The Winding Road

Dorie Clark: Taking a Long Game Approach to your Career

• Travis L. Scott / Dorie Clark • Episode 48

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Welcome to this week's episode of the Winding Road Podcast; today’s guest is Dorie Clark.

Dorie has been named one of the Top 50 business thinkers in the world by Thinkers50. She is a keynote speaker and teaches executive education at Duke University.
 
She is also the Wall Street Journal bestselling author of The Long Game, Entrepreneurial You, Reinventing You and Stand Out, named the #1 Leadership Book of the year by Inc. magazine. A former presidential campaign spokeswoman, she frequently writes for the Harvard Business Review. 


We talk about:

  • There are a lot of people building courses. How important is tying the community to those courses?
  • How important do you think it is for people to be a part of a community? If they have a non-linear career?
  • The resume is irrelevant.
  • How do you prioritise the different things you're involved with?
  • You talk about the long game in your book; what about a shorter timeframe? 
  • How do local network building versus broader entities like Linkedin etc., come into play?
  • What was the catalyst for writing your book?



Connect with this week’s guest Dorie Clark

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Ep# 48 - Taking a Long Game Approach to your Career


Travis: Dorie. Welcome to the Winding Road Podcast. I'm so excited to, to have you here. I, I guess I'm kind of on a little streak. I had Jenny Blake on, a few weeks ago, and she's gonna come back on in couple weeks to, to kind of pick up where we left off. And, and now, now you, and, and, just really thrilled that, 

Dorie: that you're here.

Well, thank you, Travis. I'm so glad to be talking with you. 

Travis: So, so yeah. I, I've read all of your books. I've been a part of your recognized experts, workshop and, and I have to tell you about that. I mean, it was tremendous workshop, but I think the, the thing I was. The most pleasantly surprised about with that was the community that you've built through that.

I mean, just an amazing group of people, people I've met there who I would consider to be friends now. And so thank you for, for putting that together and bringing those people together. It's been 

Dorie: wonderful. Thank you, Travis. It's so great to hear. I mean, that really was one of my big goals for the program because when it comes to, Online courses.

Some of the conventional wisdom, which is not wrong, is. You wanna make the course tightly focused enough so that people see immediate results and you know, they're able to get the quick win. And the problem, the sort of inherent problem is that becoming a recognized expert is kind of the opposite of a quick win.

Because the whole point is like, you know, sorry, that's not how it works. , you know, to kind of keep doing it. That's how you become a recognized expert is it's not fast, it's not easy. you can do it, but it takes a lot of time and. And the thing that keeps you going through the process when it can become hard or when it feels like a slog, is the community of people that you've built that make it an enjoyable process and give you the support and give you the encouragement and show you that it's possible.

And so for me, that was a really integral part of building the recognized expert community. So I'm, I'm so glad that it felt that way and worked that way for you. Yeah. Yeah. 

Travis: Absolutely. And do you think. If you're, you know, there's a lot of people building courses that wanna build courses. How important is tying community to those, those courses?

Dorie: Well, one of the things that I've, I've heard, and I agree with it in a lot of ways, is that people come for the course. You know, they come for sort of the content, but then they stay for the community because it's a, it's a little hard, you know, if people are like, oh, the community's great. Well, you know, I mean, people, first of all, people are kind of skeptics, right?

They're like, well, I'm glad for you, but you might have bad taste . And so, you know, like nobody, nobody believes that until they actually experience it for themselves. And so the thing that will sell them on a course is like, well, I wanna learn that thing. And that's, that's great. It doesn't necessarily have a lot of adherence, a lot of stickiness, but in order for the recognized expert process to be effective, because it's something.

Definitionally people need to be working on for a period of several years. You have to have the stickiness, you have to have people who are willing to, to do things. And so for me, community is a very integral part of it. I mean, I, I recommend that people include that in their, in their courses at least they're more intensive courses as a, a key component of it.

But it really was mandatory, I think, in terms of the formulation. What it takes for people to be successful in the journey toward becoming a recognized expert. Mm-hmm. . Yeah. Yeah. 

Travis: I, I would agree with that. And, I had mentioned before I hit record that I'm, I'm creating some courses, one's a cohort based course and, it's, and the winding road, the, the podcast and, and, careers is for people who have a non-linear career path.

