Mary Lemmer is a creative entrepreneur, keynote speaker, and author dedicated to helping individuals and organizations navigate change, uncertainty, and growth. She is the founder of Improve, a company that blends improv comedy, business frameworks, and research-backed techniques to help people and companies innovate, perform better, and handle challenges with resilience. Mary has partnered with some of the world’s largest and fastest-growing companies, empowering them to embrace creativity and adapt to unpredictable situations.
A TED speaker and Second City-trained writer and performer, Mary combines her background in comedy with her personal and professional journey—including starting and growing a gelato business as a teenager, serving as a director at a tech unicorn, and navigating unpredictable challenges in life and work—to inspire and teach others. She writes a weekly Substack newsletter, Living, Improvised, and her forthcoming book, How to Handle Anything, offers actionable strategies for thriving amid life’s curveballs.
Mary graduated from the University of Michigan and uses her unique blend of humor, insight, and practical tools to equip entrepreneurs and leaders to turn challenges into opportunities.
What is your typical day, and how do you make it productive?
A typical day for me is, well, there’s no typical day. Every day is a mix of structure and spontaneity—because who wants to live on autopilot, right? I usually start my mornings with a ton of water, a healthy dose of patience (because, you know, mornings), and 100% dark chocolate, because yum!
I like to organize my day around key priorities instead of a rigid schedule. I block out focused work periods for tasks that require deep thinking, like writing for my book or creating new content for Improve. These focused blocks are balanced with meetings, teaching, workshops, or speaking engagements.
To stay productive, I use techniques inspired by my improv comedy training and some of the techniques we use at Improve. For example, I live with the “yes, and” mindset to stay open to new ideas and unexpected challenges. And if things get a little scattered, I’ll use a technique called “Pointing” to regain focus. I also make sure to step away from work—whether it’s walking in nature with my dog, laughing with a loved one, exploring the world around me, or experimenting with new recipes (currently making date-sweetened chocolate truffles is my favorite)—because I’ve learned that some of my best ideas emerge when I give my brain space to wander, and life is so much more than just working all the time!
Ultimately, productivity for me isn’t about checking off every box, but about making meaningful progress on what matters most—while keeping the humor and dark chocolate intake high.
How do you bring ideas to life?
Bringing ideas to life starts with allowing myself to dream without filtering. I’ve found that the best way to come up with new ideas is to embrace a “yes, and” mindset—taking inspiration from everything around me and playing the scene I’m in. I try to stay open to whatever comes my way, knowing that creative ideas often show up when I least expect it.
Of course, not every idea makes it past the brainstorming stage—there’s only so much time in the day! Many get pinned to explore at a later date. The ideas I choose to pursue are the ones that excite me the most. To bring them into reality, I follow a process I call SLED: I do Something Little Every Day to move that idea forward. This consistent effort—whether it’s writing a few pages for my book, creating a new workshop for Improve, writing for my next creative comedic project, or designing a new product—helps keep the momentum going without feeling overwhelming.
I also make sure to share what I’m working on with others. I believe in collaboration and know that the right people, resources, and feedback can take an idea to places I might never have imagined on my own. By opening up about what I’m creating, I bring in support and new perspectives that help the idea come to life. Ultimately, it’s about staying open, taking small steps, and surrounding myself with the right people to help turn dreams into something real.
What’s one trend that excites you?
One trend that really excites me right now is the movement toward intentional, sustainable work. People are increasingly recognizing the importance of working at a pace that allows for deep focus, creativity, and rest. Rather than buying into the “hustle culture,” this approach prioritizes balance, self-care, and the well-being of teams. I’m a huge advocate for this shift, as it aligns perfectly with my belief that slowing down can actually lead to greater productivity and more meaningful work.
When people take the time to work intentionally—whether it’s allowing space for creative thinking or making sure they’re looking after their physical and mental health—they’re not only fostering better outcomes for their businesses, but they’re also setting themselves up for long-term sustainability. This is especially important when we look at the growing rates of chronic illness and burnout in our society. Taking care of ourselves and supporting our teams with empathy and care doesn’t just benefit the individual—it helps everyone thrive.
Ultimately, this more mindful approach to work will, I believe, be a key factor in reducing the health challenges many face due to stress and exhaustion, leading to a healthier, happier workforce. It’s exciting to see this shift happening, and I’m thrilled to be part of a conversation that champions this kind of change.
