The queen of reinvention espouses “tiny habits,” finding a wingman, and constant experimentation

What better way to prove you’re a master at reinvention than to succeed as book author, keynote speaker, branding consultant, presidential campaign spokesperson, and adjunct professor of business administration at Duke University’s Fuqua School of Business?

Celebrated business thinker Dorie Clark has written books about how to manifest change; Reinventing You, Stand Out, and Entrepreneurial You all stress the psychological understanding of oneself to become a better person. Her new book, The Long Game, blends insights into our personal and professional lives to help people define and achieve success on their own terms. We spoke to her about keeping focus, identifying next steps, and little modifications in habits that change careers.

How would you describe yourself in 30 seconds or less?

I teach at Duke University Fuqua School of Business and Columbia Business School. My work centers around how to help good people and good organizations get their message heard in a noisy and crowded environment. 

How do you keep good habits consistent and not slip up?

It’s hard. You can’t just do it on willpower alone. If you are engaging in a habit where every day you are saying, “Ugh, I have to do this thing,” you will slip up. There’s too much cognitive work forcing it to happen. I try to pick things that I know are enjoyable. Example: I knew for a long time that I would have to take morning supplements, but I wouldn’t do it for a long time because swallowing big disgusting pills is not my cup of tea. I’m a fan of the saying, “the perfect is the enemy of the good,” so I decided to take these ridiculous gummy vitamins. Sure, they might not be the optimal vitamins, but at least I am compelled to take them every day, compared to those big vitamins that I would never take because I think they are disgusting and hard to swallow.

Are there formal strategies that take this approach?

One of the strategies—I actually talk about it in The Long Game—is propounded by the Stanford researcher BJ Fogg. He talks about the importance of tiny habits, and especially two pieces: one is about hitching habits to an existing behavior, and the other is making sure it is the tiniest possible habit. His classic example is when he wanted to get better at flossing. The thought of flossing all his teeth felt overwhelming and boring, so he started with just one tooth. Of course, the hard part is just starting a task, so when he flossed one tooth he realized it’s not that hard to floss the rest. So finding a tiny anchor habit and attaching it to a preexisting routine. Brushing your teeth is a perfect time to attach certain behaviors because that’s a habit that is so ingrained, since we’ve been doing it since we were little kids. 

How do you position these exercises so they don’t feel like random chores? 

We have to keep our north star in mind. At the moment it might not be enjoyable to craft this habit. The reason we have to be conscious about crafting this habit is because it feels like an exercise. This is very similar to sales processes. They always tell salespeople to sell the benefits and not the features. I don’t care about the aspects of a fridge, just explain how it will be easier to invite all my friends over for margaritas. Similarly, we need to constantly remind ourselves that whatever we are doing in the moment is a buildup to the long-term goal we have in mind.

Speaking of long-term goals, was it hard to write The Long Game? 

Well, the good thing about it was I had more time with the whole #pandemic. I wasn’t traveling as much. For every book that I’ve written, I’ve usually interviewed about 50 people to just get a lot of data and a lot of experiences. Then over the period of two to three months, I write the first draft of it, shaping the interviews and really creating a narrative out of them. I send in the first draft to my editor, and we go back and forth on revisions. 

Who did you decide to interview? 

A lot of the people that I profiled were members of an online course/community that I run called The Recognized Expert Community — because that was in many ways the inspiration to write the book. This is a book that provides a framework for good, smart people who get discouraged too soon. So often in my coaching work and in this online community, I see people with great ideas wanting to be heard, but it’s a slow process, slower than we want. People usually drop off too soon. You have to keep persevering. I’ve learned that it usually takes two to three years of just effort before you get any meaningful type of feedback in return. 

What does this book add to the conversation? 

What I try to do is provide specific frameworks that can be used. It’s not about pure encouragement, but a palate of real work techniques. There are plenty of books out there about business strategy and plenty of career guides, but I wanted to marry business strategy to your personal life. It’s applying the high levels of corporate strategy to your own career arc so you can get closer to the life and career you want to have. 

Where did you learn about corporate strategy? 

I’ve been fortunate to have 15 plus years working and consulting blue-chip corporations. Also during my time teaching at Duke and Columbia I’ve gained a lot of insight. At this moment, I’m actually teaching a class for LinkedIn learning on strategic thinking, it was one of the most popular courses of the year in 2020. 

For those going back to the office, how do we keep focused on the long term?

