Ep. 97 - The Long Game: Principles to Help You Redefine Success in an Uncertain World - with Dorie Clark
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Dorie Clark has built quite a portfolio career since her early days as a journalist and presidential campaign spokeswoman.
Her journey to the pinnacle of success in the business world certainly wasn't a linear one, and day after day and year after year, she continues to build upon her incredible career mashup: a top 50 business thinker, branding expert, a professor at Duke and Columbia, a frequent contributor to Harvard Business Review, the host of a weekly live LinkedIn show from Newsweek called Better, and the author of three best-selling books.
And Dorie’s latest book — "The Long Game: How to Be a Long-Term Thinker in a Short-Term World" — releases the same day this episode goes live.
I had a chance to read it and I felt it really spoke to the moment that we're in right now.
Through years of work with clients and her own experiences, she's observed the many challenges that we often face in reaching our long-term goals. Too often we focus on the need to get those big wins fast, or feel the pressure to take a path that is seemingly easy or more guaranteed. And in the worst case, we give up too soon because we didn’t give these endeavors enough time.
In “The Long Game,” Dorie teaches us how to break that cycle and reframe how we look at progress and what we want to achieve so we can live happier and more fulfilled lives — one small shift at a time.
Dorie’s Unlikely Career Mashup
Dorie attended college at an early age and then went to divinity school, with the intention of being a professor. But then she got turned down by all of the doctoral programs that she applied to — and had to think fast.
After she didn’t find fit in her first few pivots toward journalism and politics, she started consulting, writing, coaching, teaching, and touring as a speaker. Her latest endeavor is creating a Broadway show, which she’s making steady progress towards by applying valuable principles and frameworks from the book.
It’s a remarkable portfolio career that reflects an incredible breadth and depth, and it enabled her to leverage those early “failures” toward consistent personal and professional momentum.
Yet she too had a linear view of career success early on. When she started as a journalist in fact, her definition of success was “move up the ladder and keep, keep getting better and better positions at bigger and bigger papers. And it really was just a march toward a fairly predictable future.”
Along the way, she’s come to understand and personally experience that none of our career paths are predictable. It’s really our ability to have these long-term plans while being nimble in their execution is key.
Why the Short-Term Mindset and Societal Perceptions of Success Hold Us Back
Dorie writes in her book, “The first step is understanding that the key to a meaningful life is to set our terms for it.” And that struck a chord with me.
Many of us have had definitions of what success should look like based on short-term thinking or societal norms/standards.
Take being busy. We live in a society where being busy and even working more hours implies a level of status and importance because we are “in demand”. Yet what we are doing and how we are doing it doesn’t necessarily equate to us making the right progress. In fact, it really may be clouding what our real priorities are.
In this case, it’s so critical that we do get clear on what OUR goals are. While we may have many, there are ones that have been instilled in us by our parents, or by society, that may not reflect what we want. Dorie shares that this is an opportune time for re-examination so we can get that clarity on our priorities and not succumb to others.
Another inhibitor to us making that shift from short-term thinking to long-term is the skepticism we face along our journey to achieve these goals we’ve set out for ourselves.
“We judge ourselves by what we feel capable of, but other people judge us by what we've actually done.” - Longfellow
Dorie shares that this can often lead to a real disconnect because while we know something will work, others may not until it’s actually happened. And in particular when friends and family who we expect to be our allies and supporters aren’t providing the positive reinforcement, it impacts our confidence and creates doubts in our minds. So much so that we can get discouraged and give up.
Staying the Course by Looking for Raindrops
We often struggle with knowing if we're doing the right thing, because in many instances we've been conditioned to think, is it right or wrong?
And in our society of instant gratification, we tend to look for the big win. That’s when we can often get off track.
One concept that Dorie shares to help us stay the course is to look for raindrops:
“When a rainstorm is starting, you almost don't even believe it. You're like, was that a raindrop? And similarly, we need to specifically train ourselves to look for those signs. You know, maybe it's not that you're keynoting at the fancy conference for 30 grand. Maybe it's you get invited to speak for free at your local chamber of commerce, which doesn't sound very sexy.
