248 - “You Be You, Boo-Boo” — But Should You?

Sep 23, 2025

This discussion dives into the mantra of radical self-expression, questioning its actual benefits. It highlights the balance between authenticity and adaptability, revealing how different settings require different selves. The paradox of choice is explored, showcasing how too many options can lead to anxiety. Faith traditions are reflected upon, emphasizing freedom with responsibility. Social media’s role in fostering conformity under the guise of individuality is also examined. Ultimately, it encourages redirecting self-expression to serve others.

Ask episode

AI Snips

Chapters

Books

Transcript

Episode notes

INSIGHT

Individuality Ripples Through Community

Radical self-expression sounds liberating but ignores our web of relationships.
Jill argues our actions always ripple outward and pure

ANECDOTE

Keeping Nerd Interests Private In High School

Jill describes hiding her 'nerd' interests in high school to fit with friends.
She later shared nerd parts with college friends, showing selective self-disclosure.

INSIGHT

Expression Has Consequences

Freedom of expression is not the same as freedom from consequences.
Jill links unchecked self-expression to health, relationship, and social costs.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

“You Be You, Boo-Boo” — But Should You?
In this episode, I explore the increasingly popular mantra of radical self-expression—“You be you, Boo-Boo”—and ask whether it really serves us, or anyone else. Is total authenticity always a good thing? Or could it sometimes lead to conflict, disconnection, and missed opportunities for deeper relationships?
Drawing from personal experiences, faith, historical insights, and observations from work and society, I break down what it really means to be “yourself” in a world that also requires connection, cooperation, and community.
Top Topics Covered
Authenticity vs. Adaptability
I share how different parts of ourselves are revealed in different settings—and how that’s not inauthentic, it’s wise. Sometimes, being ourselves means knowing when to connect over shared interests instead of forcing parts of ourselves onto others.
The Paradox of Choice
Unlimited freedom doesn’t always bring joy. In fact, the constant demand to self-brand and self-express can lead to anxiety and discontentment. I touch on how this overload of options actually makes life harder, not freer.
Faith and Freedom
From biblical teachings to ancient Rome, I reflect on how many traditions value duty over pure individualism. Christianity teaches freedom with responsibility, where our choices are weighed by how they benefit others.
Social Media and the Illusion of Individuality
We discuss how platforms push conformity under the guise of self-expression. The algorithm rewards sameness, and the result is often curated identities rather than real, unique individuals.
Living for Others
The real takeaway? Use your individuality as a gift. Whether it’s cooking, reading, or tech knowledge—bring your strengths outward to serve others. That’s where authenticity becomes transformative.
Key Takeaways
Radical authenticity, unchecked, can lead to relational damage and societal fragmentation. But balanced authenticity—where we bring our true selves to serve others—builds stronger communities and more fulfilling lives. By contributing instead of just expressing, we discover deeper joy and a more meaningful identity.
Being yourself doesn’t mean expressing every thought or ignoring social harmony. It means using your gifts for the good of others. One wing is being yourself. The other is service. Together, they let you fly.

https://startwithsmallsteps.com/248-the-myth-of-you-be-you-why-authenticity-needs-boundaries/

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.