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Be Wilful. Go Astray. Feel Your Way - Jillain Reilly (#062)
Let's know what you liked and learnt!
The 10 Permissions: From Stuck to Self-Directed in a Fluid World
In this thought-provoking conversation, author and change-maker Jillian Reilly joins Swami to explore her powerful framework — The 10 Permissions — a new rulebook for navigating today’s fluid, unpredictable world. Together, we unpack what it means to upgrade our Adult Operating System, move from I am to I can, and replace fixed plans with curiosity-driven action. Jillian reveals how giving ourselves permission — to experiment, think small, go astray, and feel our way — transforms anxiety about change into agency and adaptability. From reimagining education and parenting to rebuilding culture at work, this episode is an invitation to stop waiting for approval and start designing a life that’s responsive, alive, and truly self-directed.
Order the Book: https://tenpermissions.com/
Key Insights
1️⃣ Permission Is the Bridge Between Intent and Action
Real change begins when we stop waiting for validation and give ourselves the authority to move.
2️⃣ Update Your Adult Operating System
Bring unconscious “rules for living” into awareness — and rewrite them for today’s fast-shifting realities.
3️⃣ Experiment and Think Small
Progress now comes from micro-moves and low-stakes trials, not grand five-year plans.
4️⃣ Feel Your Way Forward
Whole-body intelligence — instinct, emotion, and reflection — is becoming as critical as data and logic.
5️⃣ Redefine Success as Relevance
In a fluid, AI-driven world, sustained success depends on curiosity, continual reinvention, and embodied learning.
———
Timestamps
00:00:00 Intro — Welcome and Context
00:04:12 “We’re Living Through the Great Unraveling.”
00:08:10 “We’re All Running on an Old Operating System.”
00:14:11 “Shift from ‘I Am’ to ‘I Can.’”
00:18:57 “Permission Is the Bridge Between Intent and Action.”
00:22:21 “You Can’t Think Your Way to Growth.”
00:30:25 “Take Small Bets. Learn Faster.”
00:34:59 “Schools Are the Blackberry.”
00:40:01 “You Are Your Best Security.”
00:43:29 “Don’t Raise Obedient Kids. Raise Capable Ones.”
00:50:08 “Look for a Teacher, Not a Fight.”
00:55:03 “Preorders Are Permission in Action.”
00:57:14 “Success Will Be Measured by Relevance.”
00:58:50 “Curiosity Is the New Career Plan.”
01:00:34 “Don’t Stifle Your Strongest Ideas.”
01:02:15 “Permission-Givers Change the World.”
01:06:07 “You Can’t Think Your Way Into Being.”
#The10Permissions, #AdultingRules, #FutureOfWork, #AdaptiveMindset, #PersonalGrowth, #WholeBodyIntelligence, #CuriosityDrivenLife, #ReinventYourself, #ThinkSmallLearnFast, #EmotionalIntelligence, #BeWilfulGoAstrayFeelYourWay, #ContraMindsPodcast, #JillianReilly
This episode was made possible by the great folks at https://www.goeffortless.ai
🔗 Links & Resources:
ContraMinds: https://www.contraminds.com
Subscribe to our Newsletter: https://blog.contraminds.com
🎧 Listen on Podcast Platforms:
Spotify: https://open.spotify.com/show/4xceASphmwAjJONTlsvo2Y
Apple Podcasts: https://podcasts.apple.com/us/podcast/contraminds-decoding-people-minds-strategy-and-culture/id1485202972
Follow ContraMinds:
Twitter: https://twitter.com/contraminds
Instagram: https://www.instagram.com/contraminds/
LinkedIn: https://www.linkedin.com/company/contraminds
Facebook: https://www.facebook.com/contraminds
View all episodes
By Swami, ContraMinds Labs
5
11 ratings
Let's know what you liked and learnt!
The 10 Permissions: From Stuck to Self-Directed in a Fluid World
In this thought-provoking conversation, author and change-maker Jillian Reilly joins Swami to explore her powerful framework — The 10 Permissions — a new rulebook for navigating today’s fluid, unpredictable world. Together, we unpack what it means to upgrade our Adult Operating System, move from I am to I can, and replace fixed plans with curiosity-driven action. Jillian reveals how giving ourselves permission — to experiment, think small, go astray, and feel our way — transforms anxiety about change into agency and adaptability. From reimagining education and parenting to rebuilding culture at work, this episode is an invitation to stop waiting for approval and start designing a life that’s responsive, alive, and truly self-directed.
Order the Book: https://tenpermissions.com/
Key Insights
1️⃣ Permission Is the Bridge Between Intent and Action
Real change begins when we stop waiting for validation and give ourselves the authority to move.
2️⃣ Update Your Adult Operating System
Bring unconscious “rules for living” into awareness — and rewrite them for today’s fast-shifting realities.
3️⃣ Experiment and Think Small
Progress now comes from micro-moves and low-stakes trials, not grand five-year plans.
4️⃣ Feel Your Way Forward
Whole-body intelligence — instinct, emotion, and reflection — is becoming as critical as data and logic.
5️⃣ Redefine Success as Relevance
In a fluid, AI-driven world, sustained success depends on curiosity, continual reinvention, and embodied learning.
———
Timestamps
00:00:00 Intro — Welcome and Context
00:04:12 “We’re Living Through the Great Unraveling.”
00:08:10 “We’re All Running on an Old Operating System.”
00:14:11 “Shift from ‘I Am’ to ‘I Can.’”
00:18:57 “Permission Is the Bridge Between Intent and Action.”
00:22:21 “You Can’t Think Your Way to Growth.”
00:30:25 “Take Small Bets. Learn Faster.”
00:34:59 “Schools Are the Blackberry.”
00:40:01 “You Are Your Best Security.”
00:43:29 “Don’t Raise Obedient Kids. Raise Capable Ones.”
00:50:08 “Look for a Teacher, Not a Fight.”
00:55:03 “Preorders Are Permission in Action.”
00:57:14 “Success Will Be Measured by Relevance.”
00:58:50 “Curiosity Is the New Career Plan.”
01:00:34 “Don’t Stifle Your Strongest Ideas.”
01:02:15 “Permission-Givers Change the World.”
01:06:07 “You Can’t Think Your Way Into Being.”
#The10Permissions, #AdultingRules, #FutureOfWork, #AdaptiveMindset, #PersonalGrowth, #WholeBodyIntelligence, #CuriosityDrivenLife, #ReinventYourself, #ThinkSmallLearnFast, #EmotionalIntelligence, #BeWilfulGoAstrayFeelYourWay, #ContraMindsPodcast, #JillianReilly
This episode was made possible by the great folks at https://www.goeffortless.ai
🔗 Links & Resources:
ContraMinds: https://www.contraminds.com
Subscribe to our Newsletter: https://blog.contraminds.com
🎧 Listen on Podcast Platforms:
Spotify: https://open.spotify.com/show/4xceASphmwAjJONTlsvo2Y
Apple Podcasts: https://podcasts.apple.com/us/podcast/contraminds-decoding-people-minds-strategy-and-culture/id1485202972
Follow ContraMinds:
Twitter: https://twitter.com/contraminds
Instagram: https://www.instagram.com/contraminds/
LinkedIn: https://www.linkedin.com/company/contraminds
Facebook: https://www.facebook.com/contraminds