody was asking me, so they use

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MS Teams and I guess the chat that's

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part of MS Teams and they were just

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about to move to Slack and they're

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all very nervous.

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Like what are you nervous about?

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Like Slack is 8,000 times better and

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way easier to use and

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yeah, you'll be loving it in no

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time.

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UiPath uses, is all Microsoft

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everything, but uses Slack.

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Yeah, that just goes to show you how

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shit Teams is.

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We've got a great topic for today,

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which is navigating through an

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uncertain world.

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We have an amazing guest for this,

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which is Gillian Reilly.

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She's the author of The 10

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Permissions.

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And she is a speaker and

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change facilitator as well.

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So before we get to Gillian, I

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just wanted to walk through her 10

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permissions and just reflect back

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on our conversation with her and see

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what we think.

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All right, so let's start with

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number one, because that's where we

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actually spent the majority of our

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time with Gillian as well, I think

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that you were most interested in.

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So the first permission is to be

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willful, which is what do I

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want to do now, not what

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do others expect of me.

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Oftentimes with operations leaders,

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we are often in service of others,

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whether it's the CEO, the wider

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company, and we're just

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fulfilling expectations of what

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people want from us for the most

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part, as opposed to really asking

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ourselves, like, what do we think

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would be most beneficial for the

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company? That is an intro,

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what's your take on that?

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So I actually have a story that's

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a bit relevant and almost

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operational.

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As yesterday, I had a conversation

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with somebody who

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has the opportunity to

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become a COO,

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but is trying to decide whether or

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not they want to.

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It's a switch within the company.

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And it was a bit of what is a

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CO O? Do I have the skills?

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Is it possible?

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And I of course pointed them in the

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direction of the podcast and episode

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number one of what does the COO.

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It's an amazing opportunity.

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And you can see that they wanted to

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do it.

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But they just had to create all of

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these reasons why

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they shouldn't, or how it could go

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wrong, or how this needs to be a

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decision to make.

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And after we talked for about 45, 50

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minutes, I basically told them that.

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I was like, you clearly want to do

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it, you light up when you talk

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about it, it's handed to you on

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a silver platter.

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Why invent reasons why you

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shouldn't?

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I think when you join companies, you

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have this duality happening

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slightly, which is, you know that

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you need to prove yourself.

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So when it comes to the CEO, the

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leadership team, the water company,

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you need exercise kind of chops

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and also some visibility

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projects to make people feel

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like, yeah, this guy's on it

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or this gal's on it and she knows

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what she's doing and there's value

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being created there.

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And it's kind of like what's being

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asked of you more than anything

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else, right?

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So for example, for myself, there

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was a clear mandate for, here are

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the five things, Brandon, that I

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think you need to focus on at the

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outset. So you obviously need to do

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that and take that seriously.

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On the parallel side of things,

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when I joined these companies, it's

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always about the end goal, which

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is, I'm getting an equity grant.

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I want that to be transformational

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for the company, but also for

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myself. What does Brandon think

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needs to get done in this business

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to get us there, basically?

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And that parallel track.

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Is what I want and what I think is

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best for the company basically and

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trying to like take those two dual

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roles and do what is

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right for the business over a time

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period.

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I think it's always like the

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challenge I think for operators and

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for myself as well.

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Number two, go astray.

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Allow yourself to explore outside

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your defined role or identity.

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What do we make of that?

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I think that is the role of COO,

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right? That's why we like it, is

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that we can stick our noses into any

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part of the business, be

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flexible, explore,

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not be sidelined or

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contained within one discipline,

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siloed into one discipline.

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I think it's like one of those

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things early in my career

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I didn't like because the

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marketing person was a marketing

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person and you knew where they were

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gonna go. The salesperson was a

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salesperson and here I was.

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Jack-of-all-trades, master-of none

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type thing, and how do I label

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myself, and I don't fit in,

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and what's my path?

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And then, as always,

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your weakness, your biggest

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weakness, and biggest strength are

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either side of the same one.

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And so as I got more senior,

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my ability to do everything and

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understand it all actually became

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my superpower, rather than

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hard to form a

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career path or an identity.

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Next one is feel your way, so

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use your emotions and intuition as

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valid decision making tools.

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Don't create all of these

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intellectual reasons why you

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shouldn't do the decision that you

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know you're already going to do.

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If you feel it and you

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know that that's what's passionate

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and where you want to go, do

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it. If you hate it in the end,

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you can always make a new decision.

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There'll be new opportunities.

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Maybe you won't have the exact same

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options you had, but you'll have a

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new set and it just keeps opening

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different branches of decisions.

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Yep, no, exactly.

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I think it's very tied to this idea

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of just taking things step by step a

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little bit, which is not

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overthinking, not having a grand

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master plan.

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But you know, what is the next best

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move that I can make?

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Sometimes you have some data points,

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sometimes you don't, but you can

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usually sense like, what is the the

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best thing to do?

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It's also just experience that

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intuition is often,

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you have experienced many things in

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the past and it's pulling it

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together.

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And then again, I think as you get

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older, you get more,

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you trust your intuition more.

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So, this one I love, by the way.

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So, think small instead of think

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big. What is the most sensible,

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small, incremental step that can be

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done and not thinking

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through all these catastrophe

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scenarios thereby stopping yourself

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by taking that very first step?

