Evolution or Revolution

Courtney Kaplan
  • 5.0 (5)
  • Careers

A podcast about people making small (or very large) professional changes. I explore how they did it and how you can, too. If it's time to make a change, when do we trim the sails, and when do we burn the boats?

  1. 1d ago

    Mary-Lynne Williams: Leaving tech at 48 for peace & purpose.

    Mary-Lynne Williams is the CEO & Founder of Buffalo Firefly in NYC and Richmond VA. Buffalo Firefly is an Energy Wellness Company whose core mission is to bring the power of sound & energy medicine to the masses, allowing us to recalibrate and elevate from surviving to thriving. Energy medicine and sound healing allow us to regulate our nervous systems as a regular practice, encourage mindful presence, & invite people to achieve more abundance in all aspects of life — resulting in a deeper connection with their soul, the universe & their infinite potential. Before stepping into this work, she spent over two decades in the tech industry as a product design leader, including roles at Microsoft, Meta, and Zillow, where she shaped complex digital products, led teams, and worked at the intersection of systems thinking, user experience, and human behavior. She left her career in 2019 at the age of 48 to pursue peace & purpose. She evolved her leadership & coaching skills, reiki master training & general ability to do whatever the f*ck she wants to build a strong, successful brand. Her career in tech was successful by every external measure. Yet over time, Mary-Lynne began to recognize a growing disconnect between the work she was doing and the way she wanted to live in her purpose. She increasingly found herself in a chronic physical & mental health crisis and bravely chose to pivot.  Her story is not about leaving ambition behind, but about redefining success—trusting discernment, and choosing work that feels sustainable not just intellectually, but physically, emotionally, and spiritually as well. Instagram: @buffalofirefly or @buffalofirefly.nyc Shop & book appointments: www.buffalofirefly.com  Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    56 min

  2. May 26

    Stacey Gordon: Building dual identities. Fiction author. Tech leader.

    Stacey Gordon wanted to be a novelist since she was a kid. She loved reading and writing.  However, as an adult she was juggling a demanding career in tech, parenting, work travel, and life...with nothing left over for her own creative pursuits.  Stacey shares how she gave herself the space for writing and creating without sitting down to type or put pen to paper. How she continued her path through Covid, putting down a few hundred words a day in a small shed outside her house.  In this episode, she talks about how she’s building a life of a fiction writer. And she's now working on her fourth book. (And, yes, she still has a 9 - 5 job). She reveals the power of community and the importance of protecting your creative space — especially in the early, vulnerable stages. Patience and persistence really pays off: her book The Pearl Farmers is out this fall, and she’s building her author brand and helping other writers alongside her day job. Maybe your creative dream is just an idea now — but with small steps, it can become real. Website: https://www.staceygordonauthor.com/ Her book: thepearlfarmers.com IG: @staceygordonauthor Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    52 min

  3. May 11

    Danielle Malik: UX Leader's unexpected and gratifying path into housing solutions.

    After 20 years in tech consulting and leadership, Danielle was laid off. She knew it was time for a change. But what? Tech didn't seem like a path forward anymore. She made the unexpected but extremely gratifying shift into housing, becoming a housing provider for people challenged by the Bay Area rental market. Her company, Rising Tide Residences offers room rentals for men, women and families from diverse backgrounds, looking for stability and a chance to level up. These are people who have just come out of prison, have aged out of foster care, or have another  difficult situation that makes it hard to find housing. She's found success in making buildings into stable homes.  Hear her story and what she plans to do next.  To connect, learn more about their offerings, or to apply for housing, visit www.risingtideresidences.org Link: www.risingtideresidences.org Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    47 min

  4. May 4

    Erin Wade: Mac and Cheese Millionaire. From lawyer to restaurant innovator and author

    "I think the journey that most of us are on with work really has to do with a process of self discovery that has followed us our whole lives.” When Erin Wade was fired from her job as a lawyer, she decided it was time to take on a big project - creating a restaurant space that prioritized purpose, culture, and  hospitality. Erin is the founder of Homeroom, a restaurant with a cult following in Oakland, California, focused on delivering the absolute best mac and cheese.  She bootstrapped her restaurant, starting by investing her own money (no investors) and worked tirelessly in every corner—from building furniture to training staff. She was committed to launch a restaurant that was counter to typical dining culture. She designed systems rooted in transparency, employee engagement, and values that resonate beyond just serving mac and cheese. Our conversation unpacks some of the lessons learned as well as her advice to others hoping to build something meaningful. Erin Wade: https://www.erinwade.co/ Erin's Book: The Mac and Cheese Millionaire Homeroom: https://www.homeroom510.com/ 2018 WaPo Editorial Link  Chapters 00:00 - From Lawyer to Mac and Cheese Entrepreneur 03:38 - Childhood Influences and Entrepreneurial Spirit 06:13 - The Journey to Homeroom: A New Vision for Restaurants 09:12 - Building a Unique Restaurant Culture 12:24 - The Financial Risks and DIY Approach 15:15 - The First Weeks of Homeroom: Success and Challenges 18:04 - Hiring and Team Building: Lessons Learned 21:04 - Creating a Transparent and Engaging Workplace 23:52 - Values-Based Decision Making in Business 27:02 - Support Systems for Entrepreneurs Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    49 min

