Selects Edition: Long-Term Thinking In a Short-Term World with Dorie Clark

This is the Selects Edition of the Eventual Millionaire, where we choose to republish the best interviews I had with millionaires. (This episode was originally published on December 31, 2021.)

Dorie Clark is a consultant, keynote speaker, and author. She has been named one of the Top 50 business thinkers in the world by Thinkers50 and was recognized as the #1 Communication Coach by Marshall Goldsmith Leading Global Coaches Awards. She teaches executive education at Duke University’s Fuqua School of Business and Columbia Business School. She also wrote The Long Game, Entrepreneurial You, Reinventing You, and Stand Out, which was named the #1 Leadership Book of the Year by Inc. magazine.

A former presidential campaign spokeswoman, Clark has been described by the New York Times as an “expert at self-reinvention and helping others make changes in their lives.” A frequent contributor to the Harvard Business Review, she consults and speaks for clients, including Google, Microsoft, and the World Bank.

“If you’re pursuing a meaningful and long-term goal, it is far more likely than not that there will be some detours and some disruptions and obstacles, and you have to understand how to persist and how to get around them so you don’t give up too soon.” – Dorie Clark

Episode Highlights:

The framework from her new book, The Long Game
How to get over that mental piece of wanting it all done yesterday but pre-planning for the future
Four questions to ask to get more white space in your life
How to figure out your strategic plan for your business
How to lower your level of resistance to testing and trying new things for your life and business
How to work on your strategic patience
How to figure out your short-term joy so that you can stick with your long-term plan

Transcript: Download

Video Transcription provided by GMR Transcription Services.

Jaime: Welcome to Eventual Millionaire. I'm Jaime Masters, and today on the show, I finally have Dorie Clark. She's been on my radar for years and years and years. I've heard her name a thousand times. She's coming out with a brand-new book called The Long Game, which we all need to know. You can check her out at dorieclark.com. Thanks so much for coming on the show.
Dorie: Jaime, think you so much. I feel the same about you, and I'm so glad to finally be connecting.
Jaime: And this book is so freaking needed. I talk to my clients all the time about short-term versus long-term, and you wrote the book on it. So, tell us a little bit more about why you went down this lane.
Dorie: Well, I think it's probably for a similar reason to what you're talking to what your clients about, because certainly, when I was starting my business 15 years ago, I realized very quickly and with a growing sense of alarm that there were things that I would need to do in order to somehow raise my profile or differentiate myself in the marketplace. And I started to do them, and it just felt like, "Wow, is this not working? Or is this not working yet? And why can't I tell the difference?"
And it was so frustrating, and I just kind of muscled through it. And for a lot of us, when we're undergoing the gauntlet of entrepreneurship, we often feel like, "Oh, well, maybe that's just me." But five years ago, I started running this online course in community, and I was working with people who were doing very similar things.
And at this point, now, we have 600 + people who have gone through the program, and I began to see this real cross-section where it wasn’t just me. It was almost everybody, and there's this sort of gulf that we have to surmount on the path to growing the business we want.
And there can be a lot of low points. It can really be discouraging, and in The Long Game, I wanted to try to create a framework so that good people with good ideas are able to persist longer and to understand what is coming down the pike, so that they actually can get to the other side and get the rewards that they want.
Jaime: 100 percent. It's like spinning plates, right? And you're like, "I only have so much energy, and then they all start crashing, and then you just think you suck as an entrepreneur, and then you throw your hands up. Tell me a little bit more about the framework.
Dorie: Yeah. Well, ultimately, in The Long Game, I break it down into three key parts, which is kind of how I think about the journey. The first part is about creating more white space, because certainly, I think all of us these days understand one of the big barriers is – I don’t think there's anybody that thinks, "Oh, thinking long-term, that's a bad idea." We all know we should be doing it, but the problem is in the execution, because we are so stuffed to the gills with all of the short-term things we have to do.
So, Step 1 is figuring out how we can strategically clear out more white space, so we can do the thinking we need. No. 2 is getting clearer on the right goals for us. How do we focus on the right things, and make sure we're actually headed in the right direction that we want to be, and that we think we are?
And then, finally, the third part is what I call keeping the faith, because inevitably, on the path, if we're pursuing a meaningful-enough goal, a long-term-enough goal, it is far more likely than not that there will be some detours and some disruptions and obstacles, and we have to understand how to persist and how to get around them so we don’t give up too soon.
