Have you ever felt stuck in a job that’s draining your energy and leaving you wondering if it’s possible to start a new career?

In this episode, I chat with Brittany Piccola, a former high school teacher who faced teacher burnout head-on and made the bold decision to leave the classroom and start a new career as a virtual assistant.

Brittany’s story is raw, real, and incredibly inspiring. After losing her mom and facing the harsh reality of juggling grief with an unforgiving teaching schedule, she realized it was time to leave the classroom and design a new career on her own terms.

If you’ve ever thought about walking away from the familiar to start a new career, you’re going to love this conversation.

Here’s what you’ll learn in this episode:

• How teacher burnout can sneak up on you—and how to know when it’s time to go.
• The moment Brittany knew she had to leave the classroom and the unexpected opportunity that helped her start a new career.
• Practical steps for anyone ready to start a new career, especially teachers facing teacher burnout.
• Why prioritizing your mental health and well-being is the key to finding joy and fulfillment again.
• The surprising opportunities waiting for teachers who want to leave the classroom and start a new career.

Whether you’re a teacher dreaming of something more, or you’re just ready for a major life pivot, this episode is packed with encouragement and practical advice to help you take the leap.

Brittany’s journey proves that it’s never too late to start a new career that fits your life.

RESOURCES MENTIONED IN THIS EPISODE:

Female Founders Collective

Midlife on Purpose: Workbook

CONNECT WITH KATY RIPP:

Submit a letter HERE for a Dear Katy episode

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

CONNECT WITH BRITTANY PICCOLA:

Website: www.brittanypiccolava.com

Instagram: @brittanypiccola_va

Ever found yourself Googling "how to start a business from scratch", wondering if you can actually turn your passion into a career?

Maybe you've dreamed of turning a hobby into a business but felt paralyzed by fear in business—worried you don’t have what it takes. If that sounds like you, then girl, you’re in for a treat!

In this episode, I sit down with Caitlin Kowalke, an incredible running coach, former pro athlete, and business owner, who took her passion for running and turned it into a thriving career. From getting into running as a young athlete to competing at the Olympic Trials, Caitlin shares how she transitioned from professional runner to entrepreneur—starting Fearless Feet Running from her closet.

But it wasn’t always smooth sailing. Fear in business almost stopped her from taking the leap. Caitlin opens up about how she faced setbacks, battled self-doubt, and figured out how to start a business from scratch—all while balancing motherhood and life’s unexpected twists.

If you’ve been waiting for a sign to finally start getting into running or take that first step toward turning a hobby into a business, this episode is it.

• How Caitlin went from Googling "how to start a business from scratch" to running a successful coaching business.
• The mindset shift that helped Caitlin push past fear in business and take the leap into entrepreneurship.
• The surprising way running builds confidence—and why it’s never too late to start getting into running.
• The exact steps Caitlin took to start turning a hobby into a business, even with zero experience as an entrepreneur.

If you've ever wondered if turning a hobby into a business is possible, how to finally move past your fear in business, or why now is the perfect time for getting into running, this episode will inspire you to run (literally and figuratively) toward your dreams.

RESOURCES MENTIONED IN THIS EPISODE:

Female Founders Collective

Midlife on Purpose: Workbook

CONNECT WITH KATY RIPP:

Submit a letter HERE for a Dear Katy episode

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

CONNECT WITH CAITLIN KOWALKE:

Website: www.fearlessfeetrunning.com

Instagram: @fearlessfeetrunning

Ever felt like life threw you a curveball so hard it knocked the wind out of you?

You’re not alone. In this episode, I sit down with screenwriter and storyteller Victoria Male, who turned her most painful losses into creative fuel.

After losing her father unexpectedly in 2017, Victoria left her Hollywood career to pursue writing full-time. Her journey through processing grief, overcoming rejection, and reinvention is nothing short of inspiring.

We dive deep into finding the silver lining in life’s toughest moments, overcoming rejection, and the incredible power of healing through creativity.

Victoria shares what it was like working in the high-pressure world of Hollywood, the crushing moments of self-doubt, and how she finally decided to bet on herself.

Inside this episode, we’ll cover:

• How creativity became Victoria’s lifeline—and why expressing yourself can be one of the most powerful tools for healing through creativity.
• The truth about overcoming rejection—why it never really gets easier, but why it also doesn’t have to stop you.
• The reality of processing grief—how it sneaks up, how to honor your emotions, and why there’s no "right way" to move forward.
• Finding the silver lining in loss—how Victoria turned heartbreak into a career breakthrough and why loss can often be the catalyst for massive growth.
• The inside scoop on Hollywood and storytelling—the pressures, the setbacks, and the moment Victoria finally realized she had what it takes to be a full-time writer.

