The Quality of Your Questions Determines The Quality of Your Freedom Life with Tanessa & Flynn Tanessa and Flynn from the Freedom Diaries

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Ever wonder if your next big business breakthrough could come from a conversation during a walk—or maybe while homeschooling your kids in Bali?

This week, we are sitting down with two very special humans: Tanessa and Flynn from the Freedom Diaries. If you’ve ever fantasized about living abroad with your family, becoming work-optional, or simply having more ease in your finances—this episode is for you.

💭 It all started with one powerful question: What if we didn’t have to trade time for money anymore?

From that moment forward, Tanessa and Flynn reimagined everything. They went from a life of hustle—mechanic shifts and jam-packed health coaching schedules—to a deeply intentional life fueled by dividends, money dates, and a mission-driven mindset.

We unpack:

• How asking better questions opens the door to radical life changes
• Why they ditched the traditional FIRE model for something faster, more flexible, and aligned
• The investing strategy that gave them the freedom to stop working for money—and what they do instead
• What it means to co-create wealth as a couple—through vision walks, strategy chats, and radical honesty
• Why Flynn’s story as an immigrant and ex-mechanic makes this kind of freedom feel possible for anyone
• How playfulness, trust, and surrender shape their relationship with money (and each other)

✨ Whether you’re dreaming of a softer pace, wondering how to create sustainable income outside your 9–5, or simply curious about what freedom really looks like—this episode will expand your thinking.

We’ll leave you with this thought:
 💡 “What don’t I know right now… that could change everything?”

That’s the power of a single question.

🌍 Connect with Tanessa and Flynn:

• Read The Freedom Diaries: https://tanessashears.substack.com/ 
• Start your own journey to dividend income with their Cashflow Investor Challenge at https://chasingfreedomfamily.com/
• Find Flynn on Instagram: @chasingtruefreedom

📣 If this episode stirred something in you, take a moment to reflect: What’s the one question you haven’t asked yet… that could unlock the next chapter of your life?

We’d love to hear what comes up—send us a m

💬 DM us to work with us.
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