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I agree.

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I think it's very tied in

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with the trusting your

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intuition.

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And this is the side where you

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talk yourself out of things that you

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know are right. And also, it's

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very helpful when leading a team and

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everybody's a bit overwhelmed and

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trying to plan out the next two

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years or five years or whatever.

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But really, often in

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the companies we work for, you

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just need to do the next thing.

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You just need do the next sprint.

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You need to just save this customer.

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I think some of it is you still

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need a North Star and you need to

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know where you're going and you have

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some principles on how

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you execute or make decisions

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and then

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need to just deal with the problem

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in front of you.

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This actually happens a lot

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in one of the teams at peak,

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the catastrophizing.

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And then suddenly this problem

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is two months

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to solve and all of these issues

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and need all of these people.

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And then it's just like, can we just

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diagnose it?

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And we're like, oh, we didn't push

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it into production.

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It's done.

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And it's a five minute process.

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Know what you're dealing with and

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then deal with that rather

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than all of the possibilities you

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could be dealing with.

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All right, last one, make believe.

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We didn't really talk about this one

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so much, but I find it interesting.

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So make believe, reclaim creativity,

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make things that don't exist yet.

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A lot of ops leaders think of

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themselves as optimizers and not

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creators.

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Yeah, I think it's great.

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I mean, whether you're in

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the ops world or

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not, or what way you're looking at

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it. Like when I had that time off,

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did my pottery class, you can see

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above, you know.

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Oh, so I didn't even know-

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that those are all your pots no

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some are my pots some are not my

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pots and there's some other pots

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and it'll be look too good.

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Yeah, the good ones are not mine.

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The really plain ones are mine.

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And I think it's the problem is

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school decides that some people are

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creative and some people aren't

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creative, but humans are just

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creative. And it depends on what

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you're talking about.

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The fact that we're working in

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startups and scale-ups and

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we're taking something that doesn't

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exist and creating a business

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is fundamentally creative.

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You're literally creating a

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businesses. You don't have to have

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pretty stars on it and be able

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and have beautiful handwriting to be

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creative.

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It's just. The way that you look at

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it. We can't help but be creative

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as humans.

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Sitting with a blank spreadsheet

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and then creating an entire business

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model, that is creating.

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You have a good point because you're

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taking abstract thoughts and

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concepts and applying them and

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molding it into a pottery dish,

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in this case being a spreadsheet.

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Yeah. And a good spreadsheet is

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truly a work of art and

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stunningly beautiful, just

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in a different way.

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So I think people are creative every

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single day and artists

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have just co-opt what creative

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means.

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So on that note, why don't we move

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over to our conversation with

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Jillian Raleigh.

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So the Book 10 permissions, can you

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give us a bit of a sense of the

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thesis of the book?

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Yeah, the thesis, the subtitle

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is Rethinking the Rules of Adulting

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for the 20th Century.

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I describe it as a playbook

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for navigating adult life in

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the current chaos and part of

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what I just referenced was helping

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people navigate profound change.

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I think we are all navigating

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profound change that has been

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coming, you know, over a decade.

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The social norms,

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the way we operate has and shifting.

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Pretty dramatically in the book

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i describe it as the great

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unraveling of sort of flattening

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of higher keys and loosening

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of social norms a

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lot of the boundaries that told us

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how to behave and how to show up and

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become much looser and of

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course now we're in this.

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Inflection point where changes about

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to accelerate or is in the process

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of selling accelerating

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tremendously.

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And the thesis is,

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if we're going to thrive in this, we

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need to give ourselves permission to

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operate very, very differently than

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perhaps we've been told or

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taught to. So those 10 permissions

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are 10 different ways to

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think about how you're supposed to

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navigate your adult life, different

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than sort of the default story that

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most of us grow up with or

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carry along with us.

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And really, in the end, it's about

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being more adaptive and responsive

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to change and prepared

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to grow and evolve throughout the

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course of your life.

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When I think about your 10

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permissions and I think about ages,

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I think there's different permissions

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that are more or less important

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depending on the age category that

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we're talking about.

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So if we think about the

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mid to late career professional that

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is doing really well,

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escalating the promotional ranks,

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they've got a family, they got kids,

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they've have the house, in that age

Speaker:

bracket of the 10 permissions,

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which ones do you think are the most

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relevant?

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I always come back to the first one,

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which is be willful, which is

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a very primary question

Speaker:

around what do you want?

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What is your desire to create?

Speaker:

What is our desire for that next

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chapter in your life or that next

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thing that you want to create,

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because I think a lot of times

Speaker:

by the time we've gotten to that

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phase in our lives and that phase

Speaker:

and our career, we've in many cases

Speaker:

detached ourselves from our

Speaker:

own.

Speaker:

Desires our own sort of drivers to

Speaker:

create something or contribute

Speaker:

something. We've been very sort of

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duty bound if you will and made all

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the right choices I

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encounter and I work with a lot of

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people who get to a point who say, I

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actually want to do something

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different. What is that?

