Chief Change Officer - #226 Sara Lobkovich: Why Playing Life on Hard Mode Might Be Your Best Advantage – Part One

Episode Date: March 13, 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 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.

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Oshul is a modernist community for change progressives in organizational and human transformation from around the world. This episode and the next are for the introverts, the ADHDs, those on the autism spectrum, trauma survivors, strategy-brained 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 experience to help us all wake up our inner strategist 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 2, we'll 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? 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 US 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 programs. I grew up in a very art-filled and creative 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 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 founded my, 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, had to make a transition again in 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. 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. 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 navigate 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.

You mentioned that starting point in 2016. And here we are now, heading into 2025, almost 10 years later. I'll let you take more 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, since 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 the same deference to 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, 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 my, 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, it's not as much about job hopping. It's that I'm non-linear and I have lots of interests. And 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.

And that wiring for this can be better, our customer experiences can be better, our employee experiences can be better, we can be more efficient, we can waste less human labor. Like all of those noticings have been part of me since my early and mid-career. And all those things made my early career, I would describe it as seeking. I was just trying to find somewhere that I could love my work and have my employer love me back. And it was in mid-career my tenure started to get longer. I was hired and, I started working, it was when I started working in actual strategy as a field that my 10 years got longer. So I can't remember exactly the year that I started. I think it was 2012-ish was the first time I took a job in an agency as a content strategist.

And when I found that discipline, it was the perfect mix of strategic and conceptual and creative and executional, and there were numbers. I could see the performance of our content. I could optimize and improve and analyze. And so that was my first ding ding. I think I found it. And working in that space then led me again into other opportunity in that field. I graduated into a larger agency that was part of a larger holding company. And that was when I got my big agency advertising experience was that chapter from 2013 ish to 20s. I can't remember when I actually left. I think it was 2018 ish. And that was, I'd say, in addition to what I'm doing now,

that was really the sweet spot of my career, working in creative agencies in a senior role, so I could actually make change. I could lead people the way that I wanted to lead people, and in a way that felt good to me. I could nurture other strategic talent, like spot and nurture other folks who are wired strategically.

Some of my proudest experiences in that agency chapter of my life was spotting potentially strategic talent from the admin pool or the intern list and being able to nurture folks who had not been considered for strategy roles into the field of strategy. So my work graduated from content strategy into actual brand strategy and planning. And then that was when I loved my work.

I loved my colleagues. I loved my team. My team was incredible. And I was the guy on the plane. So I'd be at the office and they'd say, we need you in Cleveland. And I'd stop at home and grab a suitcase and I'd be at the office and they'd say, we need you in Cleveland. And I'd stop at home and grab a suitcase. And I'd be on a plane.

And then I'd ask when I was on the plane, OK, what's the client and what are we doing? And then I'd prep on the plane and then deliver the pitch or the collaboration or whatever it was. And so I found myself always on the go, a lot of travel, trying to maintain my team at home, my leadership of my team, having at that point very little life. And my dog lived with my mom and dad for way too long during that chapter.

And that was what led me ultimately to that burnout that then had me thinking, I can't sustain this. I need to find ways to do this differently or to do something differently. And I can't just be constantly in activity without some sort of why for myself or some sort of reason or some self-set goals and so that kind of brings it full circle to that 2016 year when I started creating my own self-set goals. 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, sure, 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. Part of my work is helping people and 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. 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 set, 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 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 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. I remember telling myself, okay, I thought I was coming into a dream job. What I've actually got is this is like a mini MBA in how to work in an enterprise environment. It was my first big company job. And I'm like, all right, I guess I'm going to get some experience with how to exist in a large political organization where your length of tenure matters and there's a lot of resistance to change. So I'm just going to make this a mini MBA for myself in that. And that was what helped me start to get curious. So whenever I did experience stuckness, I think I told myself, all right,

what is this is an MBA and something, I'm going to learn something being here. So what can I make that? What can I learn here? And then I just thought of it as being able to then tap into my dedicated student and curious brain instead of only feeling the suffering and frustration. Now, you've written a book, or should I objectives and key results to get big things done. As you mentioned, you've been practicing astrology as a profession for years. Before we dive into your book, I'd like to talk a bit about the role of astrologist as a profession.

When we are in our childhood, we usually say we want to be a pilot, a doctor, a lawyer. But astrologist usually is not something of a so-called dream job. Yet, astrology consultants, especially in firms like McKinsey or BCG, often have this prestigious image attached to them, thanks to their branding and marketing. These firms have really crafted a perception around their consultants, hence the 7 figure, 8 figure fee. After spending a good amount of time in corporate consulting yourself, what are some of the

biggest misconceptions about being a strategy consultant? What's the reality versus the myth? Could you share that with us honestly? Yeah, I can share from my experience, I can't speak for the larger field because I think my experience was a little unusual. I tried to go the big agency strategy route. I had a few years where I applied over and over to the names that you just mentioned and more, and I really wanted to get in that big agency strategy consulting space.

And I never even got a call because I didn't have the right names on my resume. I didn't have the right experience. I wasn't at the right stage of my career. I didn't come from the right school. So I have worked with lots of those consultants. I've worked alongside those consultants. I have been brought in after this time. Some of those consultants have done additional work where it wasn't as successful. 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 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 that the big agency thing just wasn't something that I was a candidate for. So I worked in smaller agencies, 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 arms link 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

word 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 Mad Men 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 there 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 Baines, 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. And then there's also the side of it that is just people asking insightful questions of each other, doing research, actually reading research, doing research, finding links finding links and developing insight and then seeing what that sparks in terms of ideas. And that's more the part of strategy that I worked in. And then luckily, I always thought that I was something other than a strategist because I had seen the McKinsey's and the Baines and the large strategy. I knew what that looked like. And I just feel very lucky that I was graduating out of the field and into consulting at a time when Mark Pollard and some of the other really rebels in the field of strategy were

emerging. And that was when I started to see those people in their work and read what they were doing. I was like, oh my gosh, I have a place. Like that is my person. I'm not gonna get his last name. I need to put the pronunciation right on screen, but Rob Estronejo is another. I'll make sure that you

have the link for the show notes. These are folks who are just democratizing strategy. And this all started with you mentioning my book, but I hope to contribute to the democratization of strategy so that we don't think of it as the smartest person or as the person in the most expensive suit or with the most beautiful slide deck. But we can think of strategy as the way that we tap into our very deeply human insight to develop scaffolding for solutions to our biggest problems, including the big problems that affect human lives, not just dollars and cents. Let's continue Sarah's story tomorrow, shall we?

Thank you so much for joining us today. Shall we? Thank you so much for joining us today. If you like what you heard, don't forget, subscribe to our show, leave us top-rated reviews, check out our website, and follow me on social media. I'm Vince Chen, your ambitious human host. Until next time, take care.