Welcome to a solo episode on the fear of starting over.

I talk to people for a living, here on the pod but also in my coaching and speaking career. And in virtually every conversation, I talk to people that want to do something new.

And it’s scary as hell.

But in these conversations, something new emerges. It’s this fear of judgment that so many guests have talked about here on the podcast. So is it really your fear of starting over that’s holding you back, or is it the fear of people seeing you start over?

This topic has been a lightning bolt to the chest for me. So let’s talk about what it really is that’s holding us back, and I’ve come up with 3 specific habits we can build to move through it, and live the bigger life we deserve.

Key Takeaways

• Most of us aren’t afraid of starting over—we’re afraid of people seeing us start over.
• What feels like a huge leap to you might look like a natural next step to everyone else.
• Stories from past guests like Sensi Graves, Karl-Allen Muncy, PrettyLynne, and Greg Boyd remind us that reinvention is possible—and powerful.
• Confidence doesn’t come before action—it comes from action. The second time is always easier than the first.
• Try the Alyx Parks exercise: ask people how they’d describe you to someone else. It’s a humbling, inspiring way to see what others already believe about you.
• Judgment—especially self-judgment—is often the thing holding us back. As Sylvia Baffour says, start by writing for yourself and acting before you feel ready.
• The world sees more in you than you probably see in yourself. Let that build your conviction. Confidence will follow.

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Recommended Episodes

She’s Like the Wind with Sensi Graves

It’s Not Too Late to Create a Career You Love with Alyx Parks

Curiosity, Creativity & Connection with Sylvia Baffour

Throttle Therapy with Karl Allen-Muncey

What the Fxck are You Waiting For? With Greg Boyd

PrettyLynne: Soft Porn, Courage, Judgment and Finding Yourself

Today we talk to Alyx Parks — fly fishing guide, TV host, career coach, photographer, professor, and the self-proclaimed “girl who falls in frog ponds”.

For most of us, the idea of creating a career out of what we love is a promise we gave up on long ago. But Alyx is living proof it can be done. And she’s here to show us it’s not too late to shape a career — and a life — that actually feels like you.

In this episode, we talk about the importance of conviction over confidence, how to answer, “what do you do?” in a way that makes people pay attention, and her lessons from the river that guide her work and her life. We also dive into burnout, imposter syndrome, personal branding, and why we need to rethink our Mondays.

If you’ve ever felt like your job no longer fits, or maybe that you’re running out of time to finally find a career that suits you, this conversation is for you.

Please enjoy, Alyx Parks.

Key Takeaways:

• Conviction over confidence: You don’t need to feel confident to move forward — just have conviction in who you are and what lights you up. The confidence will follow.
• “I’m the girl who falls in frog ponds”: Alyx shares how reframing the way you introduce yourself can open doors and make people truly listen.
• The 'why tree' exercise: A powerful way to go deeper into your values and passions to build a more authentic personal brand — from the inside out.
• Say “okay,” not “yes”: You don’t need to feel 100% ready. Just be open. A lot of Alyx’s best adventures began with an “okay, I’ll try.”
• Lessons from the river: Fly fishing is full of metaphors — about uncertainty, learning by doing, casting even when you can’t see what’s under the surface.
• The power of “Mediocre Mondays”: You don’t have to crush it every Monday. Permission to show up as you are and reset.
• We only accept the love we think we deserve: A beautiful reminder to stop pushing away compliments and start seeing yourself the way others already do.
• You are the bubble: We often chase a feeling of safety, energy, or connection — but that feeling can come from you. Let people into your world.

Links and Resources:

Alyx on LinkedIn: https://www.linkedin.com/in/alyxparks/

Alyx’s website: https://www.ontarioflygirl.com/

Alyx on Instagram: https://www.instagram.com/ontarioflygirl/?hl=en

Alyx on YouTube: https://www.youtube.com/channel/UCk2DJldSE7hhQTU8rjNHeYw

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Today we talk to Mike Michalowicz, bestselling author of Profit First, a revolutionary system implemented by over a million companies around the world to make profit a habit, not a year-end event. As Mike puts it, the entrepreneurial dream of working for yourself, working as much as you want, having complete freedom - it’s a myth for most people. Most business owners I know are stressed out, working their asses off and barely getting by. That was Mike too, so he decided to start writing about it. And that was 10 books ago.

So I’ve got a confession to make. This episode was a bit of a test, a challenge to myself. I was curious…can I make a conversation about finance interesting? What could we possibly say that hasn’t been said? Well, if you know Mike you know I had nothing to worry about. This was one of the most fun conversations I’ve ever had. Mike’s got a story for everything, including the financial rock bottom that inspired his new book, The Money Habit.

I’ve never been great with money, and I know I’ve left a lot of it on the table. As I near what most people call retirement, that’s starting to concern me more than it used to. But honestly, I feel like I’m just getting started. So sure, I could have used this conversation 20 years ago. But it’s also just what I need, right now.

