Nobody told you it would be this hard. But here you are.

It’s easy to talk about our successes. But failure and hard-earned lessons are part of the journey — and it’s time we talked about them honestly.

You left a job with a reliable income and chased something better. Something that was yours. And on paper, that was a brave, smart decision.

But nobody hands you a manual.

Long hours. Wearing every hat at once. Putting your own money on the line. Delaying your own pay so the business survives another month. Dipping into personal savings. Chasing invoices. Managing super payments, tax obligations, fair work requirements, ASIC filings — and somehow still finding time to actually do the work.

You make decisions you weren’t trained to make. You do things you don’t enjoy. Sometimes you do things you’re not even good at, because no one else is going to do them.

“There’s a particular kind of lonely that comes with running a business. Everyone thinks you’ve got it figured out.”

On the outside, you’re the boss. Confident. In control. But on the inside, you’re carrying the weight of other people’s livelihoods — staff who have families, suppliers who depend on you paying on time, partners who trusted you. You’re responsible for feeding families. Doing right by staff, suppliers, business partners, contractors, fair work, ASIC, the ATO. Lots of parties to look after. Lots of bills to pay.

The pressure doesn’t clock off. The stress is almost a given. And the worst part? Most people around you don’t fully get it. They can’t.

I know this because I’ve lived it. I’ve made the costly mistakes. I’ve worn the hats that didn’t fit. I’ve had the sleepless nights and the gut-drop moments when the numbers didn’t add up. I’m not speaking theoretically — I’m speaking from the inside.

And so are the hundreds of business owners I’ve sat across from over the years. Different industries, different sizes, different problems. But the same fundamental experience: it’s harder than it looks, lonelier than people admit, and there’s rarely a safe place to talk about it honestly.

THE HONEST TRUTH

23 mistakes business owners commonly make — and almost never talk about

We love celebrating wins. It’s human nature. But the real growth — the deep, lasting kind — usually comes from the mistakes we made, survived, and eventually learned from. Here’s what that list actually looks like.

MONEY MISTAKES

01   Paying everyone else first, then taking what’s left as profit — instead of factoring profit in from day one.

02   Pricing for survival, not for growth or margin.

03   Not separating business and personal finances.

04   Confusing revenue with profit — feeling busy but broke.

05   Delaying superannuation payments — robbing your future self.

06   No cash flow buffer — one bad month becomes a crisis.

TIME & ROLE MISTAKES

07   Wearing every hat instead of hiring or delegating.

08   Being the answer to every question, thus becoming the bottleneck in your own business.

09   Doing $50-an-hour work when your time is worth $1,000, $10,000, maybe $100,000 an hour. You’re quoting jobs, chasing invoices, ordering supplies. Meanwhile, the $100,000-an-hour version of you — the one making strategic decisions, building the right relationships, thinking clearly about the future — never gets a look in.

10   Saying yes to everything — every client, every request, every opportunity — until you’re stretched too thin to do any of it well.

HEALTH & RELATIONSHIP MISTAKES

11   Sacrificing sleep, health, and fitness “until things settle”. They never do.

12   Putting the marriage or relationship under sustained, unrelenting pressure.

13   Becoming emotionally unavailable to the people who matter most.

14   Social isolation — withdrawing from friends because “they wouldn’t understand.”

BUSINESS STRATEGY MISTAKES

15   Building the business entirely around yourself, so it can’t function without you.

16   No clear vision, just reacting to whatever lands in front of you.

17   Hiring the wrong people and keeping them far too long.

18   Ignoring systems and processes until the pain of not having them becomes unbearable.

19   Confusing being busy with making progress.

MINDSET MISTAKES

20   Thinking you have to figure everything out alone.

21   Never asking for help, treating it as a sign of weakness.

22   Letting the business become your entire identity.

23   Assuming more revenue will fix everything — when the real problems run deeper.

If you recognised yourself in five or more of those 23, that's not a personal failing — it's what happens when nobody around you has actually built a business at the level you're trying to reach. 

That's exactly why there are two paths, depending on where you're at:

👉 Running lean with under 5 staff? Profit Freedom Machine is the monthly program built for exactly this stage.

👉 Got a team of 5 to 30? Express your interest in The Freedom Engine — the room Alan, Anita and I built for owners stuck at exactly this size.

Not ready for either yet? Grab the free eBook that started all this → Selling Is Out. Create Buy-In