This essay was originally published on my Substack, Where the Road Bends, where I share long-form essays on conscious change and life transitions.
Jesse stared into the camera, his face illuminated by the soft morning light streaming through his LA apartment. Despite our decade-long friendship and the casual setting—complete with his ever-present trucker hat and familiar stubble—the tension in his voice was unmistakable.
He had stood on stages with Oprah Winfrey, led mass meditations in iconic venues like Madison Square Garden, and helped shape a movement in the mindfulness space. Among millennials, his name had become synonymous with the rise of modern meditation—a figure people turned to for inspiration, calm, and personal transformation.
But now, two years after pressing pause on these large mindfulness gatherings, he was struggling. His creation, The Big Quiet, was technically still alive, but it had been put on the shelf in the wake of COVID. As the world went into lockdown, the gatherings stopped, and while the brand still lingered in people’s minds, Jesse had begun to move on to other endeavors, like public speaking and coaching.
Yet despite no longer being at the helm, the world still saw him as The Big Quiet. And that weight—the constant association with something he no longer actively led—drained his energy and left him feeling stuck, as though tethered to a version of himself that no longer existed. There was also the growing sense that he was more than The Big Quiet, that his interests and message had evolved beyond meditation.
“I know it’s time to move on,” he said, his voice wavering slightly, “but I’m not sure how to let it go. It’s who I am.”
That was the crux of it. Jesse’s identity had become so tightly woven into the fabric of The Big Quiet that he struggled to separate himself from it. Even though the events had stopped, he was still bound to the image of the brand, to the person he had been when it was thriving. It felt like he was clinging to something that no longer held a place in his life, but the fear of stepping fully away—of not knowing who he would be without it—was paralyzing.
Jesse’s story is one I’ve lived through in my own transition and have witnessed countless times before. When we pour so much of ourselves into something—especially something that defines us publicly—it becomes more than just a job or a role; it becomes our identity. And when that role ends or shifts, we’re left asking: Who am I now?
For Jesse, letting go of The Big Quiet wasn’t just about closing a chapter; it was about confronting the very core of who he believed himself to be.
Why Identities Resist Letting Go
Our identities are not formed overnight. They are shaped over many years by both external influences—our society, our family, our peers—and by our own choices and actions. The more time, energy, and effort we invest into a particular identity, and the more it’s celebrated and reinforced by those around us, the stronger it becomes. Over time, that identity can feel like an unshakable part of who we are.
Think of identity like a tree. At first, it’s just a sapling, with shallow roots that are easy to pull up if needed. But with every choice we make, every action we take, the roots grow deeper into the soil. Over time, it becomes more established, its trunk thickening with each layer of reinforcement—praise, recognition, success, and societal approval. Eventually, the identity becomes so deeply rooted that even when it no longer serves us, it remains—entrenched and difficult to uproot.
When we realize an identity is no longer serving us, there’s a natural resistance. It’s uncomfortable. It’s as if that identity—whether tied to a job, a role, or a persona—fights for survival. And it’s not hard to see why. We’ve built so much of our lives around it, and letting go means stepping into the unknown.
Take the founder selling or shuttering their company, or the executive getting laid off from a high-powered role. These moments force us to shift, but the process of releasing that identity can feel like a battle. It’s not just about leaving a job; it’s about leaving behind a piece of ourselves—the part that was validated, recognized, and rewarded by society. Even when we know it’s time to let go, a part of us clings to the power, the influence, the status, or whatever that identity gave us.
I experienced this myself when I left venture capital. The perks of that identity—the money, the access, the sense of being part of an elite group—made it incredibly difficult to walk away, even when I knew in my gut that it was time. The pull was strong, and I found myself questioning who I would be without those external markers of success. The identity of “VC” had become so ingrained that stepping away felt like stepping off a cliff.
As Annie Duke, the professional poker player turned author, wrote, “The hardest thing to quit is who you are.” This captures the heart of the struggle: letting go of a deeply ingrained identity isn’t just about leaving a role or job—it’s about detaching from the version of ourselves that we’ve become so attached to.
It’s not just emotional attachment that makes it hard to let go; powerful forces—whether cognitive or social—are also at play, subtly deepening the roots of that identity and keeping us stuck.
The Patterns That Keep Us Stuck
Even when we know, deep down, that an identity no longer serves us, letting go is rarely straightforward. There are powerful patterns—often invisible—that keep us tethered to roles and identities long past their expiration date.
One of the most common forces that keeps us stuck is the fear of losing what we’ve built. Whether it’s the status, recognition, or sense of purpose that an identity gave us, stepping away can feel like losing a part of ourselves. We hesitate because it feels like walking away from everything that defined us, and the loss seems too great.
For Jesse, it wasn’t just about stepping away from The Big Quiet; it was the fear of losing everything that came with it—the influence, the recognition, and the sense of being a leader in that space. It wasn’t about wanting to continue leading mass meditations; it was about the fear of who he would be without that identity, and everything he might leave behind in the process.
Another pattern that keeps us tied to old identities is the investment we’ve made. The longer we’ve spent in a role, the harder it is to let go, as if walking away somehow erases all the work and effort we’ve put into becoming that person. This can keep us holding on, even when we know the role no longer aligns with who we are now.
