Not all career changes are dramatic. Some are deeply deliberate—and a little serendipitous.

In Part One, Alison Stewart, COO of Overalls, walks us through her transition from 10+ years in the financial sector to co-founding a startup she discovered on LinkedIn. With two kids at home and a stable job in a Fortune 100 company, Alison didn’t jump recklessly. Instead, she asked the hard questions: Am I fulfilled? What do I want next? And how much risk am I really willing to take?

This episode unpacks what happens when you combine career intuition with operational precision—and how a well-timed DM can change everything.

Key Highlights of Our Interview:

From Corporate Climb to Personal Wake-Up Call

“Time started blending together during the pandemic. I had to ask: Am I actually happy? Or just coasting in a cycle of constant resets?”

The Treadmill of Big Company Life

“With every leadership change, we took ten steps back before we moved one forward. I was learning—but I wasn’t growing.”

Childhood Moves, Adult Adaptability

“Moving five times by age 14 taught me to see change as an opportunity. That mindset still guides me today.”

The Pregnancy + Merger Combo

“Just weeks before giving birth to my second child, my business unit was sold. The uncertainty could’ve been paralyzing—but I chose to treat it as a new beginning.”

Risk—But Not Reckless: Mapping a Smarter Pivot

“I didn’t quit cold. I asked: What am I good at? What fulfills me? What can my family support? I gave myself permission to explore—and permission to say no.”

The Non-Obvious Job Search Strategy

“Instead of applying for jobs I knew I could do, I reverse-engineered what I wanted: values, pace, purpose. I wasn’t chasing a title—I was chasing a fit.”

The Moment Overalls Popped Off the Screen

“When I read about Overalls, something clicked. I didn’t even know if they were hiring. I just knew I had to reach out.”

Why LinkedIn Isn’t Just Noise

“It wasn’t a random scroll. I used LinkedIn intentionally—to research, reflect, and eventually connect. That DM changed everything.”

Communicating Across Industries

“Moving out of insurance meant translating my skill set. I had to show how what I did mapped onto what I wanted to do.”

Community + Clarity = Career Confidence

“A networking group of MBA alumni helped me spot my own excitement. They said, ‘This one lights you up. Go for it.’ That feedback made all the difference.”

____________________

Connect with us:
Host: Vince Chan | Guests: Alison Stewart

--Chief Change Officer--
Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence
for Transformation Gurus, Black Sheep,
Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.
17 Million+ All-Time Downloads.
80+ Countries Reached Daily.
Global Top 1.5% Podcast.
Top 10 US Business.
Top 1 US Careers.

>>>160,000+ are outgrowing. Act Today.<<<

Most people retire after one successful business. Ral West kept building.

In this episode, Ral shares how she co-ran a charter airline between Alaska and Hawaii for 25 years—eventually selling it to Alaska Airlines—and then launched into her next chapters: owning cruise ships, investing in real estate syndications, and helping other entrepreneurs find sustainability without burnout.

From navigating gender bias in a family business to designing automated booking systems and letting go of control through delegation, Ral’s story is a masterclass in evolving through every season of life. Whether you’re in the startup grind, planning an exit, or rethinking what “retirement” means—her story will get you dreaming smarter and bolder.

Key Highlights of Our Interview:

The 25-Year Flight Plan: From Tourism to Aviation

“I started in Alaska tourism. My husband was in real estate. Together, we launched a charter service to Hawaii—and turned it into a full airline.”

Selling to Alaska Airlines: A Strategic Exit

“We knew they were entering the Hawaii market. Instead of competing, we showed them why buying us was smarter.”

When Cruise Ships Became the Next Chapter

“We bought five small cruise ships out of bankruptcy, redesigned the Alaskan travel experience—and then pivoted again after COVID shut everything down.”

Why Real Estate Was the Right Post-COVID Play

“We own part of over 6,000 apartment units in five states. Why? Because homeownership is becoming harder, and rental demand is rising.”

