Scary money conversations made easy

Is there a money conversation you've been putting off?

Maybe it's a client who keeps asking for more than they paid for and you haven't said anything yet.

Maybe it's someone who wants to "pick your brain" and you don't know how to say no without feeling terrible about it.

Maybe it's a refund request that's sitting in your inbox because dealing with it feels too uncomfortable.

Maybe it's a price increase you know you need to have with existing clients.

These are the scary money conversations. And October is the perfect time to face them.

In this week's episode of Chill & Prosper I'm talking about how to have the money conversations that feel most frightening, because avoiding them isn't free. It costs you time, money and energy every single day you put them off.

Inside the episode I cover:

• Why we assume the worst about how people will react (and why we're almost always wrong)
• The simple script framework that handles brain pickers, scope creepers and boundary pushers
• How to set up predictive text shortcuts so the awkward reply is already written
• Why assuming the sale and assuming people are reasonable changes everything
• The "fake assistant" trick that takes the personal sting out of boundary conversations

Because here's the thing. Most scary money conversations aren't actually that scary once you have a script. The fear is almost always worse than the conversation itself.

xx Denise

P.S. I've put together a free guide this month called Scary Money Conversations Made Easy - full of real scripts for the moments that feel most awkward. 

Refunds, late payments, brain pickers, scope creep, price increases. All of it. 

Grab it free at denisedt.com/scary. And if you want to go deeper this month, we're working through money fears live inside Money Bootcamp.

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Prefer to read?

Here is the transcript for this episode:

Hi gorgeous, it's Denise here, and today we're talking about those scary, spooky, awkward money conversations that so many of us would rather avoid.

You know the ones.

Telling someone your prices.

Following up on an unpaid invoice.

Asking for a deposit.

Saying no when someone wants to pick your brain for free.

Setting boundaries with clients.

These conversations can feel so uncomfortable that I've actually known women who've given up their businesses and gone back to jobs because they simply couldn't bear having to talk about money with their clients.

And I get it.

But it doesn't have to be that way.

One of my early money mentors, Kendall SummerHawk, taught me something that's always stuck with me.

Talking about money should be as simple as saying, "Pass the salt."

You wouldn't overthink asking someone to pass the salt at dinner.

You wouldn't spend hours worrying whether they'd think you were rude or greedy.

You'd just ask.

So why do we make talking about money so complicated?

A lot of it comes down to what we learned growing up.

Maybe you came from a family where money was never discussed.

You didn't know what your parents earned. Nobody talked about salaries, savings, or wealth. Money was considered private, impolite, or simply not something nice people discussed.

Or perhaps you grew up in a household where money was talked about constantly, but always negatively.

Everything was too expensive.

There was never enough.

People with money were greedy.

Money was dirty or evil.

Either way, those messages can stay with us long into adulthood.

I remember taking my daughter to a farmers market when she was about three.

I thought it would be a lovely opportunity to teach her about money and commerce, so I gave her a fifty-cent coin to buy an apple.

And what did she do?

She immediately put the coin in her mouth!

I instinctively said, "Don't put money in your mouth. Money's dirty!"

And then I caught myself.

Money's dirty?

Here I was, a money mindset mentor, telling my own child that money was dirty.

Of course, I didn't want her putting a choking hazard in her mouth.

But it made me realise just how deeply ingrained some of these beliefs can be.

We can consciously believe that money is good and still have old stories running in the background.

And those stories have real consequences in business.

If you believe talking about money is rude, you might struggle to tell people your prices.

If you think asking for money is greedy, you might avoid sending invoices.

If you're worried people will judge you, you might undercharge, discount your services, or give things away for free.

And of course, that's going to cost you money.

Sometimes these beliefs are generational too.

My mum was a young single parent who worked lots of different jobs. My grandmother didn't have one consistent full-time career either.

I didn't grow up seeing women regularly negotiating salaries, talking about wealth, or confidently earning money in business.

And maybe that's true for you too.

Perhaps you simply haven't had people around you who model healthy, comfortable money conversations.

That's why being around people who talk openly about money can be so powerful.

It normalises it.

You realise that you can say a price out loud and nothing terrible happens.

You can ask for payment and the world doesn't end.

And you can set a boundary without being a horrible person.

But I also think we can make these conversations easier by putting systems in place.

If you know that talking about prices makes you uncomfortable, why put yourself in a situation where you have to negotiate every single time?

Maybe having clear prices on your website would help.

Maybe you could offer online booking with payment upfront.

Maybe you could take deposits automatically.

There's no one right way to do business, but there is a way that works better for you.

I remember calling someone to enquire about private lessons.

She told me her group classes were full but that she offered private sessions.

I said, "Great! Can I book one?"

And she replied, "Oh, they're very expensive. They're $80 a session."

I was perfectly happy to pay $80!

But she was already apologising for the price before I'd even had a chance to respond.

Imagine how exhausting it must be to have that conversation over and over again.

She could have simply put her prices on a booking page and allowed people to book and pay.

Problem solved.

And the same goes for receiving payments.

I've been to appointments where nobody has told me how much something costs or how I'm supposed to pay.

Then at the end, there's this awkward conversation.

"How much is it?"

"Oh, it's this much."

"Great, can I pay by card?"

"Oh, no, cash only."

Well, tell me that beforehand!

Make it easy for people to give you money.

You can use online payment systems, Square, PayID, deposits, or automatic payment plans.

