Going off on your own as a first-time entrepreneur can be a lonely place, especially if you’re a digital solopreneur working mostly online. It’s you, yourself and I–wearing all the hats. The isolation can be a big shock, especially if you're used to being around a big team with many people to talk to, plan with and share ideas with.
That was where I used to thrive, bringing together big teams around a common goal across cultural–and geographical–divides.
The unexpected loneliness of solopreneurship
I shouldn’t have been shocked when isolation hit me a few months into my foray as a solopreneur. But it hit me like a ton of bricks. The excitement of the launch had worn off. The honeymoon period of making my own decisions without anyone breathing down my neck was officially over. I felt lost in my head, disconnected from the energizing power of being connected to a team.
I needed a new kind of community and a different kind of support. So, I signed up for a myriad of memberships, and my year-long experiment of building a new community commenced. Anything to do with women in leadership? Sign me up. A soft landing place for new entrepreneurs? Yes, please. I went to two, three and sometimes even four events a week.
How improv breaks down barriers and unlocks joy
That’s how I met Brett MacDonald, an inspiring improv facilitator who helps teams connect and thrive. In true 2024 fashion, we first met online through a local business membership, pulled together across algorithms and digital divides by shared values and passions. Both of us had reached a peak in our careers when we chose to step away from our 9-to-5 jobs and pursue entrepreneurship. Both of us felt guided by an inner voice that insisted we had more to offer the world.
We bonded over our shared commitment to bringing humanity into the workplace and our belief in the power of joy and play to foster real connections.
After crossing paths at various events and becoming superfans of each other on social media, I invited MacDonald to take a deeper dive into the power of play to break down cultural barriers and build connected teams. She’s worked with teams in over a dozen countries, so I was curious about her approach, which adapted improv for the work place, and I was eager to learn techniques beyond the more traditional team-building training I’d done.
How could improv offer an opportunity to shape–or reshape–essential business skills, camaraderie and culture? More to the point, how could improv bring diverse groups together while acknowledging differing beliefs, backgrounds and experiences? And is it possible to do all of that online?
Here are my favorite takeaways and aha moments from my conversation with MacDonald on using improv to build connected in-person and globally distributed teams through the power of play.
Improv offers a really unique way for people to practice the skills they need to be more collaborative and effective in the workplace.
When I think of improv, I picture a comedic performance in a theater. How do you adapt improv for the workplace? And how do you create a distinction between the improv space and the work environment?
In improv, we’re playing together, building skills together and being collaborative in a shared experience. We’re not performing in front of one another. The performance side is when we’re back in a meeting or a project planning session. And hopefully, we’re taking the practice elements with us into the workplace to be more collaborative and connected. This is an important separation to make as the practice element of improv makes more space for experimentation without the pressures of the real world.
What if you’re working in a virtual remote space? Can you still use improv?
Most improv exercises can be adapted for remote environments! There are things to consider, such as organizing people into a virtual “circle” so they know whose turn is next. The easiest way is to type the order into chat in alphabetical order. It’s also hard to have many voices speaking at once on Zoom, so utilizing the chat in different ways is helpful, too. Using breakout rooms for smaller group games is essential; that way, everyone is engaged, and you can even mix up who connects with who at each point. Adapting games to a remote space just takes a bit of patience and understanding that it will look a bit different, but it can work!
I think the key is, don’t try to pretend you’re in person, because you’re not. And that’s OK! But the gathering can have a similar feeling; it’s just about looking for new and creative opportunities to re-create that feeling in the virtual room.
How does improv help teams reconnect with play, and why is that important for businesses to consider?
What we’re really doing is getting back to that childhood level of figuring out how the world works and how we fit into it. Remember how you and your friends would play together to figure out roles and how to talk to each other? That’s what improv does with adults.
In essence, improv offers a really unique way for people to practice the skills they need to be more collaborative and effective in the workplace.
How do you make sure the experience of improv is a welcoming one?
It starts with modeling the aspects of presence, curiosity, authenticity and flexibility and using that foundation to bring in exercises that build connection. This often begins with people getting to know each other on a new and different level. Having them share a personal story about their name is an excellent way for others to learn about who they are, where they lived, their cultural background and family history. Individuals get to decide how vulnerable or how deep they want to go. Having everyone in the same space, experiencing some level of discomfort, and having a shared experience starts to build trust and create space for stretching comfort zones.
How do you navigate safety and comfort zones?
There’s a level of intentionality and planning required to create the conditions for safety and be able to start pushing comfort zones. Entering the area of improv can be scary for people, so it also requires adaptability and flexibility to meet the group’s needs. Each session starts with curiosity, loosening up by getting into our bodies, and then moving into creative work that builds connection and trust. The plan for a group of 60-year-olds is going to look a lot different than a brand-new team of 30-year-olds, so it’s important to know who’s going to be in the room and that there’s an intentional reason behind every activity.
