Episode 293 – The Long Game with Dorie Clark

‘You have to be good enough and you have to be persistent, [and] if you combine those two things together, then if you keep putting yourself in new situations, eventually there is going to be something that clicks.’

Dorie ClarkDorie Clark is very clear that creating content – sharing your ideas – is an essential part of building your reputation as an expert. But she’s living proof that it doesn’t happen overnight – with writing, as with relationships, you have to play the long game.

Now one of the most respected business writers of our day, she’s open about the rejections and failures she’s experienced all along the way, and right up to the present day. This is a masterclass for anyone engaged in putting their ideas into the world, but it’s also a hilarious and candid conversation, in which we find out why she once burst into tears on an Irish road…



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Alison Jones: I am here today, brilliantly, with Dorie Clark, who is a keynote speaker, she teaches for Duke University’s Fuqua School of Business. She’s the author of Entrepreneurial You, Reinventing You and Stand Out, which was named the number one leadership book of 2015 by Inc Magazine. A former presidential campaign spokeswoman, The New York Times described her as an expert at self-reinvention and helping others make changes in their life. She’s also a frequent contributor to the Harvard Business Review and consults and speaks for clients including Google, Microsoft, and The World Bank. Her latest book is The Long Game: How to be a long-term thinker in a short-term world.

So, welcome, welcome BACK to the Extraordinary Business Book Club Dorie. It’s great to have you here again.

Dorie Clark: Hey, Alison, thank you so much. Great to be here with you.

Alison Jones: It’s fantastic. If you just keep churning books out at this rate, we’ll have you back in a year or so as well, which will be brilliant.

Dorie Clark: You know, believe it or not, my last one Entrepreneurial You came out four years ago. So it’s actually been legitimately a while, not necessarily since I’ve been on your show, but since the last book came out, so I’m trying to learn to pace myself a little better.

Alison Jones: It’s more sustainable. You’re playing the long game as well. That makes sense, complete sense. But to be fair, I kind of feel like everybody’s lost two years anyway. You know, the pandemic, some people managed to sit and write their book, but most of us just lost two years really.

Dorie Clark: Yes. Yes, it was definitely strange times.

Alison Jones: And it really fed into this book, didn’t it? So just tell us a little bit about the impulse behind this latest book and how the pandemic sort of fed into that.

Dorie Clark: Yes, well, so the pandemic really kind of bookended The Long Game in many ways. I started coming up with a concept for the book and the importance of long-term thinking well before the pandemic started. I was ideating in 2018 and 19. But you know, these things take a while to germinate and I finalized the proposal in December of 2019, when it was finally accepted by my publisher, I got the email confirming that they wanted to publish it on February 28th 2020, and literally the next day was the first case of COVID in New York City.

And in pretty short order, basically within a week or so, the entire city was freaked out and locked down and things like that.

And that was the context behind the start of the book and the book writing process. So it was a very interesting time putting into sharp relief, these questions of, you know, short-term versus long-term. How do you plan and how do we think about goals and what we’re aspiring toward in our daily life, especially when it’s in the context of so much existential uncertainty?

Alison Jones: Yes, and it’s interesting because the contrast between the two worlds, in a sense, you know, you talk about that stab of loneliness as you’re going across the bridge in a taxi, another flight, another tour and that’s kind of pre pandemic, right? That’s kind of how it was. And then suddenly there’s a whole different kind of uncertainty. And actually the thinking that you’re talking about here really kind of underpins all of that.

And let’s just talk, for people who haven’t read the book yet, just kind of talk us through the structure of it, because you’ve got the point about making time, because we’re all so crazy busy. But then really kind of aligning it with your longer-term goals.

So just talk us through those sort of three strands of the book and where your logic came from for those.

Dorie Clark: Yes, absolutely. So The Long Game is divided, as you say, into three sections. The first part is about creating white space, which I feel like is really a necessary prerequisite to long-term thinking. One of the biggest problems that literally just about everybody sort of shakes their fist at the sky about these days is that we’re too busy, we’re overscheduled, we’re jam packed. And you know, that’s going to be a fact of life to a certain extent, but for many of us, it has reached legitimately pathological levels where we feel so pressured, there really is no time to think. And it just becomes a bit of an impossibility to do long-term thinking or planning in that context. You have to fix that first because otherwise there is no room to pour water into the already full glass. So it’s about extricating ourselves from some of those false obligations and creating white space.

