Dorie Clark: Playing The Long Game

Mark Bidwell 0:39
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Mark Bidwell 2:38
My guest this week is Dorie Clark, who is the author of a new book called “The Long Game.” Now, Dorie was an early guest on my podcast, way back in early 2016, and this book, in particular her latest book caught my attention, because it touches on themes that are of interest to me, such as compounding, not in the traditional financial sense, but compounding of expertise, of brand and of content; and secondly, why it’s so important and also so hard to play the long game, and how to stay in the game despite the inevitable challenges. And we also talk about her business model, as she would describe it being a recognised expert, and how it has evolved over the years. And her book complements another book, which I’ve referred to in the past called “The Good Ancestor,” as well as the work of the Long Now Foundation, which we touch on in this conversation. So here’s Dorie Clark.

Mark Bidwell 3:38
Well, Dori, it’s great to have you back on the show. You were last on this program in March 2016 talking about your book “Stand Out.” What have you been doing since then?

Dorie Clark 3:47
I’ve been writing more books, Mark, I can’t control myself. In October 2017, I published my book “Entrepreneurial You,” which is about how to create multiple revenue streams and get more passive income in your business. And then I took a bit of a writing hiatus in order to create more revenue streams for myself, and I just came out with my newest book, which is “The Long Game: How to be a Long-Term Thinker in a Short-Term World.”

Mark Bidwell 4:14
And we’ll come back to the kind of the revenue streams and the business model of Dorie Clark, if that’s all right, in a minute. But let’s get into “The Long Game.” What is The Long Game?

Dorie Clark 4:23
Well basically, The Long Game is my effort to create a framework so that people can apply the principles of strategic thinking to their own life and their own career. What I found so interesting as I dove into the world of strategy over the years with my research, was literally I don’t think there’s anyone out there that says, oh, strategic thinking is terrible, we don’t need strategic thinking. Literally just about everybody says yes, yes, that’s so important, and yet, very few of us actually do it. The gap is in the implementation, and I wanted to really try to understand that better. What is it that’s going on, what is it that’s blocking us from doing this thing that is viewed as being so universally beneficial? And how can we tap into it a little bit more to get better outcomes for ourselves?

Mark Bidwell 5:12
I guess it continues on some of the themes of the earlier books around essentially productising yourself is one way of looking at what you write about, for experts, how do you actually take your story on the market? How do you monetize that story? And I guess, if this refines that thinking, what does the strategy look like? And how do you think about it from that longer term time horizon than the one that we tend to live in? Is that a fair assumption or summary?

Dorie Clark 5:41
That’s a piece of it. Ultimately, “The Long Game” is a business book in the sense that it’s oriented around people’s careers and their professional trajectory, because that is such a big part of how we constitute meaning in our lives. But it’s not specifically about how to make more money or things like that. It’s really a book about how to make better choices, and to make sure that what we are doing now, what we are doing on a daily basis, actually, in the end adds up to where we want to be going. The worst thing you could have is to get pretty far down the road and realize, oh, wow, it’s the wrong road.

Mark Bidwell 6:26
Leaning against the wrong wall.

Dorie Clark 6:27
Totally.

Mark Bidwell 6:28
So what are the rules of the Long Game?

Dorie Clark 6:31
Well, I divide the book, Mark, into three major categories, and I feel like in some ways, these can be useful signposts, and we can, of course, get into more detail and depth about any of them. But the first part, which I think is a necessary precondition to playing the Long Game, and being able to execute strategic thinking, is creating more whitespace. Because one of the biggest impediments, of course, to strategic thinking, is that people these days are so busy, they’re so overwhelmed, they literally don’t have a moment to think. And it’s not that it takes huge amounts of time to do strategic thinking, it doesn’t. But it does take mental space, and that is something that is often in short supply. So in the first part of the book, I talk about how to reclaim some of that, how to get it back and to be able to be more thoughtful about our lives. The second part is about focusing on the right goals, and really unpacking the question of what matters to you, what is the right path for you, and how do we tune out the noise and be able to make appropriate choices? And the final part is what I call keeping the faith, because it is almost inevitable that on any long enough journey, things are not going to work out exactly the way that you predicted. It’s far more likely statistically that it’s not going to go the way you thought, as compared to, oh, yes, it worked out exactly, every single one of these, you know, 40,000 steps is exactly like what you predicted back in 2011. I don’t think so! But yet, so many times we tend to get discouraged, we tend to sometimes even question the whole enterprise or whether it’s the right path for us, or whether we’re good enough, because there’s some block in the road, there’s some gatekeeper. I really wanted to write about that process about how to cultivate more resiliency, so that we’re able to persist on journeys that are meaningful to us.

