🎤 Quotable quotes: “If you win, you will be on the precipice of achieving everything you ever dreamed of."
— Keeley Jones
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In Season 3, Episode 11 (Mom City), Jamie Tartt is in a funk. The edge is gone. The cocky sparkle is missing. Roy tries to summon the “old Jamie” with some classic Roy encouragement, which is about 12 percent (cuss) words and 88 percent intense staring. No luck.
So Roy calls in Keeley.
Keeley, in full hype-woman mode, points to the upcoming match against Man City and drops this motivational grenade: “If you win, you will be on the precipice of achieving everything you ever dreamed of.”
And Jamie does not respond like someone who just got handed a treasure map.
He responds like someone who just got handed a bill.
Because sometimes, the thing that messes with us is not the fear of losing.
It is the fear of winning.
🏟 Why This Matters for You
Success can be weird, y’all.
We tell ourselves we want the promotion, the acceptance letter, the big stage, the “finally” moment. Then it gets close and our brains go, “Cool cool cool. Let’s panic.”
Fear of success often shows up wearing different outfits:
1. Perfectionism
If it has to be flawless, we never have to finish. Convenient, right?
2. Procrastination
We delay the thing, not because we cannot do it, but because doing it means something changes.
3. Self-sabotage
We pick a fight, miss a deadline, start doom-scrolling, or reinvent our whole personality the week before the big moment.
Why? Because success can bring pressure, expectations, attention, and identity shifts. Winning means you cannot hide behind “maybe someday” anymore.
This is where The Infinite Game idea helps. Simon Sinek reminds us that the goal is not to “win” once and be done. The goal is to keep playing, to keep improving, to keep showing up with consistency and purpose.
When you see life as an infinite game, the precipice becomes less scary. It is not a final exam. It is not a finish line. It is simply the next round.
So instead of asking, “What if I fail?” we can ask:
“What if I succeed and I am still me?”
“What if I succeed and I keep going?”
“What if this is not the end of the story, but the start of a better chapter?”
That is the Lasso way. Play the long game. Stay curious. Stay grounded. Keep playing.
🫶 Stay curious,
— Nick & Marnie
Your tea sipping, long game playing, precipice approaching friends
More leadership musings
🍪 Biscuits with the Boss:
Icebreaker time:
What is one thing you are close to achieving that makes you a little nervous?
Now the fun part:
If you viewed it as one step in an infinite game, what would you do next?
📚Beard’s collection:
📖 Sinek, Simon. The Infinite Game. Portfolio Penguin, 2020.
A great reminder that life and leadership are not about “winning” once, they are about staying in the game with purpose. When success feels scary, this reframes the moment as one more round, not the final verdict.
📖 Coniglio, Nick and Stockman, Marnie. The Business of You: Ask the Right Questions, Tell Your Story, and Lead Your Life. Amplify Publishing, 2025.
For parents with high school or college kids, this is the playbook you wish came with the student handbook, especially for those “precipice” moments when a dream gets close and suddenly it feels scary. It helps young adults get clear on who they are, talk about it like a real human, and take the next step with confidence instead of backing away from success.
🌎 This week in Here - There - Every F’ing where
We were excited to be on the Strategic Shift podcast hosted by Christy Honeycutt and presented by Pepewerk!
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And if this newsletter hit home and you want to learn more about body language and polish. Check out our friend Presilah here.
Believe!
Nick & Marnie
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