The Blank Canvas

On freedom, the pursuit of dreams, and the beautiful uncertainty of becoming.

In the spring of 2013, I sat in a Marriott conference room in Los Angeles. I was 24, and about 150 of us

were sitting together. The decor was drab, and the lights above were blindingly fluorescent white.

And yet there was real warmth in the room—and beauty in the fact that each of us was exploring our deepest thoughts and feelings. We were strangers who had spent a weekend asking questions that don't usually find their way into ordinary conversation.

During the final session, the lights dimmed. The facilitator walked slowly between the rows, repeating a sentence:

“Life is empty and meaningless. And it is empty and meaningless that it is empty and meaningless.”

…

...

What?

I looked down, furrowing my eyebrows, trying to grasp the concept.

This sounds…terrible. Empty? And meaningless?

She said it again.

I looked around the room - faces went from confusion, to despair, to recognition, to fascination—and then collective euphoria. I felt it too. If life didn't come with a meaning already assigned to it, perhaps that meant I was free to give it one.

There was something intoxicating about breaking from the chains of our past - along with our resentments, regrets, judgments, and rules and assumptions we've put on our shoulders —which together were dictating (and limiting) our futures.

This was freedom from an inherited script. Freedom from a predetermined destination. Freedom from all the “shoulds” in life.

For the first time, life felt like a blank canvas.

After a little while, though, a little unease set in.

What was I going to paint?

I'd spent much of my young life looking to parents, teachers, and managers for direction and approval. Suddenly I was confronting a question none of them could answer for me: What is my life for?

Kierkegaard called this anxiety the “dizziness of freedom.” I love that phrase. Freedom is exhilarating until you realize that you're the one who has to choose.

The existentialists gave me language for what I was experiencing. As it relates to choice, Sartre insisted that our choices help make us who we are—“existence precedes essence.”

I didn't encounter these ideas as abstract puzzles. I felt them in the decisions I was making—or avoiding.

In the years that followed, I kept exploring. In one program, a coach asked me to imagine my future ten years out, five years out, and one year out. I struggled. The black-and-white boxes and straight lines that had given my life shape and structure were blurring. If I wasn't simply following the next step, how was I supposed to know where to go?

But the coach helped surface some vague ideas: I wanted a more adventurous, global, and impactful life.

That idea inspired my choice to go to business school in Spain to be among the best around the world, to open more doors to possibility, and to learn Spanish (re: “be more Cuban”) in the process. It was the best choice I've ever made.

Then the pandemic hit, and I panicked.

After graduation, I moved to New York and took a job at a bank. On paper, it was sensible. In my heart, it felt painfully far from the life I'd begun to imagine.

I'd made a bold choice by moving to Spain. Now I was making a safe one. It was humbling to discover that a single leap of courage doesn't free you forever from the pull of safety.

Later, during a stretch of travel and reflection in Southeast Asia, I began to paint a clearer picture of what I wanted: I wanted to help people wrestle with the questions that had occupied so much of my own life: Who am I? What do I want? What might I dare to create?

The vision wasn’t clear - I'm still not totally sure what the endgame is. But I was beginning to understand that waiting for complete clarity was its own way of standing still.

And I was beginning to understand that no one else could decide what was worth pursuing. The only permission I needed was my own.

So I decided to treat this journey as an experiment. Trying things. Failing. Trusting that each step might illuminate the next. And to care a little less about what other people thought.

A future worth creating

Here's what I believe now.

We don't have to spend our lives searching for a single, fixed self, or fixed purpose, as if the answer is hidden somewhere and our only task is to uncover it. We can imagine a future that doesn't yet exist, rooted in values important to us, and choose to move toward it. And that desired future can change and morph at any time.

That's what a dream means to me: a deeply desired future, believed to be possible, that would take significant, sustained effort to realize.

It might be raising a family. Making art that has been waiting in a drawer. Building a business with the money you've set aside. Moving somewhere unfamiliar that you've always felt connected to. Finding a different way to love, contribute, or live.

My parents dreamed of raising three children in a big home with a backyard, giving us possibilities not available to them in their lifetimes, and eventually retiring to Florida to travel and enjoy time with their grandchildren.

What moves me most is not the scale or novelty of someone's ambition. It's the sincerity of their choice.

And I think it takes courage to dream. To admit to ourselves—and sometimes to others—that there's something we deeply want but don't yet have. There's vulnerability in that admission. Our dreams reveal something intimate about us: what we value, what we long for, and what we believe might be possible. And dreaming doesn't necessarily mean we're unhappy with the lives we have. We can love our lives as they are and still imagine something more. And I think it takes wisdom and strength in allowing ourselves to feel both.

I find the pursuit of dreams almost unbearably beautiful. The getting up again. The quiet stubbornness of someone who keeps going when no one is clapping. The transformation of an idea, rearranging disparate particles in the universe, into something real. Magic.

And something else happens along the way. We set out to create one thing, and find, sometimes to our surprise, that the journey has changed us too.

I didn't move to Spain with the goal of becoming a different person. I wanted a life that felt more adventurous and expansive. But the choices that followed confronted me with parts of myself I hadn't fully understood: how much I wanted freedom, how easily I could retreat to safety, and how badly I still wanted someone else's permission. I learned these things on the road to my dreams, not by setting out on a project of self-improvement.

I love the hero's journey (popularized by Joseph Campbell) for this reason. The hero doesn't leave home to become a hero. They leave because something is calling them. Becoming someone different is what happens along the way.

The pursuit of our dreams isn't decoration on top of a meaningful life. To me, it is one of the most meaningful endeavors we could choose.

And the part I find most beautiful: we cannot know, at the beginning, exactly what we will create—or who we will become.

Why this became my work

I sometimes wonder what would have been different if I'd been introduced to these questions, conversations, and tools earlier. No regrets—but I think about younger me who was lost, who doubted that it was worth even dreaming at all. And I think about everyone who finds themselves in that same place now.

Today, I get to sit with people facing their own blank canvases. Some are still searching for what they want to paint. Others have chosen something that matters deeply to them, but are struggling to keep going.

I've come to care deeply about both moments: crafting a dream that lights a fire inside, and finding a way to stay with it once the excitement of choosing has faded, and things get tough. Both moments are equally significant.

That's why I've been researching and building tools alongside my coaching work. The first is Sustain the Flame, a short reflection for people who already have a dream but find that their momentum keeps fading. In my next essay, I'll share why I built it.

For now, I keep coming back to that room in Los Angeles, to the strange exhilaration of discovering that the canvas was empty and mine to paint.

Some days I still can't believe this is my work: sitting with people at the edge of their own blank canvas, and helping them keep the fire going once they've chosen what to paint.

How lucky I am.

With Love,

Chris