Speaker:

You know, how do I sort of tap a

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little bit into my

Speaker:

own desire to maybe parlay

Speaker:

whatever it is that I've learned,

Speaker:

whatever the sort of platform I've

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created to maybe pursue something

Speaker:

that feels like a little bit

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more of a reflection of my own

Speaker:

gifts, my own experience,

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you know, to I won't say finally.

Speaker:

But in a more meaningful way

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translate a career's worth of

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experience and talent and

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assets into something that feels

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like a greater reflection

Speaker:

of me.

Speaker:

And in some cases at that point in

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your life, you feel like you've got

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a little bit more leeway to do that.

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So that's one that I would always

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turn people back to because I think

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if you try and create

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change in your live without

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connecting to your own desires,

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you can often...

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Either find yourself sort of

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hesitating or adrift or confused.

Speaker:

So to me, that's always the anchor

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for any sort of change

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or, you know, pivoting

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you want to make in your life.

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That's interesting. I was at an

Speaker:

event a couple of weeks ago where

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it was C levels

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who have had more than one C level

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job.

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So we were talking about

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how we moved between

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roles.

Speaker:

And then somebody was asking

Speaker:

in the questions afterwards, come

Speaker:

more specifically, I'm a CMO and

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no matter what I do, everybody

Speaker:

just keeps making me be a CMO.

Speaker:

And I want to get out of that.

Speaker:

And we were taking about how to

Speaker:

rebrand yourself and came up

Speaker:

with idea of a Venn

Speaker:

diagram with three circles.

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One being your passion,

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one being your experience

Speaker:

slash talent, and the third

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being your network and being

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able to rebrand yourself by

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finding that intersection of those

Speaker:

three.

Speaker:

And I think so often people think

Speaker:

about their network and their

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experience, but if you want to move

Speaker:

somewhere else, you have to find

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your passion.

Speaker:

But you have to figure out what your

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passion actually is,

Speaker:

not just what you think your passion

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should be.

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Totally.

Speaker:

And you know, also kind of

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maybe lowercase P rather than

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uppercase P because I think when we

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start to talk about passion, a lot

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of people think that it needs to be

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some grand vision or

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grand contribution.

Speaker:

And, you know I really think when

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you give yourself permission to

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drill down into that in terms of

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what is it that I want to be a

Speaker:

part of? What do I want create?

Speaker:

What problem do I wanna help solve?

Speaker:

Or What kind of services

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or products do

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I want to help make available to

Speaker:

people that you sort of free up a

Speaker:

little bit of your own imagination

Speaker:

around what that might look like?

Speaker:

And I think that's such a great

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example that you've just raised of

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people getting a little bit sort of

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fixed into an identity of

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I am CMO.

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And one of the ideas that I talk

Speaker:

about in the book is an I

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can versus I am mentality.

Speaker:

So detaching

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your identity from your role,

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which I think is going to

Speaker:

happen more and more and more for

Speaker:

young professionals moving into the

Speaker:

world today. But I think for us,

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who've been at it a while, even

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allowing ourselves to look at,

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as you've just described, sort of

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our, some of our assets and

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capabilities and networks through

Speaker:

that lens of, this is what I

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can do. And how do I bring that

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to a variety of different

Speaker:

situations, depending upon

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how the is evolving depending upon

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where I am.

Speaker:

In my own life and career.

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So I love talking about it.

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Identity.

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Which one of the ten should

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leans towards that identity

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question?

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Let me go.

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To the second one which is go

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astray.

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Because I think for

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a lot of us, you know,

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we were raised to believe that

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straight lines were everything.

Speaker:

That standing in line and sitting up

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straight was how we proved ourselves

Speaker:

to be good people and we get in our

Speaker:

heads that success looks

Speaker:

like following a straight line.

Speaker:

And our identity gets shaped and

Speaker:

fixed very early by the idea

Speaker:

of, you know, conforming to an

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idea either that we have of

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ourselves or that the world has of

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us. And then we sort of stay

Speaker:

in that for the remainder of our

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lives. Because anything other than

Speaker:

that feels rebellious or as

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you get older, it feels selfish.

Speaker:

So I think giving yourself room.

Speaker:

To accept the fact that

Speaker:

you can and will be

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more than one thing over the

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course of your life.

Speaker:

And obviously the premise of the

Speaker:

book is that increasingly we

Speaker:

have to. We have to allow

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ourselves that more flexible sense

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of identity if we're going to

Speaker:

keep evolving and changing at pace.

Speaker:

So I think a lot of the books is

Speaker:

around sort of unraveling

Speaker:

our tight grip on who We

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think we are.

Speaker:

And allowing ourselves to continue

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to explore who we can be

Speaker:

and who we need to be, given the

Speaker:

changes that are happening around

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us.

Speaker:

One of the ways that I have

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been thinking about identity, and

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I'm almost more on the,

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does your work need to be part of

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your identity? Or can you have your

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work be separate to it?

Speaker:

So the game that I play

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with myself is, if I

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can only have three labels to

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stick on myself to be my identity,

Speaker:

what are those three that are

Speaker:

permanent?

Speaker:

And so for an example, for me,

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being a mother is part of my

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identity.

Speaker:

Even if the horrible thing of

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my children not still being alive.

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I would still be a mother.

Speaker:

Whereas being a wife is not

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part of my identity.

Speaker:

If my husband and I divorced, I

Speaker:

would not be forever the

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former wife of X.

