What Happens in the Messy Middle

I disappeared a little bit over the past few months.

Not intentionally, exactly. But slowly. Quietly.

I stopped posting regularly. Stopped emailing. Stopped showing up in the ways I normally do.

And the truth is, I’ve been deep in the messy middle of my own career reinvention.

You know the version of career transition that gets talked about most often? The inspiring version. The brave version. The “follow your dreams” version.

And sometimes it does look like that.

But there’s another part of the process that people don’t talk about enough.

The part where fear gets bigger than your nervous system’s capacity to hold it.

The part where disappointment accumulates.

The part where you start wondering: What if this just… doesn’t work?

Especially when your livelihood is tied to figuring it out.

Especially if you’ve left a stable career. Especially if you’ve been laid off. Especially if you’re trying to build something from scratch. Especially if your savings account keeps getting smaller while your uncertainty keeps getting bigger.

At first, maybe you’re still experimenting with curiosity.

You try things. You reflect. You pivot. You learn.

But eventually, if enough things don’t seem to work, something can shift internally.

You stop feeling creative and start feeling desperate.

Your nervous system gets overwhelmed. You move outside your window of tolerance. And when that happens, it becomes much harder to access the parts of yourself that are visionary, grounded, patient, and resilient.

Instead, you start thinking things like: What I’m trying isn’t working. I’m still not where I want to be. Maybe this isn’t actually possible for me.

And then another layer appears.

You stop fully committing to the things you try because some part of you no longer believes they’ll work anyway.

Which means your actions become less consistent. Less embodied. Less grounded.

And unsurprisingly, more things don’t work.

So the fear grows.

Maybe you start flailing a little — trying random things that don’t actually make sense because you just need something to save you from the discomfort and uncertainty.

Maybe you start looking outside yourself for someone who can tell you exactly what to do. Someone who can guarantee the outcome. Someone who can rescue you from the ambiguity of being human.

Maybe you even start trying to crawl back toward the life you left in the first place.

Not because it was aligned. But because it was familiar. Predictable. Safer.

And if the spiral continues long enough, hopelessness can creep in.

The kind that whispers: Nothing is ever going to work. Maybe I’ve been fooling myself. Maybe this whole thing is pointless.

That spiral of thinking is what I’ve been moving through over the past 6–8 months.

And honestly? There was another layer on top of all of it for me: Shame.

Because somewhere deep down, I had internalized the belief that being a coach meant I was supposed to have this all figured out.

That if I help people navigate career reinvention, then surely I should never feel hopeless or uncertain about my own path.

So when I did feel lost…when I did feel discouraged…when I did question whether I was capable of building a sustainable, aligned life…

I thought: Well, I definitely can’t let people see this.

I unconsciously decided I needed to disappear until I had everything sorted out.

But eventually I realized something important: This isn’t hypocrisy. This is humanity.

The work I do has never been about perfection. It has never been about transcending uncertainty. It has never been about becoming someone who never struggles.

It’s about learning how to stay in relationship with ourselves inside the uncertainty.

And at some point, I decided to try something different.

I took a part-time job.

Not because it was my dream job. Not because I was giving up on coaching. But because I needed new information.

I needed to run an experiment: Can I work for someone else again without harming myself?

After burnout, after chronic stress, after stepping away from traditional employment for over a year and a half, I genuinely didn’t know the answer.

So instead of staying frozen in fear and overthinking, I moved.

And movement created clarity.

The job ultimately wasn’t the right fit for me. But taking it gave me something I desperately needed: momentum, data, perspective, and self-trust.

It helped me acknowledge what’s actually true: that building a sustainable coaching business takes time. That my economic needs matter. That I don’t need to force myself into a fantasy version of entrepreneurship that ignores reality. And that I’m allowed to build a life in a way that supports my nervous system instead of constantly overwhelming it.

But maybe most importantly…

It helped me remember that the entire point of all of this is not just “success.”

It’s aliveness.

Joy. Creativity. Connection. Play. Meaning. Fun.

Somewhere along the way, I had lost touch with that.

So for the rest of this month, I’m running a new experiment: practicing infusing more fun into my workdays and my life.

Not as avoidance. Not as toxic positivity. But as nervous system medicine. As reclamation. As a way back to myself.

I created a “Menu of Fun” that I choose from each day, and I’ve been documenting the experiment over on LinkedIn.

If you’re also trying to figure out how to create a life that feels more sustainable, more alive, and more you — especially in the middle of uncertainty — I’d love for you to follow along here.

And if you’re currently in your own messy middle right now:

You are not failing.

You are not behind.

And you do not need to have everything figured out in order to keep moving forward.

If this post felt painfully familiar… you don’t have to navigate the messy middle alone.

Sometimes what helps most isn’t another productivity hack or perfectly optimized plan.

It’s having space to slow down, tell the truth about where you actually are, and reconnect with yourself underneath all the fear and pressure.

That’s the work I do in Clarity Calls.

Together, we untangle what’s keeping you stuck, explore what your nervous system might be trying to tell you, and identify what your next aligned step could look like — even if you don’t yet know the whole path.

If that sounds supportive right now, you can book a call with me here: https://calendly.com/jessparecoaching/clarity-call.