Mark Bidwell 8:25
It’s interesting, I think you use some wonderful examples of companies and people that many listeners will know. Obviously, you refer to Amazon, which has consistently played the long game in the shareholder letters, they talk about the long game, and they use that language Bezos talks about. There’s a wonderful example of the handstand in your book, you can probably tell it better than I can. Let’s start with the handstand, how does that fit into this?

Dorie Clark 8:51
Yes, it is very vivid and quite memorable, it’s true. So in the 2018 letters to Amazon shareholders, Jeff Bezos tells an anecdote about a friend of his who of all things ended up hiring a handstand coach to get better at her handstands in yoga. And what this gentleman related is actually applicable for almost all of us. He said that for the average person, if you ask them to guess, you know, hey, how long does it take to master a yoga handstand? He said, the most common answer that he gets is about two weeks now, the actual number is that it takes six months of daily practice, it takes 24 weeks. I think this is so interesting, because it is a surprisingly common problem that when we are attempting to do something, especially something we haven’t done before, we certainly have back of the envelope assumptions, but often we don’t articulate them consciously, we certainly don’t test them, we don’t research them. And you go, oh yeah, I should be able to do that in two weeks. And then you get to week 4, week 6, week 12, and it hasn’t happened. And you begin to really feel despondent, you say, oh, man, this isn’t working, this is terrible, I’m not cut out for this. Well, it’s not that you’re not cut out for it, it’s that you scoped it wrong. You think, oh, wow, this is taking me six times longer than it should. No it’s not, you’re not even halfway there, you just didn’t know it. And I think that this is really powerful in terms of understanding where we are in the journey, orienting ourselves, and making sure that we have accurate expectations so that we don’t give up too soon.

Mark Bidwell 10:35
Yeah, because I suppose the counter of that is that the vast majority of us would stop a lot of projects in their tracks once we’ve done the research, and we realise really what was required in order to hit those objectives, right?

Dorie Clark 10:45
Yeah, that’s absolutely right, and there’s nothing wrong with that. Actually, you can often gain just as much by stopping a project early, that would have been inappropriate, or would have been a needless drag on resources. Something might be worth doing, if you can actually accomplish it in six months. That same thing may not be worth doing if it’s going to take you six years. So having a clear-eyed look at it is very important, because we only have one life to live. And we have to make judgments about really where we want to spend our time. I am a big fan, I would never say oh, if it’s going to take a long time, don’t do it. There are some things that are 100% worth doing. It might take years, they might take decades. As long as it’s a goal that matters to you, then by all means, do it. But I think we need to be educated about what we’re actually committing to.

Mark Bidwell 11:37
There’s a wonderful book, I don’t know whether you’ve come across it, called “The Good Ancestor.” Have you come across that book?

Dorie Clark 11:42
No, that sounds great, though, tell me about it!

Mark Bidwell 11:45
I think you’d love it, because it’s basically making the case that a lot of our decision making is so short term now. But in the past, there were some big projects, like for example, building cathedrals. The cathedral in Barcelona, that’s a three-generational project. It’s spurred by cathedral thinking. There’s a cathedral in East Anglia in the UK, which took eight centuries to complete, but none of us are thinking like that anymore. We focus on the short term. So you take to the other extreme, which is quarter by quarter, how do you actually deliver the numbers that the analysts are requiring? And it’s just fascinating, because the reason for good ancestors is there are a number of communities, Native American communities, where they’d make a decision based on how this is going to impact the seventh generation from now? And in Japan, they make decisions, there are certain societies in certain parts of Japan where they’re thinking about big projects, and they get people to project forward as the grandchildren of the people in the room. How will our grandchildren respond to these changes we’re making? And obviously the situation the world’s in at the moment, is a reflection of the fact that we’ve lost our ability to do that somewhat, right?

Dorie Clark 12:57
Yeah, that’s absolutely right. Some of the most interesting businesses to read about or to study are in Japan, where you have something like a noodle shop that’s been around for 900 years. It’s absolutely incredible.

Mark Bidwell 13:10
Absolutely. Breweries as well seem to last a long time. There is another area, which I’m interested in, the Long Now Foundation, which you’ve come across.

