Are you playing to keep up, or are you playing to win?
The short answer
Playing to win means making decisions aimed at the result you want, not at protecting what you already have. It isn't recklessness. It's preparation, belief in what you've built, and the courage to act when the opportunity is in front of you. Kentucky head coach Will Stein showed exactly that by going for two in overtime in back-to-back weeks, and winning both games.
I love college football. I'm not a big fan of NIL money and what it's doing to the sport, but that's a conversation for another day.
Lane Kiffin vs. Kentucky
Last Saturday, even with Georgia and Alabama battling it out in a close game, I found myself watching LSU and Kentucky. Or, as I like to call it, Lane Kiffin vs. Kentucky.
Kiffin has a way of taking all the oxygen out of the room in college football. He's polarizing, and there are plenty of people who aren't fans. Just ask someone from Ole Miss.
I'll admit, part of me was watching because I wanted Kentucky to win. As an Aggie, I already knew Kentucky was no joke. After all, they had come into Kyle Field and beaten Texas A&M in front of more than 108,000 fans.
The LSU game was a battle. Back and forth, neither team willing to give in. Eventually, it went to overtime.
Kick the extra point or go for two?
LSU got the ball, scored a touchdown on the first play, and kicked the extra point. Kentucky answered with a touchdown of its own.
Now, here's where it got interesting. Kentucky head coach Will Stein had a decision to make.
Overtime. Down by one. One decision.
Kick the extra point
Tie the game. Head to another overtime. Live to fight another series. Nobody questions the call.
Go for two
One play. Trust your players and your preparation. Win it right there.
Stein's callMost coaches probably take the safe route. Kick the extra point, extend the game, and live to fight another series.
Not Will Stein. He went for two. And Kentucky won.
Two bold decisions, two wins
Here's what makes that decision even more interesting. Just a week earlier, on October 3, Stein made the same call at South Carolina. Kentucky had fought back from a 17-point hole to force overtime, scored a touchdown, and instead of kicking to extend the game, Stein went for two. Kentucky won 35-34.
Two big moments. Two bold decisions. Two victories.
And it wasn't a gut-feel gamble. Stein has said publicly that his team had that play installed for months and that they hold two-point competitions during spring practice to build their options for exactly that moment. The courage showed up on Saturday. The preparation started in spring.
Stein wasn't coaching just to stay in the game. He was coaching to win it. He believed in his players. He trusted their preparation. And when the opportunity presented itself, he didn't hesitate to take the risk.
What does it mean to play to win in business?
There's a business lesson in that. How many times do we make decisions simply to protect what we already have?
We play it safe. We avoid uncomfortable conversations. We hesitate to pursue bigger opportunities because there's a chance we might fail. We become so focused on not losing that we forget what it looks like to actually play to win.
Now, playing to win doesn't mean being reckless. It comes down to three things:
- Being prepared. Stein's two-point play worked because his team had rehearsed it long before the game was on the line.
- Believing in what you've built. You can't make a bold call if you don't trust your systems, your skills, and your people.
- Having the courage to move when the opportunity is there. Opportunities don't wait for you to feel completely comfortable.
Playing to keep up vs. playing to win
| Playing to keep up | Playing to win | |
|---|---|---|
| The goal | Don't lose what you have | Reach the result you actually want |
| Decisions | Default to the safe, expected option | Choose the option that can win, once you've done the preparation |
| Conversations | Put off the hard ones | Have them early and honestly |
| Opportunities | Wait until there's no chance of failing | Act when the opening is there |
| Preparation | Done when it's needed | Done in advance, so you're ready when it counts |
What playing to win looks like in your real estate business
In real estate, the "kick the extra point" decisions are everywhere. They're the follow-up calls we don't make, the pricing conversation we soften because it's uncomfortable, the past clients we haven't talked to in a year, and the bigger goal we keep pushing to next quarter.
Going for two might look like calling the expired listing you've been avoiding, practicing your listing presentation until it's second nature, finally building the database system you keep talking about, or getting around people who will push you to grow. Whatever it is, the pattern is the same as Stein's: prepare first, then make the call.
Will Stein could have kicked the extra point. Nobody would have questioned him. It was the safe decision. But he saw an opportunity to win, and he took it.
Your challenge this week
My challenge to you this week is simple: stop playing just to keep up. Start playing to win.
In your business. In your relationships. In your life.
Sometimes the difference between where you are and where you want to be comes down to having the courage to go for two.
Play to win. The upside is worth it.
Ready to play to win in your real estate business?
Schedule a strategy call with me. We'll talk about where your business is today, where you want it to go, and what JLA Realty – Omnia Elevate agents are doing to build successful businesses.
Schedule a strategy call with JeremyPrefer to talk now? Call 281-387-7689 or email jeremy@omniaelevate.com.
Frequently asked questions
What does "playing to win" mean in business?
Playing to win means making decisions aimed at the outcome you want rather than at protecting what you already have. It combines preparation, confidence in your systems and skills, and the willingness to act when an opportunity appears.
Is playing to win the same as being reckless?
No. Reckless decisions skip the preparation. Playing to win means you've done the work in advance, so when the moment comes, a bold decision is a calculated one. Will Stein's two-point calls worked because his team had practiced that play for months.
What did Kentucky coach Will Stein do against LSU and South Carolina?
In back-to-back weeks in October 2026, Stein chose to go for a two-point conversion in overtime instead of kicking the extra point to force another overtime. Kentucky converted and won both games, beating South Carolina 35-34 on October 3 and LSU on October 10.
How can real estate agents play to win instead of playing to keep up?
Start by naming the safe decisions you keep making by default, such as avoiding certain calls, conversations, or goals. Then prepare for the bolder option, whether that's sharpening a presentation, tightening your database follow-up, or setting a bigger goal, and commit to acting when the opportunity shows up.
How do I schedule a strategy call with Jeremy Williams?
You can book a strategy call online, call 281-387-7689, or email jeremy@omniaelevate.com.