The Long Game With Dorie Clark

by Creating Change Mag
kobo writing life

How can we shift our mindset to thinking about a long-term creative career? What can we do now that will make our future selves happy? Dorie Clark gives some ideas for playing the long game.

In the intro, sell books directly on TikTok Shop [The Guardian]; Plan for author success in 2023 [K-lytics webinar, 1 Dec]; PDF workbooks for authors []

This podcast is sponsored by Kobo Writing Life, which helps authors self-publish and reach readers in global markets through the Kobo eco-system. You can also subscribe to the Kobo Writing Life podcast for interviews with successful indie authors. 

Dorie Clark is a best-selling author, keynote speaker, executive educator, film director and producer for a multiple Grammy-winning jazz album. Her books include Entrepreneurial You, Reinventing You, and The Long Game: How to Be a Long-Term Thinker in a Short-Term World, which we’re talking about today.

You can listen above or on your favorite podcast app or read the notes and links below. Here are the highlights and the full transcript is below. 

Show Notes

  • How to balance your time as a multi-passionate creator
  • Learning how to say no in order to reach your goals
  • Figuring out what your goals are
  • Practicing long-term thinking in your author career
  • What can you can do now to make your future self happy?
  • How your (non-fiction) book can open up other business opportunities
  • The strategy behind deciding what to write
  • Adapting to changing technology — the potential impact of generative AI
  • Marketing the same book for the next 5 years

You can find Dorie Clark at

Image generated by Joanna Penn with Midjourney

Transcript of Interview with Dorie Clark

Joanna: Dorie Clark is a best-selling author, keynote speaker, executive educator, film director, and producer for a multiple Grammy-winning jazz album. Her books include Entrepreneurial You, Reinventing You, and The Long Game: How to Be a Long-Term Thinker in a Short-Term World, which we’re talking about today. So welcome, Dorie.

Dorie: Joanna, I’m so glad to be here. Thank you.

Joanna: Now, I’m excited to talk about this. But I want to ask you first, because as I was looking at your bio, I’m like, ‘oh, my goodness, you are such a multi-passionate creator,’ and a lot of people listening are as well. And you’ve got this visual art thing, the music thing, writing, teaching, speaking.

How do you balance your time between everything you do and prioritize?

Dorie: Well, one of the concepts that I actually talked about in my latest book, The Long Game, is 20% time. It was actually originally created by the company 3M, that’s famous for its sticky notes. They had something called 15% time.

And then Google popularized a related concept of 20% time. And the idea was that they would encourage their employees to spend up to 20% of their time on basically more speculative projects, things that were outside the scope of their official responsibilities.

Now, the caveat, of course, is that a lot of Google employees, even though theoretically they’re encouraged, don’t actually do it because they are too busy, you know, like all of us. 

In theory, this is something that is part of the company DNA. And that’s how Google News was created, that’s how Gmail was created, is people just exploring things and trying new stuff that seems interesting.

And so in The Long Game, I really beat the drum that I think it’s important for all of us to proactively choose to do this. Whether we work for ourselves or whether we work at a more traditional job, finding pockets of time, you know, maybe it’s 20%, maybe it’s 5%, who knows.

To invest in something that is outside the norm of what we are “supposed to be doing” I think is really valuable, both for keeping us engaged and creative, and also pushing the envelope on something that might be the next big thing. So I really actively try to invest my 20% time in things like directing of film or writing musicals or things like that.

Joanna: But even just with what you’re doing — I mean, obviously, a lot of people listening have a day job, whatever they do as a day job, and writing is their 20% time. So it’s normally the thing people do that’s separate, where with you and I, it’s part of our professional career. But you have a teaching job, I think, and you’re a speaker and all these other things.

So it’s almost like, yeah, there’s that extra bit, but even within what we have to do as part of our normal job, how do you balance your time? Because a lot of people worry about how do they create ‘from scratch’ time? And then how do you get the business stuff done, basically?

Dorie: Yes, yes, absolutely.

It’s always the balance between the long-term vision of where we want to go and the short term of just feeling the press of the things that are on us.

Whether it’s all the messages in our inbox or all the meetings or things we have to get through, and I empathize in a big way. I had nine meetings yesterday. That is extremely suboptimal. That is not how I want my days to be, but occasionally a day ends up being that way.

