Foolish Beginnings, Messy Middles, and Mastery

If there’s one thing I’ve learned over the last decade of entrepreneurship, it’s this: success isn’t a straight line. It’s a winding path filled with foolish beginnings, messy middles, and those rare moments of clarity that feel like mastery.

In this solo episode of Unapologetically Yours, I’m talking about what it means to embrace every stage of the journey—from the tender, messy start to the confusing middle to that sweet sense of mastery (which, let’s be honest, still comes with its own lessons).

I share a bit of my own path, from founding Yakkety Yak back in 2012, to stepping into the unknown with my healing and retreat work, to launching this podcast, to stepping into new territory with my healing and retreat work. 

It’s about trusting your inner compass, letting yourself be a beginner (again and again), and releasing the pressure to have it all figured out.

Whether you’re building a business, reinventing yourself, or just figuring out what’s next, this episode is a little love note to the part of you that’s brave enough to begin.

In this episode, you’ll hear about:

  •  Why I started Yakety Yak and what it’s taught me about leadership, vision, and growth

  • What I believe mastery really looks like (hint: it’s not having it all together)

  • The beauty of foolish beginnings and why I keep saying yes to them

  • The messy middle of entrepreneurship, and why it’s actually where the magic is

  • The power of letting go, setting boundaries, and doing things differently

  • How following your curiosity leads to unexpected invitations and alignment

…and so much more! 

This episode is for the dreamers, the doers, the ones standing at the edge of something new—or deep in the messy middle trying to find their footing. Whether you’re starting a business, reimagining your life, or simply learning to trust yourself more fully, I hope this conversation reminds you that your path is yours for a reason.

There is something so beautiful about just starting and taking the steps and planting the seeds and doing the thing and being unapologetic about how that looks to the outside world.
— Ashley Logan

Some Key Takeaways From This Episode:

  1. Mastery isn’t about knowing everything. It’s not about having all the answers. For me, mastery means being willing to be wrong, to do things differently, and to trust others to take the reins when it’s time.

  2. Don’t compare your Day 1 to someone else’s Day 100. Comparison will kill your momentum. Don’t look at someone else’s middle and use it as a measuring stick for your start. Come back to your vision - every single time.

  3. Boundaries create the freedom you’re craving. You don’t have to carry everything yourself. Start letting go of what’s no longer serving you—and trust that making space invites in something even better.

  4. You don’t need a perfect plan to begin. So many of the most beautiful things in my life started with a whisper, a nudge, a foolish little idea. Start before you’re ready. Just start.

  5. The magic is in the middle. The middle is where you find your voice, your rhythm, your resilience. Don’t rush through it. Let it shape you.

  6. Trust your inner compass. You know more than you think you do. Tune in, take the next step, and keep aligning with what feels right. That’s how you build a life—and a business—that’s unapologetically yours.

When you are following your heart, when you are following your inner compass, that won’t lead you astray.
— Ashley Logan

You can listen to the full episode at the links below:

If you’re in a beginning, I see you. If you’re in the middle, I’m right there with you. And if you’re standing in a moment of mastery—don’t forget to look back and celebrate how far you’ve come.

Want to keep this conversation going? Send me a message on Instagram @ashleydlogan - I’d love to hear from you! 

Unapologetically yours, 

xx Ashley

Connect with Ashley Logan:

Instagram @ashleydlogan

Website https://ashleydlogan.com/


Have a topic or guest you’d love to see featured on the Unapologetically Yours podcast? Send us an email: podcast@unapologeticallyyours.com 

Keywords

entrepreneurship, beginnings, mastery, business, personal growth, storytelling, self-discovery, resilience, creativity, purpose

Chapters

00:00 Introduction to Unapologetically Yours

02:53 The Journey of Entrepreneurship

06:10 Embracing the Messy Middle

09:00 The Power of Foolish Beginnings

11:45 Mastery and Moving Forward

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Cleaning Out The Closet: The Power of Letting Go

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Starting, Scaling, & Showing Up with Jackie Hutson