From Exhaustion to Empowerment: Lessons from the Middle Years

“Between 35 and 55, I was stretched thin—business, babies, burnout. I had to build systems and teams to stay afloat.”

The Real ROI of Delegation

“Delegation isn’t about giving things away—it’s about building trust and giving others space to shine.”

Turning Intuition into Systems

“I realized I made ad-spend decisions based on 3-day sales trends. Once I named it, I turned it into a repeatable formula my team could follow.”

Reservation System Reinvention

“We invested two years into building an online booking system that ran 24/7—freeing us from the phones and doubling our revenue.”

Not Your Typical Retirement Plan

“I could’ve retired 16 years ago. I didn’t. I love working. My retirement plan is doing what I want, when I want, with the systems to support it.”

Advice for Entrepreneurs at Any Age

“Be bold. Stay curious. Watch the world. And don’t let age—or fear—be the thing that keeps you small.”

______________________

Connect with us:
Host: Vince Chan | Guest: Ral West

--Chief Change Officer--
Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence
for Transformation Gurus, Black Sheep,
Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.
17 Million+ All-Time Downloads.
80+ Countries Reached Daily.
Global Top 1.5% Podcast.
Top 10 US Business.
Top 1 US Careers.

>>>160,000+ are outgrowing. Act Today.<<<

Comebacks rarely happen all at once. They’re built in small moments, with slow wins.

In Part Two, Athena Brownson opens up about what it really takes to rebuild when chronic illness becomes your new normal. She walks us through her mindset rituals, the power of written affirmation, and how she finally learned the one thing no athlete ever wants to admit: she couldn’t do it alone.

From retraining her brain to let go of pain patterns, to redefining leadership through delegation, Athena shares a playbook for resilience that’s part spiritual, part practical, and 100% earned.

Whether you’re healing from illness, burnout, or just life’s curveballs—this is your reminder that growth is still possible, even in survival mode.

Key Highlights of Our Interview:

Training Her Brain to Stop Listening to Pain

“Our brains get stuck in pain patterns. I use breathwork, affirmations, and routines to teach mine a new message: You’re safe. You’re healing.”

Why Routines Became Her Lifeline

“Every day starts with journaling, breathwork, affirmations. I write: I am healthy. I am healing. My body is getting stronger. I speak it until I believe it.”

Delegation as a Leadership Superpower

“Being sick taught me what being a leader really means—letting go. Delegation isn’t giving up control; it’s giving others a chance to thrive.”

How Chronic Illness Redefined Her Business Model

“I couldn’t keep doing it all. So I built a team that could run without me on bad days—and succeed with me on the good ones.”

Your Tribe Is Everything

“After ten years, I finally found people who want me well. Who care more about my health than a commission. They’re my family now.”

The Mental Game of Chronic Recovery

“You don’t need to fix it all today. Start with one percent better. That’s how I got out of survival mode.”

Accountability on Paper

“I print out my must-do list and check it off every day. If I don’t write it down, it doesn’t happen. It’s how I stay in motion.”

Pen, Paper, and Confidence

“Writing makes the healing real. Every word reinforces a new belief system—one I can see and hold.”

Jodie Foster, Masterclass, and the Simplicity of Creation

“All you need is pen, paper, and confidence. That line hit me. You don’t need a perfect plan. You just need to start.”

Her Message to Anyone Struggling

“It’s okay to acknowledge pain. Just don’t stay stuck in it. Tiny steps add up. Your healing doesn’t need to be loud—it just needs to begin.”

______________________

Connect with us:
Host: Vince Chan | Guest: Athena Brownson

--Chief Change Officer--
Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence
for Transformation Gurus, Black Sheep,
Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.
17 Million+ All-Time Downloads.
80+ Countries Reached Daily.
Global Top 1.5% Podcast.
Top 10 US Business.
Top 1 US Careers.

>>>160,000+ are outgrowing. Act Today.<<<