But I know that for me personally, I try to put safeguards around it. And I think that in a lot of ways, a problem that many of us fall into, especially if you’re a person who is competent, who can get a lot of things done, you tend to want to get a lot of things done. And if there’s a request, you want to say yes and do it.

So I actually have been really pretty vigilant in recent years about trying to put up guardrails. Occasionally, you might proactively decide, alright, I’m going to overrule it in this particular instance.

I’ve had variations in the past depending on what my particular goal is, but it might be that I will not work past 7 pm, let’s say. I’m ceasing all activity, just as a forcing function. And the interesting thing is that much like writing a sonnet causes you to be more creative because you want to say a certain thing, and you’re like, “well, damn, how do I see that in iambic pentameter?”

If you actually have a rule for yourself, whether it’s, ‘I’m not taking meetings on Friday,’ or ‘I’m only going to work until 7pm and not a drop later,’ whatever it is, it often forces you to triage in a way that can actually be helpful, I think.

Joanna: Now, I like that. And you mentioned safeguards there and guardrails, I like that. But then another thing, I mean, you’re obviously incredibly competent at everything you do too.

And what I find difficult, and I think a lot of people find difficult with their creative projects, is saying no to work after 7pm is one thing, but what if you have all these ideas? How do you know what to say no to, whether it’s those other people’s requests for a great speaking gig or something, or your own ideas? Because if we set these guardrails, we only have the limited time to achieve these things.

It’s easy to say no to bad options, but how do we say no to the good things?

Dorie: Yes, yes. I totally hear that. Because most people are smart enough, unless they’re super codependent, they’re smart enough to say no to bad things, right?

The problem comes where there’s just like too many good things. I mean, in some ways, it’s a good problem to have. Like, ‘oh, too many good options,’ you know, cry me a river. But the truth is, we can’t do them all. 

So one of the one of the things that I talk about in The Long Game, because the truth is, if you want to be a long-term, strategic thinker, if you want to actually accomplish these important long-term goals, whether it is writing a book or getting a book to market, or whatever your variation is, you actually do need to clear room upstream in order to make that a possibility.

So learning to say no and learning to prioritize is incredibly important because otherwise you’re never going to even have the bandwidth to remotely get close to your goal if your schedule is completely filled with dross and dreg.

So, as a result, I’ve spent a lot of time thinking about this, and one of the interesting frameworks that I share in The Long Game, was actually something popularized by Derek Sivers, who’s an author and an entrepreneur.

writing independence and selling direct derek sivers

Joanna: And he’s been on the show, too.

Dorie: Oh, I love it amazing. Yeah, he talks about the sort of ‘hell yes or no’ paradigm. So meaning, if it’s not a “hell yes!” then you should be saying no to it.

But I think that what is perhaps less explored that I think is important to tease out, is that the problem that that solves is the problem that actually bedevils most of us, which is this sort of medium-good options, right?

Because the trouble, again, is not saying no to bad things. It’s the sixes and the sevens, and maybe even the eights, on a scale of 10, where we’re like, “well, I don’t really want to do it, but it could be good because of blah, blah, blah.”

I mean, even this morning, I got an email first thing this morning from a friend of mine, and she’s been asked to help put together a panel of speakers for a conference. And it’s going to be in Nashville, which is a cool place to go, and she wants to know what I do it. It was going to be a pretty low fee, but I’d get to hang out with her, and she was probably going to invite some of our other friends. So it’s one of these things where you’re like, oh, there’s some good, there’s some bad.

In the past, I probably would have erred on the side of saying yes to it.

But this is very much a place where we have to revert back to —

What’s our North Star here? What are we aiming at?

And in my case, I really made a strong commitment that post-pandemic, once we were sort of getting a little bit more normalized, I realized that I did not want to slip back into the practices that I had done before where I was just like wantonly traveling all the time.

I realized that it had really exhausted me. And certainly I wanted to be traveling more than I was during the pandemic, which was not at all. But I also did not want to go back to giving 35 to 50 speeches on the road per year, which is my average for a number of years before that.

So I decided that the better part of valor is cut it out. And so I wrote back to her right away, and I was like, thank you so much, but I’m going to need to pass on this. Because I realized the biggest attraction is like the opportunity to hang out with her. And there’s a lot of other ways that I could do it that didn’t involve me flying somewhere and spending a weekend for a few thousand bucks.

