Twelve years.
That’s how long I went without a true day off.
No vacations. No real rest. No silence that didn’t include a ping from a client, a driver needing help, or a dispatch alert.
When I became an entrepreneur, I didn’t just build businesses—I became the business. I was the CEO, the after-hours dispatch, the holiday coverage, the weekend emergency contact… and yes, I worked on every single one of my birthdays.
But this year, something shifted. I celebrated my birthday—really celebrated it—with clear skies, blue water, and peace in my soul.
And now, I want to share that with you.
From Working Every Birthday to Celebrating in Paradise
Back in my 20s, I worked full-time jobs where I’d have to ask permission to take my birthday off. Half the time, the answer was no. The other half? Guilt trips.
So when I became my own boss, I thought, “I’ll finally be free.” But instead, I worked harder.
Every birthday, I was clocked in. Answering dispatch calls, fixing issues, onboarding drivers, handling crises in the background while smiling in the foreground.
But last week? I was in the Grand Cayman Islands, Cozumel, and Montego Bay—no laptop, no to-do list, just vibes.
And it wasn’t just a birthday trip. It was a milestone moment.
The Mindset Shift That Changed Everything
Here’s the truth: I didn’t let myself rest for over a decade.
I thought if I stopped, everything would fall apart. I had built my companies with my bare hands and didn’t trust them to stand without me.
But in the twelfth year, something clicked. I finally felt like everything was moving how it should—team aligned, systems flowing, clients taken care of. So I booked my first real vacation.
One turned into two. Then four. That year, I vacationed six months out of the year. And I didn’t disappear—I brought my community with me via Zoom, WhatsApp, and email. My business didn’t suffer. It grew. I grew.
Chasing the Dream Is Beautiful—But It Costs
Let’s be real. None of this came easy.
I sacrificed time with my family. Missed events. Cried in silence when things went wrong. I invested money I didn’t have. I worked through holidays, birthdays, and grief.
There were years where I paid everyone but me. When you’re building a dream, you’ll often feel like you’re doing it alone.
But you’re not. I’ve been there. I am you. And I want you to know: the rest is coming.
There will be a day when your business works without you.
There will be a day when you can take your birthday off.
There will be a day when your office has an ocean view.
Just don’t stop building.
- Me, living my best life in the Grand Cayman Islands
- Cozumel views and cocktails
- Montego Bay sunsets and smiling faces
These weren’t just pictures. They were proof that the grind was worth it.
In Closing Thoughts
I’m still that girl who used to answer dispatch calls at 11:45 p.m. I’m still the woman who coached clients with no makeup on and a messy bun because they needed real guidance, not a curated version of me.
But now, I’ve learned that freedom is the reward for faith and consistency.
So today, I’m not just celebrating a birthday—I’m celebrating the journey. The one that took me from no days off… to no limits.
And if you’re in that season of sacrificing, I want you to keep going.
One day, you’ll be sending emails like this… from the beach.
With love and legacy,
Roslyn 💛
