Chief Change Officer
#227 Sara Lobkovich: Why Playing Life on Hard Mode Might Be Your Best Advantage – Part Two
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: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 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: Who is Sara Lobkovich and what are her books about?
In the last episode, part one, We looked into who Sarah is, what she's been through, and how her past has shaped her purpose today. In this episode, part two, 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.
Chapter 2: Why didn't Sara fit into traditional strategy roles?
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 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 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 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.
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Chapter 3: What does it mean to be a strategist according to Sara?
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 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.
And then there's also this side of it that is just people asking insightful questions of each other, doing research, actually reading research, doing research, finding links and developing insights. 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 Bain's and the large strategy. I knew what that looked like. And I just feel very lucky that I was able 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 going to get his last name. I need to put the pronunciation right on screen, but Rob Estraneo is another. I'll make sure that you have the link for the show notes. These are folks who are just democratizing strategy.
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Chapter 4: How did the title 'You Are a Strategist' come to be?
I actually don't remember now. I have some working memory issues and executive functioning issues. So my memory can be a bit spotty. I don't remember. what it was that prompted the title. I think I was doing an ideation session with one of my strategic partners, because I work with a bunch of collaborators.
And I think I said something like, if I could name the book anything, I would name it, You Are a Strategist. But I can't do that. And here's why. And But that title, the minute it came out of my mouth, I knew that was the title. I knew that was the book. I had to rewrite the book to make it that book.
It's been a lot of effort to take the book from a book about bouquets to a book that really delivers on its title. But I just got the manuscript back for proofreading. I just got the manuscript back from its first proofread. And I started reading it this weekend and I think I got to page 10 or 12 and then started to cry because it's the book that I wish I had earlier in my career.
To help me know that I wasn't alone in my career. And so that for me, I've been in, I did get the feedback that I should name it. Are you a strategist or some other variation? And I've just absolutely from the moment that title was a possibility held firm to it because it's for every person who's ever been told.
You need to, I don't know how to say this without using a word that I don't usually use, but so let me find an alternative of you need to simplify your work. It's too complicated. This is too smart. Your work is too smart. You need to make it simpler. or anyone who's ever heard, you're too strategic. I need you to focus on the tactics. I need you to get executional.
But it's also for everyone who's ever heard, you need to be more strategic. And there's never been. I got that feedback early in my career. You need to be more strategic. I can tell you there was nowhere to go to get help on what to do about that. So it is, to me, this is
Definitely a passion project with that particular book because I just want everyone to have the chance to get acquainted with their inner strategist because their inner strategist is in there no matter what they do for a living. You might be a dishwasher washing dishes and noticing things in the restaurant and putting linky things together in your brain and that strategy.
Or figuring out a more efficient way to load the washer. That strategy. It's There's strategy in how you're going to decide to reclaim if your house has gotten a little away from you and it's a little messy. There's strategic play in how to reorganize your home. There's just strategic play in so many, in anything, in anything we do.
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Chapter 5: Why is democratizing strategy important to Sara?
And that the message I hope to bring with this book is strategy isn't just about being smart. Strategy isn't about being the person who can write the perfect line. It's not about being the person.
who can stand at the front of the room and sell the most effectively it's about asking and answering questions that make people say wow that's a really good question i haven't thought of that way before or i haven't had a chance to think about this before because That's how we change systems that aren't working.
And I think the more people who feel empowered to or the more people who feel like they can ask those questions instead of wondering what's wrong with me. that this doesn't work for me, the more people who can ask questions about their environment or about our world or about our cultures instead of quietly thinking, I don't know what's wrong with me that this doesn't make sense to me.
I don't know what's wrong with me that I don't understand how to succeed. What's wrong with me that I can't just do the work like everybody else? I don't want people to have to think those things. I want fewer people to have those kinds of statements running through their head and more people to know that there might be nothing, there's nothing wrong with you.
You just might be seeing things through a strategic lens in an environment where, based on your experience and my experience, that's not what everybody always wants.
Your book's first page is dedicated to quite a range of individuals and I want to read it out loud for the benefit of our listeners. This book is dedicated to introverts, people with ADHD, those on the autism spectrum, trauma survivors, strategy brain square packs, frustrated change makers, revolutionaries, a combination of rebels and revolutionaries. And lastly, thinker doers.
There are a couple of interesting terms there. So why did she choose this audience? I'm guessing you must personally resonate with these people. Maybe you were, or still are, one of them. Why did you dedicate this book to this specific group?
You nailed it. That is me. This book is a love letter to me earlier in my career. But I know I'm not alone. I know there are so many other people who are having experiences like I did. And it...
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 pole and just don't fit in.
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Chapter 6: How can strategy be applied in everyday life?
These are people who are not specifically served by a lot of our mainstream business focus on career. Mainstream businesses focus on career and a lot of what gets written in mainstream business books
either shows or speaks to the benefits of neurodivergence because lots of entrepreneurs are neurodivergent so that independent and creative and innovator streak part of neurodivergence gets played up or gets positive treatment in business press without necessarily being mentioned as neurodivergence.
But it is really important to me that people who look at business books and feel like they're not written for them, I think I have two business books on my entire bookshelf that are geared towards introverted business people. And there are more books than that out there.
But so much of business books made me and other readers who have some of the characteristics that I just described feel like we don't fit in or there's something wrong with us. They encourage those voices that are in a lot of our heads.
And it's important to me to just be very transparent and say, my work is for neurotypical people because neurotypical people can benefit from learning simple practices for communicating clear expectations.
And my work is for neurodivergent people and people who are from other cognitive styles or neurotypes and other cultural backgrounds beyond just standard American business or mainstream business culture. to learn practices for developing and communicating strategy and expectations and goals in a way that can be understood by anyone.
There was no way I could write that book without just being really honest that It is for neurotypical leaders to develop skills to work better with their neurodivergent employees, which also benefits everyone else while we're at it. And it's a tool that people who've struggled in their careers can use to improve.
take a step to put themselves back in the driver's seat of their careers and tap into their intrinsic motivation and reconnect with what they want and need and take the risk of paying a little less attention to what people expect of you or the ways that you've been coached to mask your behaviors or to
conform with some sort of professional expectation that doesn't fit you or doesn't fit your cognitive wiring and operate from your center and from your truth with tools that help you be well received by others that you work with. Yeah, again, it's For me, we started this conversation with my activism when I was nine years old and in the third grade. And it comes back around to that.
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