Whether it was traveling with the teams my dad coached as a kid, playing club soccer at an early age, monopolizing my time in high school, playing all through college, or being the focus of my first entrepreneurial venture, soccer was a part of my identity for over 20 years. I’ve since shifted toward the more secret exercise of golf, but memories remain, and sports have so many playful metaphors.
Sports and other organized activities help us push to be our best, and the sense of belonging is the real magic.
No matter the sport, it can be easy to get ahead before slipping into a dangerous trap. Instead of staying sharp by maintaining the offensive pressure that earned an early advantage, it’s natural to start playing not to lose.
In soccer, this often means a team sinks back into an overly defensive formation. Less variety invites frantic desperation, and the added pressure often leads to the opposing squad scoring an equalizing goal. Even if the need for another goal shifts your team back into a more balanced attack, the momentum has shifted.
When applied to business, getting ahead and then playing not to lose can be seen all over the map. For instance, snagging a few early adopters, then assuming customer discovery is over. Hiring new talent, then just hoping everyone can work together. Launching a new product with existing customers, then not supporting them through the chasm of change. Securing product-market fit, then avoiding innovation due to a misguided sense of risk. Finding generous mentors, then forgetting to nurture relationships. Those are just a few ways we get ahead, then play to lose, but many leaders are lulled into this trap.
Tactics to stay ahead differ based on situational factors, but when in doubt, trust that uncertainty is certain. Be strategic to avoid recklessness, then maintain pressure and stay on the offensive by leaning into the pain.
As you find fresh ways to serve customers, continue celebrating milestones and stay ahead with more initiative to keep playing beyond the fear of losing.
1 Comment
Ben McDougal · July 15, 2026 at 4:24 PM
ORIGINAL WRITING – 7/28/22
I’ve been around soccer the majority of my life.
Whether it was traveling with the college team my dad coached as a kid, playing club soccer at an early age, focusing on the sport in high school, playing all through college, or being the product of my first entrepreneurial venture, soccer was a part of my identity for over 20 years. This team sport helped me push to be my best, but the sense of belonging is what made it special.
As I’ve enjoyed the World Cup in Qatar, I’m reminded how easy it can be to get ahead in a match, before slipping into a dangerous trap. Instead of staying sharp by maintaining the offensive pressure that earned an early lead, it’s tempting to start playing not to lose.
In soccer, this often means a team sinks back into an overly defensive formation. Less variety invites frantic desperation and the added pressure often leads to an equalizing goal being scored by the opposing squad. Even if the need for another goal shifts your team back into a more balanced attack, the momentum has shifted.
When applied to business, getting ahead and then playing not to lose can be seen all over the map. For instance, snagging a few early adopters, then assuming customer discovery is over. Hiring new talent, then hoping everyone can work together without initiative. Launching a new product with existing customers, then not supporting them through the chasm of change. Securing product-market fit, then avoiding innovation due to a misguided sense of risk. Finding generous mentors, then forgetting to nurture relationships. Those are just a few, but many leaders are lulled into this trap that’s defined by a sense of scarcity.
Tactics to stay ahead differ based on situational factors, but when in doubt, trust that uncertainty is certain. Be strategic to avoid recklessness, then stay on the offensive by leaning into the pain. As you find fresh ways to serve customers, continue celebrating milestones and stay ahead with initiative to keep building beyond the fear of losing.
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