Dorie Clark 13:20
That’s right. I’ll be speaking for them next year.

Mark Bidwell 13:24
Fantastic. I was listening to one of their episodes today. It’s that kind of thinking, which is so hard, and let’s get into why it is so hard, but we’re not very good at it as human beings on a social level. But let’s go down to the level of some of the people you work with. What gets in the way of people – we talked about one thing, which is misaligned expectations or fundamentally inaccurate expectations about how long it’s going to take – what else gets in the way of playing the long game?

Dorie Clark 13:54
Certainly, misaligned expectations are definitely one. Human nature is another, which we need to battle. But the good news and I think it is empowering news in many ways, is that we can surmount this. Toward the end of “The Long Game” I allude to the well-known study, of course, by now the famous marshmallow study by Walter Michelle, about do you take one marshmallow now or two if you wait 15 minutes, this tantalizing offer for little kids. That gets talked about a lot, but the part that I think is under-appreciated is, so often in the popular discourse, it tends to circle around, well, you’re either the give me the marshmallow now person or you’re the long term thinker. Well, the actual truth is that they have shown that you can teach even little kids strategies. The issue is not that there’s these incorrigible types that are perennial hedonists, it’s that kids don’t necessarily have good strategies to follow. But if you teach them, they can learn to be better long-term thinkers and dramatically enhance their rates of being willing and able to wait for the second marshmallow. And the same thing, of course, is true for grownups, that we can all get better at long-term thinking. Now, of course, the biases toward the short term, yes, we would all like success now, yes, we’d like all the things now. Of course, I am no different, I would like them now too, that would be much nicer. But the issue is that it just doesn’t work that way. So instead of making stupid choices, or raising our fist to the sky, and saying, oh, life isn’t fair, well, there’s something we can do about it. We can actually work to reorient ourselves, to deal with the reality that things don’t always come fast. In a smart and thoughtful and gracious way, we can begin to plow a different path for ourselves.

Mark Bidwell 15:59
It’s interesting, because you touched on it, the benefits of if you’re able to tap into something exponential, the nonlinear thinking. Our brains are wired in a linear manner, right, and often, it seems to me that people bail out just before it gets interesting, just as the curve is beginning to tip. I suppose one of the things is, how do people – and I don’t pretend to understand compounding, I understand it intellectually, but I don’t understand it viscerally.

Dorie Clark 16:27
I don’t think any of us do. Compounding is freaky.

Mark Bidwell 16:32
It is, but it’s at the heart of the long game essentially, isn’t it? Staying in the game until the numbers start getting quite big. And the numbers, it could be the numbers of readers, it could be the numbers of people listening to your podcast, it could be the numbers that pop up in your bank account, whatever. But those are all, you bail out too early, and you miss that journey, of course.

Dorie Clark 16:51
Yes, that’s exactly right. There are a shocking number of metaphors, and comparisons that you can make and parallels between playing the long game financially and playing the long game in one’s career. Just as small actions started today, making much bigger impact on your bottom line when you retire, then huge amounts of savings when you’re five years out from retirement, it’s very similar in terms of the actions that we take to enable our careers to thrive, whether it is connections that you’re making, and the value of them over time, whether it is, for instance, if you want to try to get more recognition for your ideas, starting the blog now, and posting once a week, but starting it now, as compared to trying desperately to get readers all at once before your book launches, or whatever it is. Compounding is extraordinarily powerful, and I think hopeful, fundamentally, because it shows you that none of us has a huge amount of time, none of us has a huge amount of resources or energy or whatever, we just don’t. But all of us can find small amounts of time, small amounts of effort that we can apply. And that is more than sufficient for the outcomes that we need, if we are disciplined about applying it.

Mark Bidwell 18:14
It comes to the heart of it, I guess,the assumption is, having the right goals, so being clear where you want to end up and what the journey is, recognising that the journey might take longer than you initially anticipated, and there’s a number of things you need to do on that journey to stay on the path. In terms of the right goals, maybe for you given your background, how did you land on the path that you chose? And what lessons are there for others?