And if all you care about is the big win, you're going to poo poo it and say, oh, but that's not a big thing. But you know what? A year or two ago, no one would have even known you were a speaker. A year or two ago, no one would have thought, ‘oh, we definitely want her to speak, even if it's for free.’
So it's a sign of progress and we have to see those things and recognize them.”
Building the Foundation for Long-Term Thinking: Optimizing for Interesting and Thinking in Waves
We often are told to follow our passions but not all of us know what they may be. In those instances, we can often default to optimizing for money which doesn’t help us actualize what we really want.
So to help us build the right long term plans, Dorie offers another valuable concept: ‘optimize for interesting’.
“It doesn’t have to be your soulmate career, but it doesn't have to be a final answer. It's about, is it at least interesting and you do it and then you, you keep saying, well, is it still interesting?If it is you keep on moving forward, if not you pivot.”
What was refreshing in learning about that concept, is having the permission to not know, because most of us feel the pressure to have a defined path.
Even once we do have that roadmap defined we can oftentimes get frustrated however, when the results aren’t coming. Particularly when we are working so hard.
The reason Dorie reminds us is that when we dig further into why, it may be because you are doing the same thing over and over again.
“In order to be successful, sometimes we have to do different things — and you have to know when to do the different thing. And that's why I really advocate people internalize the framework of thinking in waves, because there are seasons for all kinds of different things.”
Shifting Your Mindset by Rethinking Failure
Throughout this journey to achieve our desired goals, we often run into negative thinking because of the challenges and setbacks we face. To help combat that common feeling Dorie recommends that we reframe these situations as experiments.
“If you were thinking about things as experiments, you know, is it actually a failure?
If you say, Hmm, I'm going to try a few things, let's see what happens. And then something doesn't happen. Like, okay, did you fail?
It's like if, if you and I went to a casino and you had $10 and you put a dollar down on a bunch of different squares. You lost 10 bucks. Who cares? At the end of the day, no one cares if you lose 10 bucks. The problem happens when you lose a million bucks. It's all about degree and scope.
And so if you place little bets, it literally doesn't matter if you fail because failure is too big of a term for whatever has happened. You place little bets and you get data from that. And then you just keep moving forward with that data.”
In the end, what’s important is to be directionally correct. And having the right network of people who understand what it takes to get there will be important to help you stay on your journey.
You’ll inevitably pivot along your journey to achieve your goals based on the input you get. But make sure you are clear with your priorities and take note of those raindrops along the way to guide you north towards achieving that long-term success.
Dorie’s definition of career success:
Your future isn’t predictable. The ability to have long-term plans and be nimble in your execution is really where it’s at.
Key Takeaways:
Being busy, working more hours ≠ success even though perceptually it may imply importance and status. In fact, it may actually obscure what our real long-term goals are.
Get clarity on what your true priorities are vs. what has been implanted in us by parents/society.
Anytime something is the thing that everyone wants, it's actually ripe for re-examination.
We can often get off track during our journey because we are looking for the big-win or those who we expect to support us may not be providing the positive reinforcement we need.
Look for raindrops - those signs that signal you are making progress. These little wins will ladder up into the ultimate goal you are seeking to reach and help you shift from that short-term thinking to a long-term one.
To help you determine where you may want to go long-term or what that path may be, think about “optimizing for interesting”.
It’s not about having THE answer but rather identifying what is interesting to you, trying it, seeing if there is a fit and continue doing it if there is. If not you pivot.
Shift your mindset to thinking in waves vs. a more rigid or fixed approach to how you are going to allocate your time and activities.
Rethink the way you look at failure to one that’s about small experiments that help you learn if you are directionally correct. The data you get back will help you refine or even pivot along your path.
A way to measure for being directionally correct is to build that valuable network of relationships around you.
Find those who are knowledgeable about the path you are trying to take as they will be more likely to understand what it takes to do what you want to do and keep you on track particularly in those moments where you are likely to not trust yourself.
Remember that achieving that long-term success takes time to see those signs of progress and momentum. For minor signs it may be between 2-3 years but major signs it takes about five.
It’s all about redefining how you look at success because it’s a culmination of all the small steps you make along the way to help you get there.