The second phase of The Long Game is about identifying what we really should be focusing on, you know, sort of reorienting our goals and understanding what we are optimizing for. Like: what’s the game we’re playing? Where do we want to go? What does that look like?

And then finally, the last section of the book is what I call keeping the faith because it is almost inevitable in any long enough or meaningful enough journey that there are going to be roadblocks. There are going to be setbacks. Things are not going to go precisely the way that we anticipated.

I mean, if we think about it rationally, if you have like a 10-year goal, does it even make sense that it’s going to work out exactly the way you predict? I mean, probably not. But yet in the moment we are somehow startled by that, or we’re surprised, we’re like, oh God, this was a personal rejection. I must not be good enough.

And of course that’s not true. It’s just that things shake out differently, you know, because the butterfly flaps its wings or whatever. But we have to figure out how to be resilient enough to surmount those unexpected obstacles and be able to keep going toward what we’re actually after.

Alison Jones: Yes, strategic patience I thought was a nice phrase, I did love that.

 And you’re very sort of vulnerable, actually, in the book, I was quite moved, the way you talk about the slog that you went through to get to where you are now. It’s encouraging in a sense, but that sense that, you know, everybody that you look at who seems to be doing brilliantly, has been grinding, has been putting the work in consistently.

So, I mean, just tell us a little bit about that, because I think that people who don’t know, people who just look at you and know where you are now, it’s encouraging to hear the rejections at the start.

Dorie Clark: Yes. Yes, well, I’m glad and that is why I included it. I think it’s very easy, you know, I mean, on one hand, of course, there’s often just the common narratives around success, which is where you don’t talk about failures at all. But I think a reasonably common manoeuvre, which many of us do, and I think it is helpful, but not necessarily maximally helpful, is it is not that hard or not necessarily that vulnerable, to talk about past, you know, distant past failures because it’s like, oh, well, you know, this happened when I was 20 and, look now I’m successful.

 It’s like, oh, okay, great, you know, but you’re not that emotionally attached to it. It’s not that recent, it’s sort of like, okay, you have your moment in the cauldron, and then you get forged and you’re moving forward. But the truth, as you say, is much more complicated than that, which is that literally at almost every stage in our careers, there are still going to be rejections, because presumably if you are someone who is striving in some way, you are continually looking to reach new heights and even if you have reached success up to a certain level, that doesn’t mean that the gatekeepers at that level want to help you advance. You may in fact have just as many obstacles trying to get to the next level of your journey. So it’s certainly not that you reach a certain place and then, oh, it’s smooth sailing from here.

So I, as you indicated, in The Long Game I took a recent year, I took 2019, our most recent pre-pandemic year because everything got a little wacky during the pandemic. And I described five different goals that I had for myself, that were stretch goals, but none the less reasonably plausible, reasonably attainable goals that could have worked out.

And just, as it happened, four out of five of the goals did not work out. They came very close and then they all blew up. And so, you know, up until the end of the year, when the final one kind of came into place. I was just like, oh my God, like, is anything working? So it can feel a little dispiriting in the moment, but I think by sharing it, and by talking about it, hopefully it is useful because so often when people experience the setbacks themselves, they take it as sort of a personal referendum about their talent or about their worth. And it is really, really important not to do that because there are so many other mitigating factors, just even people having a bad day or, you know, whatever.

And it does ourselves a disservice to assume that a judgment has been rendered on our talent because it really has not, and we need to keep persisting.

Alison Jones: And there’s so much there I want to pick up and dig into. Okay, two things, particularly. One I’m going to come onto in a second, which is about, I guess, that sort of resilience and when you know it’s time to do something different. So how do you know when you plug away and you persist and you have that strategic patience and when do you actually go, do you know what, this is not working out? Because I think that’s a really key question.