If you’re struggling to make your business work for you, or maybe you want to hear about how someone writes 10 best selling books about something no one wants to talk about - this one’s for you.

Please enjoy, Mike Michalowicz.

Key Takeaways

Entrepreneurial Poverty is Real: Mike defines it as the painful gap between the outward appearance of success and the inner financial struggle many entrepreneurs face. His mission is to eradicate it.

Profit First Philosophy: Instead of treating profit as what’s left over, take it first. The formula changes from Revenue – Expenses = Profit to Revenue – Profit = Expenses. It’s a mindset—and a habit—that shifts everything.

Behavioral Triggers > Discipline: Mike shares how behavioral psychology plays a huge role in money management, and why creating systems (like putting sneakers on the toilet seat) work better than relying on willpower.

Multiple Bank Accounts = Clarity: Whether for your business or personal life, setting up separate bank accounts for different purposes helps remove emotion from financial decisions and creates instant visibility.

Your Business Shouldn’t Depend on You: The entrepreneur’s job isn’t to do the work, but to create jobs. If you're doing everything yourself, you’re stealing an opportunity from someone else—and setting yourself up for burnout.

Build Wealth at Home, Too: The Profit First system isn’t just for business. Mike adapted it for personal finances after realizing he was profitable in his company, but still living paycheck to paycheck at home.

The Power of Starting Small: Mike encourages listeners to take one simple step—open a new bank account and start moving money into it weekly for the thing that causes the most financial stress. That clarity creates momentum.

It’s Never Too Late: Whether you’re 25 or 55, building better financial habits now will absolutely change your future. As Mike says: “Profit is not an event. It’s a habit.”

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Links and Resources

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This is a re-release of my original conversation with Greg Bennick from early 2024. It is simply too good not to share again. Greg is a punk rocker, activist, documentary filmmaker, philanthropist, keynote speaker, juggler and expert coin collector. He’s also written a book, “Reclaim the Moment: Seven Strategies to Build a Better Now.”

I could have talked to Greg for an hour about any one of these parts of his life - he’s got a way of making everything that interesting. We talk about Seattle’s teen dance ordinance, a real-life Footloose law that he helped overturn. We talk about how punk music is really just love songs. And we explore the central themes that tie all of his various pursuits together.

If you ever struggle with focusing on what matters, finding your purpose or trying to figure out what makes you special in this world - this conversation is for you.

Please enjoy Greg Bennick.

Key Takeaways:

1. Changing the system from within: Greg’s involvement in overturning Seattle’s teen dance ordinance showcases the power of grassroots advocacy and persistence when making changes from within the system..
2. Straight edge movement: Explore a subgenre of punk that emphasizes a lifestyle free of alcohol and drugs that is centered around the love of music..
3. Majestic failures: Nobody advertises their failures. But behind every best-selling book or successful keynote speech are dozens of failures that paved the way for the success everyone sees.
4. Re-inventing yourself throughout your career: Your journey is unique. You have more to offer the world than you think. Deciding what to do next in your career is not about what, but why.
5. Focus and Balance: Strategies to maintain focus and balance in a world filled with distractions, as discussed in Greg’s upcoming book, “Reclaim the Moment.”

Resources Mentioned:

• Podcast: Let the Kids Dance (KUOW & NPR) – A deep dive into the history of Seattle's teen dance ordinance.
• Books:
• Denial of Death by Ernest Becker
• Art and Artist by Otto Rank
• Man's Search for Meaning by Viktor Frankl
• Greg’s Book: Reclaim the Moment: Seven Strategies to Build a Better Now by Greg Bennick

Connect with Greg Bennick:

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Today we talk to Chelsea Burns —aka The Marketing Psychologist—about the connection between how our brains are wired and the brands we choose. Chelsea is uniquely qualified to talk about this - she has a Masters in Psych, has spent 17 years in marketing and has been in therapy most of her life.

So spoiler alert: most of the purchasing decisions we make, yeah we make them subconsciously. Savvy marketers know this, so we’re all vulnerable to being manipulated into buying things we don’t need. I have a drawer full of late-night Instagram purchases I’m too embarrassed to return. Chelsea shares real-life examples of some of these bad actors, and arms us with the brain science we need to protect ourselves.

But here’s the exciting part. We can use this knowledge for good.

As employees, we can build personal brands that create authentic connections with the people we work with.

As entrepreneurs, we can build ethical companies that give our customers a true sense of belonging, so they never want to leave.

This isn’t just a conversation for marketers. It’s for anyone who wants to be more conscious about the choices they make and the messages they put out into the world.

Please enjoy, Chelsea Burns

Takeaways

From Trauma to Trust: Chelsea shares how her early therapy work helped her understand the wiring of the brain—and how that same wiring shows up in marketing and branding.

Marketing Is Relationship-Building: Whether you’re selling education or granola bars, Chelsea explains how good marketing is really about building healthy, reciprocal relationships.

