259 - Escaping the Certainty Trap: Revisiting “The Gift of Maybe”

Dec 9, 2025

The discussion dives deep into the paradox of comfort, revealing how the quest for security can trap us in predictability. The host shares personal anecdotes of chaos turning into a controlled life and highlights the anxiety that change can trigger, even when it’s positive. Inspired by the concept of 'maybe,' the conversation emphasizes how this simple word can unlock new possibilities and encourage growth. Listeners are urged to rethink their addiction to certainty, allowing for a more expansive and fulfilling life.

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INSIGHT

When Comfort Becomes Cement

Comfort and routine can silently calcify into a limiting cage that narrows your life.
Jill observes that patterns meant to protect can become “cement feet” that stop growth.

ANECDOTE

From Chaotic Childhood To Overengineered Safety

Jill shares her chaotic childhood and how it drove her to build a hyper-stable adult life.
She later realized that escaping chaos led her to overvalue certainty and avoid change.

ANECDOTE

Bubble-Wrapped By Certainty

Jill contrasts a friend’s tight, risk-averse habits with her own past adventurous self.
She realized certainty had quietly wrapped her in bubble wrap despite formerly embracing uncertainty.

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Escaping the Certainty Trap: Revisiting “The Gift of Maybe”
In this episode, I explore how the desire for comfort and security can slowly become a trap. Inspired by The Gift of Maybe by Allison Carmen, this story is both personal and universal—how striving for a safe life can quietly limit our growth, and how a single word—“maybe”—can help us shift our mindset, challenge our fear, and open up to new possibilities.
I reflect on my own life, particularly how after years of chaos in my childhood, I worked hard to create a life of comfort: a stable job, predictable routines, a peaceful home. But when faced with a seemingly perfect job opportunity, I froze. The change triggered panic, not because it was wrong, but because it threatened my carefully controlled world.
That’s when The Gift of Maybe entered my life. What started as a book I planned to review for the podcast unexpectedly turned into a mirror I wasn’t prepared to look into. The author’s story mirrored mine—how unexpected change can become transformative, even when it first feels like loss.

Comfort as a Hidden Trap:
Comfort can build slowly, through routines and security, until it becomes a prison of predictability. I explore how this happened in my own life and how I didn’t notice it creeping in until change knocked on the door.
Addiction to Certainty:
Certainty feels safe, but it’s an illusion. I discuss how we can become overly attached to control, resisting anything that disrupts our expectations—even when it’s a good thing.
The Power of “Maybe”:
The word “maybe” isn’t indecision—it’s possibility. Inspired by Allison Carmen’s work, I talk about how shifting our mindset can help us embrace change without fear.
Takeaways from the Episode:
This episode is a reminder that certainty isn’t always the prize we think it is. When we cling too tightly to stability, we shrink our world. “Maybe” gives us the space to grow again. It’s okay to feel fear, but don’t let it make your life smaller. You can take small, brave steps toward a more expansive life.
If your life feels safe but stagnant, maybe it’s time to consider what possibilities you’ve been avoiding—and maybe, just maybe, it’s time to say yes to something new.
https://startwithsmallsteps.com/breaking-the-certainty-trap-lessons-from-the-gift-of-maybe/

Jill’s Links
https://abetterlifeinsmallsteps.com

https://www.youtube.com/@startwithsmallsteps
https://www.buymeacoffee.com/startwithsmallsteps
https://twitter.com/schmern
Email the podcast at jill@startwithsmallsteps.com

By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and inspirational purposes only. I am not a licensed healthcare provider, psychiatrist, or counselor. Any advice or suggestions offered should not be considered a substitute for professional medical or mental health advice. You are solely responsible for any decisions or actions you take based on this content.