Jaime: Okay, yeah. Because it's like entrepreneurs rev their engines so much, and then they burn out, and then they're like, "I can't see the results from it because I haven't stuck with it long enough," because it's – I mean, every entrepreneur that I worked with, ever, wants it done yesterday. Like, can I have it just be done yesterday?
Dorie: Totally.
Jaime: And that level of thinking is so hard when you're looking at the long game, and going, "Yeah, but I'd like it sooner." So, how do you get over that mental piece of wanting it all done yesterday, but pre-planning for the future?
Dorie: Yeah. It is a terrible human conundrum, isn't it?
Jaime: Seriously.
Dorie: And the truth is, there's good elements to this. This is not saying that short-term thinking is universally a bad thing. Sometimes it's quite important and quite relevant. When everybody was having to pivot during the pandemic, "Okay, that old 2020 plan, that's not going to be a thing." Short-term thinking is great then, because we need to dive in and roll up our sleeves and make things happen. But I think that the most important part to recognize is: Short-term thinking is great up to a point, but we cannot live our lives that way. We have to recalibrate; we have to go back to more balance by emphasizing long-term thinking, so we actually can end up in the place we want to end up. We can't always be reactive.
So, ultimately, when it comes to this sense of impatience, I have it too. I think just about every entrepreneur does. But in the book, I talk about a concept that I call "strategic patience," because regular patience has really never done it for me. I feel like when people talk about regular patience, it's more kind of like a, just, you know, "Shut up, can you please stop?" Like "Just be patient."
And that kind of wish-fulfillment thing, like, "Oh, just lean back and magic things will happen," this never sufficed for me. I wanted to actually have some agency and some control. And so, strategic patience is my version of this, which is understanding that, yes, "Okay. We get it. We are making peace with the fact that things might take a while. Things might take longer than we want them to."
And that is frustrating, but it is reality. So, okay, we'll cope with that. But the strategic part, it should not be sitting back and eating bonbons and making a Pinterest board. You are doing things. You are creating a hypothesis; you are testing the hypothesis; you are pivoting; you are observing. To me, that is strategic patience.
Jaime: I'm so grateful that you labeled that, because when I'd say "patience" to anybody, they're like, "You don’t understand me." That's not an innate capability of mine. And so, you're like, "It's not that. It's not the normal way we see patience. It's totally something different, which makes, I think, all entrepreneurs have a little sigh, deep breath right now, where we're like, "Oh. It's for a reason, and it's for more ROI later," and that makes a huge difference.
The thing that I have a question on, though, is: Everyone goes, "Well, how do I actually get more white space?" because we're in a culture of hacking time as much as humanly possible, and packing in everything, right? So, we don’t even necessarily want space. We feel good that we're busy, but how can we get more white space in our lives?
Dorie: Yeah. That is the important question. And so, in The Long Game, I actually have multiple chapters devoted to this question, because without it, most of the other stuff is not going to work, right? We just don’t have the mental bandwidth to even go there.
So, there are four questions, Jaime, that as one of the frameworks, one of the ways that I begin to suggest this that I use personally, and that I propose that might be helpful for other people. And so, just briefly, in case they are: Whenever I am confronted with some kind of an option, an opportunity – I mean, obviously, right, if it's terrible, we say no; if it's great, we say yes.
The problem so often for us as entrepreneurs is the middling opportunities, because we kind of talk ourselves into things, right? It's like, well, it's not paid, but it could be good exposure. These magic things where we try to convince ourselves.
So, if it's a middle kind of situation; if it's like a four to an eight, what I've learned to ask myself is the following four questions. So, No. 1: What is the total commitment? It is so easy to con ourselves in the moment into thinking, "Well, it's just an hour to do this webinar," and you and I know that it takes an hour to make the slides, and then they want to have three planning calls, and all of a sudden, "Oh, okay." You have to be real. You have to say, "DO I want to devote four hours to this project?" That's No. 1.
No. 2 is: What is the physical and emotional cost of saying yes to this? Because so often – this was true for me for a long time – it was always this question of, "Well, literally, does it fit in my calendar?" That is not the right question. If you've been running yourself ragged; if you have been traveling; if you have been really over-extended on a project – you are going to be less in a position to be able to do something. So, think about the overall cost, physically, and emotionally, to yourself.
