Making Time For The Long Game: On Being A Long-Term Thinker With Dorie Clark

by | Aug 31, 2023 | Podcasts

SWGR Dorie Clark | Long-Term Thinker


Many professionals are overwhelmed by the fast-paced environment. To keep up with others, they often focus on short-term goals, overlooking the bigger picture or the long game. In this episode, bestselling author and top business thinker Dorie Clark walks us through the framework we can apply to become a long-term thinker. She emphasizes the importance of long-term thinking for long-term growth. Dorie also explains strategic patience and how it plays in many successful businesses. Her expertise opens many doors of opportunity to tap into the power of small changes that will impact your future success. So tune in to this episode to learn how to start playing The Long Game.

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Making Time For The Long Game: On Being A Long-Term Thinker With Dorie Clark

My guest in this episode is the incredible Dorie Clark. Before we get to the interview, I’d like to invite you to see how your presentation skills are doing and how they’re serving you by taking our free four-minute assessment at That’s where you can see where you are showing up as a leader and it’s benefiting you and where perhaps a little bit of extra support could get you the results you need and the recognition that you deserve.

My guest is the awesome Dorie Clark. I’ve been following her for quite some time and learned about her from friends. She’s been named one of the top 50 business thinkers in the world by Thinkers50. That’s been twice, so two years in a row. She helps individuals and companies get their best ideas heard in a crowded, noisy world.

Dorie was honored as the Number One Communication Coach by the Marshall Goldsmith Leading Global Coaches Awards and one of the Top 5 Communication Professionals in the World by Global Gurus. She is a keynote speaker and teaches for Columbia Business School as well as other important universities. She is the Wall Street Journal bestselling author of The Long Game, Entrepreneurial You, Reinventing You, and Stand Out, which was named the Number One Leadership Book of the Year by Inc. Magazine.

We are going to be talking about the long game because, in this very busy world, how do you find the time to do the important strategic thinking that will advance your company or your career? Dorie’s also a former Presidential Campaign Spokeswoman, and she’s been described by the New York Times as an expert at self-reinvention and helping others make changes in their lives. She is a frequent contributor to the Harvard Business Review and consults and speaks for clients such as Google, Yale University, and the World Bank. Forbes has declared that her insights connect marketing, social media, communications, learning technologies, and personal discovery to give us a blueprint for success in the future economy.

Dorie is a graduate of Harvard Divinity School, a producer of a multiple Grammy-winning jazz album, and a Broadway investor. She’s also written a Broadway show, which is in development now. I don’t know how she has time. If you are interested in learning more, you can download her free Long Game Strategic Thinking Self-Assessment at I have been trying and trying to get Dorie Clark onto this show and we finally connected and had a most delightful conversation full of interesting things. I know you’ll have a good time. Here comes Dorie Clark.

Dorie Clark, welcome to the show.

Elizabeth, it is good to be here.

I’m so happy to have you. I’ve been following you for quite some time and took some machinations to get you. I got you. I want to talk to you about one of your many topics, long-term strategic thinking. Before we start, the question I ask all my guests is if you could interview somebody who’s no longer with us, who would it be, what would you ask them, and who should be listening?

I always have a little bit of a historical affinity to Theodore Roosevelt. He’s a little bit out of favor now for his imperial mustachio bravado. He was a really interesting guy and such a unique thinker. Some of his quotes have endured. Brené Brown has famously popularized one of his about The Man in the Arena, “It is not the critic who counts,” and all of that.

My favorite Theodore Roosevelt quote is a different one, which seems very Theodore Roosevelt, at least in terms of the brand that has come down over time, which is “In any moment of crisis or high stakes decision, the best thing you can do is the right thing. The next best thing you can do is the wrong thing. The worst thing you can do is nothing.” I’m like, “That’s right. You got to make the move.” I respect that. It would be a very interesting conversation with him.

What would you ask him?

One of his lasting things that has stayed with us is about conservation and national parks. I would be interested in getting his take on climate change. That was not a thing that 100-plus years ago people were thinking about or needed to think about at the time. I’d be fascinated with what his perspective is on that pressing contemporary issue.

