6 Leadership Lessons I Learned While Running a Failing Business at the age of 22 (Part 1)

Kacy O'Brien
8 min readNov 30, 2023

When I was 22 years old, my mom asked me for help. She thought I was really smart, and wanted to start a business together.

This was the same year I decided I wasn’t going to medical school. I didn’t know what was next in life, so I said yes.

That yes caused me both a lot of pain and suffering, but taught me massive life lessons I would not have learned otherwise.

Before I jump into those lessons and that story…here’s what you need to know about 22 year old Kacy:

  • She had just completed university, and had decided not to go to medical school
  • She was doing a lot of leadership growth and development courses
  • She felt like she was invincible
  • Newly single
  • She had no clue what she was actually doing, the perfect amount of ignorance to try new things
  • She didn’t know anything about business, but wasn’t afraid to try
  • And she bright red hair 🙂 and loved to party and travel

About my mom

She was an esthetician at the time, renting a small room in a spa. She was making pretty good money and her operating expenses were very low.

What she wanted was to expand. Bigger must mean better …*wait for it*

There was a 3000 square foot location that she had seen for rent and she wanted to turn it into a wellness studio where women could come to feel beautiful from the inside-out.

There would be yoga, meditation, massage, mani pedis…you name it! The ultimate experience.

When I heard this, I felt like it was a good opportunity. I could build something meaningful and work with my mom. This was my first real experience in the ups and downs of entrepreneurship.

It started out fun.

We negotiated rent, got the space, started designing our rooms, and it was all going great.

I felt like I was doing very important things. Like meeting with lawyers, realtors and signing leases. I didn’t know any other 22 year old doing any of that.

It kind of reminds me when I was a kid and pretended to be a doctor, or secretary, or teacher.

Now, as a 22 year old, I was pretending to know how to be a business owner.

Going through all the motions day by day, without really understanding the brass tacks of any of it.

Nonetheless, we started off strong. Had a really awesome grand opening where hundreds of people showed up. A huge party!

And then, the excitement died down.

We showed up day after day, and life just got more and more complex while at the same time, very monotonous.

Managing numbers, booking appointments, sales, marketing, hiring and firing staff. We thought we were doing relatively well, but in all honesty, this was new to both of us.

My mom was a service provider, not a business owner. And I was a 22 year old doing her best, not an operations manager with a decade of running successful organizations under her belt.

I didn’t even know what COGS meant until it was too late. [COGs = Cost of Goods Sold, aka how much it costs you everytime someone actually buys from your business]. Yes, it actually COSTS your business money when you get a customer. Crazy.

I used to pretend that we were doing okay. We made a couple hundred bucks every day and that seemed okay. Some days it was into the thousands.

We had an accountant. A business bank account. Even a corporation. Things seemed to be going smoothly.

Until one day, we got an email that changed my life forever.

When we initially signed our lease, our landlord had given us a 1 year grace period of partial rent.

Here’s what I mean — our rent for the space was $8000 per month. Yikes.

But, over the first 6 months, it was $0 in order to get us off the ground.

Then it gradually went to $3500, $6000, and then eventually at the 2 year mark it hit the full $8000. This was all good, we were doing well enough to pay this.

Everything changed the day of the email.

It was a Thursday afternoon and the email was from the landlord stating that over the past 2 years, we had accumulated over $60,000 of “back-rent”.

Remember the time that we thought we were paying NO rent? Well, that wasn’t true. It was just delayed. With interest.

When we were working with our real estate agent, we didn’t realize these were part of the terms. Just a mom and daughter duo doing their best, with little to no due diligence.

💡 Leadership Lesson: ALWAYS get contracts like this looked over by an attorney, read through them detail for detail and always ask questions. There are never ever too many questions. In fact, the more you ask, the smarter you really are.

They had now added up all the rent we weren’t charged and put it into one generous lump sum, demanding that we pay it asap.

I looked at that email, and closed it.

I didn’t think it was that serious. I definitely had some avoidant strategies. So, I tucked it away thinking to myself, I’ll get to it on Monday and we’ll figure something out.

The whole weekend went by, and I did not respond. Big mistake.

Monday Morning

On Monday morning, we made our way to work. Got our morning coffee, listened to our tunes. Another full day of appointments and clients.

We got to the front door, and my key wouldn’t work.

I kept trying, but it was not going in. *cue Michael Scott*

Heart pounding, hands shaking, I look up and see a note that’s taped to the inside of the front door.

YOU HAVE BEEN LOCKED OUT OF YOUR STORE, THE LOCKS HAVE BEEN CHANGED. YOU HAVE 5 DAYS TO PAY YOUR AMOUNT OWING. With love, your local bailiff (lol they didn’t write with love…)

I felt my breakfast come up.

