We look good on paper. We’re all a little lost.

Last week we pulled chairs into the Soberish courtyard in Serenbe, GA, twenty-five of us, drinks from the bottle shop sweating in our hands, and started talking out loud about the thing most of us only think about at 2am.

The middle. Being in it. Not knowing what’s next.

There were three of us up front. Margot Bingham, who you’ve maybe seen on The Walking Dead or Boardwalk Empire, who spent sixteen years saying other people’s lines and now coaches people to find their own. Mehrnush Saadat, an attorney who walked away from her successful law practice to open Soberish, a non-alcoholic bottle shop with two locations in Atlanta. And me, fifteen years leading marketing teams in tech before I leaped in 2025 to do well…this. Whatever this is.

Somewhere in the middle, a woman in the audience asked a question that quieted the whole courtyard:

Was there a moment your body knew before your mind did?

Oh. Yeah. Mine was a smack in the face.

I was working from home (pre covid), back when that was rare. I like to lay on the floor like a weirdo while I work, so I was on the floor, on a call with my boss, muting and unmuting myself so no one could hear me bawling my eyes out. Greg walked in, took one look, mouthed what is going on in here, and I waved him off. Go away. Let me just get through this call.

I got through the call.

Around that same time I had a rash crawling across my face that I now know was a candida thing, but at the time I was on an antibiotic loop and it just felt like my body tapping me on the shoulder. Hey. You didn’t get the first message. Here’s another one. Here’s another one.

I won’t get into the full details… but the next day I risked my job, spoke my truth to our CEO. And my boss found himself in a new role a few months later.

I almost accepted a new job during that time, but I ended up staying on that same path for five more years – through COVID, and as I became a mother. I wasn’t miserable, but that off feeling was getting louder. And behind the scenes, I was squirrelling away money, dreaming up my next chapter, and doing the deep inner work (basically redefining everything I knew about success) in order to get up the courage to do something completely new.

Margot’s moment came during COVID, in a small New York apartment, when the work she’d built her whole identity on just stopped. One morning, she woke up and couldn’t go in because the world had shut down, and she sat there thinking, what does that make me if I’m not this role. Who am I if I’m not showing up for everyone else?

Mehrnush had hives starting in 2017, and insomnia for years. Western medicine called it stress. Then a herniated disc in 2019, and she was crawling into the office to handle clients. Her body had come apart at the seams. She started listening in 2020, but a career she’d worked that hard for doesn’t unwind overnight. it took two full years to extract herself and make the jump.

It’s a very female thing, isn’t it. The no, it’s fine, I just can’t turn left, stand on my other side, it’s not a big deal of it all.

Margot named the thing almost nobody says out loud: transition comes with grief. You grieve the life you thought you’d have by now. The timeline. The certainty. The version of you that was supposed to show up and didn’t. And naming that grief doesn’t make you weak. It’s the thing that lets you move.

Fear says we can’t move until everything is certain. Intuition just asks you to take the next step. That’s the work she does now, holding up mirrors until you finally catch yourself in one.

Then we got practical, because I can’t help myself.

Before I leaped, I sat down with a pen and worked out three numbers.

1. What my life actually costs right now.

2. What my dream life costs.

3. And the bare minimum I’d be willing to risk before I’d pull my kids out of school or sell the house.

Three numbers.

Almost every time I’ve walked someone through this, they’re shocked it’s smaller than the story in their head. We get on the treadmill and we chase more, more, more, and we never stop to ask what enough actually costs. Doing it didn’t make the fear disappear. (Money is still my weak spot. I have a lot of self worth tied up in it… something im working on untangling) But it showed me the real shape of what I was risking, and that set me free.

If you want to run your own three numbers, I’d recommend starting with this Annual Money Check-In. And i’m here for you if questions pop up. (and im not a financial advisor or anything – great to start there too. This is just what I use myself)

Mehrnush told on herself beautifully. She said she just wanted to leave law and start a “cute little bottle shop boutique”. Nothing high-stress. One sweet little thing. Then…

One store became two, and two became maybe this could be a national brand, and she’d talked herself right back into the exact life she swore she didn’t want. Except maybe scale was never the thing she was running from. The wrong career was. In the right work, maybe big stops feeling like a trap and starts feeling like a plan.

Margot named a different lie, the if. If I get the house, the title, the ring, the baby, the number, then everything falls into place. Then the world rearranges itself neatly around me. We all nodded like we’d been caught.

Somewhere in there a woman in the audience said she’s trying to be a human being instead of a human doing, and the whole room exhaled at the same time. (I just love that)

Here’s the part I keep thinking about, and the part I almost didn’t write.

After the night, I got a piece of feedback that stung in the right way. One person shared that they left feeling further from their dream, not closer. Because my story, the one where I leaped, where I have a supportive partner, a flexible business degree, a network of people, and a financial runway, landed as unrealistic for the woman who is the breadwinner, has no savings, has kids who need dinner on the table tomorrow night. She heard leap and her brain went I could never.

And she’s not wrong. That is the reality for most of us.

That feedback was a mirror for me too. I sat with it. My path is mine, it’s privileged in ways I don’t get to wave away, and it is not the only door. The point was never to go quit your job on Friday and trust the universe to catch you. The point is smaller and truer than that. It’s permission to change.

What’s the tiniest step you could take this week to get a little closer to your aim?

For me, before any of the rest of it, it was building awareness and carving out time to pause, oftentimes through journaling. Writing down half-formed thoughts I didn’t even know were in there. And then over the years i noticed patterns in my words year after year.

To be clear, this wasn’t a consistent daily journaling practice. It was quarterly, yearly… sheesh sometimes every couple years. Whenever I carved out time to sit, think and get honest about the big picture of my life, and what I want from it.

The thing people kept saying after wasn’t about any one of us up front. It was that watching three women in the actual middle of it, none of us standing on some finished mountaintop, made the work feel allowed. Permission, out loud.

If your life looks good on paper and still feels a little off lately, I hope it helps to know there were twenty-five of us in a courtyard last week feeling some version of the same thing. Nobody up front had it figured out.

And the middle isn’t only a job you’re itching to leave. It’s a marriage, a body that’s changing, an empty nest, the back half of a career, the quiet after the kids are grown. It comes for all of us eventually.

We’re all in the middle of arriving.

So this is me bringing the juiciest bits home to you, which is the thing I’ll keep doing. Reporting back from rooms full of people figuring it out, so you don’t have to feel like you’re doing it alone.

Three doors before you go.

Margot. If you’ve got a talk, a pitch, or a story you can’t quite find, helping you find it and trust it out loud is her whole thing now. She works with creatives, execs, and founders alike. → t2binc.com

Soberish. None of this night happens without Mehrnush opening her doors. Soberish is her non-alcoholic bottle shop and cannabis boutique right here in Serenbe, built so women have a warm, no-judgment place to find what they actually want. Stop in, or shop online. → besoberish.com

Me. If you want to go deeper into building a life (and work around that life) that feels really freaking good, that’s what I do, through stories, gatherings, and one-on-one. → lifeatplay.co

And wherever you are in your own middle, the easiest way in is to come along. Life at Play is where I report back from the messy middle, the stories and experiments of people quietly rebuilding life on their own terms. Subscribe below.

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xx, Gina

P.S. Margot admitted she calls ChatGPT her chatdaddy, and it’s a name I will never forget. Still brainstorming something funny to call mine.

also how did we take zero pics of this night…