  5. Apr 22

    Tina Santiago-Keenan: Leaving tech, creating immersive experiences for people IRL

    In this conversation, Courtney Kaplan interviews Tina Santiago-Keenan, co-founder of Secret City, a creative design and production studio that creates immersive experiences. Tina shares her journey from working in tech at Facebook and Uber Eats to launching Secret City, which combines elements of escape rooms and immersive theater. The discussion covers the challenges of entrepreneurship, the impact of the pandemic, and the importance of community and in-person experiences. Tina also offers insights on career transitions, balancing work and family, and the future of Secret City. Links: Website: https://secretcity.studio/ Social Links: https://www.instagram.com/secretcityadventures/ Learn More: https://www.secretcityadventures.com/ Chapters 00:00 Introduction to Tina Santiago-Keenan and Secret City 05:35 Tina's Career Journey and Transition to Secret City 10:53 Challenges in the Early Days of Secret City 21:48 Navigating Challenges During COVID-19 27:08 The Importance of In-Person Connections 32:04 Advice for Career Transitions 36:29 Balancing Parenthood and Entrepreneurship 40:21 Introduction to Tina's Journey 42:53 The Importance of Patience and Testing Ideas 44:18 Leveraging Existing Skills and Collaboration Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    49 min

  6. Mar 11 ·  Bonus

    Bonus: Four dead end traps when we want to change

    Over the years, I’ve seen how we can lead ourselves into dead ends when it comes to change. There are some ways we think about change that are actually pretty unproductive and not really useful.. and are also common patterns. So, in this episode, I want to share a few of the ways we get blocked. Anything sound familiar? Getting to know how you sabotage or position yourself in dead ends is helpful to figure out how you're going to get out. I’ve also seen - and experienced firsthand - how change is navigated more successfully. How we can frame changes in our lives to be less terrifying or stressful and more fun, creative and adventurous. (Really!) But that's in the next mini-episode. I know I was squirming in my chair in recognition while recording this one. Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    14 min

  7. Mar 4 ·  Bonus

    Bonus: Change is here, but I don't wanna. Six phrases to move on.

    Today’s episode is different - it’s called: Change is here. But I don’t wanna. I wanted to share thoughts about dealing with professional change when you’d rather freak out. On the pod, I interview people who are choosing new paths. But many folks that didn’t make a decision, but have faced a layoff, downsizing, health crisis or other change that perhaps they didn’t plan for or expect. Today, I share 6 things to help you reconnect, and start moving forward when parts of you really want to fall apart. Books about change: Transitions, William Bridges - This is a classic. Whenever I refer this book online, I get comments that folks love it.The Search, Bruce Feiler - inspiring case studies of people making changes.The Good Enough Job, Simone Stolzoff - he has another one called How Not To Know which sounds like another helpful book that I look forward to reading.Mindset. The new Psychology of Success, Carol S. Dweck - counters our false ideas about how we tend to think people are “naturally” good at things.Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    18 min

  8. 10/15/2025

    Anna Bloom: Launching her product with love

    Have you thought about launching your own product? I know I have.   My guest today, Anna Bloom, has worked as a design leader at AirBnB, Facebook, and Cash App. In 2021, she took a leap to launch her own thing while still working full-time. Anna shares what it takes to get a physical product on the shelves and what keeps her going during difficult times.  PS Quick note, this isn’t a sponsored podcast. (But I am a huge fan of Anna and Lococo)  PPSS She offered listeners a one-time 10% off discount when you shop lococomagic.com  Code: ICONIC10 Website: LOCOCO Magic IG: @lococo_magic Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    25 min
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Ratings & Reviews

5
out of 5
5 Ratings

About

A podcast about people making small (or very large) professional changes. I explore how they did it and how you can, too. If it's time to make a change, when do we trim the sails, and when do we burn the boats?

Information

  • Creator
    Courtney Kaplan
  • Years Active
    2025 - 2026
  • Episodes
    15
  • Rating
    Explicit
  • Copyright
    © 2026 Evolution or Revolution
  • Show Website
    Evolution or Revolution

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