Everything was on the other side of that door. Laser Hair Removal equipment, client files (we didn’t have a digital CRM at the time), our computers, tech, ipads, etc. was all there. Thousands of dollars invested on the other side of that door.

Everything, including my pride and dignity.

💡 Leadership Lesson: Technology is your FRIEND, not your enemy. Back then, so many people were using their good old manilla file folders. Having a CRM was foreign, and confusing. Don’t let that stop you, learn what you need to learn to ensure you have solid foundation for your growth. Without those file folders, our 10,000+ client list meant absolutely nothing.

The Call to Adventure

My mom, Cameron (my now husband, then boyfriend) and I stood staring at this sign in awe. We all froze for a moment. Suddenly, the energy shifted and we knew we needed to get into action.

I walked over to our next door neighbor, and asked to borrow a sharpie, a piece of white paper and some scotch tape.

We wrote on this new sign, “Family emergency, all appointments cancelled today. Please call (my moms’s cell) to re-book appointment”. We stuck this right on top of the bailiff sign, hoping to hide that shameful message.

My mom then called the landlord and told them we’re coming to see them in person.

And so, our adventure began.

It was a 45 minute drive. It felt more like we were headed to Mordor. (for all my Lord of the Ring nerd friends 🤓)

We got to the office, and the first thing we did when we sat in that conference room with the landlord and his executives was express our gratitude.

Weird, right?

You’d think we would demand our keys back, or express our anger. But no, we chose a different strategy.

They did not expect this in a million years. Suddenly the energy of the room changed from intensity, to calm and grace. You could really feel that God was right there with us.

💡 Leadership Lesson: Start with love. Start with gratitude. Connect to your heart, and no matter what the circumstance — choose love and faith over fear. This is especially true as a leader in today’s world. We need to lead with heart, and show that the righteous path is always one of forgiveness and love.

The Heart-Centred Conversation

We talked about all that we’d been creating, and that we saw the email. We apologized for not acknowledging it sooner and took full responsibility. We understood that we owed money, but we didn’t have all of it for them.

💡 Leadership Lesson: When you take full ownership and responsibility over your actions, the other person usually becomes kinder. They realize and see that you SEE what you’ve done, and at the end of the day, human beings are good. They start to feel more empathy and kindness towards you, bringing the matter to a mutual conclusion.

I then witnessed my mom being the most powerful I think I’ve ever seen her.

“What would it take for us to get the keys back today?”

She looked them in the eyes and said:

They said at least 20k, paid in cash by 5 pm. It was currently 12:07 pm.

She remained calm and said, “Okay, I’m going to wire you 20k this afternoon. I want the key now”.

I sat there watching this in awe, and they agreed. They handed her the key, and we walked out of that office not having paid a cent.

What. Just. Happened.

💡 Leadership Lesson: Be bold. Be audacious. You have no idea until you ask. And don’t ask in a shy way, ask in a way where they know you are not messing around. Demand. Have conviction. You must feel this conviction in every cell of your body and you must stand your ground. Nobody else will take you seriously until you take yourself seriously.

Now, it was great of her to say we had 20k, but we didn’t have 20k.

But, we had the key. And that was the golden ticket.

We were so high off adrenaline as we left the office, key in hand. Knowing we could do anything.

Rather than sit in panic about how we were going to get the 20k, we started our drive back to the Spa and we were making phone calls along the way.

By the time we arrived, we had secured 20k in cash. All we needed to do was go to the bank and wire that money.

💡 Leadership Lesson: You don’t need to know the how, the how will reveal itself when you have a burning desire to accomplish your mission. And also, having a community of people around you who know you, trust you, and believe in your vision is incredibly important on this journey. There was no way we could have gotten the key, or the 20k by ourselves. We needed a mastermind and people we could lean on.

What happened next?

Well, like any good cliffhanger, I’m not going to tell you the rest of the story just yet.

The next part is a little bit more intricate and goes deeper into some pretty challenging things, where we made a lot of money but ended up declaring bankruptcy for reasons we couldn’t see at the time.

We had a cash-rich business, but absolutely no skills to manage and run the business.

I am so grateful for these hard-knock experiences that life gave me at a young age. I grew. I fell. I wept. And I felt like such a failure for a long time.

If you want to know when Part 2 comes out, make sure you’re subscribed to my newsletter. You’ll be the first to know and I’m sure you’re going to learn a few more things that can make a huge difference for your life.

For now, would love to hear what your biggest takeaway! Have you had any experiences like this that have stuck with you for life?

As always, the inner journey is the way. Trust your truth.

Thanks for reading ❤️

Originally published at https://coachkacy.com on November 30, 2023.

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Kacy O'Brien

Loving Wife | Storyteller | Making Sense of this thing called "life"