What My Trip to Vegas Reminded Me About Life After Selling My Business
May 20, 2025I just got back from four days in Vegas...well, last week but I'm still recovering 😆
And not once—not even for a second—did I feel guilty about being away from work.
I didn’t pack a laptop.
I didn’t check in with clients.
I didn’t panic over unread messages.
I just… enjoyed myself. Fully.
Which might sound like a given, but if you knew me a few years ago?
You’d know what a radical shift that is.
Because during a previous trip to Vegas, back in 2015, I was living a completely different life.
That version of me?
She packed every single meal in Tupperware—because she was deep in the world of bodybuilding.
She was also completely consumed by her business.
Every hour of the day was scheduled. Every decision ran through her. Every vacation was just a workday in a different outfit.
I’d be checking staff messages during pool time.
Running payroll from my phone.
Sneaking in workouts like it was part of my job description.
All while pretending I was “off.”
I wore high-functioning stress like a badge of honour.
And I truly believed that was just what it meant to be a successful small business owner.
Well, I can tell you now that it's not!
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The First Business: Successful—but suffocating
I spent 18 years growing my retail business from the ground up.
It wasn’t just a store—it was my identity.
When things were good, I told myself the stress was worth it.
When things were hard, I worked harder.
Even after hiring a team, I stayed in the center of everything. Delegation felt risky. Boundaries felt selfish.
I thought being needed was the mark of good leadership.
But the truth?
I had built something that couldn’t run without me—and I didn’t even realize how dangerous that was until it nearly broke me.
Vacations weren’t really vacations.
Time off meant working twice as hard before and after.
And rest? That was something I believed had to be earned.
By 2018, I hit a turning point.
The long hours, the nonstop decision-making, the guilt—it all added up.
I started to see how unsustainable it really was.
But it took me until 2021 to actually start seeing the results of my work towards time freedom.
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What Actually Made My Business Sellable?
When I sold my business in 2023, people asked me how I knew it was ready.
The truth?
It wasn’t just about profit margins or popularity (although that definitely helped).
It came down to one major thing: operational independence.
My business had systems.
My team was trained.
I wasn’t the glue holding it all together anymore.
And that didn’t happen overnight.
It took years of building infrastructure, documenting processes, stepping back slowly, and letting go of my ego as the “go-to” for everything.
Because here’s the thing most small business owners don’t realize:
If your business depends entirely on you, it’s not just harder to sell—it’s impossible to scale.
And eventually, it becomes a glorified job that you built yourself.
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The Years That Changed Everything
Between 2018 and 2021, I did the work.
The inner work. The structural work. The scary, let-go-of-control work.
I started saying no to things that weren’t aligned.
I built systems to handle what I used to do manually.
I empowered my team to take ownership.
And the result?
In 2021, I took my first real work-free vacation.
No laptop. No check-ins. No panic.
I remember coming home and realizing that everything had kept running—without me.
That’s when I knew I wasn’t just managing a business anymore. I was leading one.
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This Trip Was the Reminder I Didn’t Know I Needed
This latest Vegas trip was exactly the reminder I needed.
It was peaceful.
Uninterrupted.
Guilt-free.
And that, to me, is real freedom.
No frantic check-ins.
No just-in-case laptop.
No pretending to relax while secretly spiraling about what I’d return to.
Just fun, rest, and a lot of people-watching.
(Which, in Vegas, is basically an Olympic sport.)
It reminded me how far I’ve come—not just in business, but in how I value my time, energy, and peace.
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Signs You’re Doing Too Much (and What to Watch For)
If you’re reading this and wondering if you’re on that same burnout trajectory, here are a few red flags I wish I’d taken seriously sooner:
- You feel guilty anytime you’re not working
- You avoid taking time off because it creates more stress
- You’re the only one who knows how to “do it right”
- Even vacations require backup plans, catch-up plans, and constant check-ins
- You fantasize about quitting—but can’t imagine how the business would survive without you
These aren’t quirks of entrepreneurship.
They’re signs your business isn’t structured to support you.
And the good news?
That can change.
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Why This Matters (Even If You’re Not Planning to Sell)
You don’t have to be thinking about selling to care about sustainability.
A business that can run without you gives you:
- Flexibility
- Mental clarity
- Creative freedom
- Time with your family
- The ability to take a breath without the sky falling
Too many small business owners are operating in survival mode—long after they’ve proven their success.
But survival mode isn’t a business strategy.
And burnout isn’t a milestone.
You don’t have to earn your way to ease.
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What I Wish I’d Known Six Years Ago
If I could go back and talk to my 2015 self (Tupperware in hand, phone glued to her side), here’s what I’d say:
- You don’t have to earn rest.
Time off is not a luxury. It’s a requirement if you want to keep going. - Letting go doesn’t mean giving up control.
It means building something stronger than you. - A business that needs you 24/7 will eventually resent you right back.
And spoiler: you’ll resent it too.
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What Could Change If You Stepped Back?
This isn’t about Vegas.
It’s not even really about selling.
It’s about freedom.
The kind that comes from knowing your business isn’t built entirely on your back.
So here’s the real question:
- What could change if you stopped being the default?
- What would it feel like to build something that supports you instead of draining you?
You don’t have to wait for burnout or a breakdown or a sale to start restructuring.
You can do it now.
Little by little. One decision at a time.
Because the difference between the version of me in 2015 and the one in 2025 isn’t just that I sold a business.
It’s that I finally stopped building businesses that demanded everything from me to survive.
And if you’re ready to make that shift too?
I promise—it’s worth it 🖤