The Cost of Becoming

Photo by Jan van der Wolf: https://www.pexels.com/photo/modern-blue-corridor-with-arched-windows-31935770/

June 2025. I decided to take the plunge into full-time entrepreneurship.

Half a year of juggling a full-time job, young kids, and a side hustle had proven to be too much — and a painfully slow way of building anything. People I met with didn’t know how to place me. Was I the urban planner? The coach? So I decided to make it easy for everyone, including me, and stepped fully into my new identity.

Fueled by an energy cocktail made with hope and anxiety, I hit the circuit to reintroduce myself to the world that knew me as the identity I had inhabited for over 20 years: an urban planning and development professional who liked to tackle big, messy urban projects. My new identity was an executive coach and strategic advisor — helping civic leaders navigate the inner and outer complexities I’d spent a career battling myself.

In the last piece, I wrote about the practice of becoming — the systems and habits involved in building toward a future self. You need them to be able to face the fears.

But with each conversation, as I stress-tested and refined my elevator pitch, a different emotion kept showing up. I couldn’t quite put my finger on it. It wasn’t fear. It wasn’t doubt. It wasn’t financial anxiety. It was something else entirely.

In the discomfort, I obsessed over my messaging. I was convinced I needed to make the connection between my old identity and new one crystal clear — for my business to work, for people to get it, for it to make sense. Every time I thought I’d nailed it, I’d feel a brief flash of relief. Within a couple of hours, I could literally feel the gears in my mind turning again. It doesn’t quite make sense yet.

Here’s what I know now that I didn’t know then: I was grieving.

What? But I had chosen this. I was excited about this. I had spent years fantasizing about this version of myself. What is there to grieve?

When you make a voluntary leap, hope is in the front row. You have a vision of your future self waiting on the other side. And because you chose it, there’s an unspoken assumption that you should just ... feel good about it.

That hope is a powerful thing. Powerful enough to convince you to skip what still needs to happen first.

Here’s what the research shows: your brain has to catch up to that choice. Your mind encodes your identity — like the one I inhabited for 20-plus years — as familiar and true. It does that to make its job of processing billions of bits of information easier by creating shortcuts to predict what will happen next. When your routines and identity shift drastically, even by your own design, your brain goes into overdrive trying to reconcile the new patterns against the ones it still expects. It’s a collision in your mind.1

And it hurts. I mean it physically hurts. The same neural pathways that process physical pain also process the pain of identity loss.2 Tightness in your chest. Tightness in your throat. Headaches. Fatigue.

The pain is information. It says you are grieving the old you. The question is whether you let it do its job.

I fell down a rabbit hole of research to understand what I was experiencing. That’s where I found Frédéric.

Frédéric was a 29-year-old carpenter who suffered a work injury that ended his career.3 He didn’t choose that. But what stood out to me was what he did next.

He mourned. He sat with the discomfort rather than rush to fix it. He got curious about what carpentry had actually meant to him. Working outdoors. Measuring the physical world. Seeing something tangible take shape from nothing. Those were his values. Carpentry was just the form they’d taken.

Once he could see that, he could find a new form. He went back to school and became a geomatician. I picture his mind deconstructing the old identity brick by brick, making room for his curiosity to stretch and explore.

Then I found Daniel.

Daniel was a 58-year-old business executive who lost his job and tried to move on immediately. He applied for roles, networked, got zero responses. The resentment moved in and never left. He isolated himself from shame, when connection was probably what he needed most. And unlike Frédéric, Daniel never tried to imagine a different future version of himself. He stayed fixed on what was gone.4

Two people facing loss. Two completely different outcomes.

Why?

Moving from an old identity to a new one isn’t a straight line. It’s a tug-of-war between two orientations happening at the same time: one pulling you back toward what you lost, one pulling you forward toward what’s possible.5

You need both.

The forward pull without the backward one is Nancy’s story — a 41-year-old librarian who quickly took an adjacent role as an archivist after losing her position.6 It relieved the discomfort of being in between. But she never actually processed what she’d lost. Her old identity was still beneath the surface of the new one. She was living with it. A more comfortable version of the in-between, but not fully transformed.

The backward pull without the forward one is how you end up like Daniel. Stuck in grief.

What separates Frédéric is that he danced with the tug-of-war. He let the grief do its job. The sadness, the frustration, the anger — those aren’t obstacles to finding your new self. They’re signals. They tell you which parts of the old identity actually mattered, which values are worth carrying forward.

What I’ve learned is that the hope you feel when you make a voluntary leap doesn’t cancel out the grief about what you’re leaving. If you let the hope do all the work — if you use it to skip over the loss — the grief doesn’t disappear. It goes underground, and it will find you later. In the doubt spirals. In the exhaustion from the doubt spirals. In the strange pull back toward something you intentionally left behind.

I haven’t gotten to where Frédéric is yet. But I can see myself in his story.

He went back to school. I’m exploring through my business venture. I’d say I’m about 80 percent there.

Now when I feel the clash between my old identity and new one, I remember him. It grounds me. It lets the hope and the grief exist in the same space, instead of fighting each other. It reminds me that the friction isn’t a sign something is wrong.

It’s just part of the process. The cost of the climb.

The other thing this research called back for me was organizational change management. We all know change management is “hard.” But what if the need to grieve is the secret unlock?

That’s another question to get curious about for another day.