Joanna: Yes, it’s interesting. And I really appreciated you sharing that in the book about your burnout. I mean, you basically were having burnout from all of that and performing while sick. Very impressive, but also like, oh, my goodness.

It’s interesting, I mean, in the book, you talk about needing this white space to even think about the long term. And it’s almost like, you mentioned in that talk, things happen that we need that short-term cash sometimes and so we do these things.

In that white space, when you have that white space, let’s think that people do, maybe they go to a cafe or maybe they can get away from the house to have that white space.

What should they be asking themselves in order to try and think about what they might want for that North Star, as you mentioned?

What are some of your practices to help figure out what you want?

Dorie: Thank you, Joanna. I’m eager to answer that, but actually, if you don’t mind, I want to turn the question back on you for a minute because you are someone who’s really a polymath.

I mean, you have this business and this podcast around helping people learn to be successful writers, you have written like a ginormous number of books yourself and in multiple genres and things like that.

So I would love to just hear a little bit more about how you personally think about prioritization and fitting the different pieces together?

Joanna: But I’m interviewing you, Dorie!

But no, I mean, I do that. I have a lot of journals, I’m sitting here with about 40 journals. So, I think by writing, so for me, I have to go somewhere and I write. And then what’s interesting is I’ll look back at a journal from a decade ago.

I did this recently, I looked at 2012. I had like three diaries or journals from 2012, and I went through them all. And what was interesting is so much that I journaled about has now happened. And so a lot of it, for me, is that ideation, I guess.

It does help me to read books like yours, and why I wanted to speak to you was because I listened to the audiobook when I was in New Zealand at Christmas. So I listen to things and then I journal, that’s basically how I think about it. And I’ll come back to the future stuff in a minute. But now, throwing it back to you.

Dorie: Yes, all right. Well, thank you. I appreciate that. And that’s great to hear and to learn about your process. But I think that as we think about what questions we should be asking ourselves, or how to really just begin to structure this exercise, I think there’s a few starting points.

The first one is really super big picture. A lot of times people do have a sense of what they’d like to accomplish or where they’d like to go.

But what I’ve often found in having written a book about long-term thinking, I think a lot of people are hesitant to own it in some ways.

What I often hear is, “oh, well, I’m not really sure how to do long-term thinking,” or “I can’t do long-term thinking because I’m not sure how I would accomplish it.”

I really want to take that and push back on it because I think in a lot of ways, the whole point of long-term thinking is to be thinking about things that we have no idea how to do. It would be so incredibly presumptuous, and I daresay just flat out incorrect, to imagine that anyone can perfectly envision over a big goal — let’s say it’s 20 years, 10 years, even five years — precisely the steps necessary to do something.

I mean, the world is changing so fast, there’s so many flaps of the butterfly wings, or what have you, we really just can’t predict. And so I think it’s fine, it’s great, to have goals that you have no idea how you’re going to accomplish them.

That’s the point of living for the next 20 years is to figure out how to do it, but you don’t have to have it figured out today. So I think that sometimes it’s just honoring the sort of gut sentiment that you have today. That’s one piece.

Another which I always like to encourage people to do, and sometimes they’re afraid to go here because it feels really weird but is to examine who you are jealous of. If we tone it down, we can say, who do you admire? But frankly, something that’s even more helpful is like, no, who are you jealous of?

Who is it out there in the world, whether it’s someone you know or a famous person, where you’re like, oh my god, I wish I could have their life?

And you can peel it back. What is it about it? Is it that they have really succeeded in a particular genre? Is it that, oh my gosh, I’d really love to be interviewed on this particular NPR show or this BBC show? That’s sort of a bucket list goal.

Or maybe it’s some aspect of their lifestyle, like, wow, I wish I could live in the country and not have to commute to a day job, or whatever it is.

We often have trouble envisioning things until we see someone else doing it. And so seeing what’s causing the tripwire in your brain of like, ‘wow, I wish that could be me, I wish I could do that’ is really useful evidence for yourself. It’s the trail of breadcrumbs that enables you to figure out what would be compelling for you.

And then finally, something that I am always a really big fan of is trying to analyze what is the thing that if you did it now would make everything else easier.

Is there something that could be a kind of foundational activity that will enable all the kinds of downstream things that you hope to have happen?