No. 3: As entrepreneurs, we should never forget about the opportunity cost. It's not a question of, "Should I do this or should I not do this?" It is a question of, "Should I do this thing, or should I literally do anything else in the world that takes that amount of time?" That could be the gym; that could be your family; that could be writing your book; whatever it is.
And lastly, would I feel bad in a year if I did not do this? Because honestly, most things just kind of fade into noise. There's a few things; okay, maybe it's your best friend's wedding. You'd probably feel bad. But most things, you're not going to feel bad saying no to.
Jaime: We need this so badly. When you said "mental bandwidth" at the beginning, I think people don’t even understand that the level of stuff they have in their brain is not conducive to all the creative ideas that they could be having. Like you said, "If I choose to do this webinar, well, that just comes to me, so it's easier just to say yes, than to actually come up with something myself." Strategically, that's probably a million times better, and will get me there further and faster.
But it's just easier to receive, instead of trying to think about what we need to do. So, how do we figure out what that strategic plan is? Because some entrepreneurs are not very strategic, they would assume, right?
Dorie: Yeah. I certainly think everyone has the capacity to be strategic, but you're right that everybody has sort of natural predispositions. I think about – and it's sort of weird, right? It's not like the kind of things that you really get tested for, and it's like, "Oh, yes, I know this for a fact." You discover it about yourself in the doing. I have this one friend who is so good at titles. She can come up with a title for anything, and it's so magical to watch her.
And meanwhile, I'm proud I came up with a title for The Long Game that – the title and the subtitle, How To Be a Long-Term Thinker In a Short-Term World – I was so proud of myself. I literally was trying for a year to come up with it, because every single one of my previous books, I literally just let the publisher pick it, because I'm like, "I don't know." So, yeah, we all have the thing where we have to work at it. We can get better, but it's challenging.
So, if you are someone who does not feel like you are "naturally" strategic, and you do need to work on it a little bit, I think there's a few things. One is I always like to beat the drum on this, and I know that you're a believer in this as well, about developing for ourselves a robust peer community.
I think that that is really important, to have other people who not only are your boosters – and that's important too – but also, you need to have people who understand your field, as well, and can provide targeted advice about "This is a good idea, this is a bad idea," as compared to your mom being like, "You're amazing, sweetheart," which is its own good thing, but I think that's part of it. I also think sometimes we over-complicate things, right?
When we think about strategy, we don’t necessarily – where I see a lot of people go wrong is where they say, "I can't come up with a 20-year plan, because I don’t know how I would accomplish it." Good. You don’t need to know how to accomplish a 20-year plan. It is a fool's errand to imagine that you can predict how to accomplish something 20 years from now. The world could be underwater. I don’t freaking know. There's a lot of things that can happen. Really, it is about identifying some kind of – like a vision, a North Star you're working toward. And don’t figure out the 20-year plan; figure out what the next step is.
So, it's just sort of ideating. What do you want your life to look like? I'll tell you my 20-year plan. I want to be United States ambassador. Do I currently have a bead on how to do that? Not really. I think what I actually need to do is raise millions of dollars for a person who wins the presidency. Who is that going to be in 20 years? Damned if I know. But we figure things out as we are moving toward them.
Jaime: See, I don’t think a lot of the entrepreneurs we work with are lacking that vision, but they assume, in order to pick that vision, they need to know how to get there. I love that you shared the story where you're like, "It's way the heck out there, and I've got no clue," because most people won't admit that. They're like, "Oh, well, just so you know, I've got a 20-year plan on how we do this." And almost all entrepreneurs I've ever met don’t have anything even close to that. Like you said, you can't. The target ends up moving.
Dorie: Yep.
Jaime: With the pandemic, we never would have been able to predict it. We recalibrated absolutely everything after that. And so, knowing that you're sort of on uneven ground all the time, anyway, makes you a little bit better about not necessarily knowing, you know, A to Z. What do you say for the people, though, that do like to think longer-term strategically, but get in their own head about the right way to do something?
Dorie: Yeah, I think we need to lower the stakes, and lower the bar on almost anything, right? Sometimes – speaking of webinars – I'll be doing a webinar, and people will type these frantic questions into the chat box, and they’ll be like, "But what if I pick the wrong goal?" And it's like, "You know what? Change it. It's okay. It's super not the end of the world."
