There’s a highlight reel—and then there’s real life.
It’s easy to see the polished posts, the speaking engagements, the client wins, and think, “She’s got it all figured out.”
But I’d be lying if I said building multiple businesses was all strategy and success. It’s also been sleepless nights, payroll panic, self-doubt, missed birthdays, and lessons I had to learn the hard way.
Today, I want to pull back the curtain and share the challenges I’ve faced building Express Errands & Courier, Dream Team Digital Marketing, and Coaching with RoslynV—and the lessons that came with each storm.
Because growth doesn’t just happen in the glow-up. It’s forged in the grit.
Challenge #1: Growing Faster Than I Was Ready For
There was a point in my courier business where the contracts came in faster than I could keep up. Sounds like a dream, right? It wasn’t.
Drivers were calling off, routes were delayed, and I was drowning in operations, trying to hold it all together. I had asked for the overflow, without preparing for the infrastructure.
Lesson: Don’t pray for overflow if you don’t have a container to hold it.
I learned to build systems before I needed them, not after. Now, we automate what we can, delegate where we must, and prepare for scale with every move.
Challenge #2: Trusting the Wrong People
Whew. This one still stings a little.
Early in my journey, I hired someone who seemed perfect on paper. But their work ethic and values didn’t align. It cost me more than just money; it cost me momentum.
Lesson: Hire slow, fire fast. And trust your gut.
Today, every contractor and partner I work with is aligned with my mission, integrity, and pace. A business is only as strong as the people inside it.
Challenge #3: Wearing Every Hat Until It Broke Me
Marketing. Sales. Customer service. Bookkeeping. Social media. Operations. Training.
I was doing everything for every business. I thought I was saving money. But the truth? I was bleeding time, energy, and opportunity.
Lesson: Just because you can do it doesn’t mean you should.
Delegating and outsourcing changed my life. Now I stay in my zone of genius and let experts do what they do best—so I can lead and grow.
Challenge #4: Pricing from Fear, Not Value
Especially in the early days of coaching, I was charging based on what I thought people could afford—not the transformation I was providing.
That left me overworked and underpaid, and my clients weren’t as committed either.
Lesson: Your pricing should reflect your impact, not your insecurity.
Once I owned my worth, I attracted clients who respected the process and came ready to win.
Challenge #5: Reinventing Myself Publicly
One of the hardest things? Letting people watch me evolve.
When I stepped into the coaching space, some people were like, “Wait, aren’t you the courier girl?” When I launched a digital marketing agency, others said, “That’s not your lane.”
But guess what? I’ve built empires in every lane I chose to own.
Lesson: You are allowed to evolve. Your brand grows with you.
Every chapter of your story is part of the legacy. Don’t dim your light to stay in someone else’s comfort zone.
Final Thoughts
Building multiple businesses didn’t just stretch my income—it stretched me.
It taught me how to lead under pressure, pivot with purpose, and bet on myself when no one else understood the vision.
So if you’re facing obstacles right now, let me tell you: those challenges are shaping you into the CEO you’re becoming. The wisdom you gain in the hard seasons will become your secret weapon later.
Keep going. Keep growing. And never let the highlights fool you into thinking you’re behind.
You’re just building your own empire—brick by brick.