And, you know, when they try to create a resume, On paper, it doesn't really tell the, the full story. And, and, and the course I'm creating is how to land your next job without a resume. And so how important do you think it is for people to, to, to be a part of community? If they're, if they have a career that is non-linear, they don't fit into a box with, with recruiters or hiring 

Dorie: managers.

I, I think it's a, a great thing to build a community around something like that. So I'm very excited about the course that you're putting together. Travis, I agree with the premise that, People often when they're changing careers or when they're thinking about doing so, they fixate on the wrong things.

You know, we, people tend to fixate on the sort of particular tactical thing that's right in front of them. Like, I have to hire someone to help my, make my resume great. And you know, that's, that's the thing that takes all their psychic energy. And it's like, dude, if you take a step. You, you're, you know, as your title promises, you don't even need the resume.

The resume is irrelevant if you, if you're doing all the other things right? If you're, if you're making the upstream choices around building your network or being able to describe your value and what you can bring. And so I, I think, people kind of fixate on, what's. They really neglect the invisible part, but the invisible is what matters a lot more.

I mean, I'll, I'll give you one example about how I hired my assistant, who now I promoted him. So he is now my chief of staff, but he. I put out a call in a Facebook group that I was part of a few years ago. I, I had had a long time assistant for like seven years and she was kind of fixing the leave, like not really ready to leave yet, but, but kind of on that path.

So I'm like, you know what? I need to, I need to hire someone for at least a little bit of time. And then with the option of maybe expanding it, because I was pretty sure she would be, she would be departing. And so I realized that a good pool of people to choose from would be folks who were in my musical theater training program that I was doing at the time, because I thought, okay, you know, these are folks that would really.

Want, you know, as pre covid, you know, folks who would particularly appreciate the opportunity to work on their own schedule to work virtually, because it would enable them to spend time with their music. And also, they're usually highly educated people. They have college degrees, but they're underemployed.

And so I thought, all right, this is a good, criteria for an a. And so I put out a call in my Facebook, group, and I ended up getting, you know, maybe at least four people reach out to me about it. But one guy who, who I knew a little bit, texted me, he like texted me within five minutes of the post going up.

And I already had a good feeling about him because our. Program, like their orientation, their onboarding, for the program was a little bit abysmal and they somehow, it didn't, it didn't occur to them that we should actually have introductions, which is pretty basic. If you're gonna be doing a two year program with a bunch of people, I'm like, whoa, that might help

but they didn't do it. And so this guy had taken it upon himself at, at like an after party to arrange a kind of compos. Lyricist speed dating where he gave everybody name tags and he arranged the whole thing and I was just so impressed with his initiative. And then, you know, he went and texted me cuz he was interested in it.

Dorie: I'm like, all right, this guy's kind of a go-getter. So. You know, I, I literally did not look at his resume. I did not check references. . I mean, I don't know, maybe I should have, maybe he would've, you know, maybe he is a serial killer, secretly . But he's worked for me for four years, and so far he appears not to be a serial killer.

but he ha he, you know, never created a resume. That's not what, what it was about. But, you know, I've now given, Well over six figures of income over the past few years, through, through just impressing me through other means. So I think that your strategy, Travis, that you're teaching in the course is right on that, that's a great 

Travis: story.

And, yeah, a couple of questions came out of that. so, one is, you know, you, you have a lot of interest. You're involved with a lot of things, doing a lot of things. And I think people have non-linear career paths because they're interested in a lot of different things. I know I am. That's why I have have that in.

how, how do you prioritize the different things you're involved with? How do you stay on top of, of 

Dorie: everything that you're doing? You know, in a literal sense, I, I just like kick it old school with a legal pad and it's ado list. I, I don't have anything really fancy. I mean, to the point about people fixating on the, the kind of obvious things like, oh, the resume or whatever.

I get so many people who are like, oh, well what kind of, what kind of CRM do you use and what, you know, what kind of software do you use? And you know, it's like I use a notepad, I use Excel. I use like Google Calendar. Like money is not gonna make a difference for you. When it comes to sort of solving the problems of prioritization, it's a strategic problem.

You know, as I talk about in, in my book, the long game, it's, it's not a, a thing like, oh, if I only had, you know, an extra a thousand dollars to spend on software, then it would solve my problem of what to spend my time on. No, it does not. So, you know, one question that I always like to think about and ask is what, what is the thing that if I can do it, it will make everything else easier?