The big thing – you know, this is a drum that I beat a lot in The Long Game – we all know, and we probably are applying this, honestly, in our businesses – I mean, everybody at this point in the entrepreneurial ecosystem is down with lean start-up methodology, and minimum viable product, and all of that. You're probably doing it with your AB testing of your landing pages, right?
But you're not doing it, probably, for your own career. Let's apply the lessons that we know and that we have internalized for our business. Let's turn it back on ourselves. You only get into problems if you overextend yourself, and you put too much on the table, and you lose a bet.
The way I like to think about it: If you go to a casino, and you lose a dollar, are you going to say, "Oh, I failed." Nobody notices. Nobody cares that you lost a dollar. The point is, don’t put down $100,000.00 on a bet that you are totally unsure you're going to win, or probably you're not going to win, right? That's a terrible idea.
Put down a bunch of $1.00 bets. It's like venture capital. You can lose 900 of them, and it's not a big deal, because the whole point is not to make a dollar. The point is to get data, so that you can find the one place you put the dollar and it works, and you say, "All right, I'm putting $100,000.00 down here," and you have a high degree of confidence that it's going to work.
Jaime: Yeah, it's a feedback loop, people. It's scientific method over and over and over again, because even if the guru tells you that this is the right way to do something, they're making that up, too. Like yeah, they got data, and now they're saying it worked; and maybe you listen to it five years later, and now it doesn’t work, and you're like, "Hey" and you blame the – it's forever moving, and I don’t think people really understand that. And the good news is, with the feedback loop like you're saying, is that they're going to learn no matter what it is.
Dorie: Yes.
Jaime: So, I know we sort of discount, or at least we use the cliché like, "It's never failing. It's learning," you know? But it's true. How do you get to have either your clients or you embody that? Because it's hard. It's easy to say, harder to do."
Dorie: Yeah, well, I really – I think that it's just the point about small bets. You literally don’t even notice or care that it's small. How does it feel like a failure if you waste an hour? It just doesn’t even register. So, I think there's ways that we can just take failure off the table. For me, personally, the way that I got the book deal for my first book – it was Reinventing You – and I had had three book proposals, complete proposals that I had written before, and they had all got turned down. Nobody wanted them. It was very depressing.
And basically, the feedback I got is, "You're not famous enough. Go get famous and talk to us later." And it's like, "Okay, okay, you assholes." And so, I started blogging. Reluctantly. I did not want to start blogging, but I'm like, "Fine. Okay. I have to do this." And it turned out much to my chagrin, "Oh, they were right," because I could not guess what readers would care about. I thought I could; I couldn't. I'm not that smart. Probably no one's that smart.
The way you find out what readers care about is you test things with readers, and you see. And so, I started writing a bunch of blog posts, and there was one blog post that really took off much more than the others, and it was a piece I did for Harvard Business Review about personal branding, and reinventing your personal brand. And that became a thing, and ultimately, I was able to take it from being a blog post to being an article in the magazine.
And then, when the magazine piece came out – mind you, this is after I'd been fired by my agent, because she couldn't sell any of my proposals – three different literary agents reached out to me and said, "Hey, do you want to talk? Do you want to turn this into a book?" and I was like, "Oh, that's what it feels like to be wanted. Okay." And it was because of this testing.
But it's because I wrote a bunch of – whatever, like 800-word blog posts, that's frankly a lot more economical in terms of my time and energy than writing three complete book proposals which failed, which had been my previous strategy.
But I'm curious, Jaime, how do you think about strategic thinking in your own life? Do you have a 10-year, 20-year plan? How does this look for you?
Jaime: You turn it on me? I have so many other follow-up questions for you. Yeah, heck no. I have a vision board that I paint. That's far out when I go – I have no idea what any of this is going to be, or how it will come to fruition. In fact, I had a [inaudible] [0:18:39] movie where I put white space. This was five or six years ago. I wanted more white space. So, I took a picture of a calendar with no meetings on it, and I was like, "I need this."
Dorie: Well done, yes.
Jaime: And now I work maybe 10 hours a week, have a couple meetings, that's about it, right?
Dorie: Amazing.
Jaime: Which was completely different to my hustle sort of mode. I can achieve anything and kill myself in the process kind of way. So, I think we discount the need for contemplation time and for, like you said, strategic thinking and sort of going a little bit down that road. Even with my clients, I have them do three-month plans and while we're working on the three-month plan, then we plan the 6 to 12- month plan, and then we see how it goes, because their speed of implementation matters.