Maybe you’re standing at a crossroads, feeling the pull to create something meaningful but unsure if you’re "good enough." Maybe you’re navigating processing grief, overcoming rejection, or one of life’s many plot twists.

Wherever you are, you’re not alone. Tune in to this episode and let Victoria’s story remind you that sometimes, the hardest chapters lead to the most incredible transformations.

RESOURCES MENTIONED IN THIS EPISODE:

Female Founders Collective

Midlife on Purpose: Workbook

Episode 15: Creating a Meaningful End-of-Life Celebration with Alanna from Good Mourning

CONNECT WITH KATY RIPP:

Submit a letter HERE for a Dear Katy episode

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

CONNECT WITH VICTORIA MALE:

Website: www.victoriamale.com

CADER IDRIS Short Story

Instagram: @victoriamale1

Threads: @victoriamale1

Ever feel like your life is one big, epic story? Well, spoiler alert: it totally is!

In this episode, I’m diving into the concept of the hero's journey, a storytelling framework by Joseph Campbell. But trust me, it’s not just for your favorite movies—it’s a powerful way to understand your own life transformations.

From the "call to adventure" to overcoming trials and challenges, the hero's journey is a guide to embracing challenges and living authentically. I’m also sharing some deeply personal moments—like how my path to sobriety mirrored the hero's journey cycle—and how you can use it to transform your life.

Here’s a sneak peek at what we’ll uncover in this episode:

• What is the hero's journey, and what are some of the hero's journey examples real life?
• The hero's journey examples in movies - you’ll never watch Moana, Harry Potter, or Star Wars the same way again!
• How to overcome resistance to change using the hero's journey cycle. Why is it so hard to take that leap? We’ll unpack the role of fear and doubt and how they play into embracing challenges.
• My path to sobriety through the lens of the hero's journey. The messy middle, the trials, and the transformative rewards—it’s all here.
• Embracing challenges as the catalyst for growth: learn how facing life’s curveballs head-on and understanding the hero's journey cycle can lead to incredible transformation.

So, where are you in your the hero's journey cycle right now? Are you stuck refusing the call, grappling with embracing challenges, or standing victorious on the other side? Wherever you are, I’m cheering you on.

RESOURCES MENTIONED IN THIS EPISODE:

Sign up for the Hero’s Journey Mini Course here!

Mind Rebel Academy

Female Founders Collective

Midlife on Purpose: Workbook

CONNECT WITH KATY RIPP:

Submit a letter HERE for a Dear Katy episode

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

What if the roadblocks in your life weren’t holding you back, but were actually setting you up for a breakthrough?

In this episode, I’m sitting down with the amazing Melissa Fino, a high school dropout turned award-winning author and business coach, to talk about how to change your life completely—even when the odds feel stacked against you.

Melissa’s story is packed with lessons on resilience, authenticity, and overcoming adversity. Together, we dive into her personal transformation and her expert advice on dealing with imposter syndrome.

If you’ve ever felt stuck, uncertain, or unsure of your potential, this conversation will give you the inspiration and tools to move forward.

Here’s what you’ll hear in this episode:

• The powerful moment that inspired Melissa to figure out ways to change your life—and how you can, too.
• Why dealing with imposter syndrome is a key part of any transformation—and Melissa’s tips to get over it for good.
• The surprising role authenticity played in Melissa’s success—and how staying true to herself changed everything.
• Practical ways for how to change your life completely through resilience, community, and taking bold steps—even when it feels scary.
• Why women are dealing with imposter syndrome way more than men—and how Melissa broke free to step into her full potential.

Melissa’s story proves that dealing with imposter syndrome and embracing change are not only possible—they’re necessary for creating the life you truly want.

Tune in and let Melissa’s incredible story inspire you to figure out how to change your life completely. Whether you’re just starting out, working on dealing with imposter syndrome, or looking for ways to change your life for the better, this episode has something for you.

RESOURCES MENTIONED IN THIS EPISODE:

Female Founders Collective

Midlife on Purpose: Workbook

CONNECT WITH KATY RIPP:

Submit a letter HERE for a Dear Katy episode

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

CONNECT WITH MELISSA FINO:

Website: www.loveyourlifecommunity.com

Instagram: @iammelissafino

Freebies

Little Miss Perfect

Have you ever thought, “I want to get sober”, but felt stuck on where to start? Or wondered about the benefits of getting sober?

This week, I’m diving into a deeply personal and inspiring conversation with Whitney Combs, a health and wellness coach specializing in addiction and recovery whose journey from binge drinking to empowered sobriety is nothing short of transformative.