Dorie Clark 18:42
In terms of landing on the path that I did, I have certainly tried to walk the talk, in terms of actually doing the things that I prescribed in “The Long Game.” This has certainly been my most personal book. There’s a bit of a through line talking about my own experiences and professional journey, although I also interviewed dozens and dozens of other professionals and shared their stories in the book. But ultimately, in terms of keeping the faith and resilience, there’s a lot of that, because early in my 20s I had a million setbacks. I got laid off from my job as a journalist, I worked on political campaigns and they all lost, I got turned down from all the doctoral programs I applied to. I had a million things where gatekeepers or circumstance for whatever reason was just basically saying like, nope, sorry, not this thing. And so you have to keep climbing back and saying, alright, well, if not this, then let’s come up with something else. So there’s a certain amount of just being willing to tap into your plan B or your plan C, or your plan D. I think that also, not in every area of my life, but in certain ones, I really was conscious about trying to play the long game and to enact these principles. As one very conscious example, I knew that I had a bit of a challenge. When you start your own business, we all have different challenges, based on what our previous experience was. But mine was that I had previously worked on, as I was alluding to before, I’d worked as a newspaper reporter, I’d worked on political campaigns, I worked in nonprofits. So the one thing I hadn’t done was work with high powered and wealthy business executives. I knew that, if I was going to actually build a business with consulting and executive coaching, I somehow needed to meet those people. It was not going to be through my own network, because people know people like themselves. I knew a million people who couldn’t pay for my services. I didn’t know anyone who could, so I needed to do something differently. I decided that I would double down on a content creation strategy, because I thought that was the way that I could raise my profile, meet new people and grow my brand. I very consciously turned down work and turned down revenue, in order to be able to make more space for content creation, which was not paying or not paying very well, as part of the long game, because I knew it would be necessary for the health of my business 5 or 10 years down the road. And that was, thankfully, a bet that did pay off.

Mark Bidwell 21:16
That’s one of the core skills you allude to in the book, is saying no to stuff, getting really good at saying no to stuff, right?

Dorie Clark 21:23
It’s true. It’s in many ways just a necessary precondition, to be able to even engage in long/term thinking.

Mark Bidwell 21:31
And then another one which struck me is choosing to be bad. Can you say a little bit about that? That felt a little bit different.

Dorie Clark 21:38
Yeah, this is a very counterintuitive piece of advice, you’re right, which is part of why I love it. This was an idea that I first came across a few years ago. There is a Harvard professor named Frances Frei, and she and her partner Anne Morris wrote a book back in 2012, called “Uncommon Service.” It was a book about service industry companies, so banks or airlines or things that are dealing with customers, and they were trying to answer the question, why is it that so few companies are actually really great? Of course, everyone tries to be great, but very few actually are, most are pretty like they’ll do. And what they realized, and I thought this was so powerful, is that fundamentally, the challenge and the main reason that so few companies are great, is that by and large companies refuse to make strategic choices about what to be bad at. There’s often this level of magical thinking that companies have, where they say, oh, well, I can be great at this particular thing, and then I’ll be just fine, I’ll be average in everything else. That’s how it will work. And of course, that is not true, because there’s finite resources, and if you’re going to truly be great at something, you’re going to have to be bad at something else. And you’re going to have to be smart about what you are bad at. It’s a very important strategic choice. And because they’re just not willing to go there, they never rise above mediocrity. I thought that was so powerful, and it applies to us as well. It applies in our own lives. In order to be great, we have to be willing to choose what to be bad at.

Mark Bidwell 23:20
Just curious, what have you chosen to be bad at?

Dorie Clark 23:22
Mostly, what I’ve chosen to be bad at professionally, I would say, is my email response time, which is very embarrassing to me and I hate it. But nonetheless, if you actually want to get the most important work done, answering your email is almost never the most important work. It’s a little irksome to others, and I and I hate it, but if you really want to move forward with important things like finishing your book, for instance, it has to happen. I would say on a personal level, there’s just a lot of things I don’t do. I live in New York City so I can get away with it, but I don’t cook pretty much ever. I just buy food, and it works great, but I’m able to save a lot of time not dealing with some of the niceties of housekeeping.

Mark Bidwell 24:06
The other piece that struck me was the Drucker’s questions that you asked yourself. What should I spend my time doing? What are the 20% of my activities that yield 80% of the results? What can I stop doing? How can I use constraints to my advantage? And you talk about answering those questions several years ago. Are they questions that you continue to revisit and to refine the choices you’re making, or have you locked that down and you’re off to the races?

