Crossing the Threshold
On commitment, letting go, and what it actually feels like to cross over.
I was nervous approaching the bundle of sticks on the floor…
It was April 2025, the final day of my coaching certification program. We’d spent the past three days together laughing, crying, and appreciating each other in ways that felt almost reckless for a room of adults who’d known each other for less than a year. Now, the faculty had ushered us all out of the seminar room and into the hallway. A bundle of sticks lay at the doorway. One by one, we would be called to cross the threshold, in a symbolic act of leaving old burdens behind and recommitting ourselves to our calling.
Before we filed out, they asked us to sit with three questions:
How is life calling you? What do you need to let go of to answer that call? How committed are you?
I knew my answers. That was the problem. I knew what I wanted to commit to, and I was afraid I wouldn’t be able to follow through. Not afraid of doing the ceremony wrong; afraid of making a promise to myself that I couldn’t keep.
When my turn came, I paused at the threshold. It all felt very serious.
I took a deep breath. I closed my eyes.
When I opened them, I saw the warm smiles of my classmates and the faculty. I smiled back and proudly stepped over — maybe even with a little swagger — and stood beside them on the other side.
And then, for the first time in what had to be years, I broke down and cried.
It was relief, first. Relief at finally making a promise to myself. And then grief, for the years of putting off that commitment. For the cost of listening to the “shoulds” of others, rather than to my own voice.
Later that day, I wrote in my journal:
I need to remember those feelings, and that promise to myself, to not let my dreams and my happiness wait, not to let them be held back by the weight of expectations, or permission from others, and just proudly be who I am and pursue my purpose unapologetically. I cannot sit around waiting any longer. My development and happiness and purpose comes first; not as a wishful hope if allowed.
The promise I made wasn’t abstract. It was a commitment to stop keeping the most meaningful part of my work, and myself, on the margins. To stop treating my own priorities, the things that mattered deeply, or that made me feel alive, as something I would “fully pursue later.” To let those parts of me take up real space. Not as a side interest, not as a “someday,” but as something central and non-negotiable.
At the time, I thought that was the threshold.
It wasn’t.
Over the months that followed, life did what life does. The ceremony receded. The commitment I’d made didn’t disappear exactly, but it settled into the background, crowded out by the daily rhythm of a career that was still running on the old terms. I was still inside the same structure, still navigating the same metrics, still pulled between the work that felt most alive and the work that was most rewarded. The vow was there, but I wasn’t honoring it the way I’d promised myself I would.
I don’t say that with judgment. That’s just what happened. It’s the kind of gap most people feel but don’t talk about: the distance between what you declared in a moment of clarity and how you actually live on a workday when the pressure’s high.
Then, on an unassuming Monday morning in December, I sat down for a vaguely titled “check-in” meeting with my manager and someone from HR. And I learned I was being counseled out of the firm. Given a choice: take the Performance Improvement Plan, or enter into a Career Transition period to find something new.
This wasn’t how it was supposed to go.
For a long time, I’d been building the moment up in my head as some triumphant moment of courage and clarity. The version where I finally walked into my boss’s office and handed in my resignation on my own terms, confident in my next step, full of resolve. That’s the version I’d fantasized about. That’s the version that would have felt like a proper resolution to all those years of wrestling and questioning.
Instead, it felt like the opportunity to rewrite my own story had been snatched away.
The first emotion to surface was shame. Shame for failing — something I’d always been afraid of and gone out of my way to avoid. I’d learned early to stick to what I was good at, where performance was clear, where intellect was currency. And here I was.
The honest self-assessment was something like: I messed this up. Not that I believed I couldn’t cut it. But I wasn’t giving my best. I wasn’t buying in. And it showed. They caught it, and they were right to.
Then there was the looming thought of having to tell people. Of explaining my “tarnished” career narrative. Of feeling exposed. And the grief, not just for the job, but for the way I’d always imagined this moment going. For the big cinematic payoff that didn’t come.
But something in me had already begun crossing a different threshold.
This hadn’t happened overnight. Over time, my center of gravity had been shifting. I’d been pulled toward work that felt more human: mentoring, people & culture, DEI, coaching conversations. Over all those years, I clung to the rebellious notion that I wasn’t going to settle for continuing the hollow climb, even when I didn’t have clear answers. I tested limits. Explored edges. Followed what felt meaningful, even when it didn’t translate cleanly into the metrics that were rewarded.
So, when the time came to choose my path, even though it wasn’t the fairytale version I’d pictured, I chose alignment. Not because everything happens for a reason. Not because I had some clear vision of what was next.
I chose it because I knew what I had to commit to. I’d known since April, standing in front of a bundle of sticks on the floor.
