What’s Stopping You from Outgrowing Yourself?
Change Ambitiously. Outgrow Yourself.
At Chief Change Officer, we harness change as a superpower—fueled by globa...
#227 Sara Lobkovich: Why Playing Life on Hard Mode Might Be Your Best Advantage – Part Two
Some people color inside the lines. Others—like Sara Lobkovich—ditch the coloring book altogether and make their own rules. A proud introvert, ADHDer, and change-maker, Sara turned years of navigating life’s twists into two books designed to help others do the same. In Part 1, we’ll hear how she went from feeling like an outsider to building a thriving career by embracing what makes her different. And in Part 2, we’ll break down her books—what’s inside, who they’re for, and why they actually work.Key Highlights of Our Interview:A Love Letter To Square Pegs Who Don't Fit In"This book is a love letter to me earlier in my career. I know I'm not alone. I know there are so many other people who are having experiences like I did.If I had written this earlier in my life, if I had somehow had the capacity to write this earlier in my life, I would have written a book to people who are strategically wired and feel like they don't fit in a world that's really focused on tactics to people who feel like square pegs in their careers, like we're always a square peg trying to fit into a round hole and just don't fit in."Two Books, One Mission: Simplifying Strategy and Goal Setting“I realized I had two books: one is the No BS OKRs workbook, and the other is about modernized, human-centered strategic planning.”The Moment ‘You Are a Strategist’ Became the Book Title I Had to Write“I knew the title had to be ‘You Are a Strategist.’ I rewrote the book to deliver on that title.”Empowering Your Inner Strategist: No Matter What Job You Do“You might be a dishwasher, noticing things in the restaurant—there’s strategy in everything we do.”_____________________Connect with us:Host: Vince Chan | Guest: Sara Lobkovich______________________--Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,TransformationGurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.
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#226 Sara Lobkovich: Why Playing Life on Hard Mode Might Be Your Best Advantage – Part One
Some people color inside the lines. Others—like Sara Lobkovich—ditch the coloring book altogether and make their own rules. A proud introvert, ADHDer, and change-maker, Sara turned years of navigating life’s twists into two books designed to help others do the same. In Part 1, we’ll hear how she went from feeling like an outsider to building a thriving career by embracing what makes her different. And in Part 2, we’ll break down her books—what’s inside, who they’re for, and why they actually work.Key Highlights of Our Interview:The Milk Activist: Chocolate Milk Equality at Age Nine“I successfully petitioned the cafeteria ladies for milk equality… so that the bag lunch kids could also have chocolate milk on Friday.”Job Hopping or Scanning? Redefining a Nonlinear Career“They called it job hopping, but my career coach reframed it as being a ‘scanner’ with lots of interests. Turns out, I wasn’t hopping, I was just too excited to make things better!”The Burnout Chronicles: From Always-On-the-Go to Needing a Why“I was that guy on the plane, always on the go. My dog lived with my parents for way too long. That lifestyle led me to burnout, and I realized I needed to do things differently.”Curiosity as a Cure: How Staying Curious Helped Me Avoid Feeling Stuck“Curiosity is an antidote to stuckness and anxiety. Later in my career, I developed the ability to always have a playground in my brain—something to learn.”Turning a Job Disappointment into an MBA in Enterprise Politics“Instead of feeling frustrated, I reframed my experience as a mini MBA in navigating large political organizations with resistance to change.”Strategy Isn’t About Being the Smartest in the Room—It’s About Asking the Right Questions“Being a strategist is not just being the smartest person in the room. It’s having a toolkit of questions that uncover facts, spark insight, and develop ideas.”_____________________Connect with us:Host: Vince Chan | Guest: Sara Lobkovich______________________--Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,TransformationGurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.
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#225 Love, Logic, and a Reality Check: Waverly Deutsch on Changing for the Better – Part Three
We’re closing out Love and Logic with a powerhouse—Waverly Deutsch, the theater-loving, PhD-earning, startup-coaching dynamo. A fierce advocate for LGBTQ and women entrepreneurs, Waverly doesn’t just give advice; she gives strategies that work. At WyseHeart Advisory, she’s proving that retirement isn’t about slowing down—it’s about lifting up the next generation with tough love and a little bit of stage presence.Key Highlights of Our Interview:A Coach’s Secret Weapon“The key to trust and transformation in coaching lies in active listening. People often speak in long, winding narratives. The magic is in boiling it down to the core message—a few sentences that make them feel truly understood and heard. By distilling and refining, you don’t just hear—they feel heard, understood, and empowered to act.”AI Can Polish, But Can’t Replace the Human Spark“AI can help craft a polished pitch or refine a resume, but it can’t simulate the deep understanding and personal experience that resonate in real-life interactions. The investor meeting? That’s where your own knowledge and authenticity come into play.”The Dating Analogy for Entrepreneurs“Pitching to investors is like dating. The 10-minute pitch? That’s the coffee date. The in-depth meeting? That’s the dinner date. The term sheet? That’s the engagement ring. True commitment comes when the contracts are signed and the check is in the bank.”The Age and Cost Equation“Older professionals face a harsh reality: companies often trade senior salaries for multiple junior hires. This economic shift means adapting, whether through freelancing, consulting, or pursuing entirely new avenues of work.”Consulting as the Bridge“Many transitioning entrepreneurs find opportunities as consultants. Whether it’s an interim CFO role or building sales strategies, the key is to be willing to revisit foundational work while leveraging years of expertise to establish credibility in new ventures.”_________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.
