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How Assia Mahmood Built a Purpose-Driven Business in the Middle of Chaos
You’ve done everything right.
You’ve followed the steps.
Built a “stable” life on paper.
But deep down… something still doesn’t feel aligned.
In this episode, I sit down with Assia Mahmood, a former educator turned entrepreneur and founder of Windhaven Academy, who made the bold choice to walk away from a secure career path—mid-renovation, with young kids, and right as the pandemic hit.
This conversation is for the woman who’s felt that quiet nudge.
The one who knows there’s something more waiting on the other side of fear.
The one ready to trade comfort for fulfillment—and step into something meaningful.
Timestamped Summary
00:00 – Welcome + Why this conversation matters
04:15 – Assia’s early career in education and how the idea for Windhaven sparked
09:00 – Making the leap during renovation—and the world shutting down
14:50 – Navigating fear, uncertainty, and what kept her grounded
21:30 – The role of purpose in building resilience
27:05 – Balancing motherhood and entrepreneurship
33:10 – What delegation really looks like for high-achieving women
39:45 – Rebuilding trust in yourself after corporate burnout
44:20 – Advice for women feeling stuck or uncertain
52:30 – How to lead with values and serve with heart
Why Assia’s Story Resonated So Deeply
She Didn’t Wait for Perfect Timing
Assia’s journey reminded me that clarity doesn’t always show up with a perfect calendar or full confidence. Sometimes purpose whispers during the chaos. She launched Windhaven Academy mid-renovation, during the pandemic—with no guarantee it would work. But she kept moving forward anyway.
Courage Isn’t the Absence of Fear—It’s Moving Anyway
This episode is such a powerful reminder that bravery doesn’t always feel bold. Sometimes it looks like showing up, again and again, even when everything feels upside down. Assia leaned on her faith, her family, and her vision—and that’s what carried her through.
What Purpose-Driven Work Really Looks Like
When You Know Your “Why,” You Keep Going
Assia’s clarity around her “why”—creating a warm, values-centered space for early childhood learning—helped her navigate every obstacle. From staffing shortages to community building, she kept coming back to the bigger picture. That purpose became her compass.
Building with Intention > Hustling to Prove
One thing I loved about our conversation was Assia’s honesty around hustle culture. She talked about letting go of doing everything herself, and what it really means to trust others (and yourself) in business. Letting go isn’t weak—it’s strategic.
Redefining Success as a Working Mom
From Burnout to Balance
Before launching Windhaven, Assia was working long hours in education and corporate environments—feeling unfulfilled, exhausted, and disconnected. The moment she gave herself permission to imagine something different, her life started to shift.
Delegation Isn’t Optional—It’s Essential
We talked about the mindset shift that has to happen for high-achieving women to delegate effectively. Assia shared how she built systems, hired intentionally, and created a team she trusts—so she could lead with clarity instead of being buried in the day-to-day.
Advice for the Woman at the Crossroads
If you’re in a season where everything feels blurry…
If you’ve outgrown what once felt “safe”…
If you’re craving meaning, but unsure how to start…
Assia’s story is a roadmap. She didn’t wait for certainty. She made bold, values-aligned decisions with the information she had—and stayed grounded in her “why.”
“You don’t have to leap without fear.
You just have to leap with vision.”
Final Thoughts
This conversation reminded me that the most meaningful paths don’t always look shiny at first. Sometimes they start in the middle of the mess—in between school drop-offs, renovation dust, and a world that feels upside down.
But fulfillment isn’t found by playing it safe.
It’s found by listening to that deeper voice—the one that says: “There’s more for you here.”
If this episode spoke to you, I hope you’ll share it with a friend or fellow dreamer who’s been holding back out of fear. Your purpose doesn’t need perfect timing—it just needs permission.
Related Episodes You Might Like
- Episode 198: Burnout, Boundaries, and Coming Back to Life
- Episode 203: The Middle Ground Movement – When Work and Family Collide
- Episode 195: Redefining Success with Your Own Metrics
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