Chief Change Officer
#304 Sara Lobkovich: When the System Doesn’t Fit, Rewrite the Operating Manual
Thu, 17 Apr 2025
Sara Lobkovich didn’t pivot to be edgy. She adapted because the system never fit—and she refused to shrink herself to match it. In this first of a two-part series, Sara walks us through her nonlinear arc: from teen internet entrepreneur to lawyer, from burnout strategist to behavioral goal-setting expert. Along the way, she reveals how quiet defiance, early activism, and radical self-curiosity helped her rewire how she worked and lived. For Gen Xers tired of being told to “just fit in,” this episode hits like a guidebook wrapped in real talk.Port Townsend Roots, Strategy Brain Wiring“I was raised where being a writer or artist wasn’t a dream—it was a job.”Sara shares how growing up in a small creative town and fighting for chocolate milk equity in third grade foreshadowed a life spent rewriting systems that didn’t make sense.Corporate Doesn’t Like People Like Us“I gave 150% and learned they only wanted 25.”She opens up about being misread, underused, and professionally ghosted inside organizations that couldn’t make space for someone who thought faster than the hierarchy could handle.Law School, Big Agencies, and That One Job That Broke Her“I was the person on the plane with no life and a dog living with my parents.”Sara traces her journey through law, tech, brand strategy, and burnout—highlighting how her performance often outpaced her internal compass.Strategy as a Rebellion, Not a Resume“Strategy isn’t being the smartest in the room—it’s asking the best questions.”She unpacks how real strategy is built by misfits, introverts, and pattern-obsessives—not always the polished ones at the front of the pitch deck.Stuck ≠ Static“I made stuckness into a self-directed MBA.”For Sara, curiosity is the antidote to stagnation. She reframes “being stuck” as a training ground and offers a mindset shift for anyone feeling locked in place._____________________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.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Sara Lobkovich and what is her background?
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.
Chapter 2: How did Sara's early life in Port Townsend shape her career?
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?
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.
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.
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.
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Chapter 3: What was Sara’s career journey before becoming a strategy coach?
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.
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.
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Chapter 4: How did Sara transition from law to strategy and goal-setting?
as I was listening to your story. First off, if we were in a studio together right now, I would give you a big high five. You really hit on something that's basically me. When you mentioned getting excited about an opportunity, putting in 200% of your time and effort only to realize They just want 20 or 25% from you, and they don't even appreciate all the extra thoughts and work.
Yeah, that was me too, for sure. Thanks for sharing that, Sarah. But as I kept listening, I also picked up on something else. There have been quite a few moments when you were stuck or felt stuck. And it sounds like through a lot of self-discovery, you rose above those challenges and kept moving forward. Is that a fair way to summarize your evolution?
It's such a good question, Vince, because Now I am professionally trained as a coach. I, part of my work is helping people in organizations remain unstuck. But partly because of all my wiring and the way that I've navigated my career, early career when I would move from opportunity to opportunity based on my interest and the opportunities that were presented to me.
And then later in my career when I started to become just an insatiably curious student of career and leadership and change. I have had times in my career where, in retrospect, I think I was stuck. Like when I think back, it's like I overstayed somewhere or I had to pay the rent and I didn't have something lined up so I didn't make a move.
But I have always been so intensely curious that I don't feel like I have struggled with stuckness as much because when I get stuck, I just get intensely curious. Curiosity is an antidote for me to so many ills. Curiosity is an antidote to anxiety. It's an antidote to stuckness. And so I've always, I think, been able to shift my brain. I shouldn't say always.
Later in my career, earlier in my career, I did really struggle. It was just more kind of survival and trying to figure out desperately what was expected of me and what it would mean to succeed. So I think Earlier in my career, I managed stuckness by just trying to be more pleasing and trying to be a better mind reader and trying to figure out what everyone else wanted or needed from me.
But then later in my career... my curiosity developed and it just meant I could never be that stuck because I always had a playground in my brain and something to learn. I started one of the tactics I haven't thought about in a long time. But one of the tactics when I did have a couple of jobs that weren't a great sit, there was one in particular that was a dream job.
I was so excited to land that role. And then I had the experience that resonated with you of I was hired in to an innovation capacity. They hired me because of my passion. rebelliousness in content and social media. I had a public profile and a writing reputation in that space. And they hired me because of all that.
And then once I was in, it was the transition from the, what they thought they wanted to what they actually got. And so that is one role that I do remember feeling stuck in and also heartbroken that it wasn't the dream job that I hoped it to be. That said, I still have some of my most dear relationships are from that job. So it's never all bad. But in that job, I just remember Two things.
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Chapter 5: What challenges did Sara face with authority and organizational fit?
I have been brought in after this jump with those consultants and, um, done additional work where it wasn't as successful, um, And so I've seen that big strategy machine operate. I've also worked with folks who come from that world who are some of my dearest colleagues, incredibly talented people. They learned brilliant things.
ways of working in that environment and really strong frameworks for working in those environments. Learned how to work well and how to serve clients well. So I've observed and learned a lot being adjacent to those types. But the big agency thing just wasn't something that I was a candidate for. So I worked in smaller agencies.
I worked in creative agencies to begin with, and then I started working in smaller consultancies. And I think some of the misconceptions or misunderstandings in the workplace, I think, too often... The words strategy and smart are conflated. So being strategic or being a strategist is not just being the smartest person in the room.
Being a strategist is being someone who is curious and has a toolkit of questions. That help uncover facts and observations that then spark insight and let us develop ideas. And so I think that's the thing. that I didn't realize until really late is being a strategist. I'm looking at a book on my bookshelf right now that I always keep within arm's length by Mark Pollard.
And it's called Strategy is Your Words. But he is very much from the school. He's a rebel in strategy. He's a delightful rebel in the field of strategy. And strategy is your words. Strategy is your questions. Strategy is... the curiosity to ask questions that yield facts and observations and possibility that wasn't there before the questions were asked.
So I think we just think of, I don't, for one, I don't think a lot of people know what strategy is as a field, but for two, when we do, I think we think of strategists as the Madman reference. The Don Draper, he's an account guy, but he's also strategic.
The polished person in the suit at the front of the room that's got the line and the story and the room is captivated by the strategy that's being unfolded. And the world of strategy that I've always worked in is not that.
It's me and other collaborators from a diverse range of backgrounds standing at a whiteboard on a Saturday trying to solve a problem that we're so excited to solve together or to create possibility around that we're They're by choice on a Saturday, standing at a whiteboard together, throwing ideas or throwing facts and observations and insights around.
So I think especially what we see when we think of strategic consulting, it is the McKinsey's, it's the Bain's, it's the big ones, it's the folks in suits and the frameworks and they do brilliant research. And that's what we see in the field.
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