Speaker:

And so if you can only have

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three, does

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work play into being one of those

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three? And that's part of how I test

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my own identity.

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Interesting.

Speaker:

And you know, so I have two teenage

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boys, 17 and 14.

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Me too.

Speaker:

Oh, exactly the same.

Speaker:

No. Oh my gosh.

Speaker:

Well, and what's so interesting is

Speaker:

coincidence.

Speaker:

And when you ask that question, the

Speaker:

first thing that came to mind was,

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okay, fine, mother.

Speaker:

Of course, first one, mother,

Speaker:

is the foundational identity that

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is and will always be.

Speaker:

Well so fine, this is interesting.

Speaker:

I observe in them that

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I don't think.

Speaker:

They will necessarily have

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as tight of a

Speaker:

knitting together of work and

Speaker:

identity as I was brought up

Speaker:

to.

Speaker:

I think some of, you know, we are

Speaker:

Gen X, we, I think, or

Speaker:

sort of I am Gen X.

Speaker:

I'm on the border.

Speaker:

Sorry.

Speaker:

Suddenly I was like, oh, okay.

Speaker:

No, I am.

Speaker:

I will wave the Gen X flag and

Speaker:

say, you know.

Speaker:

It was probably maybe the first

Speaker:

generation where we were so

Speaker:

encouraged to it.

Speaker:

Our identity and our work together

Speaker:

as one.

Speaker:

And what I see in them is a

Speaker:

willingness to look

Speaker:

for things or be open to ways

Speaker:

in which they will create security

Speaker:

for themselves and create a

Speaker:

livelihood that might not be the sum

Speaker:

total of them, right?

Speaker:

And maybe that's the side hustles

Speaker:

and the, you know, over a decade of

Speaker:

people opening themselves up to

Speaker:

those types of things I think

Speaker:

is creating a

Speaker:

slightly more pragmatic

Speaker:

if you will, mindset amongst

Speaker:

coming the next generation.

Speaker:

But I don't know, do you observe

Speaker:

that in your own children or mine in

Speaker:

a specific case?

Speaker:

I'm just petrified about my own

Speaker:

children entering the workforce.

Speaker:

Yes, I understand that.

Speaker:

And I actually did a talk with

Speaker:

parents the other night about just

Speaker:

this, that we,

Speaker:

the current parents of the world,

Speaker:

need help supporting our kids to

Speaker:

move into this world.

Speaker:

Because I think it's very hard for

Speaker:

us as parents right now.

Speaker:

You know, as I said, I don't have

Speaker:

any prescriptions to offer them.

Speaker:

Like my parents could say, if you go

Speaker:

to a good school, you'll be fine.

Speaker:

You know you'll go and get a job.

Speaker:

There was a, and again, this is part

Speaker:

of what I talk about in the book, is

Speaker:

that there these if-then equations

Speaker:

that made sense to us.

Speaker:

Or what I say is requirements and

Speaker:

guarantees. So if you've fulfilled

Speaker:

the requirements, you were largely

Speaker:

guaranteed a desirable

Speaker:

outcome. And that is not the case

Speaker:

anymore.

Speaker:

It is a much looser playing field.

Speaker:

And so how we support our

Speaker:

kids to have a sort of mindset

Speaker:

instead of capabilities to

Speaker:

enable them to thrive in that

Speaker:

world, it's very, very different.

Speaker:

And I don't think we should

Speaker:

underestimate that it won't look

Speaker:

like the one we walked out into.

Speaker:

Won't.

Speaker:

I have one who

Speaker:

by virtue of just,

Speaker:

I don't know, my husband calls him a

Speaker:

surface dweller and my husband says

Speaker:

he's also a surface dwella.

Speaker:

They're not deep thinkers.

Speaker:

They just like to look for things

Speaker:

that are fun.

Speaker:

Don't have massive plans.

Speaker:

I suspect he'll

Speaker:

be The other one is

Speaker:

much more like me.

Speaker:

He's already trying to decide which

Speaker:

GCSEs he takes to maximize

Speaker:

his chances of getting a job in

Speaker:

the AI world and not about

Speaker:

what he's interested in or cares

Speaker:

about. And I'm trying to get one to

Speaker:

loosen up and one to just get a

Speaker:

little bit more structure.

Speaker:

You know, I have these spectrums.

Speaker:

They're both sitting on the other

Speaker:

side of it.

Speaker:

And so I'm worried about them for

Speaker:

different reasons.

Speaker:

I've decided we worry

Speaker:

about whatever it is.

Speaker:

We find something to worry about

Speaker:

regardless of where they are.

Speaker:

Mean, this is also true.

Speaker:

The one that was more tightly wound,

Speaker:

like he would have thrived much

Speaker:

better in a world where

Speaker:

all of the white collar jobs,

Speaker:

entry level white collar job still

Speaker:

existed.

Speaker:

I read an article the other day that

Speaker:

50% of entry level white collar,

Speaker:

jobs are going to disappear in the

Speaker:

next five years.

Speaker:

And so of course, I'm

Speaker:

freaking out as a parent.

Speaker:

Of course, we all are.

