The thing nobody talks about when their business is struggling

For many small business owners, the hardest part isn’t the numbers. It’s the shame that comes with them.

The client sat down and didn’t say hello. They just said: I’ve messed this up. I’ve done it all wrong. I’m so embarrassed.

Annè Lensink, director of Villa Chartered Accountants in Whangārei, has heard some version of this more times than she can count. Business owners – capable, hardworking Kiwis – arriving at her office carrying something heavier than a tax problem. They’re carrying shame.

“Almost all of the time, it’s fixable,” she says. “But first, you have to get them to believe that.”

It’s a dynamic that rarely makes it into conversations about financial advice. We talk about cash flow, provisional tax, the difference between revenue and profit. We don’t talk as much about the 2am wake-ups, the avoidance, the way financial stress quietly hollows out a person’s confidence – until they’re too far in to know where to start.

Annè sees it as one of the most underestimated barriers facing small business owners. Not a knowledge gap, exactly. More of a courage gap – the distance between knowing you need help and actually asking for it.

She explores this in depth on a recent episode of the Money Made Simple podcast with Simplicity, and it’s a conversation worth having out loud.

The head-in-the-sand problem

It starts, often, with something small. A side hustle that takes off faster than expected. A tax bill that arrives at the wrong moment. An accounting platform that made sense at first but now feels overwhelming.

“A lot of people start a business and the finances almost hold them back,” Annè explains. “They’re scared. They don’t understand it. So they stick their head in the sand – and that creates anxiety, and the anxiety limits their growth.”

The avoidance is understandable. But it compounds. The longer the books go unexamined, the more frightening the prospect of looking becomes. And so the cycle continues.

What Annè finds, when people finally do sit down with her, is that the reality is almost always less catastrophic than the story they’d been telling themselves.

“Often, when people realise they’re not just bad with money – they just haven’t had the right guidance – you can actually see the shift. They feel so much better walking out with a plan.”

The myth of the money person

There’s a story many people carry about themselves – that some people are just good with money, and others aren’t. That it’s a trait, like height, fixed at birth and immovable.

Annè doesn’t buy it.

In her experience, financial confidence is almost entirely a product of knowledge and guidance. Take those away, and the most capable person will feel lost. Provide them clearly, without judgment, and the transformation is often rapid.

“A lot of people think they’re not good with money. When all they needed was guidance.”

This is what shapes our entire approach to client work. Not just filing tax returns but translating financial information into something usable. Drawing timelines on whiteboards. Sitting with a client until they actually understand what the numbers mean, not just what they say.

When the money arrives

There’s another moment Annè returns to often. The first significant money hit. A new business owner sees $50,000 in their account and feels, for the first time, like it’s actually working. Like they’ve made it.

And then: the Hilux. The family holiday. The tax bill.

“The problem isn’t the earning of the money,” she’s quick to say. “And it’s not the Hilux or the holiday. It’s just making sure you’ve accounted for what’s not really yours before you enjoy what is.”

It’s a reframe that matters. Financial literacy isn’t about deprivation or discipline for its own sake. It’s about knowing the full picture so you can make decisions that actually hold up.

The habit that changes everything

If there’s one piece of advice Annè offers every business owner, freelancer, or side hustler, it’s simple: check in with your finances once a week. Fifteen minutes. No more.

“A lot of people stick their head in the sand because it feels too scary but just having a regular check-in – knowing where you stand, knowing what’s coming – takes the anxiety away. It’s not even the amount that gets people. It’s the surprise.”

Knowledge, in other words, is the antidote to fear. Not certainty. You can’t always know what’s coming but enough of a grip on the present that the future stops feeling like a threat.

Most of our clients don’t arrive in crisis. They arrive because they’re ready to stop guessing. And whatever their situation looks like on paper – however long the head has been in the sand – the conversation always starts the same way.

No judgment. Just a plan.

Annè talks through all of this in a recent episode of the Money Made Simple podcast with Simplicity.

If any of this sounds familiar, you don’t have to have it sorted before you reach out. Book a free, no-obligation chat with our team, and find out what’s actually possible.