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Playing It Safe Holds You Back | Elizabeth Weingarten
What if the very questions keeping you up at night were the key to moving forward? In this episode, AJ and Johnny sit down with author Elizabeth Weingarten to challenge the tired advice to “embrace uncertainty” and show how reframing it as an invitation—not a problem—unlocks growth in career, relationships, and life. Drawing from her book How to Fall in Love with Questions, she shares how patience, courage, curiosity, and community help us stop chasing premature answers and instead thrive in the unknown, offering a practical framework to create meaning even when the future is unclear.
What to Listen For
[00:00:00] Why “embrace uncertainty” is tone-deaf advice
[00:02:15] Defining uncertainty: doubt that delays progress
[00:05:07] Elizabeth’s personal crossroads: marriage doubts and a failing project
[00:07:02] Rilke’s Letters to a Young Poet and the idea of “living the questions”
[00:10:22] The human craving for certainty—and how it misleads us
[00:16:02] Patience as a creative and relational superpower
[00:20:05] Why patience without courage keeps us stuck
[00:26:14] Building a “questions practice” to reframe binary thinking
[00:33:19] Barbara’s story: identity shift after paralysis as freedom, not loss
[00:40:03] Loving the questions as an act of self-compassion
[00:44:13] First step: ask if your question narrows you—or opens possibility
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Curious about your influence level?
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Take this 60-second quiz to find out how your influence stacks up against top performers at theartofcharm.com/influence.
Episode resources:
Elizabeth's Website
How to Fall in Love with Questions
Letters to a Young Poet
Check in with AJ and Johnny!
AJ on LinkedIn
Johnny on LinkedIn
AJ on Instagram
Johnny on Instagram
The Art of Charm on Instagram
The Art of Charm on YouTube
The Art of Charm on TikTok
Learn more about your ad choices. Visit megaphone.fm/adchoices
View all episodes
By The Art of Charm
4.7
1046510,465 ratings
What if the very questions keeping you up at night were the key to moving forward? In this episode, AJ and Johnny sit down with author Elizabeth Weingarten to challenge the tired advice to “embrace uncertainty” and show how reframing it as an invitation—not a problem—unlocks growth in career, relationships, and life. Drawing from her book How to Fall in Love with Questions, she shares how patience, courage, curiosity, and community help us stop chasing premature answers and instead thrive in the unknown, offering a practical framework to create meaning even when the future is unclear.
What to Listen For
[00:00:00] Why “embrace uncertainty” is tone-deaf advice
[00:02:15] Defining uncertainty: doubt that delays progress
[00:05:07] Elizabeth’s personal crossroads: marriage doubts and a failing project
[00:07:02] Rilke’s Letters to a Young Poet and the idea of “living the questions”
[00:10:22] The human craving for certainty—and how it misleads us
[00:16:02] Patience as a creative and relational superpower
[00:20:05] Why patience without courage keeps us stuck
[00:26:14] Building a “questions practice” to reframe binary thinking
[00:33:19] Barbara’s story: identity shift after paralysis as freedom, not loss
[00:40:03] Loving the questions as an act of self-compassion
[00:44:13] First step: ask if your question narrows you—or opens possibility
A Word From Our Sponsors
Tired of awkward handshakes and collecting business cards without building real connections? Dive into our Free Social Capital Networking Masterclass. Learn practical strategies to make your interactions meaningful and boost your confidence in any social situation. Sign up for free at theartofcharm.com/sc and elevate your networking from awkward to awesome. Don’t miss out on a network of opportunities!
Unleash the power of covert networking to infiltrate high-value circles and build a 7-figure network in just 90 days. Ready to start? Check out our CIA-proven guide to networking like a spy!
Indulge in affordable luxury with Quince—where high-end essentials meet unbeatable prices. Upgrade your wardrobe today at quince.com/charm for free shipping and hassle-free returns.
Ready to turn your business idea into reality? Shopify makes it easy to start, scale, and succeed—whether you're launching a side hustle or building the next big brand. Sign up for your $1/month trial at shopify.com/charm.
Need to hire top talent—fast? Skip the waiting game and get more qualified applicants with Indeed. Claim your $75 Sponsored Job Credit now at Indeed.com/charm.
This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/charm
Stop needlessly overpaying for car insurance. Before you renew your policy, do yourself a favor—download the Jerry app or head to JERRY.com/charm
Connect with quality therapists and mental health experts who specialize in you at www.rula.com/charm
Curious about your influence level?
Get your Influence Index Score today!
Take this 60-second quiz to find out how your influence stacks up against top performers at theartofcharm.com/influence.
Episode resources:
Elizabeth's Website
How to Fall in Love with Questions
Letters to a Young Poet
Check in with AJ and Johnny!
AJ on LinkedIn
Johnny on LinkedIn
AJ on Instagram
Johnny on Instagram
The Art of Charm on Instagram
The Art of Charm on YouTube
The Art of Charm on TikTok
Learn more about your ad choices. Visit megaphone.fm/adchoices
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