That's, that's one way to, to think through what would be the best use of your time. But, you know, the honest truth is, some days I would say are busy enough that, that it's really just a, like, let's just get through the calendar, kind of get day. I mean, I know I, you know, alright, I have half a dozen meetings.

I've just, all I really have time for is. Executing on those meetings, being there on time and being where I'm supposed to be. And that's all I can ask of myself on those days. but there are also other days where you have a lighter schedule and that's the place where you can begin to, to make choices.

I think that a lot of the answers, we try to solve the problem downstream, but I think a lot of, a lot of. Should be solved upstream because what I realize, I've come to realize, and it became acutely evident to me as I was writing the long game and really thinking about all of this. When you agree to do anything, it usually creates about two to three times more work than you anticipate, because whatever the thing is, you've agreed.

There's emails back and forth. There's planning calls, there's preparation, there's, you know, some kind of downstream consequence or follow up, whatever it is. And so I think it's, it's important in our heads when we're saying yes to just multiply whatever our estimate is by about 2.5 in terms of being able to quantify how much time and effort it'll actually.

Travis: Interesting. Um,yeah, I was working on a proposal this morning and I just, I just added 20%, but I think I need to double double that, so, so yeah, I might be thinking about that wrong. and, and in the long game you mentioned think thinking in waves. and I, I think about that a lot now. and. That coupled with working with Jenny, Jenny Blake over the summer.

It's changed the way I do my podcast. Instead of doing them, you know, one a week and, and just this never ending process of, of feeling like I have to just keep up. Now I've started to block them together, do all the recording at once, I've hired an editor, to then edit and then ship it. And that's made things a lot easier in the, in the book.

You mentioned thinking in waves in kind of like three to six month or maybe longer waves. what about a shorter timeframe? Is it, is it a good thing to maybe think about organizing your schedule maybe in, in waves, throughout the week or throughout the month doing certain things, certain weeks, certain days?

Dorie: Yeah. Well, I mean, this is. It's kinda like chaos theory, right? Where you, you sort of, you know, the things, you know, if you, if you look. The coastline, let's say, and then you zoom down to like individual pebbles on the beach, they sort of mirror the coastline. So I think it's true. I mean, yes, there's sort of an arc of waves of like, here's how to spend your year, here's how to spend your, you know, your six months.

But it's also true that, I mean, if we bring it back down to its, its literal. Basis. We all have waves. We have circadian rhythms that are governing our day. You know, there's people, I mean, obviously there's exceptions to everything, but most people get tired at night and you're not gonna be so effective if you've already been up and doing things.

And so you need to understand, all right, that's probably not the time for me to like, you know, like 2:00 AM is probably not the best time to concentrate on doing your taxes and not making mistakes, you know? So how do. How do you apply your energy and your effort based on what's the most appropriate thing in that moment?

And so it relates to energy, but it also relates, as you were saying, to bundling activities and recognizing, okay, this is, this is a time when I should be doing more of something or less of something. So one example. It's been really clear to me coming out of Covid is that was a time where systematically for the past, you know, couple years, most people did not do enough networking because our social worlds just kind of contracted.

And partly it was because. Everybody else was scared. partly it was because conferences and large gatherings just got canceled or shut down. Partly it was because, you know, we may have had concerns about, you know, sort of reaching out, outside of our. Pre predetermined networks. You know, strangers became dangerous for this period of time in many people's imagination.

And so as a result, we spent a lot more time with people we already knew and a lot less time with people that we did not. And so I think that that implies that. We need, you know, if we were under indexing on that, it's time to rebalance the portfolio and to overindex on networking and socializing and connecting with people.

Because unless you wanna continue that trajectory where you're just sort of narrowing and narrowing and narrowing the people you talk to, which you know, most of us recognize, is not actually good for us. It's not good for our mental health, it's not good for our innovation. It's not good. Introducing opportunity into our lives.

We wanna change it. And so in order to change it, this is the wave where we need to start socializing and networking more than we did. Much more than we did in order to balance out the deficit that we had been running for a while. Yeah, that, 

Travis: that's interesting. And, and how, How does local network building versus kind of a wider range through, you know, LinkedIn and other, other non-local, entities come into play?