If somebody can do something in a week, and other people take a month or two months to do, it's totally different. You can't plan. I used to be a project manager, if you can't tell. I'm like, you put all the things in order. And so, yeah. I only go three to six months out typically, anyway, because it ends up shifting after a little while, right?
Dorie: I think that makes all the sense in the world. Yeah, absolutely. You can have the long-range vision, but you can only plan definitively a little ways out. I'm curious: What were the biggest changes? I'm sure there were a lot of changes around the edges, but what were the biggest changes that you made that enabled you to go from the sort of proverbial overstuffed schedule to having all the white space and just 10 hours of work per week?
Jaime: Enough pain for me. Mine's a different situation. The kids' dad who I co-parent with got terminal cancer, and I went, "What matters more?"
Dorie: Yes. [Inaudible] [0:20:17] function.
Jaime: Yeah. It was – and I'm stubborn. So, I had that little white space on my mind movie forever, but it was like I would do little things here and there. And then, when this happened, I was like, "Nothing," because I couldn't. And so, unfortunately, the situation sucks, but you can do – I used to be like, "Well, I can't. I'm a single mom and I've got kids, and I've got this, and I've got that." I would use all those excuses. And when push comes to shove, you can do anything that you want to.
Dorie: Yes. Right, right. That's really the key.
Jaime: I love that you turned everything on me. Wait, I have a question for you, because the three proposals: That's a lot. Those aren't $1.00 bets, to me. When you failed three times on proposals, that's a huge chunk, especially just in mindset and defeatedness, right?
Dorie: Yeah.
Jaime: And now you have a bazillion books. And let me say, one of your books was rated – Stand Out was rated No. 1 leadership book of the year by Ink Magazine. So, to go from three failed proposals to Ink Magazine's No. 1 book of the year is kind of a ridiculous trajectory, but you could have quit at Book Proposal 2, or Book Proposal 3, and you never would have achieved that. So, that's not, to me, $1.00 bets. Those are pretty heavy.
Dorie: Oh, yeah. Yeah, yeah, yeah. That was before I learned how to do things better. Yeah. I'm not saying "Do that." I'm saying "Don’t do that."
Jaime: That's awesome. So, what would you have done in hindsight? Because you didn’t want to write a blog, and you had to get pushed into it, too.
Dorie: Right. Well, what I would recommend for other people is to start at that point and write the blogs, because the three failed book proposals really didn’t give me much data aside from I wasn’t famous. Oh, surprise. I didn’t know that. And so, what did give me data was writing a bunch of different blog posts, because you're trying – you know, a blog takes you an hour, two hours, whatever, to write, and you're able to create a lot of them and see what resonates. So, that is a much better strategy, yes.
So, the whole premise, in The Long Game, is that I am writing about things; certainly I interviewed a bunch of people on sharing their best strategies; but I'm also curating it through my own lens of what I've learned over the past 15 years in business, and certainly plenty of mistakes along the way.
Jaime: Why is it that we seem to have – because I worked with a lot of entrepreneurs; I have a lot of entrepreneurial friends – we are stubborn as all heck, right? Even when I think about you going like, "Oh, I don’t want to write a blog. I just don’t want to." And the amount of pushing that sometimes has to happen, right, in order for us to get to where we need to go – it's not just like, "Oh, this is magic, and it's a small step, and I take it." Right? Like, how can we get people to not be so stubborn, or at least lower their level of resistance to testing and trying new things that they might be averse to?
Dorie: Yeah, yeah. We do have to talk ourselves into things, sometimes. I think part of it is ways of understanding that oftentimes there are other routes to a goal. I think most entrepreneurs – you want to build a business. You want the business to be successful. That's a pretty universal desire. We may be averse based on personality, based on previous experience, or whatever; just certain methods of it. And actually, I think that's fine.
I get questions sometimes from people that are thinking about doing coaching or courses with me, or whatever, and they're like, "But I don’t write. I don’t like to write. Do I have to write to do it?" and I write. I write a lot. But also, used to be a former journalist. That's what I enjoy; that's fine. But I very clearly tell people, I'm like, "No, that does not have to be the thing."
What is the thing? We just need to dial it back one more step. It's not that you have to write; it's that you have to share ideas. That is the part that's mandatory. You cannot be a thought leader; you cannot be a recognized expert in your field if you don’t have any ideas or you're not sharing those ideas so other people can hear them.