Whitney gets real about her struggles with alcohol, anxiety, and depression, and how she took her first steps toward sobriety in 2017. Now, she’s using her experiences to help others build lives they no longer want to escape from. Whether you’re looking for help getting sober, or just curious about sobriety tips, this episode is packed with actionable insights and heartfelt advice.

What you’ll learn:

• The life-changing moment that pushed Whitney to say, “I want to get sober”, and how she stayed the course.
• Why your recovery doesn’t need to follow a straight line—and how to embrace the non-linear nature of sobriety from alcohol.
• The surprising connection between vulnerability and lasting sobriety—how sharing your story can heal you and others.
• How societal pressures around drinking may be holding you back—and what Whitney says is the first step to freedom.
• Whitney’s sobriety tips that might surprise you—and why it’s all about focusing on progress, not perfection.

Whether you’re searching for tips for getting sober or exploring the benefits of getting sober, this episode is for you. Whitney’s raw honesty and practical advice will inspire you to trust yourself, take that first step, and build a life you love.

RESOURCES MENTIONED IN THIS EPISODE:

Female Founders Collective

Midlife on Purpose: Workbook

Whitney’s Recovery Resources

This Naked Mind by Annie Grace

Quit Like a Woman by Holly Whitaker

The Luckiest Club

CONNECT WITH KATY RIPP:

Submit a letter HERE for a Dear Katy episode

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

CONNECT WITH WHITNEY COMBS:

Have you ever felt the pull to change your life, but fear held you back?

You’re not alone. In this episode, I sit down with Candace Dudley, a former teacher who made the bold decision to pivot from her 13-year career in education to the world of entrepreneurship.

Burnt out and seeking something that fit her life better, Candace took a huge leap of faith. We dive into her inspiring story of transformation, discussing the courage it takes to embrace what you actually want, let go of societal expectations, and start living life for YOU.

This conversation is packed with actionable advice to help you reflect on your own life and take that first step toward change.

• The one wake-up call that made Candace realize she was burned out—and how she found the courage to act.
• Why community is critical for growth—and how to find your people.
• Strategies for overcoming fear and judgment when making major life changes.
• What made Candace pivot from teaching to entrepreneurship—and the unexpected lessons she learned along the way.
• How aligning with your values can change everything—and what that looks like in real life.

If you’ve ever wondered if it’s time to pivot, or felt stuck in a situation that no longer serves you, this episode is your sign to take that first step.

RESOURCES MENTIONED IN THIS EPISODE:

Female Founders Collective

Midlife on Purpose: Workbook

CONNECT WITH KATY RIPP:

Submit a letter HERE for a Dear Katy episode

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

CONNECT WITH CANDACE DUDLEY:

Instagram: @candacedudley

Website: www.candacedudley.com

Better Brave Podcast

Aligned Business Collective

Willow & Wren Website: www.willowwren.my.canva.site

Have you ever had a year so wild it felt like you were living in a sitcom? That was my 2024, and let me tell you—it was a ride!

In this episode, I’m spilling all the hilarious, heartfelt, and downright unexpected moments from my year. From navigating life on a scooter after multiple surgeries to adopting alpacas, to graduating from coaching school, and launching this very podcast - it’s been a journey full of resilience, self-discovery, and a whole lot of laughs.

My hope is to inspire you to reflect on your year—celebrate the wins, learn from the challenges, and step into 2025 feeling unapologetically you.

Here’s what you’ll hear in this episode:

• My recovery from major surgery, the emotional toll of immobilization, and lessons in patience and self-care.
• How setbacks like flood damage and selling a beloved lake house shaped my perspective.
• The bittersweet moments of watching employees grow and move on—and what they taught me about leadership.
• My journey to sobriety and its transformative impact on my personal and family life.
• How I’ve supported small business owners as a coach and the lessons I’ve learned from them.
• Why reflecting on your year helps you align your life with your values and celebrate your progress—no matter how big or small.

Join me for laughter, tears, and a lot of heart as I share my journey and help you reflect on yours. Let’s step into 2025 with a little more clarity and a whole lot of courage.

RESOURCES MENTIONED IN THIS EPISODE:

Female Founders Collective

Midlife on Purpose: Workbook

Episode 28: “All Families Have a Little Bit of Craziness in Them” Featuring My Siblings

Dream Bank by American Family Insurance

Mind Rebel Academy

Episode 13: How Chanlie Leavitt Left Teaching to Build Her Dream Business

Paradigm Podcasting

CONNECT WITH KATY RIPP:

Submit a letter HERE for a Dear Katy episode

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp