‘Yes, and’ your career: Improv as a practice, mindset, & tool for creativity
Drawing parallels between performing arts & marketing can boost your creativity and refresh your POV
Hi there! You’re reading the Bonfire newsletter from Kevan Lee & Shannon Deep. Each week, we highlight brand, marketing, and creative learnings from our experience as in-house marketers turned agency owners who think a lot about creativity, our relationship to work, and how all of that impacts our identities. We’ll also feature insights from our digital community of super smart folks (which you’re welcome to join).
Wishing you a great week!
I’m a grown-up theater kid. From my preteens to my mid-20s, I was writing, directing, performing, dramaturging—immersed in new plays and musical theater in Chicago and New York.
When I pivoted into brand strategy, the imposter syndrome didn’t last long. Because it turned out I could do things most corporate folks weren’t trained for: hold a room, tell a story, crack a joke, roll with curveball questions from garrulous clients, run a two-hour training in front of a full auditorium without melting down. (I even liked it.)
Turns out, I was “good in a room”—because in theater, things go off-script constantly. Hail backstage (yep), bats swooping over performers (really), a split lip mid-show (you were a trooper, Steven). The show must go on, and it must go on right effing now.
And after all that and dancing in skimpy costumes? A board meeting’s not so scary.
Basically, I’d picked up a few key improv skills. And you might want to, too.
Most people hear “improv” and picture Tina Fey or Amy Poehler doing something unhinged but brilliant, the show Who’s Line Is It Anyway?, Stephen Colbert riffing off something an audience member said, but somehow tying it back to a larger joke. And sure, improv can be that. But it’s also an underrated professional toolkit—especially for those who need to tell creative stories.
That’s why I’m so excited to share this conversation with Campout member Will Crowley—a marketer and improviser who’s spent the last decade moving between startup teams, agency life, and improv stages across the country. He’s seen how improv doesn’t just make you funnier—it makes you a better teammate, a sharper thinker, and a more confident creative.
In the chat below, we break down how improv works as a practice, a mindset, and a tool—one that helps you stay grounded, collaborative, and quick on your feet. Whether your next stage is a webinar or a QBR, we think you’ll find something useful here!
A practice: Showing up like an improviser
“There are no mistakes in improv, only opportunities.” — Del Close
Shannon: Ok, so I admit I’m not a real improviser like you are. I never did improv classes—it was too much stress for me! From the outside, it can feel like improv performers are just naturally quick or clever, but there’s so much presence required. What does “showing up” actually look like in an improv practice—and how does that translate to the work we do in marketing?
Will: Right, people think great improvisers are just up there winging it, but they’re obsessively consistent about practice, which makes “winging it” that much easier when they’re on stage. Just like any band or sports team practicing, improvisers get together frequently (often in local theater basements or, in a pinch, a teammate’s spacious living room) to work through key exercises and techniques over and over. That way, when shows come around, they don't wait or hope for inspiration; they’ve already built muscle memory through showing up and honing the foundational skills of the art form. Of course, no two shows are alike—which I think makes it so fun and alluring—but they’re all built on key concepts that improvisers strive to hone and apply throughout their careers.
Shannon: Right. It’s not magic—it’s muscle. The ease is a groove they’ve carved, not some natural state.
Will: Great marketers do the same thing—writing, ideating, testing, presenting—over and over again. For example, building a new website landing page used to take months of work and approvals to get it just right, but thanks to more modern CMS tools and an emphasis on agility and speed, modern marketers can now go from a blank page of copy to launching a page in days (or even hours) and set up a few A/B tests to learn, iterate, and improve. This kind of practice and rapid delivery builds confidence not just in your skillset, but in your ability to stay present and adaptable when things veer off-script. And in marketing, they always do. And it adds a level of resilience! Practice means you recover faster from a flubbed line—or a flubbed campaign. Because you’ve internalized the core skills, you can “improvise” in a work setting without panicking in order to manage both yourself and stakeholders appropriately.
Marketing takeaway: You won’t know every twist in a product launch or rebrand. But if you’ve worked the core skills—clear communication, quick creative judgment, trusting your instincts—you’re more equipped to handle the unexpected.
A mindset: The improviser’s approach to career growth
“Saying ‘yes’ begins things. ‘Yes’ leads to knowledge.” — Stephen Colbert
Shannon: Let’s zoom out a bit. One thing we talk a lot about in the Campout community is how modern careers feel less like ladders and more like choose-your-own-adventure books. Or, honestly, improv scenes. No script, no plan, just having to react to what happens that’s out of your control. How has the improv mindset helped you navigate the uncertainty and weirdness of career growth?