That is the price of admission, but the way that you share those ideas, that is open for debate; and if you hate writing, fine. Don’t force yourself. It's okay. It's not like there's a law that you have to do it. You can give speeches. You can do podcasts. You can do videos. You can whatever. If it's really good, I guess you could do like a slide share, or something, but there's a lot of methods to it.
But find the underlying principle and then look for a different way to meet that goal.
Jaime: Yeah, and starting them – like I blogged for six months, and I feel like you were telling my story. I blogged for six months. I hate writing. But everybody told me to blog, so I blogged, and it kind of sucked. And then I started a podcast, and it was a million times easier and better because that's my thing, and I would never have known that that was my thing until I went down the path of going, "This is not my thing," because I wouldn't have come up with a podcast without doing all the other pieces, even though – but sticking with something for six months in a culture of TikTok right now, it's just very different.
So, six months of trying to get feedback and not feeling like you're successful at something sucks. So, what do you say for people's mindset of feeling like things are going super, super slow, when they're focused on more of the long game?
Dorie: Yeah. Well, I think this – going back to a point we were talking about previously – this is where having a knowledgeable group of friends you trust is very valuable, because if you genuinely do trust their opinion, and you make it clear that you want honest feedback, we are not good judges when we are in the thick of things. Our judgment goes a little bit out the window.
And depending on the moment, or depending on our nature, we probably vacillate pretty wildly between, "Oh, I'm just going to keep hanging on, and we're almost there. We're just around the corner," and then five minutes later it's like, "It'll never work. It'll never happen for me." And it's just like, "Oh, which is it?"
So, you need people to reflect back, and to give you some guidance about it. But also, a piece that's really important is, very few people take the time to research up front what has happened for other people. We sort of make these assumptions like, "Oh, well, this person gave this speech, and then it went viral, and then all the things happened," and you don’t understand the mechanism behind it; you haven't really looked into it.
And it's very useful to understand, yes, there are outliers, but in general, there are premises that we should be aware of. Like in the business world, if somebody's a lawyer and you want to make partner at the law firm, generally it takes about seven or eight years to become a partner at a large law firm.
If you somehow think you're going to make partner in three years, I'm not saying it's not going to happen, but I'm going to say it would be extremely surprising in the history of the universe if that was how it happened. And okay, if you know something I don’t, and you bring in a billion dollar contract to your law firm, then great. But mostly, that's not going to happen.
And similarly, in your entrepreneurial field, if you look at your idols/competitors or whatever, we need to see, like: What did that arc look like? How many episodes did Jaime have of her podcast before she hit x number of monthly downloads? These are the pieces of data that are actually going to be valuable to you, as you think about what is a rational goal.
Jaime: Yes. Okay, I love talking to you, because things aren't realistic, and unfortunately, because of marketing also, people are like, "Oh, you can be profitable in a month, and blah blah blah, right?" Like there's a lot of things being touted when you actually look realistically what has happened for other people, it is never the overnight success that we are sold, and I think that's where the dichotomy comes in, too, because we're like, "I know, but so-and-so started a podcast like this." You know what I mean? And good for Don Dumas.
We went to high school together, right? And everybody's like, "He was an overnight success." I was like, "No, he was not. He worked his butt off for many, many, many, many months, and had a team before – you know what I mean? And it's easy to just sort of see the head above the water being like, "I'm great now," instead of actually paying attention to what was realistic for people. But we don’t like waiting, so, strategic patience is something we all have to work on, I think.
Dorie: Absolutely. Absolutely.
Jaime: So, how do you work on strategic patience? Because you've been in the game for 15 years, so you took a lot of experiential learning lessons, right? So, somebody who's a little bit newer, how can they test out their strategic patience? What are they supposed to be doing, if they keep going back into, "Oh, crap, I have no patience whatsoever?"
Dorie: Well, one of the things that I often think back to, as during the process where I was writing The Long Game is, a piece that sort of inspired me was just over a number of years, a lot of coaching calls that I would have with my executive coaching clients.
And we'd hop on our Zooms, and they'd say, they give me the update about what they've been doing the last few weeks, and then they'd say, "So, what now? What next?" and that was always the question. And I just felt like the meanest person in the world, because I'd have to tell them of, "You should keep doing the thing you're doing. That's what's next."
It was like every two weeks, they somehow wanted a new strategy. Like, "And now it's time for vlogging," and I'd sort of unveil the thing, and it's like, "No. No. Actually, the strategy that we decided on like six months ago, do that."