What is one habit that helps you be productive?
One habit that helps me stay productive is my practice of SLED—doing Something Little Every Day to move an idea or project forward. I’ve learned that big goals can feel overwhelming, but breaking them down into manageable, bite-sized actions makes them more achievable. Whether it’s writing a few pages for my book, brainstorming new content for Improve, or sketching out a creative idea, I focus on making steady progress every day. This habit helps me maintain momentum without getting bogged down by perfectionism or burnout. By doing something small but meaningful each day, I ensure that I’m always moving toward my goals, one step at a time.
Oh, and eating 100% dark chocolate with breakfast because a day is always better with chocolate 🙂
What advice would you give your younger self?
The advice I’d give my younger self is to play the scene I’m in and trust the process. Life is full of unexpected twists, and it’s easy to feel like I need to have everything figured out by a certain age or point. But in reality, there’s no script for life. I’d remind myself to take everything as a gift—whether it’s a setback, a challenge, or an opportunity. It’s all part of the improvisation, and you don’t have to have all the answers right away. Instead of rushing through things, I’d encourage myself to lean into the moment, play the scene, and have fun with it.
I’d also remind myself to be kind to myself when things don’t go as planned. In improv, there’s no such thing as failure—just new material to work with. Life’s curveballs are just part of the scene!
Tell us something you believe almost nobody agrees with you.
Meticulously plotted morning routines or waking up at 4 a.m. to meditate, journal, and plunge into an ice bath are NOT the key to success. While that may work for some, I believe the real key is being clear on your values and then treating life like an improv scene: say “yes, and” to whatever comes your way, embrace the unexpected, and don’t panic when your carefully crafted plans fall apart. Life is messy and unpredictable, so instead of trying to control every moment, lean into the chaos, find the humor, and make the best of whatever comes your way. Oh, and don’t forget to laugh—it’s a fun thing to do when the script goes off-track.
What is the one thing you repeatedly do and recommend everyone else do?
The one thing I repeatedly do—and recommend everyone else do—is to embrace the “yes, and” mindset. In improv, “yes, and” means accepting whatever comes your way and building on it. It’s a great tool for life because it helps you stay open to new ideas, unexpected changes, and even challenges. I believe it’s key to creating meaningful connections, pushing through creative blocks, and managing uncertainty. Life never goes according to plan, but if you approach each moment with a sense of curiosity and a willingness to see what comes next, you’ll find opportunities and solutions where others see obstacles. Plus, it’s a lot more fun that way!
When you feel overwhelmed or unfocused, what do you do?
The improv-inspired technique of “Pointing” that I use is a powerful way to bring myself back to the present moment, especially when I feel overwhelmed or unfocused. Here’s how it works:
First, I physically point at objects in my surroundings and say what they are—”chair” when pointing at a chair, “plant” when pointing at a plant, “laptop” when pointing at a laptop, and so forth. It’s a grounding exercise that helps snap me out of mental clutter and reminds me to reconnect with the immediate world around me. By labeling things with simple clarity, I restore focus and bring a sense of order to the chaos in my mind.
Then, I take it a step further and point at the same objects, but this time I say what they are not—”car” when pointing at something that is not a car, “cup of coffee” when pointing at something that is not a cup of coffee, “mountain” when pointing at not a mountain, and so forth. This shift primes my brain to think more creatively and to see things in new ways. It’s like flipping a mental switch that encourages me to approach the situation differently. If I was overwhelmed by a challenge or a decision, this helps me reframe it, allowing me to view it with a sense of curiosity and excitement, rather than stress. It’s a fun, playful way to bring new perspectives and sometimes even a sense of gratitude for what’s in front of me, instead of feeling burdened by it.
In essence, “Pointing” helps me break free from rigid thought patterns, reset my focus, and invite fresh ideas and excitement, all while adding a bit of humor and lightness into the process. It’s a little trick that makes a big difference when I need to regain perspective and shift my mindset.
And when that’s not suitable, a walk with my dog in nature helps!
What is one strategy that has helped you grow your business or advance in your career?
Improvisation has been one of the most powerful strategies that’s helped me grow my business and advance in my career. By embracing uncertainty and staying flexible, I’ve been able to pivot when things don’t go as planned and open myself to unexpected opportunities.
A great example of this was when I was invited to speak at a conference in Denmark. It wasn’t something I had planned for, and there could’ve been dozens of excuses not to go. But like an improviser, I said “yes” to the opportunity, and “and” figured out the rest along the way—flights, accommodations, presentation details, you name it. In the end, it turned out to be an incredible experience. Not only did I get to speak about the principles of improvisation in life and work with my “How to Handle Anything” approach, but I also built relationships with people from all over the world, learned to play padel, and explored the LEGO House.
In business and career growth, saying “yes, and” to new opportunities—even when they don’t fit neatly into your plan—has been key. Flexibility is vital. Instead of holding tightly to a rigid agenda, I stay committed to my core values while allowing the conversation or situation to unfold naturally, which has led to some of my most exciting collaborations and projects.
Improv also teaches me to be present and listen intently—whether I’m in a meeting, workshop, or conversation. When I’m fully present, I’m better able to respond to what others are saying and build on their ideas. This has fostered stronger connections with colleagues, clients, and collaborators, creating an environment of trust and openness.
Moreover, improvisation encourages me to take risks and embrace “failure” as a natural part of the learning process. I’m comfortable with not having all the answers right away, trusting that the next step will reveal itself as long as I keep moving forward and remain open to whatever comes my way. This mindset has been invaluable in navigating the uncertainties of entrepreneurship, turning challenges into opportunities, and building a business that’s adaptable and resilient.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
One failure I experienced in my career was a failure to communicate clearly, which led to missed opportunities and strained relationships early on. Turns out, people aren’t mind readers (a real bummer, honestly). While I was good at listening to others, I sometimes struggled to express my own views and expectations. I’d either assume my ideas were obvious to everyone (spoiler: they weren’t), or I’d dance around the point like I was auditioning for Dancing with the Stars. The result? Confusion, misaligned goals, and the occasional awkward “so… what are we doing again?” moment.
To overcome this, I had to get serious about sharpening my communication skills—and by serious, I mean embracing the principles of improv comedy. I learned to say what I mean, ask for feedback, and confirm mutual understanding instead of just hoping we were all on the same wavelength. I also started asking more questions to clarify what others needed from me, because apparently, guessing wrong isn’t a winning strategy. The results? Stronger relationships, smoother projects, and far fewer blank stares in meetings.
The big lesson? Communication is a two-way street, but it’s not enough to just smile and wave from the sidewalk. You have to get in there and articulate your own views clearly while actively listening to others. It’s like a well-rehearsed improv scene: when both parties show up, trust builds, ideas flow, and the magic happens. Turns out, when you stop treating everyone as a telepath, collaboration gets a whole lot easier.
What is one business idea you’re willing to give away to our readers?
One business idea I’d love to share is a Life Skills Escape Room—an immersive, hands-on experience where participants solve real-world challenges to “escape” within a set time. Think of it as an escape room meets personal development workshop.
Here’s how it works: the escape room is designed around everyday scenarios where people need essential life skills, like budgeting, negotiation, communication, and time management. For example, in one room, you might have to plan a group vacation while staying within a tight budget and handling surprise expenses. In another, you could face a negotiation challenge, like buying a car or navigating a tricky workplace scenario.
The goal is to make learning these critical skills fun and engaging. Instead of sitting in a lecture or reading a self-help book, participants are thrown into practical, high-stakes situations where they have to think on their feet, collaborate, and get creative.
This idea could be adapted for corporate team-building events, schools, or even family activity centers. Imagine students tackling a “Renting 101” room where they learn how to read a lease and manage utilities, or coworkers navigating a “Crisis Communication” challenge to strengthen workplace collaboration.
The best part? Everyone leaves the experience not just with a sense of accomplishment but with actionable skills they can apply in their lives. It’s practical, fun, and has huge potential to make a meaningful impact. It’s like life’s most stressful moments, but with a safety net—and maybe a prize at the end! Because let’s face it, we all need a little practice before life throws us into the real escape room: adulthood.
What is one piece of software that helps you be productive? How do you use it?
Canva! I use it regularly to design everything from posts to presentations. With its wide range of templates, stock photos, and design elements, it’s a breeze to create polished visuals quickly—no professional design skills required.
The best part is how easily I can customize templates to fit my brand’s colors and style guidelines. Canva’s drag-and-drop interface makes it simple to experiment with different layouts and typography until I find the perfect fit. The pre-made templates and design elements save me time, ensuring my branding remains consistent across platforms. And because it’s accessible from both my laptop and phone, I can stay productive with high-quality visuals, whether I’m in the office or on the go.
What is the best $100 you recently spent?
The best $100 I recently spent was on an acupuncture session. It’s one of those investments that benefits both my personal well-being and professional life. Acupuncture has helped me achieve a level of relaxation and mental clarity that makes me more focused and productive.
The experience is incredibly calming, allowing me to unwind and clear my mind. After a session, I’m able to handle stress more effectively, manage my energy throughout the day, and approach tasks with renewed creativity. It’s a simple but powerful way to refresh and recharge, enabling me to show up as my best self in both my personal life and work.
Do you have a favorite book or podcast from which you’ve received much value?
Just one?! I’ve read over 150 books in the past five years, so that in itself will illustrate how much I value books. But if I had to pick one, it would be Between Two Kingdoms by Suleika Jaouad.
I binge-read this book. It’s a beautifully written and deeply moving account of an experience that many would find difficult to talk about, yet Suleika manages to share it in such a compelling way that it’s hard to put the book down.
The impact this book had on me is multifaceted. First, it helped me shift my perspective on health and illness, encouraging me to approach both with more acceptance and gratitude. Second, it inspired me to write more courageously and vulnerably. Finally, it led me to explore more of Suleika’s writing, including The Isolation Journals on Substack, and introduced me to the music of Jon Batiste. If I could enjoy dinner with anyone I haven’t yet dined with, I’d choose Suleika and Jon. So, if you’re reading this, Suleika and Jon—you’re invited to dinner!
Big thanks to my mom for recommending this book to me and introducing me to Suleika’s work.
A close runner-up is The Boy, the Mole, the Fox and the Horse by Charlie Mackesy. I’ve read it multiple times, and it was a huge inspiration for my own illustrated book, A Girl and Her Horse. I love how the power of story and illustration can touch both children and adults, and I think this book does that beautifully.
What’s a movie or series you recently enjoyed and why?
I mean, is it too obvious to say Ted Lasso? But honestly, it’s the answer. It’s one of the most heartwarming, hilarious, and inspiring shows I’ve watched in a long time.
What I love most about Ted Lasso is how it blends humor with profound life lessons. Ted, with his endless optimism, demonstrates the power of kindness, vulnerability, and believing in people—especially when they don’t believe in themselves. It’s a show that reminds you that leadership isn’t about being perfect; it’s about showing up with empathy and integrity. Plus, the characters are so lovable and real. Every time they have a moment of growth, it feels earned and incredibly rewarding.
As someone who believes deeply in the power of comedy and humor as tools for personal growth and social impact, Ted Lasso aligns perfectly with my own approach to comedy writing. The show uses humor as a vessel for teaching important life lessons, making it relatable and accessible to everyone. It’s a reminder that laughter can create connection and that humor, when used thoughtfully, can inspire real change in how we show up for ourselves and others.
The way the show balances humor with deeper emotional moments is a masterclass in storytelling. It’s a reminder that the best way to lead—whether in business, personal relationships, or life in general—is with compassion, humor, and a little bit of belief in the people around you. If I ever need a boost of motivation or a good laugh, Ted Lasso is always there to deliver.
Key learnings:
- An improvisation practice is a great way to improve communication and collaboration skills. By embracing the principles of improv comedy, you can better express yourself, actively listen, and build stronger connections, while also boosting personal well-being and creativity.
- Life is full of surprises and things outside of our control. Learn to laugh and improvise in the face of life’s curveballs. Humor, when used thoughtfully, can create meaningful connections, alleviate stress, and serve as a vehicle for personal growth, professional growth, and social impact.
- Invest in your wellbeing. Small personal investments, like acupuncture, massage, can have profound benefits on both your personal and professional life by helping you manage stress, improve mental clarity, and recharge your energy.
- Sometimes, the key to productivity is indulging in the simple joys—like enjoying chocolate with breakfast—because the right balance of fun and satisfaction fuels creativity and energy throughout the day.