But before that, one of the things that really struck me, and has always struck me about you actually, is that you are dead clear that to get where you wanted to be one of the key routes that going to get you there was content, was creating content, was putting it out there consistently.

So I think this is particularly relevant for people listening to this podcast, all of whom are writing in some form or other. So just tell us a little bit about why content matters when you’re trying to do something that matters in the world.

Dorie Clark: Well, I think there’s a couple of reasons that content matters. The first one is at a really fundamental level, I worked over the past decade to really try to encapsulate what I call the recognized expert formula, which is, you know, understanding the key components of what it takes to be considered a thought leader in one’s company or in one’s field.

And what I realized was at its core, it distills down to three fundamental principles, all of which are important. They kind of feed on each other in a flywheel fashion. And one of the pieces, one of the corners of the triangle as it were, is content creation. And the reason for that is that unless you are publicly sharing your ideas with people in some fashion, the only people that will know that you’re any good are people who have already worked with you and you know, that’s great, but that is inherently a small number of people. And so if you want to be known more widely, it can’t just be that, you know, five people are like, oh, she’s great. Like you need a lot of people to know you’re great.

And so content is a transferrable method that enables larger groups of people to see that you know what you’re talking about, you’re smart. They relate to your approach and they say, oh yes, this person does seem really good. Whereas, if it’s just like five people singing your praises unless they’re like really, really well-connected people, the virality of that is not going to be sufficient.

You know, it’s an R0 of below one, to use our current lingo. So it does not in fact go viral.

But content, and I use the term deliberately, right? It could be writing, it doesn’t have to be writing, but it’s somehow a method of sharing your ideas, becomes really essential.

And for me personally, as well it also was a potential competitive advantage that I felt that I could lean into because I had a lot of experience in writing. And so I was like, all right, you know, there’s different things that one can do. I might as well, if I feel comfortable writing, I might as well just, you know, do that.

 So that was the particular method that I chose.

Alison Jones: Yes, because of course you were a journalist originally, and that really comes through, I think, in your writing, you bring in stories from people, you frame them really well. There’s quite a journalistic feel to it and you write punchy sentences. You’re clearly used to grabbing somebody’s attention when they’ve got a nanosecond to spare.

But I remember you saying in the book, and I’ve heard you say before, that you’re a professional journalist and you were pitching to these people offering to write for free. And they were like, yes, no, I don’t think so.

Dorie Clark: Yes, it’s very dispiriting. I mean the whole process of working to get your ideas out there, working to become a recognized expert. You really have to recognize that even if you have built up kind of standing, that you think is good. Like, you know, well come on people, why wouldn’t you have a professional journalist write for you for free? I mean, they don’t care.

We just have to assume we are living in a profoundly indifferent universe and the moment we make peace with that, then we can realise Oh, okay. Okay. It’s not that I’m not good enough. It’s not that they hate me. It’s just like, they’ve got their own deal. They don’t care.

I mean, it’s like the ocean, you know, it’s not like the ocean’s like, fuck those surfers. We’re going to get those surfers. You know, it’s like the ocean is doing what the ocean’s doing and if the surfers get in the way, then too bad for the surfers.

Alison Jones: I’m not sure if I’m encouraged or dispirited by this…

Dorie Clark: Well, I mean, I would like it better if we were in a benevolent universe of gatekeepers, but nonetheless I think that it is encouraging to me in the sense that if we are reasonably persistent, and if our quality is of reasonable quality, which I am assuming, like sometimes people think like, oh, they have to be the best, the most talented, no, you have to be talented enough.

I know I’m not the best writer. I’m a good enough writer, you know, but you have to be good enough and you have to be persistent, but if you combine those two things together, then if you keep putting yourself in new situations, eventually there is going to be something that clicks.

I mean very much for me, you know, it was not, I mean, these editors, right? They didn’t know me. They didn’t care. It’s not like anybody was like, oh, let’s do Dorie a favour. But when I was first reaching out about a decade ago, really trying to break into places, what happened was I reached out to like two dozen places. Almost all of them blew me off. A handful were willing to engage in slightly more conversation and then they blew me off.