Dorie Clark 24:34
Well, I think that it would probably be foolish to answer strategic questions once and then just say, okay, well, good, now I’m done, because the world changes around us. Of course, it’s equally silly to try to change your answers to strategy questions every week or every month, because you want to keep doing things long enough to actually see if they work, to actually see what the results are. But periodic reflection on every six months, every 12 months basis, I think really is important to understand, alright, is this still what I want? Or have market circumstances changed to the point where maybe this idea isn’t such a good idea anymore? Or maybe there’s another opportunity that’s presented itself, that’s even better, which might happen occasionally as well. But yes, I certainly continue to ask and try to answer those questions. When I think about what I want to be optimizing for, what is the 20% that yields 80% of the value right at this moment; this has been a continuing theme, certainly for me over the past few years, but at various times, I’ve focused more or less heavily, 2021 has been a time for me about focusing on launching “The Long Game” successfully and getting that out there. When you launch a book, if you’re really going to do it right, it has to be the sole focus. But broadly speaking, I would say the main thrust for me is continuing toward additional ways to leverage passive income, because that is what is scalable. So focusing on online course creation and optimizing the online courses I have. For instance, literally this morning before talking to you, Mark, I spent several hours working on it. It’s an ongoing project of continuing to improve my Recognized Expert Course, which I’ve been running now for five years, and has become a core part of my business.

Mark Bidwell 26:26
Another question which really struck me was, how could I do something once and make it count 10 times. Is that a lens through which you now look at your choices you’re making?

Dorie Clark 26:37
Yeah, absolutely. I think it’s not a bad question for us to ask ourselves as a thought problem right? Now, this doesn’t apply in every area of our life. If we think about spending time with our family or whatever, that’s a different story. But if we think about work products and work output, sometimes people will say things to me like, oh, well, social media is so exhausting, I don’t have time to do this on LinkedIn, and this on Twitter, and this on YouTube. So I try to think about, alright, well, how is it possible that we can create one core piece of intellectual property and then optimize it? It’s equally ineffective if you just take literally the same thing, and like, oh, I’ll just slap it up and reshare it everywhere. That gets old pretty fast, and if you see something that essentially is a tweet, that is optimized for Twitter, and you see that on LinkedIn, it’s going to look weird on LinkedIn, it’s not going to perform well, it might even damage your brand. Because it’s like, what is this with all the symbols and all the hashtags, and it doesn’t look right there. But I do think, if you take the time legitimately to create something, let’s call it an article that you’ve written, let’s say it takes you an hour to do that for the sake of argument, you actually don’t have to spend 15 minutes creating a LinkedIn post, and 15 minutes creating a tweet and whatever, that’s not very effective. But what you can do is take two minutes to take that article you’ve already written and come up with a better, LinkedIn specific way to share it, so that you get more views and more power and more leverage off of the thing that you already invested in. So the question for me is really, how can you take, let’s call it 10% more time and be able to get 10x the returns in terms of the attention on, and the views for that article that you so lovingly crafted?

Mark Bidwell 28:40
If we just step back, I’m very curious, we’ve touched on it a couple of times, the not residual but different revenue streams. So if we look at your business, you have obviously writing books, you have writing articles, and forgive me if I’m missing anything, but then you have coaching, executive programs, and then I think you have online groups which you’re leading, and do you also have asynchronous online programs where they might be running at three o’clock in the morning, New York time, but people are still participating, I guess there’s a bit of that as well, right? Is that the universe?

Dorie Clark 29:18
That’s largely the universe. When it’s not COVID, I will periodically do, maybe once or twice a year, topical workshops that people can sign up for in person. I also run a mastermind group, which is a year long program, again, primarily, it was in person pre-COVID. It went virtual now, it’s probably going to be hybrid, like a lot of things. But yes, roughly, that’s the universe of activities.

Mark Bidwell 29:46
And presumably then there are the pieces of content or expertise that you’ve developed in one area, which are then cycled or recycled or repurposed and repackaged and delivered in different forums.

