Chief Change Officer
#226 Sara Lobkovich: Why Playing Life on Hard Mode Might Be Your Best Advantage – Part One
Thu, 13 Mar 2025
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 Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.10 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.130,000+ are outgrowing. Act Today. --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.12 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>140,000+ are outgrowing. Act Today.<<<
Chapter 1: Why is Sara Lobkovich an advocate for introverts and change-makers?
are for the introverts, the ADHDs, those on the autism spectrum, trauma survivors, astrology brain square packs, frustrated change makers, revolutionaries, that's rebels and revolutionaries combined, and thinker doers. Why? Because our guest today, Sarah Lobkovich, is part of these groups and she is not holding back anymore.
In fact, she's spent months writing two books that bring together her life lessons and business strategy experience. to help us all wake up our inner astrologist and achieve big goals with no BS. In this episode, part one, we'll dive into who Sarah is, what she's been through and how her past has shaped her purpose today. In the next episode, part two,
will dig into the book, her why, her audience, her objectives, and her vision. That said, Sarah's story and her book aren't just personal. They are also deeply rational. She's packed it with tools, analysis, and a lot of business concepts.
For anyone familiar with business school models and buzzwords, you'll find her approach balances speaking to a specific audience while delivering real business value. Let's get started. Welcome, Sarah. Welcome to our show. Let's dive right into your story.
For sure. So now I am a, I call myself a strategy coach and goal nerd. I'm really fascinated by goal setting and the role that goal setting and then organizing behavior change to support goal achievement can have for people's lives.
So it sounds super intellectual, but to me, it's really a passion and a movement around helping people tap into their intrinsic motivation and their purpose and their why, and then be able to operate their careers and run their businesses with more of that connection to their why and their purpose and the larger meaning instead of just chasing extrinsic rewards or external expectations.
How did you end up doing what you're doing now? Maybe we can dive deeper and go down memory lane. Where are you originally from? I know you are now on the West Coast in the United States, but let's talk about the early part of your life. Where did it all start for you?
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Chapter 2: How did Sara Lobkovich's upbringing shape her career?
You either get a long answer or a short answer when I talk about my work life. The longer story, I am from a little tiny town out on the Olympic Peninsula that's called Port Townsend. So it's still here on the west coast of the U.S. in western Washington. But Port Townsend is a relatively small town.
It's a ferry ride and an hour and a half drive from Seattle, so it's not really close to an urban center. And it is the kind of place where there's a massive arts and creative community, incredible writing programs. I grew up in a very art-filled and creative community. environment where like being an artist is a way to make a living or being a writer is a way to make a living.
Chapter 3: What early experiences fueled Sara's passion for activism and creativity?
And so that was how I started. I had two parents who were public employees. and lived in this place where my creativity was nurtured and encouraged from very early on. So my upbringing helped me find, and my early childhood, I think I've been an activist since birth. I successfully petitioned our cafeteria ladies to, for milk equality, which sounds so silly now, but I was in the third grade.
I think I was nine years old and the brown bag kids had regular milk on Fridays and the hot lunch kids got chocolate milk on Fridays. So I petitioned the schoolyard kids, successfully petitioned the cafeteria ladies to achieve milk equality so that the bag lunch kids could also have chocolate milk on Friday.
And once I had a taste of that, it's like the combination of growing up somewhere where creativity was really nurtured and that early taste of successful activism You can just draw a straight line from that to what I'm doing today in terms of enabling people to
really change systems change workplaces and change how we operate in ways that are more human-centered so it's for high performance but also with these practices that really help us operate from our why and our shared purpose and what really matters beyond just the generating of revenue So that's the early childhood. And then from there, I got really into technology. So I was an early adopter.
Chapter 4: How did Sara transition from law to a career in strategy?
I co-founded an internet content company in the mid-90s when I was still in high school with a couple of my amazing teachers. And Worked in online community and online content from the jump. Just got a really early start in that space. And that led me into my first career in technology. And then my second career was practicing law.
I wanted to do something where I felt like I could really help people. And for me, that was becoming a lawyer. So I became a lawyer. I practiced law for almost five years and then Because of some life circumstances, I had to make a transition again from self-employed. I was self-employed as a lawyer to having a job. And then that was when I started working in outreach.
I went back to marketing roles. I got into strategy. My first real strategic work was in that chapter after my years as a lawyer.
And it was that work in strategy and then beginning to lead people in strategy, having my career develop into an executive career in strategy, where I got to see the challenges that people experience, trying to understand what's expected of them, which I had struggled with my whole career.
Chapter 5: What key transformations did Sara undergo in her career journey?
But I also experienced the pressure of being a leader and trying to deliver clear expectations and trying to manage up and trying to support CEOs who are accountable to boards and just saw the complexity of all of the expectations and the overwhelm and the too much information and the not enough information that people navigated. leadership and their careers with.
And that was really what drew me to this form of goal setting. I started experimenting with self-set quantifiable goals that I cared about my career when I was in a phase of pretty bad burnout. And it was just like a light switch flipped for me.
The minute I was getting up every day and thinking about goals that mattered to me that I could measure, it gave me a way to feel like I was driving in my career instead of just trying to mind read and understand what everyone else was expecting of me. And that was really the, that was in 2016. That was the birth of my obsession with goal setting. And I haven't looked back.
I've been in that space ever since.
Chapter 6: Why does Sara embrace nonlinear career paths?
You mentioned that starting point in 2016. And here we are now heading into 2025, almost 10 years later. I'll let you tell more about about what these last 10 years have been like for you in a moment. But before 2016, like you said, you've gone through several transformation points. Transformations are unique for everyone. Even for me, each of those moments felt very different from one another.
Looking back now, especially since people who write books tend to have reflected deeply on their experiences, I'm curious, what were some of those key transformation points or challenges you faced that really stand out to you? More importantly, how did you manage to get unstuck We are living in a world where so many people feel stuck in some way.
So I think your story could really resonate with anyone who might be going through that right now.
Yeah, Vince, that question gave me goosebumps. For one thing, this is a funny place to start my answer to the questions, but I have had issues with authority for my entire life. So I have never had the same deference to authority. institutional power or authority that comes from an org chart as opposed to from the experiences that you have with humans.
I believe that authority and respect are earned not awarded or not due to something other than being earned person to person. So I have had a career where for one thing, I just got, I'm just going to own it. I got really lucky that I started in technology as early as I did because for my early career career,
Because I had that technology and community and content and internet content experience so early. That created opportunities for me whenever I decided I was ready to move on in a role. So I did have, I would have been called a job hopper if we had that language back then. But I worked with a career coach who reframed that for me to use the language of being a scanner at the time.
So it's not as much about job hopping. It's that I'm nonlinear and I have lots of interests. In my early career, those issues with authority manifested themselves in frustration. I would get into a role. I'd be super excited. I would bring my 150% to the role and then I would realize they don't even want 25% of what I'm bringing.
It's just not, they just want someone to sit down and do the widget building or sit down and do whatever the tactical thing was. And so that was my struggle early in my career.
Part of the job hopping was I would get hired in with a change remit or hired in with a more strategic title and then find out that it was actually just a tactical execution role, which there's nothing wrong with tactical execution. I'm just a person who I can't help but see how things can be better or how things can be different or how we can innovate or improve.
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