Charlie’s Toolbox

American Patriarchy Explained: What's Happening to Women Right Now and How to Survive It | Dr. Anna Malaika Tubbs

We're the most educated generation of women in history. We're choosing ourselves in ways our mothers couldn't. And we're being punished for it.
If you're feeling anxious, confused, or like you're being pushed back into a box you fought to get out of, you're not imagining it. There's a pattern. A system. And once you can see it, you can navigate it differently.
Anna Malaika Tubbs (PhD, 2x NYT bestselling author of The Three Mothers and Erased) breaks down what we're actually up against and, more importantly, how to survive it while choosing yourself anyway. This is about recognition, strategy, and hope despite knowing the cost.
You can find more of Dr. Tubbs' work here:
The Three Mothers: How the Mothers of Martin Luther King, Jr., Malcolm X, and James Baldwin Shaped a Nation 
Erased: What American Patriarchy Has Hidden from Us 
How Moms Shape The World | Anna Malaika Tubbs | TED
Learn more about Anna here. 

How 'What About the Men?' Articles Weaponize Male Suffering

There's a genre of journalism that's exploded over the last decade. On the surface, it seems reasonable, even necessary. Articles about boys falling behind in school. Men struggling with loneliness. The crisis of modern masculinity.
But here's the question nobody's asking: Who benefits when we frame it this way?
Today, we're pulling apart the machine. Looking at what these articles do, not just what they say. And once you see it, you can't unsee it.

What Following Your Intuition Actually Looks Like With Kara Brothers I President of Starface

What does it take to choose passion every single time, even when it's uncomfortable?
In this episode, we sit down with Kara, a woman who has spent her life following one unwavering voice: the one that tells her when something isn't alive enough, passionate enough, worth it enough. She's left Google. She's left the presidency of Starface.
She's moved her family to Italy. Not because things were falling apart, but because they weren't lit up enough. This is a conversation about living for the feeling. About refusing to settle for work, environments, or choices that don't serve you. About the discomfort of pivoting away from what looks good on paper toward what actually makes you feel alive. And about what it costs to live this way, and why it's worth it.
Kara doesn't just talk about passion as a nice idea. She builds her life around it. She protects it. She keeps choosing it, over and over again, even when everything else is pulling her toward safety and stability. For anyone who's learning to trust that voice, the one that says "this isn't it, but that is," this conversation will remind you why it matters to keep listening.
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Where to Find Kara Brothers
-Instagram: @karabrothers
-YouTube Podcast: https://www.youtube.com/@sayit.outloud
-Say It Out Loud; available audio only on all platforms as well
-Community: For The Play Collective or 1:1 Coaching Opportunities
- Shoot her a note at kara@playcollective.co -Newsletter sign-up: https://substack.com/@sayitoutloudnow
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Ready to stop living life on autopilot and start designing it intentionally?
- **The Shop:** Discover exclusive tools, curated workshops, and guides for the radical woman ready to step fully into her power.
- https://www.charliestoolbox.com/shop
- **Substack Newsletter:** Read deep dives and stories about women choosing themselves, money, self-trust, and building power outside of old systems. - https://charliestoolbox.substack.com/
- **Website:** Find more resources, learn about our methodology, and explore all our offerings in one place.
https://www.charliestoolbox.com/
- **The Podcast:** Listen to real conversations with women who've built lives beyond approval, expectation, and limits.
- https://charliestoolbox.podbean.com/
- **Take the Free Assessment:** Learn where you are on your decentering men journey.
- https://www.tryinteract.com/share/quiz/68b71e8eeb218c0015ec5c4f
Your sovereignty is your foundation. My role is to help you use it as a launchpad.
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**Follow for Daily Inspiration:**
- TikTok: https://www.tiktok.com/@charliestoolbox
- Instagram: https://www.instagram.com/charliestoolbox/
- LinkedIn: https://www.linkedin.com/company/charliestoolbox
**Take Action Now:
** Hit **subscribe** if you're ready to stop waiting for permission and start choosing yourself. New episodes drop weekly with tools for building a life that's authentically felt and beautifully lived. Ready to stop living life on autopilot and start designing it intentionally?
- **The Shop:** Discover exclusive tools, curated workshops, and guides for the radical woman ready to step fully into her power.
- https://www.charliestoolbox.com/shop -
**Substack Newsletter:** Read deep dives and stories about women choosing themselves, money, self-trust, and building power outside of old systems. - https://charliestoolbox.substack.com/
- **Website:** Find more resources, learn about our methodology, and explore all our offerings in one place. - https://www.charliestoolbox.com/
- **The Podcast:** Listen to real conversations with women who've built lives beyond approval, expectation, and limits. - https://charliestoolbox.podbean.com/
- **Take the Free Assessment:** Learn where you are on your decentering men journey.
- https://www.tryinteract.com/share/quiz/68b71e8eeb218c0015ec5c4f
Your sovereignty is your foundation. My role is to help you use it as a launchpad.
---------------------------------------------------------------
**Follow for Daily Inspiration:**
- TikTok: https://www.tiktok.com/@charliestoolbox
- Instagram: https://www.instagram.com/charliestoolbox/
- LinkedIn: https://www.linkedin.com/company/charliestoolbox
**Take Action Now:** Hit **subscribe** if you're ready to stop waiting for permission and start choosing yourself. New episodes drop weekly with tools for building a life that's authentically felt and beautifully lived.