Oftentimes, for me, for instance, with the clients that I work with, people come in and often their starting point is that they want to write a book, which that was the case for me too. I wanted to write a book because I wanted to write a book. That has just been my goal since I was a kid.

But the truth is, if you do certain other steps before writing the book, and in the case of authors or executives or entrepreneurs that I work with, it is writing for high-profile business publications.

If you do that before you write the book, it makes everything downstream easier, including getting the book deal, including being able to publicize the book when it’s out, including landing interviews of the people you want to interview for your book, et cetera, et cetera.

So that’s often a sort of first domino that I think can be useful. And so asking yourself what is that first domino is not a bad question to ponder.

Joanna: Yeah, I completely get that. And as you said, if you did it now, would it make everything easier?

And I was just thinking there —email list. Starting an email list early, I started mine in 2008.

By starting my email list back then, it makes it far easier to sell books now.

You’ve got one as well, right? I mean, we have to do some of these things knowing that there’ll be nobody on our list, or no one listening to our podcast, or nobody knows who we are now.

But if we don’t start it now, it’s that whole planting a tree thing, right? If you haven’t done it yet, you’ve got to do it today.

Dorie: Yeah, you’re so right, Joanna. I mean, most people who are writing books, they don’t want to grow an email list. There’s like literally zero people in the world for whom growing an email list is the dream that they’ve held in their heart. It’s the instrumental thing that we have to do.

But yet, to your point, it is something that if you work on it now, like future you in five years is going to be like, wow, thanks for doing that. That was really awesome. Good job.

So I’m always very interested in the question of ‘what is it that we can do that will please future you?’

Joanna: That’s a great way of doing it. I mean, there’s so many things like fitness and health and stuff like that. But that’s why it’s so hard.

I mean, there’s some psychology studies out there where they age people, they artificially age you and show you a picture of you when you’re like 65, and then say, “would you like to put money into your pension, little 22 year old?” And far more people put money into a pension when they can look at a physically aged version of themselves. It’s just human brains just find that hard, right?

Dorie: Yeah, I mean, studies have shown that essentially people view their future self as literally a different person. So it’s like, well, who cares? You know, who’s that jerk?

Joanna: Yeah, I’ll probably be dead! People say that too. And I’m like, but what if you’re not?

Dorie: Exactly.

Joanna: I wanted to ask you about publishing, in particular, because the book is the long game and long-term thinking, and yet publishing itself has this kind of ridiculous model focused on bestseller lists, on spike sales — traditional publishing in particular, independent publishing is different — but this sort of idea that if you don’t sell lots in the first month or so, you’re not successful.

So how can authors, in particular, think about the ‘long game’ of a creative career when there’s so much focus on short term spikes/launches/lists?

Dorie: Well, I think this is a really important question. Because you’re right, there is such an unhealthy focus and emphasis on bestseller lists.

And it’s interesting, because even in the popular imagination, if people think you’re good or if they somehow think you have stature, they will often call you a best-selling author, whether you are or not, which is interesting. I mean, I know you actually are.

I’ve now done four books, three of them, my first three books, were not bestsellers. I mean, I wish they were, but as you know, it’s very hard to have a best seller. Because all it means is that you have been able to sell a certain threshold, let’s call it generally a minimum of 5000, sometimes depending on the list, 10,000 or 15,000, within a given calendar week. And if you don’t do that, no matter how well your book does over time, you are not in fact a best-selling author. 

I’m not talking about Amazon bestsellers, which as we know, can be gamed up the wazoo, but I’m talking about the more official lists. Finally, my recent book, The Long Game, was able to be a Wall Street Journal bestseller. But that was a process of about a decade of brand building and list building to enable me to reach the point where I was able to do that.

But it’s really interesting, because for a long time, people were like, she’s a best-selling author. And I have to be like, actually, technically, no. It is really interesting. But I think you’re exactly right. I mean, it depends in the end, of course, why you are writing the book.

If you are a businessperson, which again, primarily the group of authors that I’m working with are entrepreneurs or executives. In general, yes, they want to write a great book. Yes, they would like it to be a bestseller.

Ultimately, the goal is typically that they want it to drive business or to drive professional opportunities for them.

And so if that’s the goal, it’s really important to look beyond the bestseller status.

I mean, yeah, it’s a nice piece of social proof, but you want to continue promoting this book on an ongoing basis.