Jaime: Yes. Keep going.
Dorie: And they were just like, "Oh, really? Keep doing" – and I'm like, "Yes, keep doing that." But I think, God willing, that was helpful for them, because so often, the tendency – our always – this is true for all of us: We kind of look for the magic bullet. We sort of half understand there's not a magic bullet, and then we keep looking for the magic bullet. Like, "Oh, now. But now if I do this," and again. Sometimes there's a crazy miracle, but mostly it's slogging, and mostly it's just being a good person who is persistent at doing something well.
In my book Entrepreneurial You, where I wrote about John Lee Dumas and a number of different people, one of the folks that I profiled, who you probably know as well, is Jordan Harbinger, a fellow podcaster. And he told me – the thing about Jordan, he started podcasting in 2006, or 2007. Most people had no idea what a podcast was. They certainly didn’t even know how to find them.
And he said he looked at his statistics once, like he figured out how to find them and he looked it up, and he was like – he saw, basically, that like three people had listened to it. And then, he said that he proceeded to not look at his statistics again for seven years. And he just kept making episodes anyway.
And I love it, because that is really what we need to do. At the end of the day, we have to just be running our own race, and come up with a strategy and execute it. And I think part of the issue with strategic patience, as well: We often, at least a part of us, is kind of looking for the big score. Like, "Oh, a million downloads, or whatever."
Well, it's probably going to take a while. And so, we have to find a way to make the activity meaningful for us even while we're doing it, and even if we never get to the million downloads, because that's what will enable us to do it.
And it can be different goals. It can be the self-mastery of just learning how to do a new thing. It could be that you are interviewing people and you like networking, and this is a great way to – so, it's a great vehicle to meet new people. It could be a way that you think about doing professional development, because you're talking to cool people, and you're asking them all the cool questions you want. Whatever the motivator is. But you have to find a short-term motivator to con yourself into playing the long game.
Jaime: Yeah. Okay, yes, because aligning with your strength, and actually enjoying the journey, that's the other cliché, right? Enjoying the journey. But literally, I hate writing. If you made me write a blog forever, I would just be gritting my teeth and going, "This sucks" forever, right? It's totally different than actually trying to, at least, enjoy what you're doing, because there's no way you'll stick with it for longer, and you have to, even though we don’t necessarily want to.
How do you figure out your strengths, to? Especially for somebody like you. You knew writing beforehand, if you were a journalist. But you worked with a lot of people, also. How do they figure out what actually can give them that short-term joy, so they can stick with it long enough?
Dorie: I don’t necessarily know that it's about strengths, per se. Even having been a journalist, I look back on my early blog posts that I wrote. And nowadays, I look at them, and I'm like, "Eh, I wasn’t that good." It wasn’t the worst thing in the world. I was at least literate, but I had not found my "editorial voice." So, I think most of us start not that great at different things. I think the question is less about strengths, and it's more about enjoyment. It's more about what do you find pleasurable enough or interesting enough that you will be willing to persist at it long enough to be good at it.
Jaime: I love that. Yes, because otherwise, it's done, and then you hate your job or your business or your life, and you're never going to make money or stick with it long enough to be able to make money on what you want to do, also. But did you always know that you wanted to be a writer?
Dorie: I always liked writing. So, that was sort of a piece of it. But there were different things that I wanted to do. Really, what I wanted to do out of school was go into academia. So, I got a master's degree, and then I applied to doctoral programs, and I thought I would just be a professor. But I got turned down by all the doctoral programs. So, I had to find something else to do. So, journalism was actually my fallback job, because I'm like, "Well, I can write and think about ideas doing this." So, that was sort of the Plan B from the failed career as the academician.
Jaime: My face is still in awe, because Ink Magazine, they voted your book the No. 1 book of the year, and you're like, "It was my fallback." Right? We never know what life is going to hand us for opportunities. Not that you haven't worked your butt off in order to get where you are right now. But like you said, those little pieces at one time, and you keep going, and keep going, and keep going.
What's the one thing from this book right now that you really feel like somebody needs to know?
Dorie: So, when it comes to playing the long game, I think that for me, one of the most important things, which was not at all on my radar when I was writing the proposal for this book, which took place entirely before COVID – but I actually got the email saying, "Hey, we're going to buy this book for my editor," February 28th of 2020, and then, literally, the next day was the first COVID diagnosis in New York City. So, this was all happening at a really interesting time.