Dorie: Well, you know, I, I'm keenly attuned to this, having, this past December bought a place in, in Miami and, and moving down here, you want a need to. Both. I mean, we now have the ability to have these sort of virtual networks and to stay in touch with our preexisting friends and, you know, have, have all of those relationships.

But it's also true that for most of us at least, you wanna have some people over that, like, you know, oh, it's a Friday night on board. Who can I hang out with? You'd like to live in a world where you have at least somebody you could call . So that doesn't happen by accident. And I, I think a lot. A lot of people feel very, you know, I have a whole chapter in, in the long game, about relationship building and networking, and I wanted to make a point of doubling down on that and talking about it because I think frankly, a lot of people don't have the skills or don't feel empowered to be.

The person doing the inviting. And I really want to encourage people if, if someone listening is in that position where they're like, oh, you know, yeah, I mean, I'd like to go out, but like, I don't know where to start. I don't know who to ask. You know? Oh, would it be weird? I really wanna push back on that and say, no, it's everybody's responsibility to do this.

Like, you know it, it might. It might feel to you like, oh, I don't know how people would respond, or, you know, gosh, I, I don't wanna be presumptuous, but in reality, you're basically saying, I want everyone else to do the work. I want people to come to me and fill up my social calendar. And that's actually not right.

we, we all need to carry the weight of this. And you know, as my mom used to like to say, if you wanna get an invitation, you need to give an invitation. We all need to be hosts. We all need to step up. People appreciate invitations. In many cases, they might be just as lonely on a Friday night. And so being an organizer and reaching out and doing.

Is really a mitzvah. If we would, if we would get started and embrace it, it's much less hard than you might imagine. Mm-hmm. . Yeah. Yeah. And 

Travis: it is, it is scary because you're, you're wondering like, will people say no? will anybody show up? Right? So. I know you have regular dinner parties, right?

Where you invite people over for dinner and, and is it, how, how do you determine who, who to 

Dorie: invite? Well, to be clear, mostly I don't invite them over because we live in a world Travis, where, You know, if you have, if you have, a dinner party with six people, there are eight dietary restrictions and,

And, you know, I mean, I, I take full responsibility. I'm vegetarian, which I know is, you know, somehow mentally challenging for people as well. So, you know, it gets, it gets really hard to, to manage, when you have to be the host, figuring all that out. But I do like to have gatherings at restaurants, which I think are better equipped for.

Figuring out food things. But yeah, I mean, honestly, You can have a pretty loose value proposition. And easy thing is if people have something all in common, you can pick a theme. And I've done a million different themes, you know, just based on like who you know or what, what group you wanna establish. You could, you could have a thing for, you know, I've done one for female journalists, you know?

Mm-hmm. , it's like, You just say like, Hey, you're a female journalist. Do you wanna need other female journalists? And the answer is probably yes, I do. And so they come to the party, or I did one for musicians, friends who were professional musicians, you know, they loved meeting each other in networking. But it, do, you know, I've done a million for business authors.

you know, people loved to sort of trade tips and best practices and like, oh, how'd you get so many Amazon reviews? Tell me your secret. You know, like, whatever. Everyone wants to talk shop. But it's also true that you can have just sort of mixed parties and by mixed I, I mean, you know, you could just say, Hey Travis, I'm having a gathering next, next Thursday night of really interesting people.

would you like to come And you know, if you're the right type of person, if you're the kind of person that's like, yes, I would like more interesting people in my life, you will probably say yes to that. And that's actually part of the fun is like, you might not normally meet an astronaut and a dog breeder and a comedian and a, you know, a university provost, but hey, they're all together at the dinner and all of a sudden you get to, you get to meet a bunch of people that you wouldn't have otherwise, which is cool.

Travis: Yeah. Yeah. That's, that's awesome. And when I was working with Jenny over the summer through her Voxer coaching that, that she was doing, which was a great experience. I had asked her that like, cause I knew she had moved from the Bay Area to New York and didn't really know anybody. And, I moved from Spokane, from Seattle to Spokane in 2016.

Worked remotely that whole time, for a company in Denver and, and really didn't get out and meet a lot of people locally. And then during Covid, my network like exploded internationally, which is crazy. Yeah. That through workshops and communities. And you know now once a month I have a, a call at five in the morning with someone in Finland and, and Singapore.