Dorie Clark 29:58
Yeah, that’s exactly right. I think you’re touching on something important, Mark, which is, when people think or first hear about, oh, create multiple income streams, they often think, oh, wow, that sounds so overwhelming, how can I do this? How can I build up these different audiences and do all these radically different things? And of course, if you are actually building up different audiences, and marketing radically different things, that would take a lot of time, that would be incredibly hard. But what I am talking about specifically is something a little bit different, which is taking your same audience and your same core intellectual property, and just coming up with slightly different ways of presenting it, because some people really want to work with you, or they want to buy from you, But certain things just might not be appropriate for them. So if you have somebody that loves your stuff, and all you offer is high end executive coaching, if they can’t afford it, you get zero and they get zero. But if you write a book where you encapsulate your principles, they can buy it for $20, And you are able to help them, And they’re providing you with a certain amount of revenue, not a huge amount, but nonetheless, it keeps them in orbit. Similarly, let’s say you only do in person workshops, so that’s great, but what if there’s somebody in Hong Kong that really wants to participate, but it’s just too hard and too expensive for them to fly from Hong Kong to do it? Well, if you go into virtual, now you’re offering a reasonable way that someone who would have been an eager customer, that would have been shut out, now can suddenly access your work, so you’re helping both of you. It’s just thinking about different platforms, different methods, so that you can capture the full value of the work and the audience you’ve created.

Mark Bidwell 31:45
Yeah, yeah. And I’m curious, when you started writing for one of the traditional print, I think it was Forbes, I can’t remember which magazine you published lots of articles.

Dorie Clark 31:59
Yeah, a number of years ago, I was a Forbes contributor.

Mark Bidwell 32:02
So right at the beginning, did you have this vision in mind that in 2021, you would have this universe, almost like a hub and spoke model in place, or has it evolved over time? I’m just interested in how the strategy, having the right goals, has evolved over the years from your point of view?

Dorie Clark 32:21
I certainly didn’t have all the pieces figured out. And I think you don’t necessarily have to, it’s like driving in the fog. As long as you can see a little ways in front of you, you can get to your destination. In my case, when I was writing for Forbes, I understood pieces of where it was getting me, although perhaps not the whole picture. What I did know was, number one, it was because people had heard of Forbes, and they liked the idea of being written about in it, I was able to connect easily with folks that might have been harder to access otherwise. It gave me an excuse to build my network in that way. Hey, can I interview you for my Forbes blog? Most people would say yes. So that was advantageous in the short term in terms of building my network. And additionally, it gave me the social proof of writing for publication people had heard from, that was helpful. I just thought, okay, I will probably, because people are seeing my articles on this platform, I’ll probably be reaching readers, and people will become familiar with my work that I wouldn’t be able to access on my own. So I thought, just in general ways, alright, this will help, this will do good things for my business, but I didn’t necessarily know what form that would take. I’m curious, Mark, how do you think about your business model? What did things look like for you?

Mark Bidwell 33:38
Thank you for asking me, I’m on a similar path. At the moment, I’ve got business activities, which tend to be separate, but they’re connected. I’m on the board of companies, I invest in startups. But I have my passion project, which began in early 2016, which is a podcast, znd now I have a book project. I’ve always seen that as an investment, and it’s an investment of my time in learning out loud or learning in public projects if you like. But then I also have a mastermind group called Outside Views, which is quite a distinct program, and I have a book project underway. I don’t have all the pieces, but I’ve got a lot of things, and I’m on a journey of unlocking them. It’s about time and it’s about making the right choices. I’ve made some terrible decisions on this journey, some of them I won’t talk about, but I’m still in the game and things are moving forward very nicely for all sorts of good reasons. But one of the things that I’m really interested in is, where I was going, and I don’t want to over characterise it incorrectly, but you’re published by a traditional publishing house, you taught in a traditional business environment, and you’re also very active in what are now very well established networks like Facebook, like Twitter and YouTube, I’m assuming these are the incumbents. What seems to be happening now is that these platforms are shifting and they’re under threat from Web03, from decentralized networks that appear to be developing. And if you look at the world, and again, I’m just starting on this journey so I’m at the edge of my knowledge anyway, but if you look at the world, some of the creator activity that’s going on with music, with writing, with Substack, it seems to me that the the power is going to shift over time far more to the creator than it has done in the past. The days where you can get shut down by Twitter changing their algorithms, or you lose a significant amount of your audience are fast approaching an end. And I’m just curious about how you, it’s a long-winded way of thinking, how do you look at five years, ten years out? I’m assuming the content and messaging will continue to evolve, but it’s going to be built on the themes, insights you developed. But I’m just interested in how you’re thinking about future streams of revenue, future opportunities? People listening to this today, there’s a playbook they can follow, but I do think it is changing quite quickly, or potentially going to change quite quickly. So I’m interested in how you’re looking at that? Does that resonate, or do you feel that I’ve been drinking the Kool Aid too much, and it ain’t going to happen on your watch?