It becomes your calling card, it becomes the thing that that draws people to you. And however much money you make from the book, it is almost guaranteed, you know, aside from just a tiny, tiny slice of the population, that you will make much more money on the back end of your book, rather than the front end.

So rather than money from people literally buying your book, if you were a businessperson, you’ll make a lot more from the speeches, from the consulting engagements, from the coaching engagements, etc., that result from inquiries that are driven by your book. So keeping that in mind is a really important perception shift.

Joanna: Yes, and I think this is really important. And I often stress there are multiple streams of income that business and entrepreneurial writers have. You mentioned their speaking, and I know you’re a high-profile speaker, often on big stages.

Do you feel that more highly paid speaking gigs become easier if you have a traditionally published book?

Or do you think these conferences and events are open to independent authors or self-published authors?

Dorie: I think with speaking, as with all aspects of publishing, the difference between commercially published and self-published or hybrid is eroding every day. I mean, it used to be a decade ago when I first published my first book, Reinventing You. It was a really stark difference in terms of how it was perceived, in terms of the cache. It was really important to be commercially published.

Now, there are so many people who have chosen for a variety of reasons, many of which the reason is not that they couldn’t cut it with a commercial publisher, which is how it used to be viewed.

Instead, they’re proactively making the choice to be self-published or hybrid-published because they want a faster release schedule, or because they want higher royalty rates, or they have a niche audience where it’s really important for them to publish a book in terms of establishing market credibility, but a mainstream publisher wouldn’t be interested because they think it’s too small of an audience, you know, whatever it is. 

I think that the distance has really diminished. And so yeah, it probably is still a little helpful to have a commercially published book when it comes to speaking, but I think that the distinction is much less.

And I think that if you are someone who is a self-published or hybrid published author, and you have other forms of social proof as well, to validate that you are a legitimate expert or legitimate professional in your field, then I don’t see any problems at all in terms of landing fairly high profile speaking engagements.

Joanna: I was at a WIRED conference the other week, and every speaker had a book, and every book was traditionally published. Which I kind of find hilarious, because WIRED is supposed to be a future-focused publication, but they are actually traditional publishing. It’s really funny.

But I also wanted to ask you, because you do write quite a bit in the book about your own book process and getting published and some of those challenges, and obviously, again, you have lots of ideas.

How do you decide on a nonfiction topic to write about, in terms of tips for people listening who either want a traditional publishing deal, or they want to focus the book more as like a business card, or as the beginning of an entrepreneurial thing?

How do you decide what book you’re going to write? Or is it just what you ‘feel’ like writing?

Dorie: Well, I’ll answer the question two ways. One way is the way that I would advise people to do it, which is if you want to be hyper strategic, I have not always been hyper-strategic myself, but if that is your goal, then ideally you want to tie the book content as closely as possible to the services that you provide.

So the ideal thing, which of course does not always happen, but in our dream world, it is you write a book, somebody reads the book, they say, “oh my god, this is exactly what I need. I need to reach out right this minute and hire this person to do this thing for me that she has written about.”

So if you can kind of create that, where the book touches on the themes where you help people and the thing you’re talking about is exactly what you do, then that’s the best pathway. It’s just kind of 200-300 pages of indoctrinating somebody into trusting you and knowing that whatever service you’re providing is exactly what they need.

So that’s a great way to think about it if you’re somebody who, for instance, runs a consultancy or something like that. What I have personally done is a little bit different, but I think still interesting and valuable, although perhaps less immediately remunerative.

I wrote books that were the things that I wanted to learn about.

So I used it as kind of a learning and research project. Specifically, I’m talking about my book Stand Out and in Entrepreneurial You.

Reinventing You was a book that I wrote because I had written a blog post for Harvard Business Review about it. And essentially, that was the post that caught on, and there just opened up an opportunity for me and I seized it. So I was happy to write a book about it, but I didn’t really need to write a book about it. 

Stand Out was a book about me trying to understand how someone becomes a thought leader in their industry, because that was what I was attempting to do. And I wanted to have an excuse to interview a lot of really smart people about their journey.

And then Entrepreneurial You is a book that I wrote, again, for my own knowledge and benefit, because I wanted to answer the question, how do you monetize thought leadership?

Once you’ve gained a certain level of respect in an industry, what can you do to create multiple revenue streams and really be able to leverage the value of the brand that you’ve created?

