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What I Learned About Strategy from Fantasy Football

AJ Oberlender • January 7, 2025

Winning Insights for Both the Field and the Boardroom

A football strategy is drawn on a blackboard with chalk

I’ll admit it: I take fantasy football way too seriously. It’s not just a game to me; it’s an obsession. But here’s the thing—fantasy football is more than just a Sunday pastime. It’s an unexpected masterclass in strategy, decision-making, and leadership. As someone who splits time between parenting my two little daughters, and strategizing for businesses, I’ve come to see that the lessons I’ve learned managing my fantasy league roster apply just as much to business as they do to crushing my cousin's hopes of making the playoffs.


Let me break it down. Here’s how fantasy football taught me a thing or two about strategy—and how you can use those lessons whether you’re managing a team on the field or in the boardroom.


1. Play the Long Game


In fantasy football, the goal isn’t to win Week 1—it’s to win the whole season. Sometimes, that means making short-term sacrifices, like benching a star player who’s nursing an injury or picking up a player on waivers with potential for breakout weeks down the line.


Business is no different. Too many leaders chase quarterly numbers at the expense of long-term growth. It’s tempting to go for the quick win, but real strategy means thinking about sustainability. Whether you’re investing in branding or developing a new product, always ask yourself: Will this decision help me win the championship—or just this week?


2. Know Your Stats—But Trust Your Gut


Fantasy football managers live and die by the numbers. Target shares, yards per carry, red-zone opportunities—you name it. But stats only tell part of the story. You also have to factor in intangibles: Is the player in a slump? Are they motivated to prove themselves?


In business, data is invaluable, but it’s not the whole picture. As a branding consultant, I’ve seen companies overanalyze and miss opportunities because they were waiting for the “perfect” data set. Trust your instincts, especially when it comes to things like company culture or customer relationships—those aren’t always quantifiable, but they’re crucial to success.


3. Be Ruthless When Necessary


One of the hardest parts of fantasy football is cutting a player you were so sure would be a star. Maybe you drafted them high, or maybe you just like them. But if they aren’t delivering, you’ve got to make the tough call.


The same goes for leadership. Sometimes, you have to let go of an underperforming product line, pivot away from a beloved but failing strategy, or (gulp) make hard personnel decisions. Sentimentality can cost you the championship—whether it’s in football or business.


4. Adapt, Adapt, Adapt


Remember when everyone thought the Dolphins’ Tua Tagovailoa was just a middling quarterback, and now he’s leading one of the most explosive offenses in the league? (Okay, maybe that’s just my Miami pride talking.) The lesson? Things change quickly, and you’ve got to stay flexible.


In business, your “star player” might not be delivering anymore, or the market might shift. When I started our websites offering at DoorLoop, I had to pivot my approach several times to meet client needs and stay competitive. Success belongs to those who can adapt.


5. Collaboration Wins Championships


Even in fantasy football, you can’t do it all alone. Whether you’re reading expert rankings or trading players with other managers, collaboration is key. No one wins in a vacuum.


As Director of Custom Websites at DoorLoop, I’ve seen firsthand how collaboration between teams—design, development, marketing—creates a better product. The best leaders know when to lean on others’ expertise. Remember: even Michael Jordan had Scottie Pippen.


The Takeaway: Strategy Is Universal


Whether you’re chasing a championship ring or a corner office, strategy is about making smart decisions, staying adaptable, and playing to win—not just for today, but for the long haul. And honestly? It’s about having fun along the way. Because what’s the point of all this if you can’t enjoy it?


So next time you’re sweating over a fourth-quarter trade or a Q4 business decision, think about what your fantasy team would do. And if you need advice, just let me know—I’m happy to share my roster wisdom.

And hey, if you’ve got a league of your own, feel free to invite me. Just know I play to win.

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