Dorie Clark 36:24
No, no, I think these are certainly the right questions to be asking. I’ve certainly been following Substack closely. Initially, starting my career as a journalist, I’m very interested in people who themselves are former well-known mainstream journalists like Andrew Sullivan, whose blog I subscribed to, or Bari Weiss or John McWhorter, who have these Substacks. Interestingly, John McWhorter was recently lurred back from Substack to write for the New York Times, so there’s a lot of interplay that’s going on, but that’s a fascinating model. Almost immediately, Andrew Sullivan basically announced that he doubled his income with Substack subscribers as compared to the income that he was making from his salary at New York Magazine. It is a way of insulating yourself, as you say, from different gatekeepers or platforms that might decide to cut you off either deliberately, or as an inadvertent consequence of algorithmic changes. So I’m very interested in all of that. But broadly speaking, drum up and beating for a long time is the importance of building your email lists as your direct way of connecting with your audience, with your customers, because you really should not, it’s just such an illusion for people, you should not be relying on third-party outfits, which are only concerned with shareholder profits, as your primary vehicle for connecting with your customers. It’s the height of, frankly, irresponsibility, and so we need to own those relationships. And when we do, it enables us to monetize in a lot of different ways. It gives us way more optionality, so making sure that we have that control is very, very crucial.

Dorie Clark 36:44
Yeah, absolutely. So beginning to wrap up, I know you’ve got a hard stop. I’m just curious how – a lot of work obviously went into this book, and you’ve launched it, and obviously talking to a lot of people about it – what are the things that really resonate most in the book? What are people saying, this was so insightful, this has changed how I’m thinking about my career?

Dorie Clark 38:36
One of the things that I’ve found that I actually get a lot of questions on, and a lot of interesting ones, is a framework that I use called optimize for interesting. There is so much discussion. In our culture, we seem to have a sort of bifurcated framework, where people seem to assume that you either are optimizing for money, and it’s just, okay, well give me the highest paid investment banking job you have, or the polar opposite is optimize for your passion, and that’s sort of the “morally correct” choice in our culture. And okay, there’s some truth to these things. But like a lot of stuff, it’s a gross exaggeration, and I think that polarization is not helpful to us. Because, if you have this lionized thing about following your passion, that’s great, and God bless if you have this great passion you want to follow, but also, there’s a lot of people that maybe are not sure what their passion is, maybe they have a lot of passions, or maybe they’ve been doing something for a long time, it no longer Is that exciting for them, but they’re not sure what the next thing is. And I think there’s a lot of stigma around like, oh God, poor you, you don’t know what your passion is. First of all, I find that annoying, but secondly, it’s not helpful, because the implication is that you just can’t do anything until you know what your passion is. You better just sit there and meditate until you figure it out. Not helpful. What I like to suggest, instead, optimize for interesting. We don’t want anyone, of course, to be stuck in some job or career that is not interesting to them, that would be terrible. But it also doesn’t have to be your great calling in life. We find our calling through doing, through experimenting. And so if we can at least make choices based on what is interesting to us, and just continue holding it lightly, and following that path until it stops being interesting, in which time we can do something different, then I think that’s often a kinder and healthier way to look at it.

Mark Bidwell 40:42
Yeah, this resonates because I have a son who’s about to go into the workforce the year after next, but he’s already beginning to think about it. And I think one of the challenges is, he can follow what his parents did, which is a bit dull, which is consulting in the corporate world, I don’t know whethere those jobs are gonna be around. But the reality is that, I was speaking to David Allen just before now, who I think was in one of your earlier books, and he was saying he had 36 jobs by the age of 36. He remembers that, because he sat down when he was 36 and wrote down. But he was saying that there are jobs being developed, and parts of the industry, which don’t even exist today, that in 10 years time we’ll be talking about. There are loads of jobs today that didn’t exist 10 years ago, and categories of jobs. And so it’s just so terribly difficult, so I think you’re optimize for interesting is a nice compromise. I agree with you that the passion piece doesn’t work for me, the downside is too enormous in my mind. But the idea of following the path of optimizing for money is pretty horrendous as well. I like that, I can understand why that resonates. Super. So, Dorie, let’s just begin to wrap this up with the three questions I sent through to you earlier on. First one, what have you changed your mind about recently?

