Stop Shrinking Yourself: On Owning Who You Are Later in Your Career | Victoria Woods

In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon welcomes back a guest listeners already know and love, Victoria Woods, founder and CEO of Chapelwood Financial Services and a chief investment advisor with over 30 years of experience. Victoria is the author of It's All About the Money, Honey and has hosted a weekly radio show by the same name for over 20 years, and she and her team provide the "Millionaire Experience" with a special focus on empowering women investors to take control of their financial futures. Their first conversation was so good they came back for a second, this time on a subject both women are living in real time: what it actually takes to grow a business in your 50s, 60s, 70s, and beyond, at a stage when their own parents were handed a gold watch and shown the door.

In this conversation, Victoria challenges the most entrenched piece of conventional wisdom about age: that you're supposed to wind down, retire at 65, and get out of the way. She's having none of it. If you choose to stay on planet Earth, she says, you need to be contributing value every single day, and ambition doesn't expire. What gets better with age, she argues, is that you finally figure out who you are. She calls it being bulletproof: you know your values, your work ethic, and how you want to show up, so when someone tells you that you can't wear pink nail polish in financial services or that you'd better "pull back the reins," you can simply say "next" and keep moving.

That theme of self-editing runs deep, and it's where Victoria and Kim meet most honestly. Victoria recounts the Dallas executive who told her, decades ago, "this is not Dallas, you might want to pull back the reins just a little," and how that kind of comment lodges in your head and sends you spinning. But both women land on the harder truth: often no one has to shrink us, because we do it to ourselves. Kim admits it's taken her a long time to stop self-editing and fully embrace the whole gestalt of who she is, and they celebrate the view from this stage of life, bulletproof, unapologetic, occasionally lonely, but entirely their own.

Much of the episode is a practical masterclass in energy and time. Victoria's non-negotiable belief is that the one thing you can never replace is time, which is why her firm runs on a simple promise: we don't waste time, money, or opportunity. When you're young, every opportunity feels like the last one, so you take them all and wear yourself out. Older and wiser, she runs each one through a filter, does this align with my vision, values, and goals?, and protects her energy fiercely, choosing just three speaking engagements each spring and three each fall. Her structure is tight but not rigid (80% planned, room to pivot on a dime), she does the three hardest things first each morning, and she's made her health a first priority after years of treating it as sporadic. Kim adds her own version: working smarter, guarding downtime, and releasing the guilt, echoing a friend's line, "you're allowed."

This episode explores:

• Why retirement at 65 is an outdated idea, and ambition doesn't expire
• Finally figuring out who you are, and becoming "bulletproof"
• Refusing to shrink yourself, and catching the ways you self-edit
• Why time is the one thing you can never replace
• Running every opportunity through your vision, values, and goals
• Protecting your energy and choosing commitments out of desire, not obligation
• Structure, doing the hardest three things first, and prioritizing health
• Releasing the guilt around rest: "you're allowed"
• How ambition matures into legacy and pouring into your team
• Why a book is thought leadership, not a marketing trinket
• Turning down a big opportunity to protect your reputation
• Why not every opportunity is really an opportunity
• Handling discrimination and the raise that changed her life
• Why it's never too late to start, and doing it scared
• "Don't take advice from broke people, physically, financially, or spiritually"

If you're building a business later in life, or anyone who's ever edited themselves smaller to make others comfortable, this conversation offers practical wisdom on energy, ambition, and legacy, honest talk about courage and discrimination, and a refreshing case that it's never too late to skid in sideways yelling "what a ride."

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Guest Details:

• Guest: Victoria Woods
• Company: Chapelwood Financial Services
• Book: It's All About the Money, Honey (also available as an audiobook)

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