And that's the only time make it work. And so I want to build a more vibrant local network, cuz I'm still working remotely, just not getting out there. And so Jenny. Recommended Nick Gray's book to our cocktail party. And, and then it reminded me of, of your, how you host people. And I thought, I just need to do this.

It, it feels uncomfortable. but when I first opened Nick's book, he said, all right, whatever you do, like three weeks from now, from this time of reading this, like plan a party. So I did. And I just said, okay. Oh, fantastic. I'm gonna do this. I'm gonna host it in my backyard. It was still nice out. And I, I did it with some neighbors, some people I knew locally.

and, and then I put it out on LinkedIn and had a few people show up that I didn't know. and they just came and, and one actually turned out to be a local, like morning reporter for Crem, the, the CBS affiliate. So that was, oh my gosh. So that was kind of fun. And and then just with the kind of people I knew here in Liberty Lake, the tiny town we live in.

Travis: I had the mayor come, my neighbors an F 15, former F 15 pilot, so like, it was just a really cool, eclectic group of people and it was just kind of the. The spark I needed to say, okay, this isn't that hard. It, it was really fun. I wanna do this again. And so now I'm, and, and now I'm gonna host another one in November around a theme similar to, to what you mentioned.

And what's your theme? My theme is gonna be local marketing. Operations and revenue operations people. Oh, cool. Because that's the space I'm in now. Yeah. there's some cool people I've met and I already have three kind of tentative RSVPs and so I'm gonna do that in three cause I'm not gonna host it this time cause that was fun.

But it's just, I'd rather do it somewhere else. We have a local like hard cider place here called trail break and they've lots of room to meet, and people can order their own food, their own drinks, whatever. Just much easier. Right. And so I'm gonna do that and then, Gonna do another theme of, of local people who went to Indiana University where I went, because there's not a lot of us here being so far from, from Bloomington, Indiana.

And so thought that would be a good kinda easy theme to get people excited about and just start to practice and get better at it. And good 

Dorie: for you, man. I'm impressed. You're, you're just taking, taking it into your own hands. That's exactly what I would recommend. I love that. 

Travis: Yeah. And I mean, it's, it's fun and, and, and I think.

Maybe start to expand it virtually and, and maybe have Zoom. I don't know how that, well, that would work, but, but more tighter themes with it, you know, like marketing ops, revenue ops. But, a funny story, that when I was working with Jenny on that and I was starting to plan, plan my party, She, she had mentioned she was coming to one of your, your gatherings and she, she sent me a boxer and said, guess who's gonna be there?

Nick. Nick Gray's gonna be there. And so That's right. So I thought it was just kind of, good timing or as Jenny likes to, to mention serendipity happening and, and, actually got a Voxer from. Jenny, but it was Nick who, who, who used her Voxer and sent me a message about the party and gave me all kinds of tips cuz it was gonna be the next week.

Travis: So. Oh, that's so cool. Just thought that was kind of like, okay, I read about and heard about Dory's parties and I'm trying to do my own and, and now I get a call from Nick at and Jenny at Dory's party. It was just kind of cool, but 

Dorie: totally 

Travis: full circle. Yeah, definitely, definitely. And so, so yeah, what, You usually probably get this question asked first, but gotta backed a little bit, but what, what was the catalyst for, for writing this book?

Like, what made you think, yes, I need to, I need to write it and now is the time? 

Dorie: Well, you know, there were a couple of things going on that prompted me to wanna write the long game. The first, this, this is all happening pre covid. I just kept certainly feeling myself. Hearing so many friends of mine just say some variation of, wow, I wish I had time to think, I wish I had, you know, just a moment to catch my breath.

You know, some variation of being like to the wall. Busy. Mm-hmm. . And I realized, you know, around the same time I was, I was asked to give a speech, at a conference honoring Peter Drucker, the late management thinker, and they wanted me to give a talk about strategy and. As I was thinking about what I could say about strategy, what I realized was okay.

You know, there's pretty much no one that thinks that strategic thinking is a bad thing. Everyone thinks it's a good thing, everybody loves it, but the problem is they don't do it. And a big part of it is that feeling of just like being so, oh my God, I've gotta do this, I've gotta do this, I've gotta do this.