But there was one place which was Forbes and Forbes as it happened, right at that moment, was making extreme expansion of their blogging network. And so they really wanted people and that, you know, it was luck. I mean, it was not luck that I had nothing to do with, because I did have something to do with it in that I was reaching out.

But you have to reach out to the 24 places to find the one that’s like, oh yes, we need bloggers right now.

So I think, you know, for all of us the key is not to get discouraged because none of it’s personal. And if we keep giving ourselves at bats, that’s the crucial variable.

Alison Jones: Yes, yes, it’s so true. Isn’t it? Because, I mean, take it back to your analogy of the sea and the surfer, the big difference is that actually the ocean needs the surfers, in that the whole internet is a content feeding machine. And you need people to put content in there. So you’ve got a little bit more leverage than you might think, if you’re, as you say, putting the right stuff out to the right people and being really persistent about it, and it is a numbers game in a sense, isn’t it, you know, you apply to enough people, you get one brilliant, but you have to apply to that number.

Coming back to that question about persistence and strategic patience. And just give us a little kind of litmus test. How do you know when you just need to stop and do something different? And how do you know when you need to just double down and keep it going?

Dorie Clark: Well, I think there’s a couple of ways to think about this. First of all the strategy and the tactics are different. So it doesn’t necessarily mean that the strategy is wrong, if the tactics are not working. It may mean that you need to just, you can have the same goal you just may need to approach it in a different way.

So you know, let’s say you have a goal of getting your ideas out there and you want to be writing for places. If you keep submitting to one publication and they keep rejecting you, all right, maybe it’s never going to be a fit for that publication, but maybe there’s plenty of other ones that might want it.

So I think first is we have to separate that out, but secondly, something that I am really a big fan of is, this is why professional communities are so important. I run across folks, you know, sometimes people through coaching or colleagues or whatever, that have never really taken the time or never really seen the need to build up a community of professional peers and colleagues, because they often will say, well, why should I bother with other consultants, authors, coaches whatever. What I want is clients. I want to be in the room with prospects. And that is true that that is a good thing to do, but that is not the only thing to do because we need to have trusted, professional colleagues because they are the people who, in those moments where we are irrational – and honestly, if we were in the midst of a slog, it is easy to lose perspective and become irrational – they are the people that actually, if they, number one care about you and number two are competent and thoughtful in your field, they will have the right motivation and the right information to be able to guide you appropriately during those times when you either are clinging too long or when you are ready to give up too soon and they can help you calibrate more appropriately.

Alison Jones: Yes, the point that you make in the book about networks really challenged me actually because I think I’m not good enough at this. You talk about when you moved to New York, you didn’t know anybody in terms of friends, so you created this network. You know, you started the dinners and you had people along, and it was just a really good challenge.

But that point you make as well about the reason that you connect with people and the infinite perspective. So not because they have something immediately that’s useful to you. That’s such a turnoff, isn’t it? When you meet somebody and you email and go, Hey, I wonder if you can get me in to this organization that you’re part of. But just connecting with people because you’re following your interest or you think that they are just worth knowing, and there’s no agenda there.

I thought it was a really wholesome way of thinking about networking and a much less, it made you feel less unclean than most of the ways that you think about networking.

Dorie Clark: Yes, Yes, well, thank you. I mean, yes, if we think about networking and this is not just a frame, this is literally how I think we should think about it, if we think about it as, how do you make friends as an adult, which is incidentally not an easy thing to to do.

Alison Jones: We’ve moved. I can tell you it’s not easy.

Dorie Clark: Absolutely. So, I mean, I think more people would be interested in that, you know, that’s a sort of nice thing in one’s life. I think things have really gotten kind of muddled up when we’ve put it in the frame of it being something about professional gain.

I mean, as it happens, I mean, yes, this makes sense, when you have more friends, you know more people and therefore have more access to opportunities. That is true.

If you’re aiming at that thing, then yes, it becomes weird, it becomes fake. But if we can just imbue it as like, come on people, like, you know, who wants to be the person that made all your friends when you were 20 and now you’re just like drafting off of that? Like that’s kinda lousy, things change, you know?