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#224 Love, Logic, and a Reality Check: Waverly Deutsch on Changing for the Better – Part Two
If there’s one thing Waverly Deutsch doesn’t do, it’s fluff. In Part 2 of Love and Logic series, she shares her bold journey from STEM to stage, academia to entrepreneurship, and why she built WyseHeart Advisory to help founders thrive. A champion for LGBTQ and women entrepreneurs, Waverly proves that real mentorship isn’t about hand-holding—it’s about giving the kind of feedback that sticks.Key Highlights of Our Interview:Blending Heart and Head“Whether it’s calming executives’ cautious approaches or reining in overly ambitious young entrepreneurs, success lies in balancing heart (vision) with head (practicality). It’s about building a compelling story that resonates with both emotions and logic.”Executives: Breaking the Incremental Mold“Executives often pitch ideas that feel safe but lack innovation. They’re so aware of corporate barriers that their creativity gets stifled. My role? Push them to think beyond incremental improvements and aim for groundbreaking changes that truly stand out.”“Executives often present highly calculated plans—‘$5 million investment for $7 million returns.’ While safe, it doesn’t excite investors. Encouraging them to aim higher, to envision $50 million, injects the passion and ambition their pitches often lack.”Unleashing Undergraduate Imagination“Undergraduates are brimming with ideas because they haven’t yet encountered the roadblocks of the corporate world. The challenge is teaching them the process—how to take their boundless creativity and add logic, research, and structure to turn dreams into sustainable ventures.”Overzealous Optimism Meets Reality“On the flip side, young entrepreneurs brim with optimism, promising billion-dollar outcomes for modest investments. The challenge? Bringing logic into their bold dreams—helping them see the steps, resources, and realistic pathways to scale.”The Power of Experimentation“Sometimes, all it takes is encouraging an entrepreneur to think bigger—just as an exercise. That simple shift in perspective can unlock enormous potential, as it did with Simple Mills, now a model for blending passion and pragmatism to scale innovation.”_________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.
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#223 Love, Logic, and a Reality Check: Waverly Deutsch on Changing for the Better – Part One
Welcome to Part 1 of “Love and Logic,” where Waverly Deutsch shows us how balancing passion and reason leads to real impact. Today, we explore her journey—how she carved her path and why she’s committed to helping others find theirs. In later episodes, we’ll cover her work at Chicago Booth and WyseHeart Advisory, where she dishes out “tough love for entrepreneurs.”Waverly is famous for her blunt yet brilliant coaching style—think “Simon Cowell of Chicago Booth,” but with actual solutions. She’ll tell you your business pitch makes no sense, then hand you a roadmap to make it airtight. If you’re looking for sugarcoating, look elsewhere. If you want to grow, listen in.Key Highlights of Our Interview:A Love for Theater and Logic“I fell in love with theater and acting as a child. My mother and I would go to the theater together—it was a special time for us. At the same time, I was good at math and logic puzzles. I ended up with two majors, one in theater and one in computer science. They were separate disciplines, but in my mind, I was always bringing them together.”The Gut-Driven Leap“At 29, with a fresh PhD, analysis didn’t guide my career move. Joining Forrester was pure gut instinct. I saw it as a chance to dive back into technology, learn from brilliant people, and expand my horizons—no spreadsheets, no market evaluations, just a leap of faith.”Academia or Impact? The Career Crossroads“Graduating with a PhD in theater history during a recession, teaching jobs were scarce. Colleges were cutting back on theater programs, and the research focus in humanities felt too esoteric. I wanted to do something more contemporary, more impactful.”Burnout and Breakthroughs“After nearly eight years at Forrester, experiencing explosive growth, an IPO, and 60-hour weeks, I needed a reset. By 1999, I was ready for a new direction and decided to approach my next move more strategically.”Empathy for Everyone“Emotions aren’t just a ‘women’s thing.’ I’ve sat with many men who’ve cried during challenging discussions. The key is understanding that emotions are human, not a weakness, and they have a place in even the most logic-driven conversations.”_________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.
What’s Stopping You from Outgrowing Yourself?
Change Ambitiously. Outgrow Yourself.
At Chief Change Officer, we harness change as a superpower—fueled by global role models who candidly share their insights, hindsights, and foresights—what we call deep human intelligence.
This isn’t digitized knowledge or AI-generated advice. It’s real, time-tested, experience-driven wisdom—the kind that blends logic and love, art and science.
For me, this show marks career transition #18. Over 17 transitions, I’ve been guided by countless role models, emerging stronger, better, and happier at every critical juncture. Now, I’m here to pass that superpower on to you, bringing together global role models as your guides for personal and professional transformation.
If you’re a growth progressive, a black horse, a visionary underdog, a transformation guru, or a bold-hearted changemaker—this podcast is for you. Because you are the Chief Change Officer.
Our mission?
To help you become wiser in action, clearer in thought, and more ambitious—so you can outgrow yourself and achieve outcomes beyond imagination and calculation.
A better you awaits.
110,000+ followers are already outgrowing.
Subscribe now @chiefchangeofficer on LinkedIn, Apple, Spotify, and YouTube.
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