How to Talk About Money Without Feeling Awkward

Talking about money shouldn’t feel like walking into a room where everyone suddenly stops and stares but for many of us, it does. Whether it’s chatting with a partner about budgets, asking a client to pay on time, or sitting down with your accountant, money talk can feel awkward, exposing, or downright terrifying.

But here’s the truth: if you run a business, freelance, or are even vaguely responsible for your own finances, you have to talk about money. Avoiding it doesn’t make it go away. It just makes it louder in the background. So let’s make it less scary.

Nick speaks accountant… Liv does not

At Middlebrook Accountancy, we have this running joke: Nick speaks fluent accountant, and Liv… does not. Many of our conversations start with Liv saying, “I don’t understand…” and Nick patiently translating the numbers into something that sounds like actual English.

Before Middlebrook Accountancy, Nick spent years training companies to become more digitally savvy with their accounting systems. He’s brilliant at explaining things without making anyone feel silly. He knows how to talk about money in a way that feels calm, kind, and completely judgement‑free.

And honestly? That’s a life skill we should all have. Because money conversations aren’t something we’re taught in school, yet they shape almost every part of our lives.

Why money talk feels so awkward

If you cringe when someone brings up “the numbers,” you’re not alone. Money is emotional. It’s tied to security, identity, childhood messages, and sometimes shame. But when you start a business or become self‑employed, you can’t avoid it anymore. You can’t put your head in the sand. Money talks whether you’re listening or not.

So, time to be brave and have the conversation.
Here are a few gentle, practical tips to help you get over money‑talk phobia.

Tips for Talking About Money Without Feeling Awkward

1. Start with honesty, not expertise

You don’t need to know everything. You don’t need to pretend you understand VAT thresholds or cashflow forecasting. A simple “I’m not sure what this means. Can you explain it?” is powerful. It opens the door to clarity instead of confusion.

2. Use neutral, non‑emotional language

Instead of:
“I’m terrible with money.”
Try:
“I’d like to understand this better.”

Instead of:
“I feel awkward asking you to pay this invoice.”
Try:
“Here’s the updated invoice. Let me know if you have any questions.”

Neutral language keeps the conversation grounded rather than personal.

3. Prepare before the conversation

A few notes, a screenshot, a list of questions. Anything that helps you feel anchored. Money conversations feel scarier when you’re winging it.

4. Remember that clarity is kindness

Whether you’re talking to a partner, a co‑founder, or a client, being clear is not rude. It’s respectful. Clear expectations prevent misunderstandings, resentment, and awkwardness later.

5. Practice saying the numbers out loud

It sounds silly, but it works.
Say your prices.
Say your budget.
Say the thing you’re scared to say.

The more your mouth gets used to forming the words, the less your stomach flips when you say them to someone else.

6. Borrow confidence from someone who has it

If you’re not a “money person,” find your Nick! Someone who can help you understand, rehearse, or sense‑check what you want to say. Confidence is contagious.

7. Remember: money conversations are normal

You’re not being difficult. You’re not being rude. You’re not being “too much.”
You’re running a business.
You’re taking care of yourself.
You’re being responsible.

Money conversations are part of being an adult human in the world and the more you have them, the easier they get.