Dorie Clark 41:50
In terms of changing my mind, I would say in a broad sense, I’ve changed my mind a bit more politically, because for a long time, for many years in the early part of my career, I was working for what at the time would be considered very progressive Democrats in the United States, and have become increasingly dismayed with some of the ideological inflexibility among the progressive movement. I still care about the causes that I always cared about, but I think that on all sides, of course, the political tenor has gotten rather rancorous, but as someone who has been affiliated, and therefore has a little bit more stake in some of the Democratic Party activities, I would personally like to reshape things, if I could. And therefore, I would say I’ve changed my mind about some of the types of candidates that I might have backed in the past, and think that we need to take on a more conciliatory tone.

Mark Bidwell 43:01
I always stay clear of politics on the podcast, but I suppose I’ve been lured into the conversation now, but it feels like there are some good takeaways from what has happened, and it’s not just in the US. It’s in Brazil, it’s in Poland, it’s in the UK, and more engagement, more reflective thinking from the populace about what kind of societies we want to live in. That has to be a good thing. Second question, where do you go to get fresh perspectives, especially when facing tough challenges?

Dorie Clark 43:30
In terms of fresh perspectives, I’ve learned so much from the people in my Recognized Expert Community. I feel very lucky to be facilitating this community for the past five years. Just as one example, I mentioned in some posts or some webinars, something that I was having was muscle trouble with my shoulder. And I got these great suggestions from people from my Recognized Expert Community, and one member turned me on to something called the Egoscue Method. There’s this great book called “Pain Free” by Peter Goscue. It’s like a form of physical therapy, but it’s about postural adjustment and things like that. And I think it’s quite smart, so I’ve been reading that and learning more about biomechanics, and that’s been really helpful.

Mark Bidwell 44:18
It sounds like in your group, in the Recognized Experts group, there is a lot of fresh thinking that you can tap into as a resource, essentially.

Dorie Clark 44:25
It’s people who are very smart on a lot of different subjects, and we all try to learn from each other.

Mark Bidwell 44:30
Lovely. And then the final question, how has a failure set you up for success?

Dorie Clark 44:36
In “The Long Game,” one of the things that I took a bit of delight in doing, because it was something that felt risky, and so therefore was appealing to me; it’s not that hard to talk about failures from a long time ago, because, oh it’s the ancient history, and now everything’s great. But I picked a bunch of recent failures. I had a whole chapter literally, where I talked about plans that I had for myself in 2019. I had five big stretch goals, and over the course of 2019, four of them completely blew up and failed to come to fruition. And I recounted that process. On one hand, I guess, it’s just this continual exercise in humility. We never reach a point where it’s like, oh, yeah, now everything’s easy. Presumably, if you’re a person who still has goals, or a person who is ambitious in some way, you continue to try to reach for different things. And you keep hitting ceilings, you keep hitting situations where people don’t want your thing, whatever your thing is. So therefore, I feel like those were failures that I’m not sure in a literal sense that they set me up for success. There’s plenty of ways to continue to salvage things, and so, I will continue to do that, but I think that it’s a constant reminder, even for me in writing “The Long Game,” that one has to work the program and understand that it is never going to be smooth sailing. It is not a referendum on you, and we just have to keep moving forward.

Mark Bidwell 46:04
Yeah, absolutely. As you say, it’s like driving in the fog, as long as the engine is running and you’re making reasonable progress in a measurable period of time or measurable progress in a reasonable period of time. Wonderful. Super, Dorie, it’s been great to catch up. So where can people get in touch with you?

Dorie Clark 46:17
Yeah, thank you so much, Mark. People can certainly get in touch with me and access a bunch of free articles that I’ve written for places like Harvard Business Review and Forbes, and things like that all for free on my website at DorieClark.com. And for folks who are especially interested in “The Long Game,” I have a free long game strategic thinking self-assessment to help you apply the principles of strategic thinking to your own life. You can get it for free at DorieClark.com/thelonggame.

Mark Bidwell 46:45
Wonderful. As I said, I really enjoyed reading your book. I’ve been reading around the subject for some time, so I was thrilled when I saw in my feed that you were bringing something out on this. And I also look forward to your upcoming talk at The Long Now, which is a remarkable organization. Many thanks, Dorie, great to catch up and next time you’re in Switzerland, let’s catch up in person as it were.

Dorie Clark 47:07
Thank you, Mark. It’s a treat to be reunited five years later on your show. So thanks again for having me.

Mark Bidwell 47:13
Not at all, have a good day.

Dorie Clark 47:14
Thanks.