How to Find Your Voice When Family Expectations Drown Out Your Truth | Decentering Family for Self-Discovery

Have you ever felt like your family's voice is so loud, you can't hear your own? In this episode, we're diving into one of the most challenging but necessary journeys of adulthood: learning to prioritize your own voice over family expectations.
This isn't about abandoning the people who raised you; it's about creating the space you need to discover who you actually are beneath the layers of inherited beliefs, expectations, and advice that may not align with the life you truly want to live.
Whether your family is warm and supportive or domineering and rigid, this episode offers practical tools for anyone who's ever struggled to separate their own desires from what they were taught to want.
You'll discover:
Why distance (physical, mental, or spiritual) is a tool for growth, not a punishment
Five practical strategies for stepping back and protecting your energy
How to finally hear your own voice after years of listening to everyone else
The role your body plays in recognizing what's truly aligned for you
Why "clearing the field" is essential before you can grow into who you're meant to be
This episode is for the woman who's ready to stop living by someone else's blueprint and start honoring her own truth—without guilt, without apology, and with full permission to be beautifully selfish.
If you've ever needed validation that it's okay to choose yourself, this is it.

Are You Hiding Behind Heaven? Why "God's Will" Might Be Keeping You Stuck (And What to Do Instead)

What if the very beliefs meant to guide you are actually keeping you stuck? In this episode, we explore a hidden pattern that traps millions in cycles of repeated mistakes, unclear direction, and unresolved problems. You'll discover why certain phrases you've relied on your entire life might be stopping you from thinking, and what to do about it. By the end, you'll have a framework to recognize when you're giving away your power and practical steps to reclaim it. Warning: This conversation will challenge what you've always been told.

The Fleabag Effect: What a Chaotic Character Taught Us About Self-Acceptance

What if the voice in your head didn't have to be your worst enemy? In this episode, we explore the exhausting cycle of perfectionism, why we replay our failures on loop, and what it takes to finally make peace with the messy, complicated parts of ourselves. Through the lens of one beloved TV character's journey from self-destruction to self-acceptance, we uncover what it really means to be worthy of love, flaws and all. If you've ever felt like you need to fix yourself before you deserve compassion, this conversation is for you.

How to Choose Yourself Part 3: Career Architecture

What if everything you were taught about career success was designed to keep you working harder while staying trapped? In this episode, we're dismantling the traditional career playbook and rebuilding it around one goal: your freedom.
This is pillar five of choosing yourself: Career Architecture. We're getting strategic about money, security, and designing work that actually serves your life. We're talking about how to navigate systems that weren't built for you, why single women especially need to be ruthless about income, and the truth about what freedom actually costs. Should you climb the corporate ladder? Build multiple income streams? Work remote? Hire help? We're breaking down exactly what career architecture means when the goal isn't just success, it's sovereignty.
If you've ever felt like you're working hard but not building toward freedom, this episode will change how you think about your career.

How to Choose Yourself Part 2: The Foundation That Changes Everything

What if the reason you can't seem to stick to choosing yourself has nothing to do with willpower? In this episode, we dive into the two pillars that determine whether all your other self-improvement efforts actually last.
I share a conversation that completely shifted how I think about relationships, plus the family dynamics that tried to keep me small (and how I broke free). We're talking about the systems that either support your sovereignty or undermine it at every turn.
This is Part 2 of our series on the five pillars of choosing yourself. If you missed Part 1 on financial autonomy and body freedom, catch up first, then come back for the foundation that makes it all possible.
Ready to stop letting other people's comfort zones determine your life choices? Let's get into it.
Subscribe for more episodes on choosing yourself unapologetically.

What does it really mean to "choose yourself" as a woman?

Beyond the buzzwords and Instagram quotes lies a practical framework for reclaiming your power in five critical areas of life. This isn't about self-care Sunday or positive affirmations; it's about the concrete choices that determine whether you're living on your own terms or someone else's.
In this episode, we dive deep into the real-world strategies that transform abstract concepts like "self-love" into actionable steps. Through powerful personal stories and sociological insights, discover why certain life decisions can be the difference between freedom and dependence, between thriving and merely surviving.
If you've ever wondered how to move beyond theoretical empowerment to actual autonomy, this conversation will give you the roadmap. Some truths might be uncomfortable, but they're the ones that change everything.
Ready to stop living someone else's version of your life?

What to Do When You've Never Been in a Relationship

Have you ever wondered what happens when romantic love just... doesn't happen? In a world obsessed with finding 'the one,' we rarely talk openly about what it's like to navigate life without ever experiencing a romantic relationship and the complex emotions that come with it.
In this episode, we explore the deeper questions many are afraid to ask: Is it personal? Is it fixable? And how do you find peace when society tells you something essential is missing from your life?
This isn't about dating tips or promises that love is just around the corner. Instead, we dive into a different perspective entirely, one that might challenge everything you've been told about love, worth, and what makes a life complete.
Join me for an honest conversation about yearning, societal expectations, and finding a way forward that doesn't require you to change who you are or wait for someone else to validate your existence.
If you're ready for a different kind of conversation about love and life, this episode is for you.