Entrepreneurship

Winning Strategies for Playing the Long Game in Business

Dan Nicholson

Let’s face it—business is a marathon, not a sprint. It’s so tempting to chase those quick wins, but the real game is about thinking long-term, building something that lasts. In a recent episode of the UnConventional Wealth Podcast, I sat down with Jedediah Collins, a guy who’s gone from the NFL to teaching people how to win with their money. We got into the nuts and bolts of what it really takes to succeed in the long run. If you’re serious about building a business that’s not just here today, gone tomorrow, you’re gonna want to stick around for this.

The Power of Strategic Patience: Lessons from the NFL

One big takeaway from my chat with Collins is this—strategic patience isn’t just a buzzword; it’s a game-changer. Collins, who made the leap from a college basketball player to an NFL fullback, knows a thing or two about playing the long game. He didn’t end up where he is by chasing quick wins. “I wasn’t going to be a shooting guard. I was going to be a power forward rebounder,” he said, which is a fancy way of saying he embraced his role, focused on the big picture, and didn’t worry about being the star every time.

This is exactly what we need to do in business. I always say, first, we optimize, then we maximize. In other words, get your processes and strategies dialed in before you even think about scaling. Why? Because if you don’t, you’re setting yourself up for a world of hurt—think premature expansion, unsustainable growth, and a whole lot of stress.

Building Sustainable Habits: The Secret to Long-Term Success

Let’s talk about habits, because they’re not just for athletes—they’re for anyone serious about succeeding over the long haul. 

Building sustainable habits is a cornerstone of long-term success in any field, and it’s a principle that has been reinforced by numerous business experts. Sustainable success isn’t about dramatic changes; it’s about small, consistent actions that compound over time. This is what makes habits so powerful—they transform daily routines into lasting success by creating a foundation that supports ongoing growth​. For example, in the business world, setting incremental goals and sticking to them is crucial. While big goals can be motivating, it’s the smaller, consistent achievements that truly drive long-term success. This means regularly revisiting and adjusting your habits to align with your overarching goals​.

The key is consistency. Whether it’s managing your finances, keeping up with customer engagement, or continually refining your products, the small, everyday actions you take—those that are aligned with your long-term objectives—will ultimately lead to the biggest wins. This approach is backed by the idea that sustainable habits help you navigate challenges and maintain momentum, even when external conditions change.

Moreover, creating an environment that supports these habits is essential. Your surroundings play a crucial role in habit formation. This could involve setting up physical spaces that make it easier to engage in positive behaviors or surrounding yourself with a supportive network that reinforces your goals​.

To sum it up, sustainable habits aren’t just about doing the right thing once—they’re about creating a system that makes doing the right thing easier every day. Whether you’re running a business, managing a team, or just trying to improve your personal life, the habits you build today will define your success tomorrow.

The Chess vs. Checkers Mentality: Planning Ahead

Collins also dropped some wisdom on the difference between playing checkers and playing chess. Here’s the deal—checkers is all about reacting to what’s right in front of you. Chess, on the other hand, is about thinking several moves ahead, planning your strategy, and anticipating what’s coming next.

In business, the winners are playing chess. They’re not just reacting to the day-to-day; they’re thinking long-term, just like companies like Amazon, which is all about playing the long game. Gary Vaynerchuk preaches this too—give up some short-term gains if it means winning big down the road. To paraphrase, he said, your lack of patience will be your own worst enemy. That’s the mindset you need if you want your business to last.

Putting It All Together: Actionable Takeaways for Playing the Long Game

So, how do you actually start playing the long game in your business? It’s all about breaking things down into actionable steps that you can implement every day. Here’s a roadmap to get you on the right track:

Define Your Role and Success: Before you do anything else, get clear on what success looks like for you. What’s your role in the big picture? Maybe you’re the visionary, the strategist, or the executor. Whatever it is, knowing this helps you prioritize and align your efforts. Once you’ve got this figured out, everything else starts to fall into place.

Build Consistent Routines: Consistency is key—there’s no way around it. Take a page from Drew Brees’ playbook and establish routines that align with your goals. Whether it’s a daily check-in with your team, a regular review of your financials, or a morning ritual that sets the tone for your day, sticking to these routines will keep you grounded and focused.

Focus on Incremental Gains: Don’t stress about making massive strides overnight. The real progress happens with small, consistent improvements. Focus on the little wins—those tiny steps that, over time, add up to significant change. It’s not about quick wins; it’s about steady progress.

Think Like a Chess Player: Always have the long-term in mind. Think a few moves ahead and consider the impact of your decisions down the line. Whether it’s a strategic partnership, a new product launch, or an investment, make sure each step you take is moving you closer to your ultimate goal.

These are the building blocks for playing the long game. By defining your role, sticking to routines, focusing on incremental gains, and always thinking ahead, you’ll set your business up for sustainable success.

Conclusion

At the end of the day, playing the long game isn’t just a strategy—it’s a mindset shift. It’s about moving away from instant gratification and focusing on what really matters: long-term growth and sustainability. As Jed put it, “Success is a fleeting moment gone by, satisfaction in a moment. But if you don’t enjoy the hunt, if you don’t enjoy the process, the kill is never really going to satisfy you.” In other words, true success is about the journey, not just the destination.

Sources

Harvard Business Review

Forbes

Entrepreneur

Dan Nicholson is the author of “Rigging the Game: How to Achieve Financial Certainty, Navigate Risk and Make Money on Your Own Terms,” deemed a best-seller by USA Today and The Wall Street Journal. In addition to founding the award-winning accounting and financial consulting firm Nth Degree CPAs, Dan has created and run multiple small businesses, including Certainty U and the Certified Certainty Advisor program.

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