The Power of Self-Awareness: Only 5% of our decisions are conscious—Chelsea breaks down how emotional triggers and subconscious pathways shape what we buy and why.

Manipulation vs. Persuasion: The line gets crossed when there's no real value for the customer—especially when companies prey on insecurity, fear, or false urgency.

The Role of Belonging: Chelsea’s research showed that a strong sense of belonging increases well-being and business success. Brands that create belonging don’t just sell more—they change lives.

The Cost of Broken Trust: Chelsea unpacks how Target’s rollback of DEI efforts broke trust with values-driven customers (including her 9-year-old daughter), and why regaining that trust isn’t just about PR.

Ethical Branding Is the Future: Brands that invite instead of sell, co-create with their customers, and stay grounded in values are the ones that build lasting relationships—and loyal communities.

Practical Tools for Conscious Consumers: Chelsea recommends the Yuka app to help identify harmful ingredients in everyday products and encourages people to stay informed and curious.

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Originally recorded in the spring of 2024, my conversation with Sylvia Baffour stays with me every day. Sylvia is a keynote speaker on emotional intelligence and has worked with leaders in 460 major corporations to help them better connect with their teams and customers. She was voted one of the top 15 female inspirational speakers alongside Mel Robbins and Oprah.

Sylvia’s early journey was already unique and inspiring, but it was a chance meeting with writer and activist Dr. Maja Angelou that launched a life-long relationship that shaped her life.

We dig into what emotional intelligence is and what leaders need to do better if they really care about the culture they’re building.

But probably my favourite takeaway - the power of curiosity. How it’s the secret to making people feel heard and creating a lasting emotional imprint on those around you.

This conversation really stayed with me - one of my favourites so far.

Please enjoy, Sylvia Baffour.

Takeaways

• Emotional intelligence is not about being “nice” — it’s about being aware of your emotions and how they affect others, especially in challenging moments.
• Sylvia’s global upbringing, and her father’s example, gave her a deep understanding of people, which fuels her work today.
• She was mentored by Dr. Maya Angelou for over 12 years, and one of the most powerful lessons she took away was how to leave others feeling seen and valued.
• “Shifting phrases” — like Is it possible they’re seeing things differently? — can help us manage emotional triggers and avoid reacting from a place of anger or defensiveness.
• Sylvia encourages us to “mind our monologue,” paying close attention to how we speak to ourselves during tough moments.
• Before any conversation or meeting, ask yourself: How do I want the other person to feel when we’re done? That simple intention can change everything.
• Public speaking is a privilege, and the best communicators always ask, Why should the audience care?
• Creativity thrives when we replace judgment with curiosity. Whether you're writing a book, a song, or giving a talk — just start. Don’t wait to be perfect.

Connect with Sylvia

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Today we talk to Chris Paul Rainbows, a storyteller, strategist and queer educator on a mission to make everyone feel like they belong.

Chris talks about growing up queer in a small border town, struggling with OCD and anxiety, building a successful company only to have a breakdown, and tearing it all apart to start over. We touch on PRIDE as a mix of celebration and rebellion, what it means to be an ally and how this is not the oppression olympics - we all have hard stories that make us who we are. And we need to embrace them to find our people.

But the best part is the stories - every one of them full of joy and hope. We’ve got a pumpkin empire, gay cakes, and a tortoise with a prolapsed butthole named Rock Hudson. If you’re ever struggled to find your voice, or need inspiration to chase a bigger life, Chris will make you believe anything is possible. Or maybe you just need some 100% joy in your life today.

Please enjoy, Chris Paul Rainbows.

Every other week, join your host Bob Mathers, keynote speaker for conversations designed to push you out of your comfort zone. Each episode delivers boundless insights and ideas that matter by inspiring you to get off autopilot and keep chasing curiosity.

Takeaways

• Pride has evolved for Chris from partying in their 20s to giving talks, reading books to kids, and spreading queer joy by simply living openly and authentically.
• Growing up queer in a small rural town with no representation on TV felt isolating and led Chris to leave home at 18 to find community.
• Chris’s mental health struggles with OCD reached a breaking point while running a stressful business, but therapy, medication, and support from their husband helped them rebuild their life around what truly made them happy.
• Chris launched The Unicorn Rebellion to do the creative work they love on their own terms—without the stress of a big agency—and created a life with chickens, parrots, bunnies, and a tortoise named Rock Hudson.
• His viral “Pumpkin Empire” taught them the power of storytelling on social media and how curiosity, kindness, and including your community can make even the strangest moments into something beautiful.
• Chris’s story of the world’s gayest cake, or “gayke,” shows how small, joyful acts of visibility can ripple out to inspire and empower others in ways you can’t predict.
• Allyship isn’t something you call yourself; it’s something you earn by consistently showing up, learning, and using your privilege to open doors for others.
• Finding your voice means discovering what you’re passionate about changing in the world—and knowing that everyone’s story, no matter how big or small, has the power to help someone else.

Links and Resources

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