If the lovely older ladies selling homemade marmalade outside my local shopping centre can figure out how to use Square, you can too!

Because here's what happens when you don't have a payment system.

Someone says, "Oh, I've only got $50."

And suddenly you're saying, "Oh, that's fine, I'll just take $50."

Not because you wanted to discount your service, but because you weren't prepared to receive the full payment.

So set yourself up for success.

Another area where money conversations get awkward is when people want your expertise for free.

You know those messages.

"Can I just pick your brain?"

"I've got a quick question."

"Could you just have a look at this for me?"

And if you're someone who struggles with boundaries, you can find yourself spending hours helping people without getting paid.

One of the simplest solutions is to create scripts.

Now, I know some people think scripts feel fake or impersonal.

But they don't have to.

You can customise them to sound exactly like you.

The point is that you don't have to invent a response every single time.

For example, if someone asks to pick your brain, you could say:

"That's a great question! That's exactly what I help people with in my one-on-one sessions. Here's the link to book."

Simple.

Friendly.

Clear.

You haven't been rude.

You've simply explained how someone can work with you.

I used to create text shortcuts on my phone and computer for responses I sent regularly.

For example, I'd type a few letters and it would automatically expand into a message directing someone to my team.

You can do the same with your booking links, frequently asked questions, and boundary-setting responses.

And here's the important part.

Sometimes people won't accept your boundary the first time.

They'll come back with:

"Oh, but I only have one question."

"I don't really need a whole session."

"Can't you just tell me quickly?"

And that's where you practise repeating your boundary.

"Absolutely, that's exactly what we cover in that session. I'd love to help you with it."

You don't need to justify yourself.

You don't need to explain why your time is valuable.

And you certainly don't need to feel guilty.

You can also create a specific paid session for these requests.

Call it a Pick My Brain session, a Golden Hour, a Problem-Solving Session, or whatever suits your business.

Then whenever someone asks for your advice, you've got somewhere to direct them.

You might also direct them to an ebook, course, or other paid resource.

That's what I do now.

I don't offer one-on-one coaching, so when someone asks me a question that's covered in Money Bootcamp, I can simply point them towards it.

The key is to assume that people are reasonable.

So often we approach these conversations expecting the worst.

We imagine someone will think we're greedy.

We worry they'll be offended.

We convince ourselves they'll think we're a bitch for saying no.

But think about how you'd respond if you asked someone for help and they politely directed you to their paid service.

You'd probably say, "Oh, of course!"

You wouldn't send them an angry email demanding they work for free.

So why do we automatically assume other people will react that way?

Most people are perfectly happy to respect a clear boundary.

And if someone isn't, that doesn't mean your boundary is wrong.

Another thing I've learned is that boundaries actually make the client experience better.

When I used to offer one-on-one coaching, I sometimes let sessions run over time because I wanted to help with absolutely everything.

But eventually I started being more intentional.

At the beginning of a session, I'd say, "We've got 60 minutes. What's the most important thing you'd like to work on?"

Halfway through, I'd check in and help us move to the next priority.

And it wasn't just better for me.

It was better for the client.

They knew what to expect.

They knew I was managing our time.

They didn't have to worry about whether they were taking advantage of me.

I've been on the other side of this too.

I've worked with people who haven't clearly communicated their boundaries, and I've accidentally overstepped them.

Then I've sensed that they're annoyed with me.

But how was I supposed to know?

They could have simply said:

"That's outside the scope of what we've agreed."

"That's a great idea. Let's park it for phase two."

"I'm happy to add that. It would be an additional $1,000."

Or even:

"We can absolutely do that. What would you like to remove from the current scope to make room?"

Those conversations aren't unkind.

They're helpful.

They create clarity.

And they stop resentment building up on both sides.

You don't need to change everything in your business overnight.

Start with the money conversation that makes you most uncomfortable.

Maybe it's saying your prices without apologising.

Maybe it's following up on invoices.

Maybe it's telling someone that additional work will cost extra.

Maybe it's saying no to unpaid requests.

Create a script.

Put a system in place.

Practise saying it.

And then keep practising until it starts to feel normal.

Because the truth is, your business needs to work for you too.

We've all heard that the customer is always right, but that doesn't mean their preferences should always come before your wellbeing.

If your business is constantly draining your time, energy, and money, it isn't sustainable.

And if it isn't sustainable, eventually you won't be able to help anyone.

That's why clear boundaries are a kindness to yourself and your clients.

People know what they're paying.

They know what's included.

They know how to pay.

They know what to expect.

And you get to run a business that supports your life instead of exhausting you.

One of my favourite affirmations is:

"I serve, I deserve."

I serve, I deserve.

You're allowed to be paid for your work.

You're allowed to talk about money.

You're allowed to have boundaries.

You're allowed to say no.

And you're allowed to create systems that make your business easier to run.

None of that makes you greedy, selfish, or difficult.

It makes your business sustainable.

If this is something you struggle with, I've created a free ebook called Awkward Money Conversations Made Easy.

You can get it at denise.com/awkward.

It's full of scripts to help you navigate these conversations without feeling like you have to come up with the perfect words on the spot.

And I'd love you to think about one thing you could change in your business this week.

One boundary.

One script.

One payment system.

One recurring awkward conversation that you could make a little easier.

Because talking about money doesn't have to be scary.

It's just money.

And you're allowed to talk about it.

I'll see you next week on another episode of Chill and Prosper. Take care. Bye!