Speaker:

I mean, you can't be alive and not

Speaker:

be freaking out about the fact that

Speaker:

the entire mental

Speaker:

model that has shaped the

Speaker:

trajectory of coming into

Speaker:

adulthood is falling apart.

Speaker:

And so the way I describe it

Speaker:

is the shift from following the way

Speaker:

to finding your way.

Speaker:

When we were growing up, there were

Speaker:

a certain number of paths, you

Speaker:

picked the one and you followed it,

Speaker:

which is what you're describing,

Speaker:

sort of your second son is still

Speaker:

trying to do to some extent, to say,

Speaker:

if I follow this, if i make one big

Speaker:

bet and I think it's the right one,

Speaker:

then I can stay in that and it'll

Speaker:

sort of take me along.

Speaker:

Whereas the other one is to say

Speaker:

you're going to come out and

Speaker:

there'll be a range

Speaker:

of possibilities you might have to

Speaker:

make your own.

Speaker:

You won't know which ones are good,

Speaker:

you know, You're going to need to be

Speaker:

far more.

Speaker:

Exploratory and that's going to come

Speaker:

much more naturally, as you said,

Speaker:

for your surface dweller.

Speaker:

But yeah, I think of it sometimes

Speaker:

as the difference between being in a

Speaker:

hiking with a paved path,

Speaker:

then you follow it and then the

Speaker:

premium is on your ability to

Speaker:

keep going and follow the signs and

Speaker:

versus being put down in the middle

Speaker:

of the woods and saying, okay,

Speaker:

you got to find your way.

Speaker:

And we all know that when we do find

Speaker:

our way through those situations,

Speaker:

it's absolutely exhilarating, right?

Speaker:

You feel like a million bucks.

Speaker:

So that's why I think

Speaker:

there's potential for

Speaker:

something hugely satisfying to

Speaker:

come out of this, but it is

Speaker:

gonna require a very different way

Speaker:

of finding your way forward.

Speaker:

So this topic of uncertainty

Speaker:

and kind of a future that we can't,

Speaker:

it's not knowable in front of us,

Speaker:

that seems very unpredictable,

Speaker:

I suppose. A lot of your permissions

Speaker:

revolve around this idea, I think.

Speaker:

Can you maybe just give us a bit of

Speaker:

a shape on that?

Speaker:

Yeah, thanks for picking up on

Speaker:

that. Yeah, the original

Speaker:

premise for me was what I called the

Speaker:

explorer's way.

Speaker:

And it was this need that this

Speaker:

uncertain world is requiring of

Speaker:

us to be more exploratory.

Speaker:

And the ones that you've just

Speaker:

mentioned, those permissions that

Speaker:

you just mentioned are sort of

Speaker:

operationalizing that, if you will.

Speaker:

So for me, they're about

Speaker:

how you expect to

Speaker:

be able to move through

Speaker:

your adult life.

Speaker:

And I think.

Speaker:

As much as we know that we are

Speaker:

living in a time of uncertainty,

Speaker:

there's still this kind of

Speaker:

expectation that success

Speaker:

will look like

Speaker:

ease and accumulation

Speaker:

and a sort of

Speaker:

one thing leads to another, that

Speaker:

that's what you buy for yourself if

Speaker:

you are reasonably

Speaker:

successful, then you will

Speaker:

expect to have a line of sight

Speaker:

that's long enough for you to make

Speaker:

plans, etc.

Speaker:

Etc.

Speaker:

And I think that the lived

Speaker:

experience today is not

Speaker:

that, and I think it's very easy for

Speaker:

people to start to then feel like

Speaker:

there's something wrong with them,

Speaker:

they're doing something wrong,

Speaker:

everybody else has a plan, everybody

Speaker:

is sort of moving smoothly through

Speaker:

their lives.

Speaker:

And as you say, I think particularly

Speaker:

for young people, you know,

Speaker:

the anxiety sets and the

Speaker:

self-recrimination sets in when

Speaker:

it's kind of like...

Speaker:

But this doesn't feel the way that I

Speaker:

sort of expected it to feel, right?

Speaker:

I expected it to be a little bit

Speaker:

more, you know, get a job,

Speaker:

get an apartment, get a car

Speaker:

vibe, even though that's

Speaker:

not what's happening for a lot of

Speaker:

people.

Speaker:

So, so yes, I think it's

Speaker:

normalizing.

Speaker:

And leaning into

Speaker:

a way of moving forward

Speaker:

that might not have

Speaker:

all of the predictability and

Speaker:

all of this certainty, and therefore

Speaker:

your own lived experience of it is

Speaker:

going to be quite different.

Speaker:

You might feel at times like,

Speaker:

I am working in three-month

Speaker:

increments or I'm working in

Speaker:

year-long increments.

Speaker:

I'm creating something and

Speaker:

I'm worried that

Speaker:

I don't have a plan for next year

Speaker:

sort Thank you for listening.

Speaker:

And so that permission is to say,

Speaker:

it's okay. You know, there will be

Speaker:

times in your life where you will

Speaker:

have to kind of pull your locus

Speaker:

of control in, find your

Speaker:

way through some deep uncertainty.

Speaker:

And that doesn't mean you're a

Speaker:

failure. It doesn't that, you know,

Speaker:

your life is falling apart.

