Why I Try to Be the Dumbest Guy in the Room

Lessons learned in social circles

Author

Skip Flanagan
September 30, 2025 • Estimated Reading Time: 2 minutes

Here’s the truth…
If you’re always the top dog in your environment, you’re in the wrong room.
Growth happens when you’re surrounded by people who push you, challenge you, and sometimes leave you feeling a little outmatched.

Why This Mentality Matters

If you’re the strongest in your gym…

Find a new gym.

If you’re the best player in your facility

go sign up for tournaments where you know you’ll get tested.

If you’re the most knowledgeable in your group, it’s probably time to find a new circle—one that FORCES you to level up.

Being the “dumbest” in the room isn’t about lacking confidence. It’s about refusing to settle.

It’s a mindset that keeps you learning, humble, and hungry.

Can’t Find That Group? Go Virtual

Maybe your dream circle isn’t local. No problem.

Text, email, or DM people who inspire you.

Join online communities. Set up regular check-ins with mentors and peers who are a step ahead.

Bottom line: If you’re not a little uncomfortable, you’re NOT GROWING.

Your Challenge This Week

  • Audit your environment: Who’s pushing you to get better?

  • Where are you the least experienced, and how can you spend more time there?

  • Who can you reach out to—right now—to raise your game?

Don’t settle for being the best in the room. Seek out the spaces where you’re challenged, stretched, and forced to grow. That’s how you become unstoppable.

Stay relentless,

Skip