In my own experience with venture capital, I found myself clinging to that identity long after I felt misaligned. I had invested years of my life into building connections, rising to Partner, and carving out a name for myself in the tech and venture world. Leaving wasn’t just about walking away from a job; it was about releasing everything I’d built around being a “VC.”
Then, there’s the pull of the familiar. Even when we know a role no longer fits, the comfort of the known can feel safer than stepping into the uncertainty of what’s next. The routine, the validation, the expectations—they all reinforce the idea that staying put is easier, even when it’s not what we truly want.
These patterns create a kind of internal tension, keeping us stuck in identities long after we’ve outgrown them. But once we can recognize these traps for what they are, we can start to question them. The fear of loss, the investment we’ve made, and the comfort of the familiar are not reasons to stay tethered to an outdated version of ourselves. Letting go doesn’t mean abandoning everything we’ve built—it means making room for something new, something more aligned with who we are becoming.
Letting Go and Embracing the Grief
Letting go of an identity isn’t just an intellectual decision—it’s an emotional one. Even when we know it’s time to move on, there’s still a real sense of loss. When we begin to step away from an identity, it’s natural to feel grief.
Grieving the loss of an identity is a crucial step in the process of letting go. Without acknowledging the emotional weight of that identity, it’s hard to fully move forward. This grief isn’t just about mourning what was, but also about accepting what no longer will be. We’re not just letting go of a title or role; we’re letting go of the version of ourselves that was attached to it.
Jesse went through his own grieving process when he stepped away from The Big Quiet. Rather than bypass his emotions, he allowed himself to fully feel the sadness of letting go, recognizing this as a necessary part of his transition. To honor the process, Jesse produced and shared a powerful video, announcing that he was moving on from this chapter.
His friends organized a viewing party of the film, and together, they watched it the week of the announcement. The film became a catalyst for hundreds of people to share their reflections on The Big Quiet and how it had impacted them, giving Jesse and his team a beautiful and comforting sense of closure.
In addition, Jesse wrote a long letter to The Big Quiet, thanking it for everything it had given him and saying goodbye. By ritualizing the completion of The Big Quiet’s cycle, Jesse found that it didn’t just bring closure—it also opened up a whole new channel of energy for what came next. The ritual and public announcement became his way of fully releasing the old identity, embracing the grief, and stepping into a new chapter with intention.
In my work with clients, I’ve found it essential to honor the process of letting go. We often create a moment of reflection where they can express gratitude for everything that identity brought them—whether it’s the success it fostered, the lessons it taught, or the ways it shaped their path. Acknowledging its value helps clients see that the identity served a purpose, even if it no longer aligns with who they are now.
For some clients, we take this a step further by marking the transition with a small ritual or ceremony, like Jesse did. This can be as simple as lighting a candle or writing a letter to that past identity, expressing both gratitude and closure. These rituals provide a way to symbolically release the identity, creating a sense of finality while honoring what it meant. The act of creating a tangible moment to say goodbye helps ease the transition from one version of themselves to the next.
This practice of honoring and releasing is something I encourage everyone to experience during times of transition. Whether through a simple ritual, a moment of reflection, or a conversation with someone they trust, creating space to acknowledge the grief is crucial. Letting go doesn’t erase the past; it honors the previous identity while embracing the possibilities of what comes next.
By marking the transition, we open ourselves to new identities more aligned with who we are becoming. While the process may feel uncomfortable, it’s a necessary step toward growth. Grieving the old identity creates the emotional space for something new to emerge—something more authentic, more alive, and more connected to the path we want to walk.
The Fluidity of Identity and the Liberation in Letting Go
Our sense of self fundamentally changes when we realize that identity is fluid. The roles we take on, the titles we hold, and the way we define ourselves—they’re not fixed. They’re constructs we shape, often without even realizing it. We’re not bound by who we were in the past or by who others expect us to be. Instead, we open ourselves to the possibility of conscious choice and self-authorship.
As we grow and move through transitions, what once felt like a defining part of ourselves becomes more transparent. These identities are not the essence of who we are, but simply characters we’ve played and chapters we’ve lived.
There’s fear in letting go, but there’s also immense possibility. Releasing an old identity—whether tied to a job, a title, or a way of living—doesn’t leave us empty. We carry with us the stories and experiences that shaped us. In letting go, we make room for something new to emerge. We gain the freedom to consciously decide who we want to be next, how we want to define ourselves, and what values or goals we want to prioritize.
The liberation that comes with this process isn’t about change for the sake of change—it’s about recognizing that we are always evolving, and our identities can evolve with us. We don’t have to stay stuck in roles that no longer fit, nor do we have to reinforce identities that no longer serve us. The fluid nature of identity means we can step into new possibilities and embrace new versions of ourselves at any time.
It’s true that the fear of not knowing “who we will be” is real. But the cost of staying bound to an outdated identity is far greater than the uncertainty of stepping into the unknown. True liberation isn’t found in clinging to who we’ve been, but in the courage to release what no longer serves us and trust that in letting go, we create space for who we’re meant to become.