Speaker:

It means you're in a time of

Speaker:

creativity and change.

Speaker:

So.

Speaker:

It's sort of accepting the fact

Speaker:

that some of what worked for us, you

Speaker:

know, late 20th century sort

Speaker:

of big plans and big, you

Speaker:

now, five-year visions might

Speaker:

not be feasible anymore and that's

Speaker:

okay.

Speaker:

That doesn't mean that everything's

Speaker:

falling apart. It means you've got

Speaker:

to be extra attentive

Speaker:

to learning and adapting and

Speaker:

sort of being on your toes and, as

Speaker:

you said, keeping that optionality

Speaker:

alive for yourself.

Speaker:

Lots of problems to solve all the

Speaker:

time. And we have some people

Speaker:

who just catastrophize and

Speaker:

will turn the task that's needed

Speaker:

today into

Speaker:

three months of required

Speaker:

resource and things that could go

Speaker:

wrong and an inability to

Speaker:

start because it could roll

Speaker:

into something massive.

Speaker:

And I feel like with that team, I'm

Speaker:

constantly saying, okay, well,

Speaker:

that's a possibility, but

Speaker:

we haven't diagnosed any

Speaker:

of it. So what's the thing that we

Speaker:

do today.

Speaker:

To find out whether or not that's

Speaker:

going to be an issue.

Speaker:

And stop the catastrophizing

Speaker:

so that people's brains

Speaker:

are wasting so much energy on

Speaker:

so many what ifs of the future

Speaker:

versus what's the reality of today.

Speaker:

So that's Think Small.

Speaker:

I'm here.

Speaker:

This is what I can control.

Speaker:

And the story, I cut it from the

Speaker:

book, but a lot of that for me came

Speaker:

out of traveling through really

Speaker:

wildly weird and wonderful places

Speaker:

where I

Speaker:

could have had a panic attack at any

Speaker:

time if I what if too much.

Speaker:

So I had to just keep.

Speaker:

Staying in the moment, staying very

Speaker:

present, keeping my locus of control

Speaker:

tight, looking around, figuring out

Speaker:

what I could control and what I

Speaker:

couldn't. But yeah, totally,

Speaker:

it's your brain will,

Speaker:

you know, take you on the worst

Speaker:

kind of ride if you let it in this

Speaker:

in this world.

Speaker:

And then you waste your energy

Speaker:

on that versus

Speaker:

solving today's problem.

Speaker:

I think it's so interesting how

Speaker:

catastrophizing has become

Speaker:

kind of our default.

Speaker:

I mean it's now completely

Speaker:

normal and totally accepted

Speaker:

and almost if you're not

Speaker:

catastrophizing then you're not

Speaker:

awake.

Speaker:

So I think that's

Speaker:

our collective response to some

Speaker:

extent to the uncertainty.

Speaker:

It's like to

Speaker:

throw all of our anxiety and

Speaker:

doomsday into the

Speaker:

ether and feel somehow better that

Speaker:

we're not alone.

Speaker:

But, you know, if you try and enter

Speaker:

into those conversations with either

Speaker:

a more optimistic or a more

Speaker:

pragmatic voice, it's often like,

Speaker:

oh, you just don't get

Speaker:

it. Whereas I think,

Speaker:

as you've described, actually what

Speaker:

you're trying to do is find a way

Speaker:

forward that will hopefully have a

Speaker:

better outcome than sitting around

Speaker:

worrying about, you know,

Speaker:

potential terrible.

Speaker:

Outcomes.

Speaker:

Okay, I was going to get back to

Speaker:

I think is actually, we

Speaker:

haven't gotten very far. I think

Speaker:

we've gone from like one to and

Speaker:

whichever one is things small

Speaker:

for five.

Speaker:

But I'm going to go back to one,

Speaker:

which is

Speaker:

how do you figure out?

Speaker:

What you want.

Speaker:

No, I mean, for me, it's the most

Speaker:

transgressive thing of all, right?

Speaker:

And for me it came out of

Speaker:

a career in change and

Speaker:

realizing that you were

Speaker:

trying to push people to sort of

Speaker:

evolve through change when they

Speaker:

hadn't even connected

Speaker:

to their own desire to move

Speaker:

through that change to get to

Speaker:

sort a better place.

Speaker:

And I realized how much people's

Speaker:

sense of what they want.

Speaker:

Is what I would describe as outside

Speaker:

in rather than inside out.

Speaker:

So you let the world tell you what

Speaker:

you want.

Speaker:

You outsource your wants to either

Speaker:

your family or your community

Speaker:

or your culture or your corporate,

Speaker:

whatever, you know, and then you let

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them tell you what you wanted.

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You say, yes, let's go.

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And that worked, you know, in

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a very hierarchical traditional

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world, you scored points and

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earned benefits from doing what

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other people wanted.

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The simple reality is that now.

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First of all, you don't get as many

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points or rewards for just being

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compliant and saying yes.

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They're not going to protect you

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just because you do that.

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Your loyalty will not get you what

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it used to.

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And second of all you've got so many

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more options and so many more

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choices so you can get overwhelmed

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by them.

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I always say I see it as

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like a muscle and for

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most of us it's a muscle that

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doesn't get exercised very much and

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possibly hasn't and exercise since

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childhood.