And they, they never take the space to be strategic. And so I, I wanted to try to understand what's happening here. And how can we overcome that so we can actually start to do more of what say we wanna do and actually do more of the kind of long term thinking that as we know when applied leads to better outcomes.

Travis: Nice. Yeah. and after writing it, did you, Did you, you started in 2019 and, and were writing it through, through Covid. Right. And, and so how did that shift? So did you go into, go into it having a clear idea of, of what you would write about and did Covid change 

Dorie: change that? You know, one of the things that I tell, in the introduction of the book is that shortly after, so I got the, the contract for the book.

My editor approved it February 28th, 2020, and then literally the next day was the day that the first Covid case was detected in New York. And that it just all. Downhill from there very, very quickly. And so within like a month, you know, everybody's on these like pathetic Zoom calls, nobody's leaving their house, all that.

And so I was on this Zoom call and everybody's talking about like, well what are they working on? What are they doing? And I'm like, well, I got this book contract. And you know, they're like, what about? And I said, long term thinking. And there was this guy who like literally laughed at me. He's like, he's like, nobody needs that anymore.

Too bad for you, . And, I, I was like, oh man. But, you know, I, I, I knew even then, I, I, I disagreed with his premise because it was true. It was true, absolutely. That during the pandemic, I mean, There wasn't space to do long-term thinking. We were in a crisis. I get that. It's not, that short-term thinking is never good.

There is a place for short term thinking and a crisis is it? That's when you have to pivot. You have to move really, really quickly. But it's also true, I mean, It's not that like cortisol is a bad chemical, right? Like there's, there's a place for cortisol when, when the proverbial bear is in your face, you want the stress hormone being like, get the F out of there, right?

That's very helpful. But the problem is when cortisol is in your system all the time and it starts to wreak havoc on your body and very similar. Short term thinking, not a problem in a crisis. Great thing in a crisis, but it becomes a problem if you can never back away from that if, if that's the only trick that you have in your arsenal.

You need to have long term thinking and you need to be able to toggle between them appropriately. And that was what I realized in the course of writing it. 

Travis: Yeah, I mean, I think in the pandemic you have to start to think long term cuz it's not gonna last forever. Right? And, and how do you come out on the other end of this?

What, what can you do now to, to protect yourself to, to come out better on, on the other end, right? And so I think the timing was, was perfect. so, so hopefully that that person read it and learned something. and. In the book you talk about saying no to things. I have a, a big time problem with, with this.

I say yes to too many things. And what, what if, you, something comes across and, and you know, you say, hell yeah, that, that, you know, I wanna do that. That sounds awesome. I, I want to spend my time there, but then. It elicits fear and imposter syndrome. Like how do you balance that? How do you get over that?

Because you want to do this thing, but now you are your own block. 

Dorie: Yeah. Yeah, absolutely. I mean, in, in it might feel terrible, but in some ways that's actually a good problem to have because the problem that a lot of people have is the much more pedestrian. I said, yes, and now I realize this is like so boring and such a waste of time, and now I can't get out of it

So that's, that's slightly more horrifying and more common. but you know, if you have, if you have the sort of problem I'll say in air quote, Of having said yes to something that's actually very cool, but it just is like stretching the limits of your ability and therefore making you uncomfortable. I mean, first of all, like life is never gonna be free of problems, right?

Mm-hmm. . So we need to, we need to just like choose the better problem, and that's a much better problem to have. So I think in that case, it becomes a question of, you know, it's, it's sort of like a decision tree. It's like, okay, I don't know how to do this thing. Can I do this thing? You know, I mean, I suppose there's a circumstance where you may have agreed to do something that like literally under no circumstances could you ever do, and in which case that would be unfortunate and you'd probably have to apologize and retreat pretty quickly.

But in most cases, you know, in most cases, people actually. You know, they have enough sense to be like, you know, if, if I'm like, Hey Travis, I'll give you 10 million if you can, you know, jump 50 feet, you'll be like, wow, I'd really like, you know, 10 million. But unless there's a trampoline involved, I can't jump 50 feet.

Like, you know, that that's the case. in most cases, What people are stressed out about is that the thing that they have agreed to do, like there was, there's, it's, it's within the realm of possibility. It's not like it violates the laws of physics. It could be done, but they just haven't done it before, or they don't quite know how to do it.

