299: From fit-in to stand-out: How midlife entrepreneurs can build a personal brand with soul - with Judy Winslow
- S10E299
- 47:34
- July 16th 2025
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
CRANK THE 3RD: Exploring the entrepreneurial + creative side of life post 50
CRANK THE 3RD is a weekly podcast in which we explore the entrepreneurial and creative side of life post 50.
You've survived the first two professional chapters of your lives - 20s to mid-30s (chapter 1) and mid-30s and through your 40s (chapter 2).
Welcome to the 3rd chapter! By this stage of your professional life, you've seen a lot, done most things, made some cash, expanded your horizons and probably are more comfortable in your skin than at any other time.
But it’s not necessarily all sunshine and roses either. At some stage, many of us reach a point where we ask: “Is that all there is?”
While we have oodles of experience under our belts and are a lot more sure of ourselves and confident in our own abilities, we also live in a fast-paced volatile world.
Technology is ever-changing, and the AI wave has only just begun. A sense of uncertainty is never far away. We know that if we stand still, we run the risk of losing relevance.
No matter how savvy, experienced and connected we are, certain challenges remain.
But on the upside, the number of opportunities staring us in the face is enormous, and unprecedented!
The goal of CRANK THE 3RD is to inspire energised, forward-thinking 50 and 60-somethings to continue to think expansively and creatively about their current situation, and to ponder, plot and plan the exciting road they have ahead of them.
You’ve put in the hard yards: now it’s time to capitalise!
Let’s dive in!
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