Will: Improv teaches you to treat every new scene or line from your stage partner as a gift, and that can be such a great perspective we can apply to our careers! Instead of asking, “Does this fit my five-year plan?”, ask, “How can I build on this?” That simple shift of yes, and turns potential “detours” into growth opportunities. Saying yes to online courses, consulting/freelance gigs, or virtual coffees with marketers I admire has created opportunities and opened doors throughout my marketing career.
Shannon: Yeah, we can definitely internalize that there’s some “right way” to get ahead, or a clear series of right steps to follow, which can blind us to other possibilities.
Will: But here's the thing—none of this works without listening, which is arguably the most important skill in improv. And that looks and feels like true active listening, not just waiting for your turn to talk. In improv, you work to be completely present and receptive to what your scene partner is offering so you can build on it authentically. The same can apply to your career journey.
Listening deeply becomes critical on two levels. First, listening to others—mentors, colleagues, and friends—for the subtle opportunities they're presenting or doors they could be opening. But equally important is listening to yourself through intentional self-reflection. What energizes you? What patterns are showing up? What do you want to say yes to next? Most people rush past these internal signals and dive into the more tactical steps of what’s next - networking, applying, interviewing, etc , but they're often the most valuable data you have, especially when you’re considering your next career move.
Marketing takeaway: The best career moves come from listening deeply to both external opportunities and internal signals about what energizes you, not making a plan and sticking to it.
A tool: Collaboration at the core
“Why work alone if you don’t have to? It’s all give-and-take…improv classes are great because they teach you about conversation.” — Catherine O’Hara
Shannon: Something that I’ve always loved about live performance of any kind is that it is inherently collaborative. With only extremely rare exceptions, it’s not actually possible to do it alone. And that feels so true in marketing too, especially when your ideas depend on buy-in or collaboration to actually come to life. How have improv principles shaped how you show up in creative partnerships or cross-functional teams?
Will: The teamwork element is one of my favorite aspects of the art form! In improv, your job is to make your scene partners look good. And in modern marketing, it’s pretty rare that any big initiative is done completely in a departmental silo; you’re co-creating with product, sales, design, customer success—sometimes all in one day. Great marketing and great improv require trust, adaptability, and a shared commitment to the outcome, even when the path looks different than expected.
You can use improv principles to run more fluid brainstorms, build stronger creative collaborations, and stay agile when plans change mid-stream. It's about creating an environment where everyone feels safe to contribute and build on each other's ideas.
Shannon: What’re some examples of principles you could use?
Will: In improv, the scene only takes off once everyone’s clear on the who, what, where, and—crucially—the why that drives the characters in that scene. These key anchors create a shared reality and let the action unfold naturally. It’s great to apply that principle when framing campaign briefs: name the audience (who), the deliverable or message (what), the channels and timing (where), and the business goal it ladders to (why). Once product, design, and sales understand those elements up front, you can skip some of the confusion and get right into riffing on the best ways to execute—collaboration suddenly feels a lot more like a good improv scene.
And if you’re a freelancer or a marketing team of one (been there!), actively seeking out communities becomes even more important. Marketing and improv are both collaborative arts—you need other people to play with, whether that's in a formal improv class or a marketing community!
Marketing takeaway: The strongest marketing teams operate like improv ensembles—building on each other's contributions rather than competing for the spotlight. Recognize the necessity of collaboration and lean in!
Whether you’re rethinking your career path or just trying to make the next brainstorm less soul-sucking, improv offers a surprisingly sturdy toolkit: trust, presence, generosity, and a willingness to try the thing before it’s fully baked.
We’re big believers that your best work (and most meaningful career) doesn’t come from control—it comes from collaboration, curiosity, and saying yes to the unexpected.
Notable links, convos, and events
We’re always talking about the crossover between your professional life and your creative expression over in our Campout community.
In case you’ve missed any of our free public events, you can catch all the replays here! This includes:
Find Your Fit: Reshaping Your Work, Not Yourself with
Beyond AI Prompts: How to Sound Human When the Robots Want You Basic with Meg Moore
Personal Brand on Your Terms & Conditions with Callie Rojewski
We’re building up quite the library!Craving an IRL experience to help guide your next steps toward a more meaningful and creative career? You’re in luck… We’re hosting an in-person retreat this fall in the French countryside! We’d love to eat some cheese with you, so check it out!
But wait! There’s more…
Wanna be friends?
If you love this newsletter and wish it were more interactive, you’re in luck! Join us over in Campout, our digital community for creative marketers and the creative curious.
Wanna work with us?
If you need help with brand strategy and storytelling, fractional brand and marketing leadership, and bringing your brand strategy to life in impactful ways, send us an email at hello@aroundthebonfire.com to get in touch.
As always, you can find us on LinkedIn, Instagram, and Threads.