So, when I was first envisioning the book, I thought of it as, "Oh, Instagram culture and comparison, it's so deleterious, and we have to be playing the long game, and not be so worried about what other people are doing, or why am I not succeeding as fast as I want." And as I was writing it, during COVID, I realized there was also something different, which was: COVID was sort of a forced detour into short-term thinking, and as with a lot of things, it's easy once you're doing something for long enough for that to become the new habit, or for that to be the new default.
A lot of people are like, "Oh my god, I totally forgot how to relate to people," or things like that. It's like, no, no, no. We need to retrain ourselves, because it is not a good thing to forget how to talk to people. We need to fix that.
And similarly, I think it's very easy, almost the default, because it ties into human nature, is to default to short-term thinking. But we need to forcibly correct that. I really believe that. It is not a way to live, and if we want to have the kind of entrepreneurial careers that I think most of us do, where we accomplish something; we have a vision; we set out to achieve something, and then we do achieve it: You can really only get there through long-term thinking.
So, to me, I now view the long game as a kind of corrective to that. It's a way of replanting our stake in the ground after COVID, and saying, "Take that, COVID." Now is the time, there's a new sheriff in town, and I'm going to come up with the identity and the vision and the goals for myself, and not just react to the circumstances around me.
Jaime: Yes. Yes. If we all get to do that, we will have a better world, instead of feeling that reactive, everybody's going crazy; this, which we've been in now for quite a few months, and it's –
Dorie: Yes, we have.
Jaime: Yeah, and burn-out is real, because of that short-term thinking. And so, we have to change the game. We have to have the new sheriff, otherwise we're going to burn out, and medically, we're going to have issues, because we can't live like that forever.
Oh, refreshing. Okay. So, I'm going to ask the last question. Besides buying your book – because everybody should go get the book – what's one action listeners can take this week to help move them forward towards their goal of a million?
Dorie: Yes. Well, Jaime, I'm going to revert back to a theme that I talked about with my previous book, which is called Entrepreneurial You. The subtitle is, "Monetize your expertise, create multiple income streams, and thrive." And so, what I want to suggest is, if we're thinking about a step that people can take to raise up their incomes to a million dollars: One of the things that I feel really strongly about is the importance of creating multiple revenue streams.
I got laid off from my job as a journalist – this was sort of a formative experience for me – on September 10th, 2001, and my job search the next day didn’t quite unfold the way that I thought it would. It was this very geopolitically traumatic reminder that the safe job isn't safe. And as entrepreneurs, we know that. But also, the safe client isn't necessarily safe.
And so, if we are too over-reliant on one client, or frankly, one line of business, it just puts us at existential risk. And I realized that one of the things that we have the ability to do as entrepreneurs is to diversify that risk, and be thoughtful about it.
And so, I'm not saying we have to do a million totally different things. It's not like, "Oh, you should be a windsurfing instructor and a lawyer and a dog breeder." What my saying is that your core IP, the core thing that you do, you can transmit it in different ways. Maybe you do coaching and online courses, or you run a mastermind, or you have a product line. Whatever it is, but you kind of come up with different things, because there are people out there that are probably interested in what you offer, but they may be interested in it in a different form than it currently comes in.
And I like to suggest, we shouldn't overtax ourselves and try to come up with 10 new things this year. But my challenge to your listeners is to try to come up with one new line, one new product or offering this year, as a way of diversifying your revenue stream.
Jaime: That's the long-term thinking that you were just talking about, because everybody that got hit by COVID, that had one stream, and it was really affected by COVID went, "Oh, crap. Now what?" And you're saying there's all sorts of different ways we can diversify now, so we don’t find ourselves out on the streets, if something, who knows, happens. You've had crazy bumps in your career.
So, everybody, check out this book. Tell us more about where we can find you online, your blog, and all your books, because you've got a lot of books.
Dorie: Thank you so much, Jaime, yes. The best place, the central hub, is dorieclark.com. And for folks that are interested in diving in more fully to the long game, of course you can get the book, which is fantastic. I also have a free long game strategic thinking self-assessment, and folks can get it at dorieclark.com/thelonggame.
Jaime: Everybody go check that out, and find out how strategic you are. Thank you so much for coming on this show, today, Dorie. I so appreciate it.
Dorie: Thanks, Jaime. Great to be here.

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