On Downturns, Improvisation & Instinct
I’ve been thinking about creativity, specifically improvisation, as a key skill for navigating the current moment (waves around). No matter where you are in the world, you’ve probably noticed, or experienced, that many are being forced to work and move differently. The economy is trash. Funding is drying up. Growth is stalling (or worse). It’s a scary time, especially for entrepreneurs, or the entrepreneurial, who were counting on traditional systems to build something new. The usual formulas aren’t working like they used to. For some, they were never quite working, but still felt worth attempting, just in case the stars aligned.
I believe creativity matters more than ever. The ability to think beyond constraints, move without a blueprint, or act without a fully formed plan and fully realized resources might be your greatest asset.
During the 2008 financial crisis, I was interviewed for a Wall Street Journal article about how entrepreneurs were navigating the downturn. The piece was titled “It Just Isn’t Working? Some File for Customer Divorce” because, for me, survival wasn’t just about cutting costs. It meant questioning everything that quietly drained resources, including underperforming services and even misaligned clients.
The truth is: when resources are scarce, the most creative thing you can do is stop wasting energy on what no longer works, and lean into discovering what does. That shift takes courage, clarity, and a willingness to think differently.
When you’re constantly navigating systems and other people’s playbooks, it’s easy to lose touch with your own instinct. There’s always a framework. A formula. An expert with 10 steps to get you from here to there.
But sometimes, the way forward has to come from you.
If you’re feeling stuck, here are three to consider:
3 Ways to Challenge Your Thinking
Redefine The Rules.
What or whose rules are you following, and are they still serving you? Notice where a process or playbook no longer fits. What would it look like to step outside those constraints? What would you do if you could change or ignore the rule entirely?
Redefine “Product”
There’s the product that reflects your long-term vision, and all the smaller ones in between. Sometimes, the product is the process: the insight, clarity, or data gained from collaborating, experimenting, or shipping. What would an iterative approach look like for you? How can each step provide value?
Start With Enough.
What would you build if you knew, with certainty, that all you have is all you can use? Constraints can be a creative advantage. Start there.
Be Prepared Not Predictable
I’ve started a Creative Practice series exploring how routine, hands-on work can sharpen thinking, shift mental models, and unlock new possibilities. This summer, I began a creative sabbatical to recharge, rebuild my creative muscle, and leave space for high-impact work. I recently revisited an old hobby by taking a collage workshop. It had been a while since I took a course, especially in visual art or mixed media. This post offers a behind-the-scenes look at preparing for class, exploring how structure, curiosity, and improvisation interact and why presence matters when plans fall apart.
Breaking Linear Thinking
“What If?” is my new blog series exploring speculative scenarios that spark curiosity, imagination, and big-picture thinking. This post is inspired by skip-reading, a surrealist technique used by artist Frederick Sommer. By intuitively selecting words, the method disrupts linear thinking, clears preconceived ideas, and sparks creativity through unexpected connections. A shift in viewpoint can change how we see problems, make decisions, and determine what is real.
Tools I’m Trying.
I use voice notes to capture thoughts for blog posts or daily work journals, especially when I’m on the go. Since I usually need to transcribe those notes later, I set up a lightweight system that does it automatically, using tools I already have. Now, when I record and save a voice note, it’s transcribed in the background. A few moments later, the transcript appears in a shared folder accessible from all my devices.
Creating the Conditions for Big Ideas.
I had the honor of opening Richmond’s 2025 Big Dipper Innovation Summit on a panel that explored what innovation really looks like in legacy industries like medicine. As a Virginia native and longtime Richmond resident, I shared how I launched Time Study here. But our growth was fueled by partners beyond the region, helping us scale to over 100 leading health organizations. That experience shaped my message: innovation isn’t just about invention. It’s also about creating the conditions for ideas to launch, grow, and thrive.
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