There’s a big difference between teaching business… & actually running one.
You can read the books.
Learn the frameworks.
Sit in the workshops.
But until you’ve had to make payroll with nothing in the bank, deal with a team issue that keeps you up at night, or watch something you built fall apart…
You don’t really get it.
And I say that with complete honesty, because I’ve lived both sides.
I’ve Built Businesses… & Lost Them Too
Over the years, I’ve built five businesses.
Two were successful.
The kind that gave me financial freedom & the lifestyle I enjoy today.
Two were massive failures.
Not the quiet kind you can sweep under the rug. The kind that hit hard.
One was so severe I lost my house.
And yes, the Porsche went with it.
And then there’s the fifth.
A fresh start-up, still finding its feet. Still in that messy, unpredictable phase where things don’t always go to plan.
That’s business.
It’s not a straight line. It never has been.
The Highs Are Real But They Don’t Last Forever
I’ve had the moments most business owners chase.
Landing major international brands.
Seeing something you built gain traction.
Watching growth happen quickly.
I’ve also been recognised as one of the top six businesswomen & one of the top 30 women in New Zealand.
Those moments matter.
They give you confidence.
They give you momentum.
But they don’t protect you from what comes next.
The Lows Teach You More
Because business has a way of humbling you.
I’ve borrowed on credit cards just to make payroll.
I’ve had someone inside the business completely derail it due to a core values mismatch.
And I’ve experienced what it’s like to have something you’ve built come crashing down due to factors completely outside your control.
Covid did that to one of my businesses.
No warning. No time to prepare. Just impact.
That’s when theory stops being helpful.
And real experience becomes everything.
I’m Not Talking About the Past. I’m Still in It
This is the part that matters most.
I’m not reflecting on something I used to do.
I’m still running businesses every day.
Our EOS Practice operates across Australia & New Zealand, with a growing team & increasing demand.
I run Integrated Executives, placing fractional leaders into businesses that need capability quickly.
And I hold a shareholding in Uneo, an AI business operating in a fast-moving, constantly evolving environment.
This keeps me sharp.
It keeps me current.
And it keeps me grounded in the reality of what it takes to run a business today.
Why This Matters for You
Because when you’re sitting in the leadership seat, the pressure is real.
You’re making decisions without perfect information.
Balancing people, performance & cash.
Trying to grow without breaking things.
Trying to lead without becoming the bottleneck.
You don’t need more theory.
You need practical tools that work in the real world.
That’s why I believe so strongly in EOS.
Not because it looks good on paper.
But because I use it. Every day.
Sometimes a Mentor. Always a Student
I’ve always believed there’s more to learn.
In fact, I’ve got a tattoo that reminds me of that.
A Chinese symbol that translates to:
“Sometimes a mentor, always a student.”
Because no matter how much experience you have, business will keep teaching you.
If you’re paying attention.
Final Thought
Sometimes people assume they know your story.
They see the role.
The title.
The results.
But not the journey behind it.
So I wanted to share this for a simple reason.
If you’re in the middle of the highs, the lows, or somewhere in between…
I get it.
I’ve been there.
And I’m still there.
If you’re looking for someone who understands both the structure of EOS & the reality of running a business, then let’s have a conversation.
Written by Debra Chantry-Taylor, FBA Accredited Family Business Advisor, Certified EOS Implementer & Founder of Business Action.
Business Action is focused on helping Entrepreneurs lead better lives, through creating a better business. We have a small team of accredited family business advisors, EOS Implementers & Leadership coaches, as well as access to a huge range of advisors through our Trusted Partners Network.