It would be interesting to ask him about the political opposition he faced in creating national parks and saying, “Not every resource belongs to us, the privileged elite. Maybe we should save some for the people or the planet.” I am sure he got a lot of pushback for that. That would be an interesting conversation. That would be lots of fun. I’ll tell you that quote, the one that Brené Brown talks about, my dad had it on his wall for years when he retired and then set up a little office in an extra room of the many things from his official office. That’s the one that went up on the wall in the back bedroom when he set up his desk back there. I know it well. I read it many times long before Brene Brown.

There we go. I like it.

Dorie, you talk about so many things, but I’d like to ask you about long-term strategic thinking, why it’s so important, and why we don’t make time to do it.

One of the things that set me on the path to thinking about this was in 2018, I was invited to speak at a conference in your hood in Austria. Every year in Vienna, they have an annual tribute conference to Peter Drucker, the great management thinker. I was asked to speak there and give a short talk about strategy. The mandate is something about the strategy, which is fairly broad. I was trying to think about what would be interesting and what would be useful.

As I was pondering it, what I realized was that to me, the thing that was interesting about strategy is the fact that, unlike a lot of things in contemporary business life, there’s not any opposition. It’s not like there’s an anti-strategy faction. Everyone agrees that strategy is a great thing. “We should do that. We should all be long-term thinkers.” The problem is not that we don’t think it’s a good idea. The problem is that we think it’s a good idea and we don’t do it. It’s almost like going to the gym. There’s no one who thinks that exercise is horrible, but we still don’t do it.

SWGR Dorie Clark | Long-Term Thinker

The Long Game: How to Be a Long-Term Thinker in a Short-Term World

I began to go down the rabbit hole of trying to understand, “What is the problem? What gets in the way here?” That ultimately led me on the path to writing my book, The Long Game: How to Be a Long-Term Thinker in a Short-Term World. One of the interesting statistics that stood out to me most when I was researching it was there were a pair of studies that were done just around the same time as each other.

One study that was conducted by the management research group was of 10,000 senior leaders. They asked them, “If you have to pick one thing, what is most important in being a successful leader?” Ninety-seven percent had the same answer. They said, “Long-term thinking strategy, that’s what’s important.” Meanwhile, in a separate study, they surveyed executives about the challenges they were facing, and 96% of them said they did not have time for strategic thinking. That pair together, 97% say it’s the number one most important thing and 96% say they don’t have time for it. Clearly, there’s a disconnect and it’s one that is worth solving.

This is something I work with my clients all the time. They’re always putting out fires. To take the time to think about the long-term, about your career, and about setting yourself up as a thought leader, you actually have to do the homework. You have to sit down and think about what your talking points are and what you think. In writing a book, you’ve got to take the time. How do you do it?

There are a lot of answers to that and we can go into depth about any of them. For me, what I’ve discovered is the starting point in a lot of ways. The things that crowd out our ability to do strategy, some of them are more subterranean and more psychological. Sometimes it’s avoidance, trying to bury yourself in work, etc. At a pedestrian level, almost all of us are plagued by very banal things. We have too many meetings and too many emails. As a result, we feel like we can essentially never get to the good stuff because we’re always triaging our inboxes.

At a really pedestrian level, almost all of us are plagued by very banal things. As a result, we feel like we can essentially never get to the good stuff. Share on X

One of the most important things that we can do is to set up rigorous barriers and boundaries for ourselves so that we have some white space and have some time to attend to things. I’m not perfect at this either. Part of the reason I’m doing this work is to teach myself as we often do. If you have a day that is interrupted in such a staccato fashion that you’ve got a meeting, then you’ve got 15 minutes, you’ve got another meeting, then you have maybe 30 minutes, then you’ve got another 2 meetings, you’re not going to be able to do any intellectually meaningful project during that time.

For a big project, it takes a while to get into it to remind yourself of the nuances. All you’re going to have time to do is answer a few emails and then you’re onto the next thing. A lot of it, the starting point is about getting clear and creating systems for yourself to have the necessary white space. That is hard. It’s hard emotionally for people to turn things down and to say no. That is the necessary prerequisite to be able to give yourself this space for strategy.

What do you mean by white space?