So I wrote Entrepreneurial You to answer that question and to have the opportunity to connect with a lot of smart people on that. And then The Long Game was a little bit different. It was not so much that I wanted to learn something per se, but it was something that I was rolling around in my head. And it was a philosophical question that I wanted to ponder and I thought might be helpful to other people.

Joanna: Yes, I write because I want to either learn something entirely, or just codify what I’ve learned about something.

I was getting loads of questions about podcasting and audiobooks a few years ago, so I wrote a book on audio books and podcasting so that it answered all the questions. But I’m like you too, it’s kind of curiosity driven.

I did want to come to your questions in the book, and I’m pretty obsessed with the future of creativity, so this question in the book has really resonated with me, which is:

What are my hypotheses about the future, and how do they inform my actions today?

So I wondered about what are some of yours. So given that we’re thinking about the long game and you mentioned before how fast things are changing.

So what are some of your hypotheses? And how were you changing your actions?

Dorie: Well, I’ll start by answering the question, actually, with a past hypothesis of mine that relates to publishing. So about a decade ago when I was getting started, I landed my contract for my first book in 2011. I had a hypothesis that the commercial book publishing industry was going to completely collapse within a decade.

I recognized that at that time, as we were discussing, there was still a branding value to having a commercially published book. And I thought, okay, if I’ve got this contract now, and I’m able to leverage the value of a mainstream publisher, I need to take advantage of that. Because eventually, that’s no longer going to be an advantage.

I think that’s largely playing out, although it’s not that publishing has collapsed per se, but I think it is true that the difference between hybrid and traditional, just most people don’t care. They don’t know, they don’t even see it, you know. So I decided, as a result of that hypothesis, that I was going to write as many books as I could, as quickly as I could, in order to take advantage of that toehold that I had achieved before it collapsed.

And so as a result, I really went on a writing spree. And I published three books within basically a four-year period. 2013 was Reinventing You, 2015 was Stand Out, 2017 was Entrepreneurial You. And I then slowed down the pace.

And so four years later, 2021, I wrote The Long Game. My plan for myself, my strategy has now changed.

I am intending to promote The Long Game for five years.

So I have vowed not to come out with another business book until at least 2026 because I really want to be riding this wave.

My actions were very deliberately based around a hypothesis that it was important for me to leverage the advantage that I had managed to attain in breaking in with a commercial publisher, and just creating as much IP as I could as quickly as I could.

Now, I feel like four books in and it’s a little bit like diminishing returns, like I don’t need to be pumping things out the same way anymore. But I do think it was actually pretty helpful to me early in my career to just create a lot of stuff so that I had a lot of stuff to talk about.

Joanna: So looking ahead, for example, I know the metaverse can be a dirty word for some people, but as a speaker, I find it very interesting. I mean, after we finish recording you do these LinkedIn live things, and like we’re all used to doing online presentations and stuff. But let’s face it, they’re a bit crap. But doing the other thing, going and speaking in a stadium or a theater or whatever, is tiring and all that.

So virtual reality, to me, seems like it may well have a really good application for speaking, education, learning, that kind of thing. And it probably is a decade off, right.

So what are your thoughts on how you might adapt to coming technological changes?

Dorie: The thing, Joanna, that really has been fascinating me lately is less so the metaverse, I mean, I agree with you and I agree with Mark Zuckerberg that eventually it’s going to be a thing. But quite clearly, it’s not a thing this minute. I think it’s probably not going to be a thing next year either. It is a long-term play.

But AI is really interesting to me, in particular, GPT-3, and DALL-E as well.

Joanna: We’ve done shows on both of those things. So yeah, people know what they are. Yeah. I’m glad you’re interested in those. Yeah, amazing stuff, right?

Dorie: It is so interesting. And to the point about what is a competitive advantage you have and being mindful where that advantage might erode. Something that I think is both interesting and concerning, is that AI pretty well can — and I mean, give it another year or two and I think it will really, really can — write all the articles for us.

It used to be a few years ago, it was like, oh, you know, AI is taking the job of like a reporter because it could take scoreboard statistics from like a baseball game and write up an article based on the data of what happened in the baseball game. You know, okay, great, that’s easy.

But now you can basically say, “hey, GPT-3, can you write a blog post in the voice of Joanna Penn, talking about the five top mistakes that rookie writers make?” And it will do it better than you.

