S4-EP1: Author Dorie Clark on Playing “The Long Game” to Get the Most Out of Life and Work

Oct 8, 2021


Debbie Weil talks to author and renowned business thinker Dorie Clark about applying long-term thinking to optimizing life and work after 60 – and why that matters.



Welcome back to Season 4 of the [B]OLDER podcast!

Today, Debbie Weil brings author, entrepreneur, and renowned business thinker Dorie Clark on the show, a perfect way to kick off Season 4.

Dorie is a 42-year-old business consultant whose life and work resonate strongly with Debbie.  She was a Philosophy major in college, graduated from Harvard Divinity school, worked as a journalist (something Debbie did for two decades) and was a presidential campaign spokesperson. 

Then, in a very intentional way, over a period of eleven years, she became a highly respected business author and speaker. Dorie is on the Thinkers50 list, the top 50 business thinkers in the world, and has just written her fourth book: THE LONG GAME: HOW TO BE A LONG-TERM THINKER IN A SHORT-TERM WORLD. She now teaches at Duke and Columbia’s business schools and consults with clients like Google and Microsoft and the World Bank.

But – and this is the part that applies to midlife reinvention – it took repeated rejection along the way for her to get to where she is today. She tells us those stories and more in THE LONG GAME. Her new book is aimed at a mid-career business audience but Debbie was struck over and over, as she read it, how Dorie’s approach applies to life and work after 60 or 65 or 70.

Dorie is also a documentary filmmaker, a Broadway investor, and a trained musical theatre lyricist and composer.

She writes in THE LONG GAME about creating white space in your calendar, meaning give yourself unstructured time to think “differently” and to explore and experiment. She also talks about optimizing for meaning (instead of for money, usually the default) and optimizing for interesting: follow your curiosity even if you don’t know exactly where that will take you. 

Wow, she could be writing a script for a grown-up gap year and for optimizing a post-career, non-retired chapter of life – the focus of this podcast.

Needless to say, Dorie is also a huge proponent of trying new things even if they are way outside your current area of expertise.

This is a great conversation full of useful nuggets about how to think long-term and why that matters.


Mentioned in this episode or useful:



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Thanks to our media partners

Encore.org, our newest media partner, is an ideas and innovation hub tapping the talent of those 50+ as a force for good. Founder and CEO Marc Freedman is an award-winning social entrepreneur and author, most recently, of How to Live Forever: The Enduring Power of Connecting the Generations. Looking for a great gap-year transition program? Check out Encore Fellowships, which match skilled, seasoned professionals with social-sector organizations in high-impact, paid assignments.


Modern Elder Academy is a program dedicated to navigating mid-life transitions. MEA, based in Baja California, Mexico, provides the place and the tools to start reframing your lifetime of experience. Grow whole, not old. Founder Chip Conley is a New York Times bestselling author, award-winning hospitality entrepreneur and a rock star of the mid-life transition movement. His newest book is Wisdom @ Work: the Making of a Modern Elder.


Next For Me is an important new resource for the 50+ crowd focused on rewriting life. Taking a gap year or timeout may be the best way to figure out "what's next" when you're in this stage of life. Founder Jeff Tidwell explains, Next For Me "connects and inspires our generation to evolve our post-50 lives through new work, a new purpose, or a new social contribution."