White space is a very literal term. It means if you have a calendar, whether it is a paper calendar or an electronic calendar, when you have a meeting on Monday at 9:00 AM or whatever, you’re either filling it in with black ink and writing it or on your computer and now it’s a blue square that gets filled in. If you are scanning your calendar and it’s an ocean of blue or whatever your chosen color is, you are not going to have the ability to do a lot of deep thinking because your nominal presence is going to be required for so many things. There’s not an oasis in the day for you to do it. You’re going to be racing around like a chicken with your head cut off. You need larger, unstructured blocks of time. That is necessary. That’s not to say you need six weeks at ashram. That’s probably not possible or likely. Do you need more than 30 minutes in a day? You probably do.

The ones that have worked the best for me is when I have an acquaintance who wants to do the same thing. We have it every two weeks if we can, but we have to get it done on time. We turn on Zoom and minimize it, but we stay online so that you can see that the other person is actually working because promising you will still don’t work because you’re still going to get distracted. For those of us who are working from home, the things you need to do about laundry and fixing that spot that’s broken and things like that, which I never allow enough time for. “Here’s something I can postpone because I have to do the laundry instead.” That’s something to recognize that you need those times.

I love your strategy. There’s a whole business that has come up based on the premise of what you’re talking about. People can do it informally like you have, but I have a colleague who started a business called Cave Day and people will pay money if they don’t have a friend who will do it with them. They get paired with a group of people or one-on-one and do that sustained focused work as a forcing function or an accountability mechanism.

If you have an admin who is managing calendars, don’t tell them not to let you book something during lunch. Have your admin say, “Don’t let me say yes.” I’ve had quite a few clients who’ve done that. They say, “I have no time to think.” I said, “You didn’t take time to eat. Who said yes?” You could say no. It is a systemic issue. I know that’s one of the things. Say you’ve got two hours every other Friday blocked off, how do you make sure you’re using that for the right purposes? You’re going to get something out of it.

It’s a good question because a similar analogy would be like writing a book. There are a lot of people I know who want to write a book and this is their goal. Part of the battle is allocating time on your calendar to write the book, freeing up all the stuff, “Now I’m going to do it.” This is great, this is a victory. Let’s say they put two hours on their calendar Friday afternoon, “I’m going to write this book.” Because they haven’t gotten down to a level of granularity about what this is going to look like, all they have on their calendar is, “Write a book.” They sit there and they’re like, “How do I write a book? Where do I start?” They sit there and are overwhelmed for two hours, which is not terribly helpful.

Many people have a similar view of the portent nature of, “Do strategy.” This is world shatteringly important thing that has to be done with a stentorian voice. That almost necessarily intimidates people. It means they get frozen up, they don’t do it, and they procrastinate even when the time is on their calendar. You’re right that this is worth drilling down on.

Here is the quick back-of-the-envelope way that I like to define doing strategy. There are a lot of ways you can do it. You can do it with your team and things like that. When we’re doing it for ourselves, I like the frame and asking the question, “What is it I can do today that will make tomorrow easier and better?” That is the question that I ask myself. That brings it down to a more human level essentially. I may not know what my life purpose is. I may not know what should be my strategy for the next couple of years, but I can probably find something I can do now that will make tomorrow better. Tomorrow can be defined however we want.

At a minimum, let’s say you’re taking a couple of hours on a Friday, something that I feel is almost always a good thing to do. This is a good habit, but if you can’t yet make it a habit, try it as a one-time thing and see how it works. Look at your schedule for the next week or possibly the next two weeks. What I like to do is say, “What do I need to do to prepare for the things that are coming my way?” I skim the calendar and say, “I’m meeting with this person. I need to read that article because I’m supposed to talk to them about this article. Put this down and read this article. I’m giving a speech, did I make the deck yet? Did I send the deck to the organizer? I’ve got to do that.”

It’s all of these little things, “I’m meeting with the accountant, which means I need to send him last year’s tax returns.” You do these things and it does make your upcoming week or weeks simpler because there’s an enormously large number of things that if you have to do them last minute, it becomes a bit of a crisis or an emergency. If you do them three days in advance, then all of a sudden it’s not that hard. The difference between doing something three days in advance and doing something the night before or the hour before on both a practical and an emotional level is enormous. Even that can make a big difference in your life.

I love that. You talked about strategic patience. What do you mean by that since we’re talking strategy?