I mean, there’s a lot of people out there that are lonely, that don’t have enough friends and, you know, and I don’t mean losers. I mean, like really nice people, but it’s hard to make friends as an adult.

And so if we can just create more of an ethos where this becomes a normalized behaviour, then I think it’s better for everybody.

Alison Jones: And I think content feeds directly into that because if people discover you by your content, people connect with you because you’re talking about things that resonate with them in a way that connects with them as well. And there’s a real kind of point around the relationships that come out of your content as well as the clients and the work.

Dorie Clark: Yes, that’s a hundred percent true. When you’re creating content, it makes it a lot easier for people to connect with you because they understand who you are. They’re getting a feel for your vibe. And some people are going to be drawn to that. Which is great. Cause it kinda does the work for you.

Where did you move to and from Alison?

Alison Jones: So, well, we moved from Hampshire to Cheshire in the UK. You spend what, 14 years there building a life, building connections and so on. Tell you what though, I can recommend having a dog, you walk a dog, people talk to you. It’s like pushing a pram, except I’m never going there again. So yes, that’s really helpful.

Dorie Clark: I can imagine, yes, everybody likes the cute icebreaker, so okay, for Americans who don’t really understand these things, where in relation to say, London is Hampshire and where is Cheshire?

So Hampshire is about 50 miles kind of West and slightly, well, my bit of Hampshire, was sort of out West and slightly South and Cheshire is about 200 miles North and slightly West.

It’s 200 miles north of Hampshire?

Alison Jones: Yes

Dorie Clark: Okay. Got it. Cool.

Alison Jones: Which I know is just around the corner at American scale, I do get that. But here it’s quite a long way because we have roads that you can’t drive on because there are too many cars on it.

Dorie Clark: Yes, no, absolutely. Absolutely, I completely understand. I’ve never driven in England, but I did try to drive in Ireland once. And it was one of the saddest experiences of my life. I actually had to, I’m not joking, I pulled over on the side of the road and started crying because it was so traumatic because the roads were so small and people were going so fast and they were on the wrong side of the road, at least as far as I was concerned.

And it was extremely cognitively taxing. And I thought I was going to die.

Alison Jones: That’s hilarious. Yes, driving is a much more relaxed affair in the States. Partly because your cars are so much bigger and more comfortable.

 Anyway, sorry people, back on content and stuff I’m going to ask you about writing itself, Dorie, because I mean, and actually just side note, that thing about people connecting with you, reading you and listening to you, it’s the same thing. So I’ve heard you talk a couple of times, you read the book, I hear that voice in my head. So you do something really smart with capturing how you speak in the book, which I think is a knack that probably you don’t even think about because it just comes naturally to you. But it’s a really good trick.

If somebody is listening to this and they aren’t professional journalists and they haven’t already written four books, what would you say to them is the key to writing in a way that connects with people maybe?

Dorie Clark: Oh, well, well, thank you. And thanks for your compliment. Actually, I will say I do think actually a lot about the style of my writing. I think that most people who have been to college and, or graduate school have had their writing a little bit ruined by that process because it is optimizing for what I would consider to be the wrong thing. It teaches you to be a little bit more abstruse, a little bit more pedantic, a little bit more Latinate. And you know, that’s fine for academia, but most of us don’t really want to sound like critical theorists in day-to-day life. That’s just not super fun to read.

And if you want to be successful as a writer in connecting with people, you need to make it fun to read, which means it needs to be conversational. Obviously one starting point for some people, depending on the way that they like to think, some people actually, talk into a recorder and sort of capture the rhythms of their speech.

Although I think that’s not a bad starting point for people who have trouble with the blank page, although there is enough of a difference between spoken English and written English, that it actually has to be edited pretty heavily because there’s lots of stops…

Alison Jones: …you’ve got some work to do…

Dorie Clark: …and starts and…

Alison Jones: …but it’s a good way to get started, as you say, you never have a talking block, do you?

