Making Work Fun Again: A Conversation with Jake Brown
Jul 31, 2025
What if your biggest challenge at work, whether it’s a bad boss, a chaotic brain, or burnout from building your own business, was really the doorway to something better?
In my latest episode of the Writing & Influence podcast, I sat down with Jake Brown: author, speaker, coach, and self-proclaimed workplace mischief-maker. Jake’s book Leadershit (yes, spelled exactly like that) is packed with stories and strategies for surviving bad bosses and thriving in environments that weren’t built for neurodivergent minds.
He’s funny and wildly practical. And yes, he once kicked off a serious conference session by teaching a room full of executives how to doodle. I was there.
Elaine: Let’s start with something that made a big impression on me. I watched you lead a session at the GROW conference earlier this year where you somehow got a room full of caffeinated, distracted professionals to calm down and get present... by drawing robots. Why doodling?
Jake: Doodling is this incredible reset button. I learned it from my grandpa. Now, I use it to help people step into presence and get past judgment—especially the self-judgment that shows up in high-pressure work environments.
When we doodle, our brain stops spiraling. The noise fades. I’ve done this with thousands of people now, from kids to C-suite execs. It never fails: silence falls, stress melts, and focus returns.
Elaine: I watched it happen in real time. Everyone relaxed. No one cared about whether they could draw or not. And suddenly, we were ready to listen.
Jake: Exactly. It’s about creating a moment where you’re fully present. Doodling gets you there fast and it’s judgment-free.
Elaine: You talk a lot about ADHD in the workplace. What do leaders often misunderstand about how ADHD shows up on the job?
Jake: That accountability and pressure don’t work the same way for everyone. People with ADHD don’t thrive under scrutiny. They thrive in spaces of hope, encouragement, and novelty. That’s why I suggest coworking Zoom calls with cameras on and music playing. It’s not about micromanagement. It’s about nudging people gently into focus.
Elaine: You’ve also talked about how hard it is to switch tasks with ADHD. That struck a chord.
Jake: Oh yeah. For someone with ADHD, an interruption can throw you off for two weeks. Doodling helps with that too. It acts like a bridge between tasks. It gives your brain a safe place to reset so you can come back strong.
Elaine: Let’s talk about your book. First of all, I had to put your title in quotes just to get Amazon to cooperate—Leadershit with the “sh!t” right there in the name. How did it come to be?
Jake: It started as a typo. But that little typo changed everything. I was talking to so many people who hated work, and I kept telling the same stories over and over. I thought, maybe it’s time to write them down.
Elaine: You recorded yourself telling the stories out loud first, right?
Jake: Yep. That’s how my brain works. I recorded, then transcribed, then edited. My wife says there’s “Jake” and “Head Jake” in the book—me in the moment, and me reflecting on it later. I didn’t want to write a lecture. I wanted people to laugh, then realize they weren’t alone.
Elaine: What about when the writing got hard?
Jake: A lot of things helped: encouragement from people like you (you once told me “never stop writing” and I’ve still got that email flagged). Also, someone in my family doubted I’d finish. And nothing motivates me like doubt. But the big push came when a woman said, “My son needs this book.” That was it. I wrote it for him.
Elaine: You introduce a tool in the book called the WIPE framework. That’s funny but it’s also effective. Give us the quick version.
Jake: It’s a self-assessment model that helps people figure out where they are at work:
- Winner: You’re aligned and empowered.
- Intern: You’re aligned, but not yet capable or allowed.
- Prisoner: You’re capable but not aligned.
- Expert: You’re capable and allowed but disconnected from the mission.
Once you know where you are, you can decide: do I stay here, grow, or move on?
Elaine: And this isn’t just for employees, right?
Jake: Definitely not. I used it on myself after launching my own company. Turns out, I was the worst boss I’d ever had! Entrepreneurs, solopreneurs…we can be our own toxic bosses if we’re not careful.
Elaine: Before we wrap, tell us where people can find more of your work.
Jake: You can grab the first chapter of the book at leadershit.co—it’s available in PDF or audio. And if you want to explore my ADHD coaching or team workshops, head to jakebrown.co. There are plenty of free resources there.
Elaine: Thank you, Jake. I love your heart, your humor, and the realness you bring to tough topics.
Want to work with a publisher who understands how to turn your stories into powerful tools for change? Sparx360 Publishing specializes in business books—and under our imprint, The Cookbook Creative, we also publish culinary titles that stir the soul. If you're ready to bring your book to life, schedule a call with us.