Strategic patience is a topic that I have talked about in the long game and I called it out specifically because it is true. The unfortunate truth is that if you are working on long-term projects, almost by necessity, they take a long time. We might wish that the path to whatever the goal is, the path to the C-Suite, to becoming a multi-millionaire, to becoming a bestselling author, whatever the thing is you’re trying to do, it would be great if like, “I can do that in three months,” but mostly not. There are a lot of things that do take a number of chess moves. It’s over a period of years. They don’t happen as fast as we want them to.

SWGR Dorie Clark | Long-Term Thinker

Long-Term Thinker: If you are working on long-term projects, almost by necessity, they kind of take a long time.


The question we have to ask ourselves is, “If I’m serious, if I mean what I say that this is important to me, then I need to deal with the reality on the ground that this is something that’s going to take a while. I don’t have to love that, but that’s probably how it is.” It’s not to say that a miracle can’t happen, but most likely it will probably take quite a while. That’s where strategic patience comes in. Patience has gotten a bad rap justifiably because, a lot of times, people in power will use the language of patience as a way of shutting you up. “Just be patient, it’ll come to you. Don’t worry. Stop complaining.”

That’s not what I’m advocating because that is patronizing. Nobody wants to have that done to them. I like to think of strategic patience as essentially just making friends with reality. Sometimes things do take a while and we have to understand that, be ready for it, and cope with it, and then that’s what’s going to allow us to get the outcome.

Making friends with reality, I love that. I talk about it a lot because I want everything to happen overnight. My wife wants everything to happen overnight. I’m a little bit more patient than that. On the subject of being patient, for you, for instance, how do you set up times to check in to recognize the progress you’ve made? If you haven’t gotten to the absolute goal, how can you keep yourself going and remind yourself that the patience was worth it?

It’s true. Once you’ve attained the goal, that’s great. That was worth it. I did it. I describe attaining long-term goals as almost being like entering a long dark tunnel. The problem with this long dark tunnel is that you don’t know how long it is. You can guess sometimes. Something really helpful is upfront to try to make as educated a guess as you can about it by researching what other people have done or certain milestones or things like that. We never know for sure. Is this tunnel 1 mile or 100 miles? Is it 1,000 miles? When you’re in the thick of it, it feels like it’s never going to end, which is why a lot of people quit. Understanding milestones becomes critical because otherwise, the great irony is it feels like the rational choice to quit.

Attaining long-term goals is like entering a long dark tunnel. Many people quit because the tunnel feels like it will never end. Share on X

I hear from so many people that I talk to and they’re like, “I tried it and it didn’t work.” They feel so good about themselves, “I tried it.” You dig a little deeper and come to understand the human mind craves certainty so badly that it often will try to forcibly create the conditions, even if it’s a negative outcome. It feels better to have that negative outcome than not to know. “I tried submitting my book proposal, and four people turned it down. It just wasn’t going to happen.” There are a lot of authors that did it 20 times, 100 times, or scrapped that proposal and started on another proposal. It depends on how badly you want it.

To answer your question, there is a concept that I talked about in The Long Game called Looking for the Raindrops. It is essentially identifying in advance and looking for small telltale signs that the ultimate success, in this case, the thunderstorm, is coming and they are very subtle. They often literally are a raindrop, which the average person might ignore or like, “It was probably an air conditioner.” You need to train yourself to look for them, whatever those signs are. If you’re trying to get a book deal, it could be something as small as, “I seem to have a trend here where the last few weeks I’ve had 15% more email subscribers to my list.” That might be five people. The average person would be like, “Whatever, it’s five people.” You need to look for those signs and those patterns because they actually could be telling you something useful.

This is a question I think about a lot and I don’t think I’ve ever asked anybody. You hear all the time people say, “Don’t give up before you’ve already gotten to the end.” How can you tell the difference between keeping going so you don’t give up too soon and going down the wrong path and that you’re wasting time, money, and energy on something that you’re never going to get to? How do you know when it’s a blind alley? How do you know when it’s time to pivot to use the popular term and see what you’ve learned and maybe you go someplace else?

