I recently had the opportunity to host a virtual conversation with Stanford Life Design Lab founders Bill Burnett and Dave Evans. It was one of those discussions that stays with you well after it ends.
We explored a question that I believe resonates across careers and life stages, particularly for founders, entrepreneurs, and leaders:
How do you build a meaningful life when the future is inherently uncertain?
For much of my career, I have believed deeply in planning. Business plans, estate plans, succession plans. There is comfort in structure, in the idea that with enough foresight and discipline, we can map the road ahead.
But what Bill and Dave offered was something more dynamic, and more human: a life is not found, it is designed.
As Dave put it simply, “The 10-word version of designing your life is get curious, talk to people, try stuff, tell your story.”
What followed was a practical philosophy for navigating ambiguity with intention.
Designing for the “Wicked Problem” of Life
Not all problems can be solved with logic alone. In fact, the most important ones, like how to live, what to pursue, and where to go next, rarely can.
Dave described life itself as a “wicked problem,” one where “you don’t know what you’re looking for until you find it… and you can’t reapply that answer to anybody else, because it’s totally context-sensitive.”
Traditional approaches, such as analysis, optimization, or process, fall short in this terrain. Instead, design thinking offers a different path: you build your way forward.
“You have to build your way forward by having ideas and trying stuff,” he explained. This mindset replaces the pressure of certainty with the discipline of experimentation.
You Are Not Static, You Are Becoming
At the heart of Bill’s perspective is a simple but profound idea: identity is not fixed.
“You really are not a static thing, you’re a becoming. All humans are becoming.”
This shift reframes how we think about growth. Rather than needing a fully formed vision of the future, we evolve through action, engaging in conversations, experiences, and reflection.
“You talk to people, you try stuff, and you change yourself. You become a new person if you’re paying attention.”
A well-designed life, then, is not one that follows a predetermined script. It is one that adapts, expands, and deepens over time.
Prototyping a Life
One of the most practical tools Bill and Dave emphasize is prototyping, or running small, low-risk experiments to explore possible futures.
Rather than making high-stakes decisions based on limited information, you can “start prototyping your life by having experiences that fill in the blanks of what you’re really interested in.”
This might take the form of conversations, short-term projects, or trying on new environments or roles. The goal is not immediate answers, but continuous learning.
“And repeat that until something sticks,” Dave noted, “and that’s called a life.”
Direction Over Certainty
In a world that often demands clear plans and definitive answers, Bill offered a more flexible metric for progress.
“You don’t necessarily need to know exactly where you’re going, because the future’s uncertain, but you can know you’re going in the right direction.”
This idea introduces a powerful distinction. Direction matters more than precision.
Through reflection and intentional design, individuals can build a kind of internal compass, one that guides decisions even when the destination is not fully defined. I have seen this play out repeatedly with founders. Starting a business is inherently imprecise. As long as the approach includes a direction, the process will get you there.
A Life of Engagement
So what does a well-designed life actually look like?
Bill described it not in terms of titles or milestones, but in terms of experience: a person “deeply engaged in the world.”
Engagement, being present, curious, and connected to what you are doing, becomes a core indicator of meaning. Rather than chasing a singular definition of success, we can design for moments of energy, alignment, and contribution.
The Throughline
If there was a unifying message throughout the conversation, it was this: you do not need to solve your life in advance, you need to participate in it.
By staying curious, taking action, and remaining open to change, we can move forward with intention, even in the absence of certainty.
Or, as Bill reminded us, the process is ongoing.
“All of these experiences start to add up… and you become.”
A meaningful life is not built in a single decision. It is shaped, step by step, through the choices you test, the people you meet, and the stories you’re willing to revise.
And in that process, design becomes not just a method, but a way of living.