There’s been some great research being done by Teresa Amabile at Harvard Business school. She wrote a book called The Progress Principle. She discovered that when our work is highly motivating the biggest thing is that our work is filled with meaningful progress, even a tiny amount of progress. That’s the key distinction. For many people returning to the office, we can still often create control and autonomy in our lives. For example, during COVID maybe you wanted a career change or a new hobby. But if you use your commute time to learn about this new passion, maybe by listening to a podcast or reading a book, you will feel empowered, because even if it’s just an hour a day, you are still advancing your project. 

How about those that have so much free time during COVID that everything seems overwhelming? 

When we are thinking about a long-term goal, we don’t need to know when the goal should be met. What we do need to know is the next step. I’m a really big fan of imposing structure on yourself. Sign up for a class that can “force you” into a regiment. For example, in 2017 I made a ten-year project to write a musical that would be on Broadway. Now, let me tell you I had no idea how to do this. I had no previous experience. But after research, I found out that BMI, the music publisher, has a musical theater course. My next goal was to get into that course. It was intense and hyper-focused. My next steps focused on how to apply and get into this program. Having that structure was like going on an amusement park ride, because once you are strapped in you are forced to continue. 

How do we prepare for failure when talking about long-term goals?

In the Long Game, I make the point that it’s not really a failure. It’s more like an experiment, especially in the early stages of your long-term goal. You do a lot of things and try a lot of different things out. Place small bets to see what works, and then when you know what works, you double down on those bets. You never want to be in a situation where you are creating an enormous risk where you couldn’t survive the loss. I would never tell someone to mortgage their house before you have a reasonable degree of certainty that things are going to go really well. Instead, write a blog post and see how that goes. Offer something for free, because if they don’t want something for free they won’t want to pay for it! At each checkpoint, you can get a better sense for the market and what the market will bear. By the time you are putting down substantial resources, it really doesn’t look like a risk. Any failure along the way is negligible because it’s not failure, it’s a test. 

What is your definition of success? 

It’s a difficult question because I want people to succeed on their own terms. I would define it roughly as accomplishing the highest and best use for yourself. What do you want to be? Okay fantastic, if your life becomes that, that is success. For some people that means, “I want happy and healthy kids,” for others that means, “I want to be a CEO.” Great! I don’t want to prescribe what it should be, but I do want to create a world where people can enact their vision. 

What are the essential elements to success? 

I tie them into how I structure The Long Game

We all struggle with the first one: there feels like there is very little time for long-term thinking. We are always pushed to the max, running around going to meetings. We don’t need gobs of time for strategic thinking, but we do need some time. To get there, we need to be willing to make parameters so we have room to breathe. 

Number two: understanding what we are focusing on. This means separating our voices from those around us who are telling us what we “should” be doing. It’s really about understanding what success does look like for us. 

Finally—what I call keeping the faith—there are always going to be setbacks; there are always going to be detours. We can’t let them crush us. If we did we would be done after the first bump in the road. 

How do people sell themselves, not just to others but to themselves? 

It’s always a challenge I see far too often. One strategy that I talk about in my first book Reinventing You is about the importance of finding a wingman. For many people, it might feel super embarrassing promoting themselves, but most people feel great promoting a friend of theirs. If you can get a buddy and make a pact with them—of course, it needs to be somebody you respect. This is somebody that can talk you up at a cocktail party or a meeting and you can do the same for them. You won’t be stressed out about how to impress others with your success, because you’ll have a friend who will do that for you. 

Do you have a morning routine to keep you focused?

To be honest, I’m a little too rebellious to have a strict morning routine, but the best part of my mornings is this COVID gift to myself. I bought myself a way too expensive espresso machine. It took me–I’m not joking–about five hours of reading manuals to learn how to use the thing. But now I make really nice espressos and cappuccinos. On Instagram I was trying to perfect latte art, and now I can do a pretty good heart. 

What’s next for you? 

I’m planning on promoting this book [The Long Game] for the next five years. For my three previous books, I feel like I didn’t promote them long enough. I worked hard and I promoted them hard, but I feel like my attention was always focused on the next thing, on the next book I was going to write. I was cycling through that too quickly. I realized that if you want something to have an impact, you need staying power. What’s next for me is that I’ll be promoting this book for a very long time. 

 You can download Dorie Clark’s free Long Game strategic thinking self-assessment at dorieclark.com/thelonggame.

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