What happens with hierarchies and cultural differences in improv?
In an improv workshop, everyone is an equal participant regardless of culture or levels of management and leadership. It’s a level playing field where we’re back to engaging at a human level, outside pre-defined roles.
There’s also no set leader in improv—you’re constantly switching roles between leader and participant. Your role instead is to listen, participate and take care of other people in the group. There’s also more space to explore comfort levels and discomfort with a new environment. Everyone in the improv container is present with their nerves, worries, passions, thoughts and family stories, but ultimately, everyone is in a shared experience together.
Laughter and humor are a big part of improv. How does that fit in with work and business?
A big part of improv is creating situations of shared laughter. We’re in an unexpected, spontaneous environment that builds a common humanity where we enjoy something together. Humor and laughter are how most of us get through difficult situations, and it becomes a practice of getting curious about where we can infuse joy and laughter out of the improv space and into the workplace.
What skills are teams building in improv?
Beyond play, one of the most important parts of improv is the self-reflection afterward. You’ve had the shared experience of improv, and now you get to reflect on what you felt, what you noticed and how this relates to the real world. Sure, you’re not going to take a clapping game or storytelling directly into the workplace, but what did you learn about yourself, how you react in different situations and how you work in a group? By meeting this knowledge with curiosity in a low-stakes environment, participants can have a deeper level of self-learning that can be translated into the workplace.
How can businesses start to capture the power of play to build connected teams?
It all starts with curiosity. Get curious about where there could be more playfulness and lightheartedness throughout your work day. Start to notice where the moments of joy, playfulness and connection are happening versus the moments of disconnect. And what’s the difference between the two? That’s where the magic of connection starts to happen.
Going from intention to action: improv games to spark creativity and connection
Whether you’re a solopreneur struggling to tap into the joy of your work, or you’re curious about ways to use improv to bring your team together, here are a few of MacDonald’s favorite games.
Airport Security
This game uses everyday objects to spark creativity and fun during virtual gatherings. Each participant should gather a couple of nearby objects—preferably unusual ones—and keep them within reach. Participants take turns holding up an object as if it had been discovered in someone’s luggage at airport security. They then challenge another participant to explain or justify why this object would be in their bag.
This activity encourages creativity, as the person being asked must think outside the box to justify the object's presence. It also brings a playful element by incorporating random objects into the virtual space, shifting the focus away from just participants' faces. Often, the game prompts curiosity and storytelling as participants share personal anecdotes related to the objects.
Shared Memories
This is a group improvisation game suitable for both virtual and in-person settings. It works best with four to five participants but can be adapted for larger or smaller groups.
Participants collaboratively create a fictional holiday memory. The first person begins by saying, “Remember when we went to…” and names a location. The next participant continues by saying, “Yes, yes, yes, I remember, and when we were there, we…” and adds to the story. The process continues around the group, building a collective memory piece by piece.
This game is excellent for fostering connection and teamwork. It emphasizes the key improv principle of “Yes, and,” while also creating a joyful, shared experience. For added variety, groups can all start with the same initial location and later share the unique adventures they’ve created.
To adapt for different numbers of people, try these approaches:
Daily warm-up exercises for solopreneurs: try a quick round of Shared Memories with yourself. Start with: "Remember when I achieved [a small business win]," and build on it to reflect on positive milestones. This helps shift your mindset before starting work.
For small remote teams: use 10 minutes of your weekly team call for a simple exercise like Airport Security. It sparks creativity and laughter, setting a positive tone for the meeting.
For Slack or asynchronous teams: create an improv-inspired thread. Share a fictional scenario (e.g., "We're stranded on a desert island! What's the one tool you'd bring?") and invite team members to contribute asynchronously.
If you’re still feeling intimidated by the prospect of introducing improv to your teams, try to embrace play in your business by taking three small steps that will help you move from intention to action:
- Host a small virtual improv session using breakout rooms
- Encourage small, playful exercises like storytelling in team meetings
- Identify moments in the workday for laughter and connection
Improv isn’t just for performers—it's a tool for any team looking to strengthen communication, embrace vulnerability and foster playfulness. It allows us to reconnect with the childlike curiosity we once had about the world, and that sense of play is exactly what businesses need to build strong, connected teams. By creating safe spaces in-person or online to experiment, laugh and reflect, teams can cultivate the skills needed to thrive in today’s fast-paced, diverse work environments.
Whether you’re a solopreneur or part of a larger organization, embracing the principles of improv can lead to more authentic connections and a more engaged, effective team.