Oh, Good! What Improv Teaches Us About Uncertainty
How We Future with Dan Klein
I met Dan Klein about 15 years ago when I took a continuing education class at Stanford on creativity and improvisation. I thought it was going to be a fun night to learn some new facilitation skills. Instead, it was a totally transformational experience.
Although the session was only 90 minutes, I left feeling thunderstruck—not just because Dan’s expertise helped unlock a whole new way to think about creativity, collaboration and innovation, but also because of the way in which he did it: experientially, joyfully, holistically, with the lightest touch and a welcoming invitation filled with good humor and care.
It was the kind of experience that makes you realize you thought the world was black and white, but it’s actually a vibrant technicolor: filled with all of the possible combinations of colors, hues, tones and blends.
I remember saying to him after that day, “Dan, what phone call would you like to get from me so that we can do more work together?”
What Dan taught me that day—and in the many collaborations and adventures we’ve had since—is that the best preparation for an uncertain future is not a better plan. It’s better practice.
Most people think improv is about being quick-witted or funny on demand.
But Dan’s work goes much deeper.
Improv, he shows us, is a rehearsal space for dealing with reality as it actually is—messy, collaborative, and full of surprises we didn’t see coming. The principles Dan teaches aren’t party tricks. They’re survival skills for a world that refuses to follow our scripts.
In this next episode of How We Future, I talk with Dan about improv and why it’s such a powerful approach to navigating uncertainty, building relationships, and collaborative futuring. Over the years, we’ve co-hosted high stakes gatherings, designed innovation programs steeped in reflection and mindfulness, and have even incorporated ice curling into our practice (those Olympians make it look easy... it’s much harder than it seems). It honestly doesn’t matter what we’re doing because I know that when I partner with Dan, I’ll never be alone, and I’ll never be without options.
Here are just a few of his approaches that have completely shifted how I think about leading, creating, and living.
1. Shoot For Average and Fail Cheerfully
Dan believes in proactively and cheerfully practicing failure. And for lowering the stakes…by a lot.
“I’ve taught improv to Stanford students for nearly 20 years. One of the first things I tell my students is: ‘Your job in this class is to shoot for average and to fail cheerfully.’”
Wait, what?
He later goes on to say “They can’t believe it! It’s not the message they got to get into that room. I also think that whatever message they’ve been getting is not sustainable. In too many cases, we’re on a collision course that’s internalized pressure. It’s become a mental health crisis for so many. ‘Shoot for average and fail cheerfully’ is a release valve for them, and it changes everything.”
This isn’t about being cavalier or reckless. It’s about rewiring our relationship with failure—especially in teams. In most organizations, the fear of failure keeps us playing small. We hedge. We hold back. We don’t share the wild idea that might actually change everything.
Dan’s improvisers practice celebrating mistakes until it becomes muscle memory. Not to encourage carelessness, but to create psychological safety—the kind where people take creative risks, learn faster, and recover with grace.
Imagine a team meeting where someone’s idea falls flat and instead of awkward silence, everyone cheerfully acknowledges it and moves on. What becomes possible when failure isn’t fatal?
2. “Oh, Good”: The Reframe that Opens up Everything
When something unexpected happens—a plan falls apart, a curveball arrives, reality refuses to cooperate—improvisers are trained to say: “Oh, good.”
Not as toxic positivity. Not as denial. But as a genuine reframe that asks: What can I do with this?
Dan shared how this practice, drawn from improv legend Patricia Ryan Madson, transforms how we meet the world. Instead of resisting what shows up, we accept it. Instead of mourning what we expected, we work with what we’ve got.
“When we’re on stage, lots of things go right. Things also go ‘wrong.’ Improvisers get excited when things go wrong because it’s a new opportunity, and we say, “Oh, good,” and we see what can happen from there. It turns out that that’s actually true in many ways in life as well….There will be bad things that happen, no matter what we do. This principle of ‘oh, good’ reminds us that we have a choice of how we respond to them.”
3. Your Job Is to Set Your Partner Up for Success
Here’s where improv becomes a fundamentally different way of being in the world.
In improv, success isn’t about individual brilliance. It’s about making your scene partner look good. You listen deeply. You build on their ideas. You accept their offers and add to them—”Yes, and…”—creating something neither of you could have made alone.
In improv this is the practice of “accepting offers.” From others. From the world. From yourself.
Setting your partner up for success isn’t just about getting to better ideas, it’s also an antidote to loneliness.
In a culture obsessed with personal genius and individual achievement, improv says: You’re not supposed to have all the answers. You’re supposed to find them together.
When teams practice this—really practice it, like improvisers do—something shifts. Competition becomes collaboration. Ego becomes generosity. And suddenly, everyone’s winning.
Practicing for What We Can’t Predict
The future isn’t something we predict perfectly. It’s something we co-create, moment by moment, offer by offer.
The improvisers I know aren’t better at predicting what comes next. They’re better at responding when it arrives. They’ve logged thousands of hours practicing the micro-skills of adaptation: listening deeply, building on ideas, celebrating failures, staying present instead of script-following.
That practice matters. Not just on stage, but in meetings where plans fall apart. In relationships tested by change. In the quiet moments where we decide whether to contract in fear or expand into possibility.
“We’re practicing flexibility in low-stakes moments,” Dan explains, “so we’re ready for the high-stakes ones.”
Every “yes, and” is a tiny act of world-building. Every “oh, good” is a choice to work with reality instead of against it. Every time we make someone else look like a genius, we’re practicing the kind of generous, collaborative leadership the world desperately needs.
Dan shares so much more in our full conversation, including our shared appreciation for Stephen Colbert and wisdom from improv legends Keith Johnstone and Patricia Ryan Madson. You’ll learn specific practices you can try with your team tomorrow, and why laughter is actually a sign of learning (not just entertainment).
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Because the truth is: We don’t need to know exactly what’s coming next. We just need to get better at dancing with whatever arrives.
Yes, and…
What’s your relationship with uncertainty? Have you found practices that help you stay flexible, present, and generous when plans change? I’d love to hear what resonates (or what you’re skeptical about). Drop a comment below.
What a brilliant summary of improv’s life lessons! Can’t wait to listen to the fun podcast. Yes - And forever! Thank you, Lisa.