Maybe: The Power of Uncertainty

"As far as the laws of mathematics refer to reality, they are not certain; and as far as they are certain, they do not refer to reality.

--Albert Einstein

When I was a child, the answer I most hated getting from my parents was “maybe.”  I fiercely disliked the limbo “maybe” created. The most dreaded answer was, “We’ll see.” Those answers were ambiguous and uncertain. As a developing child, my brain functioned in the black-and-white world of legalism and certainty. Hearing “maybe” made me wonder what was next, when things might happen, and how to prepare for the unknown. If I’m honest with myself, even today, I am frequently anxious when things seem uncertain, when I don’t know whether I’m doing the right thing, or when I am unsure about my ability to navigate a problem. 

 I’ve been reading Uncertain: The Wisdom and Wonder of Being Unsure (Prometheus Books, 2024) by Maggie Jackson, and it turns out that my parents’ “maybe” was a great gift to me. In this beautiful book, Jackson points out that uncertainty brings a sense of honesty and helps us move forward. 

 I experienced that stripped-down sense of honesty four years ago, at the height of the COVID-19 pandemic. I was leading an independent school. Once schools shut down, I had no idea what would happen next. I met with other school leaders on video calls where we collectively wondered how long this would last, how we would open again, what kinds of policies we needed, and how to keep children safe AND encourage their natural and social development. None of us had answers, and this period rates among the most stressful of my life. At the same time, the lack of certainty allowed us to deconstruct school and think about what learning provides at its best. We supported one another in developing new strategies for learning, new ways to help families, and new ways to learn together. We had to get honest and dig.  

 Human beings are wired to develop mental shortcuts. We all have things we can do “without thinking”—even complex things. For example, I never thought about the mechanics of walking until an accident left me limping. Several months after the accident,  my therapist helped me see that my biggest obstacle was my brain. It had re-wired itself to limp in response to pain that no longer existed. I was functioning in auto-pilot based on that old experience. I was certain that walking normally would cause pain. By injecting uncertainty into my conviction, my therapist helped me break through. She broke down the mechanics of walking with me, helped me strengthen my weakened muscles, and, most of all, helped me think. Once I was no longer certain that I needed to limp, I could re-wire and learn to walk differently. (It took some time, but I'm there!) 

 It turns out that certainty usually has to do with past experience and past success. Certainty works well when there is a technical challenge in front of us. A technical challenge is evident, can be solved by experts, and the people experiencing it are happy when help is coming. The expert draws on their experience and applies expertise to solve the problem. When my computer takes a long time to process, I pull up my Apple support chat. A bot walks me through potential solutions, and if those don’t work, I am connected to an expert who solves the problem. While frustrated about the situation, I am happy to turn it over to someone else.  

 Unfortunately, the most obstinate challenges we face are not technical; they are adaptive. The problem isn’t apparent, and we cannot rely on technical knowledge to solve it. Our past experiences will help us with the challenge, but we cannot turn on autopilot and rely on our gut. Adaptive challenges demand that we face our uncertainty and learn something new. 

 To be experts at adaptive solutions, we must become experts at living with uncertainty, tearing down assumptions, and wondering what might be possible. This is what great Process Consultants do. They come to an organization without a known solution. Instead, they walk alongside their Clients and wonder why. They humbly ask to listen, to help, and to learn. The Client then also listens, helps, and learns. By embracing the uncertainty, they move their knowledge forward profoundly. They discover new solutions together. 

 When we embrace uncertainty instead of relying on past knowledge, we open our minds to possibility and to wonder. When we give up on the certainty of having the answers, we embrace the opportunity to unleash possibility boldly.  

If you’re ready to step into uncertainty, here are the things Jackson suggests to cultivate comfort in uncertainty: 

1. Actively seek novel (and potentially uncomfortable) experiences. 
2. Cultivate the ability to hear voices of dissent and encourage disagreement. 
3. Take another person’s perspective and work to understand their point of view. 
4. Set problems aside for a while to come back to, daydream, and create space for your brain. 

 And for my mom and dad, I’m sorry I didn’t recognize the gift within “We’ll see.” to understand their point of view. ms aside for a while to come back to, daydream, and create space for your brain.