Dorie Clark: Yes. Yes exactly. But I’ve had to really consciously work to make my writing conversational and feel like, okay, I’m writing to a person and to make that connection. I would say also as part of it, something that I literally did for The Long Game was I re-read The Tipping Point by Malcolm Gladwell. I mean, of course he’s a beautiful writer and part of what makes his work interesting is that his business books read like detective novels in some way, you know, there’s sort of cliffhangers and it’s sort of exciting. You really are propelled forward because you want to find out more about what’s going on.

And I re-read it from a structural perspective so that I could remind myself of ways to do that more effectively.

Alison Jones: I think that’s such a great point. I mean, Malcolm Gladwell’s a brilliant example, but generally, you know, learning to read like a writer so that you notice when something has an impact on you and you kind of reverse engineer, how did they do that? Is a really good thing. And just reading widely, it’s one of the best things you can do, isn’t it, as a writer.

Dorie Clark: Yes, absolutely. And, specifically, you know, to a point that Malcolm Gladwell makes where he’s cribbing from Anders Ericsson. It’s not just, you know, oh, like you practice 10,000 hours where you’re kind of like, blah, blah, blah. I’m doing the thing, you know. It’s not just reading, that’s part of it, because it kind of familiarizes you and it gets you in the rhythm, but it is actively studying and reverse engineering. That’s the key, is that you have to be asking yourself constantly what are they doing here? Why is it this way? This is really effective, why is it effective? And understanding the method.

I mean, it reminds me of when I was a teenager and I would like write out the lyrics to songs that I liked because of course we didn’t have you know Genius, the site that gives you all the lyrics. And I was like writing it out by hand and, you know, trying to analyze what the song structure was so that I can understand that.

Alison Jones: Yes, and that’s a really cool idea. Isn’t it? I mean, basically you got Malcolm Gladwell to coach you in writing. He didn’t know, but that’s what he was doing. And I recommend you as a coach, to anybody who’s reading your books as well.

 But you can do that. You can just ask yourself the questions, really engage consciously with it and learn a huge amount as you read.

I’m really interested to hear this actually. I always ask my guests to recommend a business book that they think people listening to the podcast would like, are you going to recommend a Malcolm Gladwell book or a different one? What would you say?

Dorie Clark: Well, I will say that one book that I would recommend is actually, it kind of ties in because he also was someone who I think did a brilliant job of writing, just sort of the art of writing and also was an editor you know, informal sort of friend editor for my book. But it’s a book by my friend, Ron Friedman and his book is called Decoding Greatness.

And it came out last year or this year, earlier this year.

Alison Jones: We’re speaking in November 2021.

Dorie Clark: Yes, completely lost all sense of time.

But anyway it’s a really, really, well written business book and interesting business book. So I think that it’s both a super enjoyable read about, you know, what the nature of success looks like and just very, very well done from the point of view of craftsmanship.

Alison Jones: Yes, brilliant. Thank you. I actually haven’t read it. I know of it, but I haven’t read it yet. So I’ll shift that up the to-read pile, which is teetering, which you can imagine.

Dorie Clark: Yes.

Alison Jones: And Dorie, if people want to find out more about you or about The Long Game and all your other books, where should they go?

Dorie Clark: Alison, thank you so much. Well, for folks who want to learn about The Long Game, I mean, it is of course available in all the places that one purchases books in England, if you’re in England, it’s on amazon.co.uk and they’ve got it at Waterstones too. But I’ll also mention too that in particular, because we’re talking about content and about writing and things like that, I have some free resources that I created specifically actually about business writing and about how to do it faster and more effectively.

And folks can download this sort of checklist that I’ve created about rapid content creation quick tips. These are the principles that I use in terms of writing my articles and folks can download that for free at dorieclark.com/content.

Alison Jones: That’s gold. Thank you. Absolutely brilliant. And I should say as well, I subscribe to your newsletter, which is an absolute master class in newsletter writing. So I thoroughly recommend that as well.

I’ll put those links up on the show notes at extraordinarybusinessbooks.com along with a transcript of this conversation.

And, yes, thanks again, Dorie, I knew it was going to be a fascinating conversation. We’ve ranged very, very widely and philosophically and tactically and it’s been really fun. Thank you.

Dorie Clark: Thank you so much. Great to be here, Alison.

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