Success Feels Like a Mess (And Maybe That’s Okay)

Is it just me, or does success feel a little messier than expected?

I always thought there would be a moment. A revenue milestone. A team win. A shiny new client logo that made it all click—Yes. This is it. I’ve made it.

But instead of feeling like I’ve arrived, most days feel like I’m juggling five different versions of myself: the founder, the mom, the boss, the partner, the scheduler of orthodontist appointments, and the one who definitely forgot the laundry in the washer again.

And the weird thing? I am proud of what I’ve built. I do love what I do. I feel incredibly lucky to run a business I care so deeply about, alongside a team that inspires me every single day.

But I’m also tired.

And if I’m being honest, I’m not sure I know how to rest. I rarely stop to celebrate the wins because I’m already thinking about what’s next. The pressure to keep going—to not drop any of the balls I’m juggling—feels constant. And when you’re responsible for your business, your team, your clients, your family… the stakes feel high. Like, don’t-blink-or-you’ll-fall-behind high.

I know I’m not the only one who feels this way.

So I said it out loud in this week’s Work in Progress episode. I admitted the thing we don’t always say on LinkedIn: that behind the highlight reels and polished wins, there’s a whole lot of mess. There are late-night tears, missed milestones because we were too busy cleaning up the chaos, and days where “success” feels more like survival than anything else.

I don’t have all the answers. I’m still figuring it out in real time—like most of us are. I don’t know how to slow down, or what “balance” really means, or how anyone keeps their house clean while leading a company. (Seriously. Please tell me.)

But I do know this: we’re not meant to figure it out alone.

That’s the whole reason Work in Progress exists. To create space for honest conversations—about leadership, motherhood, burnout, ambition, and all the contradictions we carry.

So I’ll ask you what I asked on the show: 

👉 What does success really look like for you? 

👉 Do you pause to celebrate, or does it all blur together in the pressure to keep moving? 

👉 Are you secretly wondering if you’re the only one dropping balls—or are you just really good at pretending you’ve got it all together?

Send me a message. Leave a comment. Share your “Is it just me?” moment. Because if I’ve learned anything, it’s that the more honest we are, the more connected we become.

We don’t need to have it all figured out. 

We just need each other.

Much love,

Gayle