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So start small with.

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Trying to tap into what do

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I want to eat, what do i want to

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do on Saturday, what do I wanna do

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with my friends,

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like literally just connect to

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the parts of you that feel something

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to the voice inside of you,

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that says hey I want spaghetti

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versus pizza or whatever it

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is.

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I think a lot of us try and figure

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out what we want to do with our

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careers and we can't figure out what

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we wanna eat on Saturday night

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and you can't make big choices

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if you're totally unused to making

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small ones with any degree of

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intentions.

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So there's a workbook that comes

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with the book and a lot of it is

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really focused on super small,

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activating your agency and your

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intentionality through some of the

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smallest low consequence

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choices.

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Because if you leapfrog to the high

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consequence ones and then go, oh

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gosh, I can't decide if I want to

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quit my job or not, it's like, well,

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yeah, that's pretty serious.

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So why don't we work on just

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getting in touch with you

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as a person who has desires

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and is allowed to act

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on them, and maybe some of them

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not, but at least if you're

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connected and more aligned in that

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way, it allows for a better

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conversation with yourself when

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you get to some of the higher

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consequence, more serious choices in

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your life. I think that's fantastic.

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Another one that really resonates

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with me is I feel like a lot of my

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life has been spent trying to

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figure out myself and what I'm

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feeling.

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One of the things I've noticed is

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the stories that I tell

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because for a

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while – and this comes back

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to my original question of is

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this about your personal life or is

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it about your career?

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There was definitely a part of me

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that was like business

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was not who I was and

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business is what I did and

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was not part of what I enjoyed.

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I might have been good at it, but I

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didn't enjoy it.

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And yet I've had multiple career

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breaks and then keep going back to

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business. And then at a certain

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point I realized, oh no,

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I actually enjoy it, even though

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I felt like I shouldn't.

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It's something that I enjoy.

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So it's also like, what are those

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things that you enjoy that you tell

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yourself you shouldn't enjoy or

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can't enjoy, or it's not an

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acceptable thing to enjoy and

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embrace those as well?

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Oh, I think just the idea

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of desire, pleasure,

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enjoyment, I think some

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of what I've observed is we've

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moved into discipline and

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grit and rigor as

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our collective response

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to the increasing uncertainty, you

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know, if I cold plunge,

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if I get up at 5am, if my journal if

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I If I

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have this unbelievable structure

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overlaying my life, I will be

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able to somehow immunize

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myself against all the crazy out

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there. And it's like, great, if that

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works for you, fantastic.

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However, there's a whole scope of

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there's something to tap into around

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enjoyment, around pleasure,

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around what lights me up,

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what makes me feel good.

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Because from that space

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you are much more generative

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you are a much better contributor

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when you are in that

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space and i think we underestimated

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the extent to which you know

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contentment happiness.

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Is a wonderful place to operate

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from because you are then

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able to take advantage of

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what's around you and contribute

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better and i mean having

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the conversations around what do i

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enjoy.

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It sounds so basic and yet

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the more you slip into your dutiful

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adult role the more those

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conversations feel indulgent

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they live on the ever near

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edges of your to

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do list.

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And it's like, actually,

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that's pretty important because I

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can't serve anybody from

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a place of deficit and

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duty and always like

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my outgoings always

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exceeding my incoming sort of

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energy and stimulation.

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So.

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Again, I think some

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of what's happening right now might

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allow for us to connect to

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those things and engage

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with them more than our

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parents could or maybe even

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I could from an early point

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in my career.

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So that's where I see some potential

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right now.

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So maybe we can circle to the last

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one in your lesson. I'm very curious

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about this one, the make belief

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number 10.

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So I have a couple different

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thoughts in my head. One is, you

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know, obviously when you're a child,

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it's all about make belief and

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slowly but surely it's beaten out of

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you as you get older for the most

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part.

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This is one other thought, which is

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I just did the all hands meeting.

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I hosted, I was the moderator last

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Thursday.

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And whenever I go into moderate all

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hands sessions, this is like an

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improv set and I'm just like.

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You know it's like silly version of

Speaker:

brand and having fun with people

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doing a bit of a back and forth and

Speaker:

all that jazz but never can make

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believe bring someone this one.

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Yeah, well, I mean, you've picked up

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already in the conversation that so

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much of this is about

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reconnecting to some

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sort of innate ways of being

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and doing that in many ways we lose

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or we have lost as we

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seek to become adults.

Speaker:

And this one, perhaps the

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most, as you've just said,

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I think a couple things.

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So I describe it as make things you

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believe in, and perhaps more

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importantly, believe that you can

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make things. Which, as you

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say, we lose that belief

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really quick.

Speaker:

I think we probably all have some

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sort of experience that scarred us

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in an art class early on when

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we decided that we

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could not make stuff, that we were

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not artistic or creative.

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And from that point on, we

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don't engage with that piece of

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ourselves.

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And I think, we've seen that

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as a capability for the few.

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The rest of us just go out and

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collect a paycheck and execute on

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somebody else's ideas.

Speaker:

And obviously what's happening right

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now is the scope opening up

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for, and a requirement opening

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up, for us to tap more into

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that capability to

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make things big and small.