You’re asking the right question, Elizabeth. This is a really important thing. Nobody wants to waste time on some stupid quixotic venture. Also, you don’t want to quit too soon if success is around the corner. How do you know? I will venture to say that there are two key elements. Where a lot of people go wrong is that they try to figure it out in midstream. They’re in the tunnel and they’re like, “What do I do?” The answer is, “You’re in a tunnel. You have no idea.” Anybody’s guessing. If you’re in the tunnel, you have no idea. You have no guidance.

Where people go wrong is that prior to entering the tunnel, you need to set up a list of criteria. One piece is about proper scoping. It’s about doing enough research, and a lot of people skip this step. They just jump right into it. It’s about understanding the thing you’re trying to do. Has anybody in the world ever done it? The answer is probably, in most cases, unless we’re talking about intergalactic exploration, most things have been done. People have written bestselling books, people have gotten X amount of money to speak on a keynote stage, or people have gotten a big promotion to SVP or whatever they’re seeking.

The question is, can you research or identify at least one, but hopefully, multiple people who have done it, either because you know them and can ask them, or, if you don’t, using the internet and publicly available sources? It is easier than ever, thankfully. Reverse engineering and trying to understand how long did it take them between the start and the finish and what did they do? What were the steps? Work it back to try to get as much clarity as possible.

Your path is probably not going to be identical to theirs, but it is useful. If it takes most people ten years to do something, it’s probably not going to take you two years to do it. I’m not saying it could never happen, but it’s probably going to be 9 or 11, but you know the ballpark to expect. That is useful. Knowing that enables you to do part two. Part two is about asking yourself essentially what you can tolerate. If it takes 10 years or 12 years, is it worth it to you? That’s a really important question. If the answer is yes, great. Also, it’s useful for you to ask how much you can afford to lose. That’s a literal thing as well as a metaphor.

If you’re starting a business, for instance, you may say, “I can afford to lose up to $100,000 getting this started, but I can’t lose more than that. If we get to $100,000 and we’re still not seeing X amount of traction or X amount of profit or whatever the thing is, then I’m going to pull the plug.” You create these certain if-then conditions. You could also say in terms of time, effort, or whatever it is. It’s important to set the criteria upfront so that you’re not trapped. When you’re in the middle of the cycle, it’s a terrible time to make decisions. Your emotions are very clouded at that point. I’m curious for you, Elizabeth, how do you think about these things? What does strategic patience or the arc of achieving long-term things look like in your life?

SWGR Dorie Clark | Long-Term Thinker

Long-Term Thinker: It’s really important to set the criteria upfront so that you’re not trapped. The middle of the cycle is a terrible time to make decisions.


I know that I will break promises to myself. My whole life I’ll put something up on the wall and say, “I’m going to do that,” and it doesn’t happen or I stop seeing it. I have to do it with an accountability partner. I have a course called the Visible and Valued course for executive women. It’s a leadership certification. The key part is having somebody else, a partner, a cohort who will hold you accountable because I wish I would be accountable to myself, but I’m not. “I’m good at a lot of things.” That’s not one of them. That’s one question. The other thing is I’ve been through the point of saying, “This was the thing I built. It was my baby, it was my identity, and it is no longer sustainable. It’s time to leave.” It’s a huge emotional thing.

I hired somebody to work with me to say, “Can we pivot this company so that we can get something else that will work?” After about six months, I said, “I think it’s time to close.” The coach or the consultant who was a friend and who had helped me build the company said, “I knew that was going to be the answer, but I knew you were going to need those six months to be ready.” That was a gift she gave me. You know you could decide to stop.

My whole identity was tied up in my company. We’ve all seen people like that. Someone like you and I are our product. What I tell my clients now is, “Your thought leadership is wonderful. Make sure things change and you change.” Don’t discount the emotional part of making that decision because not being willing to let go of the identity I had built took me a year and a half. I’m relationship-oriented. I will be accountable to another person. I had this brilliant consultant and I just paid her to help me along the path, and that was worth every penny.

That’s such a great point because you have to know yourself and you have to know what works for you. Everybody’s different. For folks who are not familiar with it, Gretchen Rubin has a great book dealing with this called The Four Tendencies. You could call it a personality assessment, but it breaks down different types in terms of your ability to self-motivate or what enables you to get things done. One quadrant is the people who like, “I make a promise to myself and I keep it. No problem.” These are the people who are extremely annoying to everybody else.