Joanna: Oh, yes, it can totally do that. Absolutely. And also you, I mean, you’re the same. Both of us have put out a lot of content over more than a decade. So it probably could just write in our voices.

Dorie: Yeah. 100%. And so on one hand, I feel like there is an advantage in the sense that “I” could create a lot more content. Because I’ve done the sort of groundwork of putting my voice out there, GPT-3 can kind of take it and run with it and create something that is “mine.” I say an air quotes, but it’s not really mine, because like anybody can create that. So I don’t really know how that’s going to play out.

There was an observation back in the 70s by a Carnegie Mellon professor, that in a world where information is abundant, something else becomes scarce.

And that thing is attention. And that has played out a lot over the past 50 years. And so the question that I always like to ponder, which I don’t yet know the answer to, is —

When the ability to write high-quality articles quickly becomes abundant, what is the thing that becomes scarce?

Something will, and that’s the thing that’s going to be valuable. That’s the thing that’s getting monetizable. But we have to figure out what that is.

Joanna: Yes, I think we’re already at the point where curation is so important. And this show, for example, a lot of people will be listening to your interview, but also a lot of people come along just for the introduction, where I curate the news, and a lot of its AI news as well in the creative sphere. And so the curation of the massive amount of information out there is important.

But I totally agree with you, and to me, it’s also not despairing about technology, but taking advantage of technology as a lever and using it for our creative purposes. So for example, the image that will go on this blog post that accompanies the podcast is generated by Midjourney, which you probably know is AI art generation.

So instead of stock photos, which I’ve used for more than a decade, I now generate each post myself because I find it super fun. So it’s incorporating AI into our creative work rather than running away from is my thought.

Dorie: Yes, absolutely. And of course, there were recent headlines about the guy who won an art competition with his Midjourney art, and the scandal of, oh my goodness, did he “really do it?” You know, what does it mean for art if you’re able to tell an AI to do something and then it does it. And it’s rather philosophical, right?

Like if you’re an artist who has assistants that help you with welding a sculpture, we’ve sort of determined that like, okay, well, they did it because they told them what to do. But somehow, we’re still feeling different about AI. So watching those things play out and shake out, I think is really going to be fascinating.

Joanna: And then one final question, because we’re almost out of time. But you mentioned that you’re going to promote The Long Game for five years, which I think is brilliant. You’ve got this great book, so promote it. 

What are you doing for book promotion and marketing?

Dorie: Absolutely. Well, certainly around the launch, I mean, I did do all the maniacal things that that one does. A million podcasts, in my case, for the last three books that I’ve done, I’ve managed to do about 160 podcasts a piece for each of the three launches. So over the past, I’m going to call it about eight years, I’ve done over 700 podcasts. So there’s a lot of them.

But a mistake I think that I made was that in past launches I became so burned out from doing 160, as you can imagine, I mean, like yap, yap, yap. Like you think you’re the most boring person in the world after that. It’s like no more, I can’t take it. So after those launches, I just like stopped for like a year, I’m just like, no, I’m done, I’m done. I can’t do any podcasts.

What I’ve decided to do is, you know, you have to keep fanning the flame, so one thing that I am doing is I have committed to do two podcasts per week, basically over the five year period, which I think is a reasonable pace that I can maintain without making myself insane. And so continuing that, but also just being mindful.

Instead of like rushing to write the next book or rushing to the next thing, it’s continuing to do things like write articles and try to place them in high-profile publications that deal with the themes in The Long Game around long-term thinking and strategic thinking and things like that. It’s continuing to give talks about it.

I mean, essentially, the biggest thing is just not writing another book so that I’m not competing with myself and stepping on my toes about like, well, here’s another thing I could do.

Joanna: That’s brilliant. I think that’s going to give people a lot to think about.

So where can people find you and your books and everything you do online?

Dorie: Joanna, thank you so much. So the new book is called The Long Game: How to Be a Long-Term Thinker in a Short-Term World. And if folks want to learn more about me and get a bunch of free articles and resources and things like that, my website is

And you can actually download a free strategic thinking self-assessment based on The Long Game that helps you apply the principles of strategic thinking to your own life and career and your writing career at

Joanna: Brilliant. Well, thanks so much for your time, Dorie. That was great.

Dorie: Thank you. Great speaking with you.

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