299: From fit-in to stand-out: How midlife entrepreneurs can build a personal brand with soul - with Judy Winslow

CRANK THE 3RD: Exploring the entrepreneurial + creative side of life post 50

In this episode of Crank The 3rd, we dive into what it really means to stand out in your 50s and beyond.

Host Trevor Young sits down with Judy Winslow, founder of Unforgettable Brands, to explore how experienced professionals and entrepreneurs can build a soulful, authentic, and unforgettable personal brand in the so-called “third chapter” of their careers.

Judy shares her powerful personal story - from facing depression and feeling out of place as a young woman, to discovering her purpose through creativity, business, and brand strategy.

Together, Trevor and Judy unpack the importance of embracing your unique twist, reconnecting with your values, and getting comfortable with being a “unicorn”—someone who dares to be different in a world that often rewards blending in.

You’ll get practical tips on how to bring out your individuality, what it means to infuse your brand with real soul, and why your past experiences are the raw material for your finest work.

Judy also pulls back the curtain on her process for helping clients get braver and bolder, whether you’re building a team, scaling your business, or preparing for a big-stage moment like a TEDx talk.

If you’re ready to stop playing small, own your story, and amplify your impact, this conversation is packed with wisdom, humour, and actionable steps.

Let’s get started!

QUOTABLE QUOTE FROM JUDY:

“No one speaks quite like you. No one articulates quite like you. No one sees your industry quite like you, nor do they have the experience. So… just being you—that's so fabulous.”

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Visit Judy's website - https://unforgettablebrands.com/

Connect with Trevor on LinkedIn - https://www.linkedin.com/in/trevoryoung