There’s another category that is like you, “What if I make a promise to somebody else? I’ll do it. If I make a promise to myself, eh?” The answer there is you have to learn it over time, but it is relatively straightforward, which is to hire a personal trainer if you want to go to the gym or get an accountability buddy if you want to accomplish the business thing that you say that you need to do. It’s a way to force yourself to do the behavior that you know you need to do. Learning the tricks to outsmart our own personalities is useful.

Get an accountability buddy if you want to accomplish the business you say that you need to do. It's a way to force yourself to do the behavior you need to do. Share on X

Dorie, I’ve got four other questions I want to ask you. I want to respect your time. Buy the book, The Long Game. If someone is reading this and is motivated now this minute, where’s someplace you can start?

I’m going to give you two answers, Elizabeth. One, above and beyond folks who want to dive directly into The Long Game, I do have a free strategic thinking self-assessment that people can try on and might be helpful. They can get it for free at I will also say that going back to a point that we made early on in the conversation about white space and how to create more of it, I have four questions, a checklist that I like to go through personally when a new possibility, a new invitation, or a new engagement is presented to me. So often when something comes in, we stress about it, “Should I do it or not? I don’t know.” It becomes hard. If you can go through a systematic checklist, it can become faster and easier, the decision-making process around it.

The four questions that I like to ask when evaluating something, and I hope it might be helpful to other people. One is what is the total commitment being requested? What I mean specifically is we often make little mental shortcuts. “They want to have coffee with me. That’s 30 minutes.” No, somebody wants to have coffee with you. If it’s in person, first of all, it’s almost never 30 minutes. Let’s call it 45 at a minimum, maybe it’s an hour. Depending on where it’s going to be, maybe it takes you 40 minutes to get there. You’ve got to park and do all this stuff, and you realize, “This coffee will be quick.” It’s like a three-hour invitation. Do you want to spend half your day with this person? That’s worth asking.

Number two, what is the physical and emotional cost? Your criteria should be higher. Let’s say somebody wants to meet with you, Elizabeth. They want to meet with you on a day, which is the morning after you’ve just flown from Austria to Oregon. It should be a higher bar because you are going to be in bad shape probably. If you’re like most people, you’re going to be jet lag and miserable. If somebody wants to meet with you on that day, it needs to be pretty damn good.

Number three, what is the opportunity cost? People often forget this really basic question. It’s not about whether should you do it or not, it’s what else could you be doing with that time and if that is more valuable. The final piece is how will you feel about it in a year. A year from now, would you feel regret? Would you be like, “I really missed that opportunity?” Is it equally likely that you’re like, “I don’t even remember it?” Time can be a useful filter as well.

I love that last one. How will I feel about it a year from now, was it worth it? That’s great. That gives me all interrelationships, which was a subject I wanted to dive into and I never got there. Thank you. Dorie Clark, I’m so glad I finally got you. You’ve been on my wishlist for quite some time, so this is yay. I’m thrilled this worked out. May the rest of your time be wonderful. It’s early for you as well.

If you enjoyed this, please subscribe to the show and check us out on YouTube. Most importantly, leave a review on Apple Podcasts. That’s the one that counts. Tell your friends so many more people can hear this wonderful conversation with the amazing Dorie Clark. Thank you, Dorie. I’ll see you on the next one.


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About Dorie Clark

SWGR Dorie Clark | Long-Term ThinkerDorie Clark helps individuals and companies get their best ideas heard in a crowded, noisy world. She has been named one of the Top 50 business thinkers in the world by Thinkers50. She was honored as the #1 Communication Coach by the Marshall Goldsmith Leading Global Coaches Awards and one of the Top 5 Communication Professionals in the World by Global Gurus. She is a keynote speaker and teaches for Columbia Business School.
She is the Wall Street Journal bestselling author of 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.” She is a frequent contributor to the Harvard Business Review, and consults and speaks for clients such as Google, Yale University, and the World Bank. Forbes has declared that “her insights connect marketing, social media, communications, learning technologies, and personal discovery to give us a blueprint for success in the future economy.”

She is a graduate of Harvard Divinity School, a producer of a multiple Grammy-winning jazz album, and a Broadway investor. You can download her free Long Game Strategic Thinking Self-Assessment at