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And I think podcasts are a brilliant

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example of that, a space

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that's opened up over the last, you

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know, and obviously boomed over the

Speaker:

last five years in particular

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where people were like, hey, maybe

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we can make something that is of

Speaker:

value to the world.

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So I think it's happening.

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I think it needs to accelerate that

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our understanding of our

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kind of generative capacity to

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make things that are responses

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to current problems

Speaker:

that are sort of reinterpretations

Speaker:

of old things.

Speaker:

One of the things I talk about in

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the book is think DJ,

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not DaVinci.

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So, you know, a DJ is remixing

Speaker:

stuff that already exists to make

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something new to meet a specific

Speaker:

need for a specific group of people

Speaker:

of an eye. He or she is not some

Speaker:

grand master who's making something

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that will exist forever, but

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the need to mix and remix

Speaker:

and reset for

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a specific need.

Speaker:

You know, pop-ups, places

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where people are finding ways to

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create things that are

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responsive and adaptive.

Speaker:

And your reference to sort of

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improv, the need to behave

Speaker:

more improvisationally to accept

Speaker:

the fact again that when you're

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improvising, I think we used to kind

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of feel like, oh gosh, I don't have

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it all together because I'm

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improvising here.

Speaker:

And it's like, no, that's just what

Speaker:

you're going to have to do a lot of

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is to figure things out on the fly,

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to come up with a new solution to

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make something that just works for

Speaker:

now, but might fall apart.

Speaker:

You know, in the next day, that's

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okay.

Speaker:

And that again is a mindset that

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I think we've got to allow ourselves

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to play around with and engage with

Speaker:

in a way that I certainly did

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not.

Speaker:

And again, for our listeners

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who are a little bit older, I think

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there's so much scope to

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get in touch with this.

Speaker:

And, again, I would say start small

Speaker:

and just play around with things

Speaker:

that interest you.

Speaker:

But Yeah, that's almost the

Speaker:

culmination.

Speaker:

You know, it bookends the, what do I

Speaker:

want? And what's my contribution?

Speaker:

These two things bookend everything

Speaker:

in between.

Speaker:

And I think we're moving

Speaker:

into a period where that

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conversation with self,

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embedding that into yourself

Speaker:

will become so important

Speaker:

to us moving through the next five

Speaker:

years, the next decade, not feeling

Speaker:

like we're just responding and

Speaker:

becoming irrelevant.

Speaker:

But actually you know figuring out

Speaker:

how to make our best contribution to

Speaker:

a world that's changing very very

Speaker:

quickly we

Speaker:

unfortunately, are rapidly running

Speaker:

out of time, but

Speaker:

nobody gets away without answering

Speaker:

our final question,

Speaker:

which is, we've

Speaker:

covered so much today, if

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our listeners can only remember one

Speaker:

thing, or take one thing

Speaker:

away, I should say, what is it?

Speaker:

I think it's that you're allowed

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to have a life that looks very

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different perhaps than the story

Speaker:

that you were sold or the story you

Speaker:

told yourself and that this world

Speaker:

is requiring us to sort of

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loosen our grip on the

Speaker:

notion of what good looks like as

Speaker:

an adult, okay?

Speaker:

So, it's okay.

Speaker:

Give yourself a break, allow

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yourself more room than maybe

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you thought you needed to

Speaker:

discover what's possible of

Speaker:

a moment, of a season

Speaker:

in your life.

Speaker:

Because the more that you listen to

Speaker:

that voice that wants to explore

Speaker:

something other than the status quo,

Speaker:

the more you're oiling your own

Speaker:

receptivity and adaptivity to

Speaker:

a changing world.

Speaker:

And I think that that, in the end,

Speaker:

is what all of us need to really

Speaker:

nurture in ourselves, is how do

Speaker:

I evolve as the world does?

Speaker:

I'm allowed.

Speaker:

It's okay.

Speaker:

It might not always be neat.

Speaker:

It might feel very messy, and

Speaker:

adult life isn't supposed to feel

Speaker:

messy. But maybe

Speaker:

in all that mess is a lot of

Speaker:

the beauty.

Speaker:

And a lot of the joy and a lot

Speaker:

of the sense of discovery and

Speaker:

possibility that I think most of us

Speaker:

need in spades right now.

Speaker:

So yeah, give yourself permission to

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go and discover what's

Speaker:

possible and know that it's

Speaker:

okay.

Speaker:

Lovely. So I will give us permission

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to end this podcast today.

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So thank you Jill Riley for joining

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us on the operations room.

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If you like what you hear, please

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subscribe or leave us a comment and

Speaker:

we will see you next week.

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About the Podcast

The Operations Room: A Podcast for COO’s
We are the COO coaches to help you successfully scale in this new world where efficiency is as important as growth. Remember when valuations were 3-10x ARR and money wasn’t free? We do. Each week we share our experiences and bring in scale up experts and operational leaders to help you navigate both the burning operational issues and the larger existential challenges. Beth Ayers is the former COO of Peak AI, NewVoiceMedia and Codilty and has helped raise over $200m from top funds - Softbank, Bessemer, TCV, MCC, Notion and Oxx. Brandon Mensinga is the former COO of Signal AI and Trint.

About your host

Profile picture for Brandon Mensinga

Brandon Mensinga