You know, let's call it like a 10 or 20% stretch from where they are. And if that's the case, then you know, the question just becomes, well, how do you figure out how to do. Is there a person that you could ask? You know, is it, is it a skills gap? Is it a knowledge gap? Like, you know, are you just like literally not sure what the next step is?

Or is it that you need to practice first? Like, okay, is there a way that prior to doing whatever the thing is, maybe it's, you know, oh, Travis, will you keynote this big conference for 500 people? You're like, oh my God. Well, , you know, is there a place where you could speak to 10 people, the week before so that you can practice your talk and get more comfortable?

Like what are the ways that you can make it happen? I think that this is also. You know, a concept that, you know, I talk about quite a bit in my first book, reinventing You, which is probably especially relevant for Winding Road type people, cuz it is about career change and reinvention is, the importance of having a mentor board of directors.

And, you know, the, the reason that's important frankly, is that. We tend to be very aware of what our flaws are, and it's often harder, much harder for us to see our strengths because we consider them to be normal because we are our own baseline of normal. And so it really is helpful to have friends and colleagues that you trust around you who are able to say, actually you can totally do that.

Travis, I've seen you speak before. You're pretty good at this here. Just, you know, do this and this, and it'll be all good. So sometimes they can be the ones that talk you down from the ledge. 

Travis: Yeah, that's, that's great. Great advice. And I think I'm gonna have to go back and reread that book. I read it when I didn't need it, and now I need it.

So I'm gonna, I'm gonna pull it off the, the bookshelf. cause I have a tendency to say yes to things that I maybe haven't quite done before, or I know. I get it, but maybe haven't done it, you know, in the trenches. And so Totally, I have a, a habit of that because it sounds interesting, it sounds fun, and I wanna learn, right?

I wanna see how, how's the sausage made with this stuff? And so I, I say yes, and then I'm like, oh shit, now I gotta figure this out. How am I gonna figure it out? And, so, so yeah, I do that a lot, but that's how I've grown and that's how I've learned. But 

Dorie: yeah, sometimes a forcing function is not a bad 

Travis: thing.

Yeah, absolutely. Absolutely. And, I think kinda one, one last question for you. kind of along those lines of, of kind of thinking in waves and saying hell Yes. And then also you mentioned in the book, heads up, heads down, and I'm guessing you are heads up right now since you agreed to do this. what, what have you said?

Hell yes to? that's, that's on the horizon. That's your next head down. Wave that you're really excited about? 

that's a, a great question. So there's, you know, there's, there's a few things. You have to, you have to sort of, pick and choose wisely, of course. But in, you know, one of the concepts we haven't talked about yet that.

Dorie: I cover in the long game is 20% time. Mm-hmm. , which is, you know, borrowed from Google, which sort of popularized it where you spend 20% of your time on a kind of exploratory project. You know, something that may or may not work out but could, could be really good. You know, I'd like to think of it as sort of like your own personal venture capital portfolio.

And so in my case, part of, part of, you know, where I've been going heads down is writing musical theater, which is part of what I'm really interested in. So, I'm, I'm working on multiple shows right now. in particular, I've, I, I've spent a lot of the year refining one of my shows, absolute Zero, and, I now have a second show where the next heads down piece is like getting, I wanna get a first draft of the show written by the end of the year.

So that's probably my next big, heads down thing. Nice. 

Travis: That's awesome. Yeah, I meant to talk about 20%. We, we talked about it before I hit record because I, I, I should probably be doing 20%, but I'm doing 100%. So we'll see how that, how that goes. That's right, man. But yeah. yeah. Well, I really appreciate you coming on the show.

It's been, its been great to have you on and, and to, to rift. 

Dorie: Thank you so much, Travis. I really appreciate it. It's great to have the chance to talk to you, and I'll just mention for any of your listeners who are on the winding path themselves, in case it's helpful, I have a free resource, which is the Reinventing You Self-Assessment, and folks can get that for free at dory clark.com/reinvent.

Travis: Awesome. Yeah, I'm gonna go, go, re-download that again today. Perfect timing. So yeah, thanks and, and really 

Dorie: appreciate it. Thank you. Great to talk to you, Travis.



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Travis L. Scott

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