10 Lessons from My First Two Years in Business

Two years ago, I had no idea what I was doing.

The start up I was launching ran out of money, I was a single mom with three kids, and I had bills to pay. I didn’t have a plan, a roadmap, or even a clue if people would want a “fractional COO”. What I did have was experience, decades of it, and a fierce determination not to fail.

Fast forward to today: I run a seven-figure business with a team of 12, clients across industries, and more opportunity than I could have imagined. But getting here wasn’t a straight line. It was messy, humbling, and full of hard-earned lessons.

So if you’re building something of your own, or thinking about it, here are the ten biggest lessons from my first two years in business.

1. You Always Start Clueless

No one starts a business knowing what they’re doing. You think you know, but you don’t.

I started On Call COO without researching pricing, competitors, or even whether the fractional COO industry existed. I built my offer based on instinct and experience, not a business plan, and somehow, it worked.

But here’s the truth: being clueless is part of the process. Every entrepreneur starts from zero. What matters is how fast you’re willing to learn.

2. Find the Helpers

When you realize you’re clueless, your next move is to find people who can help.

Early on, I invested in a mastermind and a training program that connected me to entrepreneurs who were farther ahead. It was terrifying, I didn’t have the cash to spare, but that single decision changed everything.

Skill acquisition and community will shorten your struggle more than anything else. Don’t walk the path alone.

3. Try Everything Until Something Works

In the beginning, my strategy was simple: throw everything at the wall.

LinkedIn posts. Virtual coffee chats. Cold DMs. Paid ads. Free masterclasses that no one showed up for. I did all of it.

And for a long time, none of it worked.

Then one day, something did, paid advertising. Once that started to click, I stopped doing everything else and doubled down.

That’s the secret: experiment relentlessly until you find what works, then focus.

4. Just Keep Going

Entrepreneurship is not for the faint of heart. It’s lonely, frustrating, and often humiliating. But success is always on the other side of struggle.

When it gets hard (and it will), remind yourself that consistency beats perfection. You don’t need to be the smartest or the fastest, you just need to keep showing up.

5. Know Where You’re Going and Be Open to Change

My first goal was survival: make enough money to keep the lights on.

Then it became “fill my plate.”

Then “work only with aligned clients.”

Then “build a team to handle demand.”

Now, two years later, my goals are so much bigger than I could’ve imagined back then.

The point? Let your goals evolve. As your business grows, so will your vision. If you keep aiming for the same target you set at the beginning, you’ll end up limiting your potential.

6. Experience the Losses, Don’t Wallow in Them

Loss is inevitable. You’ll lose clients, opportunities, and confidence.

The trick is to let yourself feel it without getting stuck there. Process the emotion, then ask, “What can I learn from this?”

Every setback teaches you something valuable, if you’re willing to look for it.

7. Ignore the Critics

People will talk. as Mel Robbins says, let them.

When I was in the C-suite, I had plenty of critics trying to tear me down. That experience prepared me for entrepreneurship, where the judgment just moves online.

If you’re worried about what other people think, you’ll never build anything worth building. Take their attention as fuel, not feedback.

8. Stop Lying to Yourself

The most dangerous lies are the ones you tell yourself.

That something’s working when it’s not.

That a client is “fine” when they’re not.

That this shouldn’t be so hard.

When I finally got brutally honest about what wasn’t working, my network, my messaging, my offers, I was able to fix it.

Clarity starts with truth.

9. Celebrate Every Win

Big or small, every win deserves recognition.

When I left corporate, I bought myself my first luxury handbag to mark the occasion. Now, I celebrate each milestone, onboarding a new client, hitting a revenue goal, hiring someone amazing with something that brings me joy.

Entrepreneurship can be lonely. Celebrating your wins is how you remind yourself that the hard work is worth it.

10. It’s Okay to Go Dark

We live in a world that expects you to share everything. You don’t owe anyone that.

When I was building the foundation of my business, I went quiet. I didn’t post, I didn’t overshare, and I didn’t explain myself. I stayed focused on building.

You’re allowed to do the same. The world will still be there when you’re ready to come up for air.

Two years in, I’m still learning. Year three will bring its own lessons, and I’ll share them when I can.

But if you’re in the messy middle, building, pivoting, or just trying to figure it out — know this: you are not alone. Every successful entrepreneur has stood exactly where you are right now.

Keep going. Keep learning. Keep building.

Because if I’ve learned anything, it’s this:

Success doesn’t happen overnight. But it always happens to those who refuse to quit.