When honesty stops helping

Vulnerability is meant to carry the team forward, not ask them to hold you up

Last week, one of my Substack notes did something I still don’t quite have the words for.

In seven days, I went from 49 subscribers to 173. My content was, for lack of a better word, popping off.

This type of engagement is a dream come true, a decade in the making. It’s the kind of momentum that creators are told to celebrate loudly and immediately. But since this is my first time, alongside the immense gratitude came a kind of pause, a flicker of stage fright.

It’s easy to hit “post” when no one is really watching. But when people suddenly have raised their hands and said, this resonates, I want more, the responsibility gets a little heavier. I try to work through it, to keep on keeping on.

In the middle of that reconciliation, I felt the urge to acknowledge it honestly, and publicly. To post a note saying something like: “Wow, this is wild. I’m so grateful. Also, give me four seconds to get over myself and recalibrate… Now what do we talk about?”

Self-aware, light, with a hint of self-deprecation.

When I floated the idea past my fiancé, he shut it down immediately. “No one wants to follow an insecure leader. People want confidence. Stability.”

I understood what he meant, but I couldn’t fully agree either. It’s part of my ethos to shine a light on the internal experience of growth. As I went back and forth with myself arguing, I got hung up on an important question that creators, and all leaders, should be asking themselves:

How much of the process should we show? Gary Vee would tell you to show everything, but when does transparency stop building trust and start asking too much of the people watching?

The difference between honesty and asking to be held

I’ve always believed in shedding light on the full entrepreneurial experience. The beauty, the challenges, and the friction in between.

Part of that comes from how I process. I’m an external processor. I talk things through out loud, write them down. Naming the feeling is how I make sense of what’s happening. For a long time, that instinct has served me well.

But leadership, whether in a company, or an online community, changes the equation. Transparency isn’t a moral virtue. It’s a tool. And like any tool, it has a time and a place.

At its best, transparency creates shared reality. It reduces uncertainty by helping people understand where you are and where you’re going. It builds credibility not by pretending everything is easy, but by orienting people inside of chaos.

But there’s a subtle line transparency shouldn’t cross.

There’s a difference between, this surprised me and, I don’t know if I’m ready. On one side you have vulnerability that is an honest reflection of reality, and on the other side, vulnerability that asks the audience to hold you up.

As leaders, its our job to carry the team. If you’re leading with transparency, but don’t see this distinction, it will erode your hard work.

Holding without spilling

I’ve always admired my boss for this exact reason.

She never pretends stress doesn’t exist. But she also won’t let it spill indiscriminately either. Every day she shows up to the office grounded and a ray of positivity. If something’s weighing on her, she processes it privately, on a walk, in a closed room, or in a one-on-one.

The team has never seen her sweat. And because of that, we trust her. We rely on her. There’s something deeply stabilizing about leaders who can say, this was hard—without saying, I don’t know what to do next.

That kind of leadership isn’t about suppression. It’s about recognizing that not every feeling needs an audience. Not every wobble needs a microphone.

Image sourced via Pinterest

The slippery slope of curated vulnerability

In online spaces, vulnerability is often rewarded, and I think it is important in building connection. I’ve seen a lot of influencers get massive audiences because of their willingness to hit record every time they start crying. But over time, if you become “known” for being vulnerable, I imagine there’s an unspoken pressure to keep going deeper. To share more and make each moment more raw than the last.

At some point, vulnerability risks becoming performative. Moments that could have passed quietly are seen as content. And sometimes, we just didn’t need to know.

I think what people are looking for nowadays is not you weeping in the party bathroom (a cheeky nod to my swifties), but instead what you learned from the experience. We don’t need to processes it live with you. In fact, the most honest thing you can do is process privately, integrate the experience, and then share once you know what you actually believe about it.

So what is transparency for?

If it’s a tool, when do we use it? What I’m learning through my own experience is that transparency is slightly different from letting people see everything. It’s about letting them see how you choose to react to situations.

Instead of asking ourselves, “am I being honest?” The better questions is, “what am I asking of the people on the other side of this honesty?”

Am I offering clarity? Or am I offloading uncertainty?

Am I setting the direction? Or am I creating instability while I catch up internally?

For those of us who process externally, that distinction is critical to internalize. Communicating how you process could potentially erode the trust you work so hard to build. Choose wisely where that processing belongs and communicate what comes after.

Journal, yes.

Trusted conversations, yes.

Asking an audience to carry your uncertainty? Mmm, probably not.

Resist the rush to resolve

Being a leader is a funny experience. Some people say you’re born with it, others don’t set out to become them but have to grow into the role. From this experience, I’m learning that, whether you’re a creator, a founder, or a manager, when we become responsible for other people, our honesty carries weight.

And that needs to be respected.

So I’m still thinking about it. About what it means to be real without asking to be held. And how to lead with openness and steadiness at the same time. So I’m curious, when has honesty made things lighter for others, not heavier? And how do you know when vulnerability is an act of care, not just release?