What happens when you’ve done everything “right” — the job, the marriage, the boxes checked — and still feel empty inside? I know firsthand how scary (and freeing) it can be to admit that something isn’t working, and that’s why I am so grateful for this conversation with life coach and truth-teller Amanda Lipnack-Radel. In this episode of The Hurray Show, we open up about mid-life awakenings, why grief can make space for joy, and what it really looks like to step into your “second act.” This one’s for you if you’ve ever wondered: is it too late to start over?

Disclaimer: Psst! Some of the brands linked or mentioned in the podcast are proud partners of mine or I may get a small thank you commission if you purchase through me. Your purchase through those links helps a lot in keeping articles like this coming your way. Either way, I always share items that I truly love and can help you say hurray!

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Show Notes

Hurray! In this episode of The Hurray Show, host Kimmay Caldwell is joined by life coach, podcaster, and truth-teller Amanda Lipnack for an honest conversation about mid-life awakenings, messy emotions, and what it means to start a “second act.”

Amanda knows firsthand what it feels like to “check all the boxes” and still feel deeply unfulfilled. At 40, in the midst of her second divorce, she found herself numb, sad, and convinced she wasn’t worthy of love or joy. But by finally allowing herself to feel the sadness she had been running from, Amanda discovered something surprising: grief created space for joy.

Together, Kimmay and Amanda explore how feeling the full spectrum of emotions—sadness, joy, fear, hope—can open the door to authenticity, healing, and a life that feels real (because it is!). They also dig into the myths of mid-life, why menopause might just be “cougar puberty,” and how to build boundaries that keep you safe while still letting love and connection in.

This episode is a compassionate reminder that even if your life doesn’t look the way you thought it would, change is possible – and you are absolutely worth it.

Key Takeaways:

• The “Second Act” is possible. Life doesn’t end at 40 (or 50, or 60). If what you’ve been doing isn’t working, you can rewrite the script.
• Feel the full spectrum. Sadness isn’t the enemy – allowing grief creates space for joy to flourish.
• Authenticity outweighs approval. Hear Amanda’s advice on how to worry less about what others think, and why it is freeing, even if it feels scary at first.
• Boundaries are self-care. Not everyone gets full access to your heart. Kimmay and Amanda discuss the “Hurray House” method for letting the right people in.
• You are worthy of change. Therapy, coaching, books, and community can all support you, but the first step is deciding you’re worth the work.

Mentioned in this Episode:

• Brené Brown – Atlas of the Heart 
• Elizabeth Lesser – Broken Open
• Augusten Burroughs – This Is How & Running With Scissors
• The Hurray Show S1: E3 – How to Anti-Airbrush Your Life
• Tom Boy X Underwear

Get in touch with Amanda Lipnack-Radel at:

Amanda Lipnack Coaching: amandalipnack.com

Instagram: @amandalipnack & @alrcoaching

Facebook: Amanda Lipnack Coaching

Podcast: Little Miss Recap

All that and more on this episode of The Hurray Show. Tune in and celebrate your story – one HURRAY at a time.

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Get To Know The Guest

Amanda Lipnack-Radel

Amanda Lipnack is a heart-centered life coach, podcaster, and project manager dedicated to helping midlife women reimagine what’s possible for their next chapter. At 40, she realized she didn’t want to spend the rest of her life feeling unfulfilled, so she committed to understanding what truly makes happiness stick and discovered that grief doesn’t block joy, it creates space for it. She combines warm curiosity with practical tools like coaching, action plans, and emotional boundary-building to help women align their adult lives with their deepest desires. Amanda believes that you are worthy, exactly as you are, and that your “second act” can be built on love, creativity, and bold self-trust. 

Follow Amanda on Instagram and Facebook, hurray!

On this episode:

Your Turn: Have you ever reached a point in life where you realized the “script” you were following wasn’t bringing you joy? What did you do next? Share with me on Instagram or TikTok!

Free Fit Guide & Video

Want to wear a bra without ripping it off at the end of the day? Watch Kimmay’s video tutorial on getting a comfortable fit, plus a printable guide and checklist to take shopping. Don't spend another minute feeling uncomfortable in your bra.