And I felt relief. Maybe it didn’t feel free and soaring, the way I’d always fantasized about. It was mixed, heavy even. But it was honest.
The day I formally chose the Career Transition, I sat down and wrote a letter to myself. Not polished or planned. Just letting the feelings land on the page. I wrote:
I’m here to remind you, Will, that the circumstances around your transition should in no way diminish the reality of this opportunity you’ve carved out for yourself by doing the challenging work of listening to that pull deep down. Long before today, you declared your intentions to pursue work that felt meaningful and true.
And this:
I’m so glad that you learned to reflect back on your winding journey, with all of its ups and downs, and realize that those twists and turns were all part of becoming exactly who you’re meant to be.
And this, which I needed to hear most:
The path ahead won’t look exactly like you imagined it would, but what matters is you’re walking it now. And there’s real wisdom in the messy reality that doesn’t quite map to the storybook ending.
Here’s what I didn’t expect about the other side: how ordinary it would feel. Not ordinary in a disappointing way, but in the sense that it just became my life. Quickly. Naturally. Without the fanfare I’d always imagined would accompany a moment like this.
Lynea was the first to name it. A few weeks in, she told me I seemed different. Lighter. More present, especially in the evenings (or when peak “Sunday scaries” used to show up). Not performing “doing well.” Actually doing well. She could tell I was doing something I believed in, and it showed up in ways I wasn’t even tracking yet.
My family started to notice too. For years, I’d gone vague whenever anyone asked about work, deflecting, keeping it surface-level. I was scared of being seen as a failure or not living up to my potential, so I just didn’t let people in. When I started publishing my essays, my dad told me, “I never realized you were carrying all of this.” He wished he’d known, because maybe he could have helped. I told him I was glad we could finally talk about these things freely now. And then we started doing actual coaching sessions. Him opening up about things he’d been sitting with, me showing up with the part of myself I’d spent years telling myself “maybe someday.” I didn’t plan that. It just grew out of the space that had opened up, and it’s brought us closer than either of us expected.
When my sister calls me mid-week now to talk through a work dilemma, I’m genuinely excited to be the person she calls. That kind of thing never used to happen when I was guarded about my own career. Something about finally being honest opened the door for everyone else too.
I’ve also been reaching out to old friends, former colleagues, people I’d lost touch with. Not because I need anything from them, but because this new chapter has made me want to tend to those connections in a way I never made time for before. And what keeps surprising me is what comes back: conversations that go deeper than the usual catch-up; people sharing what’s actually going on. Something about showing up from a more honest place seems to invite honesty in return.
It’s not all smooth. There’s real uncertainty in this, and Lynea and I are navigating it together: what the finances look like, what the timeline is, what “working” even means for a practice this new. When a discovery call doesn’t land, or a prospective client goes quiet, it stings in a way that’s more personal than any performance review ever was. I care about this deeply, and that means the stumbles hit closer to home.
But there’s something else I notice now, almost daily. I’ll spend an hour at a friend’s coffee shop, just talking about life and work and whatever’s on our minds, and I don’t feel the old pull of guilt about the “real work” I should be getting back to. Those conversations are the work now. Same with losing myself in a book, or mixing a mini DJ set in my home office at the end of the day. In my old career, those things always felt like stolen time I’d have to pay back. Now they’re just woven in as part of how I show up.
And when someone from my old world says “I could never take a risk like that,” I don’t hear flattery. I hear the threshold they’re standing at. And it makes me want to keep going, to keep showing up as an example that something more you is possible. Not my version of the story. Theirs. It doesn’t have to be a dramatic exit. It can be feeling less stuck. Or showing up with more energy and less dread on an ordinary Monday.
I don’t have this all figured out. I don’t know that I ever will. But I’m free, and I’m committed, and I’m doing the thing I promised myself I would.
Your threshold probably doesn’t look exactly the same. Maybe it’s the tension you feel on Sunday night that you’ve gotten too good at explaining away. Maybe it’s the promotion you don’t want as much as you thought you would. Maybe it’s the insistent thought you keep having and keep dismissing: I can’t keep leaving myself out of this.
Crossing over doesn’t always look the way you imagined. Sometimes it comes with shame. Sometimes there’s grief. Sometimes, the most honest thought is just: why haven’t I done this sooner? But once you see clearly what you need to commit to, not crossing begins to carry a weight much heavier than you expected.
You don’t need a ceremony or a threshold made of sticks. You don’t need HR to force your hand. You just need to be honest about the questions — and willing to let your answers really mean something:
How is life calling me? What do I need to let go of? How committed am I?
If you’re standing at your own threshold right now, nervous and unsure, give yourself a second to pause. Take a breath. Look around for the warmth that’s already there.
And then step. Because waiting on the other side is a life that feels like yours.
My favorite post yet!