How to Play "The Long Game" (according to Duke & Columbia business professor Dorie Clark)

Plus, my latest book recommendation for you...

What do I know about playing “the long game” as a 25 year old?

Even if I’m soon-to-turn 26 in October, the reality is I’ve now been an entrepreneur for over a decade in a world where institutions are crumbling, new industries are popping up left and right, and relationships are easier than ever to develop and maintain via social media. Relationships are also easier than ever to f**k up.

Someone I’ve known since my late teens, who has always played the “game” the right way is Dorie Clark, business professor at Duke and Columbia, Harvard Business Review contributor, and author of The Long Game: How to Be a Long-Term Thinker in a Short-Term World among other popular business books.

The pandemic reminded me of how important it is to play the long game with my relationships at work and home.

I acquired Network Under 40 earlier this year from an entrepreneur I met when first moving to Atlanta more than four years ago, and had we not developed rapport, stayed in touch, and treated one another with respect during the negotiation efforts, we would not have pulled off a great deal and transitioned the business successfully while keeping the main team intact.

When starting Offsite, I raised our pre-seed round primarily from long-time friends who (almost entirely) placed their faith in me to shepherd their money well and generate returns for them over the coming years/decades while creating a company that would create a positive ripple effect in the world, bringing more remote work flexibility to high-growth startups and some of the most promising companies in tech who are planning their team retreats with our help.

Side note - if you are planning a team retreat in Q4 or early 2022 for 10+ people at your company, please reply to this email to learn more about Offsite. I’m happy to give you 40% off any Offsites you book with us between now and September 30th.

As for Meeting of the Minds, the only way we remained solvent during the pandemic was because my team stayed with me during our lowest months, our clients continued attending our events virtually without cancelling annual memberships, and our partners continued promoting us to business owners who were able to benefit from our brain trust during the toughest moments of their business life cycles.

It’s now more important than ever to remind ourselves of the benefits of long-term thinking.

While others might lack follow-up, lose their edge, or forget about some of their most valued relationships because we aren’t face-to-face, in-person as much as we were pre-pandemic with teammates, clients, and fellow industry folk, we are going to provide value to others, build relationships with intent, and keep in touch with our networks.

Dorie wrote a piece for the Harvard Business Review magazine this month based on the book, and if you find value in that, you can pick up a copy of The Long Game here.

Some of the ideas Dorie shares in the article and book are as follows:

Research the Target and Terrain

“Reach out to colleagues who have accomplished what you’d like to and push them to identify the markers along their paths. (‘How long did it take you to make your first six-figure sale?’ you might ask. ‘How many prospect meetings had you held? How many phone calls did you have to make to land those meetings?’) In most cases, unless these people view you as a direct competitor, they won’t object to sharing that information. They may be surprised by the level of detail in your questions and have to refresh their memories, but that’s typical because no one else asks about these things—which can give you a competitive advantage.

Mapping the terrain enables you to create checkpoints at which you can reflect on your progress or lack thereof. Say you’re a start-up founder and you know from your research that successful companies in your industry typically hit $2 million in revenue by the end of year two, but you’re 18 months in and your projections are barely half that. That’s a sign that you need to shift your approach quickly or perhaps get out of the business.

After all, the goal isn’t to charge forward with all ambitions. Instead, it’s to nurture the right ones, jettison the wrong ones, and avoid giving up too soon on viable initiatives that are simply taking a while to gain traction.”

Recognize That Progress Can Be Barely Perceptible

“There’s a long phase in the development of technologies that improve at an exponential rate (like artificial intelligence, 3D printing, and self-driving cars) in which advances are so minimal that even though they’re regularly doubling, it seems as if nothing is happening. Authors Peter Diamandis and Steven Kotler call this period the “deception phase,” because it prompts many to prematurely dismiss the technology. But once the advances hit a certain threshold, the improvement curve turns sharply up, and success is stunning and swift. (Think of the transition to digital cameras.) The same principle is true in our careers…

That said, in the absence of clear movement toward your goal or even the milestones you’ve set out, you should be able to find small, motivating wins. I call these “raindrops” of progress. They start out intermittent and barely perceptible—praise from a boss or a client, LinkedIn requests from strangers who have started to hear about your work, an invitation to lead a committee, and the like—and on their own, they’re not worth popping open the champagne. But in the aggregate, they’re leading indicators of forward momentum, and they can keep you motivated when progress is slow.”

Leverage Your Relationships in the Right Way

“Surround yourself with trusted advisers and have them help you evaluate your progress and determine if it’s time to pivot. When you’re wrapped up in pursuing a certain goal, it’s not uncommon to lose perspective and either cling to a failing approach or despair too quickly about a viable one that’s percolating slowly. That’s why a reality check from a trusted colleague is so necessary.”

Stop Moving Your Goalposts

“There’s a term in environmental science—shifting baseline syndrome—which refers to the tendency to change the reference point or norms we measure something against…Because we’re often so fixated on large-scale goals (the promotion, the invitation to be a keynote speaker, the industry award), we write off some achievements as no big deal, forgetting that five years—maybe even a year—before they would have felt like huge accomplishments. When we keep moving the goalposts, we distort and erase the progress we’ve already made, which obviously feels discouraging and makes us far more susceptible to quitting. But if we can instead notice and honor where we started and how far we’ve come, it inspires us to keep moving forward.”

Aim for “Directionally Correct”

“It’s rare that any of us will attain everything in the exact form we predicted. Circumstances change over time (your spouse receives a compelling overseas job offer), and some possibilities are blocked to you through no fault of your own (your company was acquired and your role got eliminated). Instead of dogmatically pursuing one goal, consider striving to make directional progress.”

I hope you’ll enjoy The Long Game as much as I did, and I’d love to hear from you about your favorite ways to play the long game in business with your network.


Jared Kleinert is the founder of Meeting of the Minds (, as well as a TED speaker, 2x award-winning author, and USA Today's "Most Connected Millennial".

Meeting of the Minds curates "super-connectors" and subject matter experts as invite-only attendees to 3 day summits in places like Napa Valley, Bermuda, and elsewhere, as well as “deep dives” such as this Marketing and Biz Dev strategy & implementation workshop. Members of the MOTM network include CEOs of 7, 8, and 9-figure businesses, creators of globally-recognized brands and social movements, New York Times bestselling authors, founders of pre-IPO tech unicorns, c-suite execs from Fortune 500 companies, and others.

Jared's career began at 15 years old when he started his first company, and took off at 16 while working as the first intern, and then one of the first 10 employees, for an enterprise SaaS company called 15Five, which today has raised over $40M and has almost 2000 forward-thinking companies as monthly recurring clients.

Later, Jared would become a delegate to President Obama's 2013 Global Entrepreneurship Summit in Malaysia, write multiple books including the "#1 Entrepreneurship Book of 2015", and speak at TED@IBM the day before he turned 20. 

As a highly-sought after keynote speaker and consultant, Jared’s clients range from organizations like Facebook, Samsung, Bacardi, Estee Lauder, IBM, Cornell, Berkeley, AdAge, and the National Speakers Association. His insights on entrepreneurship, networking, marketing, and business development have been featured in Forbes, TIME, Harvard Business Review, Fortune, NPR, Entrepreneur, Mashable, Fox Business and more.