2021 Is the Year You Conquer Your Fear of Money Talk

Does money talk make you cringe? Don’t fret - there are simple ways to help you turn those awkward conversations into easy (and automatic) exchanges.

When I started my writing business, I dreaded and avoided money conversations like the plague. Clients would ask me what my rates were and I’d change the subject by asking a question: “What’s your budget?”

I told myself this was the right decision because it allowed me to gauge whether they were worth working for based on what they were willing to pay me. The truth was that I felt uncomfortable telling clients what my rates were in fear that they would balk at them.

I hated talking about money.

Similarly, I feared chasing clients for late payment because I imagined that they would see me as someone who’s only interested in money and drop me like a hot potato. I was fearful of money talk because I thought it would lead to a strained relationship and a lost client.

Overcome Imposter Syndrome and Get Comfortable With Money Talk

As my business grew, I grew. I realized money talk was unavoidable. I also quickly learned that if I wanted to get paid and have a thriving business, I would have to learn to deal with them.

And deal with them I did. The more conversations I had, the easier they became. When clients asked me my rates, I told them. When payments were overdue, I reminded them.

In hindsight, I see why I was so uncomfortable having these conversations. And no, it wasn’t only the fear of losing clients… It was much deeper than that: I disliked conflict, felt like an imposter, and didn’t understand my worth. Who was I to be charging clients? What value was I actually providing?

These questions consumed me. Doubts festered and affected my ability to make money. But you know what? Over time I developed a sense of self-worth and became more comfortable with these conversations.

Money Talk is a Key Part of Your Small Business

I eventually became so confident that I put a stake in the ground: “These are the services I offer and these are my prices. If you don’t like it, that’s okay; I’ll simply find someone who does.”

That’s not to say that I’m entirely comfortable talking about money today; I’m not. But my improved self-worth, recognition of the value I provide, and acceptance that these conversations are part of running a business have helped me build a thriving one.

And I want the same for you. I acknowledge that these conversations are more difficult for some. So difficult that many struggle to assert their worth and don’t even bother starting their business in the first place.

Perhaps this sounds familiar?

I get it, I do. You’ll do anything to avoid these conversations. I’d like to say that you can build a business without having them. But you can’t – these discussions are unavoidable. What you can do is invest in tools that will make them that much more manageable.

How the Right Tools Make Awkward Money Conversations Manageable

Just as social media made it easy to create new connections, the right tools have made those painful money conversations a little less painless by letting you put much of the process on autopilot. Here’s how.

1. You Can Automate Late Payment Reminders

You’ve sent an invoice to a client and the payment is now overdue. Sound familiar?

Traditionally you’d have the cringe-worthy task of creating and sending an email to remind the client the invoice is overdue. You’d likely sit there and wonder: How am I going to word this email without sounding pushy?

You’d probably also worry about how the client will respond and how you’re going to deal with it. This entire process can cause a lot of anxiety. I’ve experienced this time and time again in my writing career and, to be honest, I still experience this today. I don’t think it will ever go away.

Thankfully, invoicing tools (like FreshBooks!), let you set automatic late payment reminders as soon as you send the first invoice. That reminder is sent when the invoice becomes overdue and you don’t even have to lift a finger. More importantly, you avoid all that unnecessary anxiety.

2.You Can Quickly Set Late Payment Fees on Your Invoices

I do not have a late payment fee policy, but I do know of fellow freelancers who do. They typically set a monthly finance charge based on the value of the invoice.

These fees may prevent the need for sending late payment reminders altogether and encourage clients to pay you on time or risk facing penalties.

Of course, charging late payment fees may not always be the best idea and that’s why it’s important to follow some guidelines:

  • Make sure the client is aware of the charge at the beginning of a relationship. If they aren’t you’ll only open yourself up to those uncomfortable money conversations.
  • Know when not to enforce the policy and be empathetic. A regular client may be going through a personal challenge such as the death of a loved one.
  • Ask yourself: Were they happy with my service? Some clients don’t speak up when they’re dissatisfied with your service. You should establish how satisfied they are before you enforce those fees because it’s highly unlikely they’ll want to pay if they feel you haven’t delivered.

3. You Can Easily Create Killer Project Estimates

How often have you had to have a conversation with a client who thinks that you’ve whacked on surprise charges?

While you may feel that these extra charges are warranted, your client may not. This usually happens because they weren’t discussed at the beginning of the project.

You can avoid these scenarios by creating project estimates. These estimates help you manage client expectations and prevent disagreements about price. They detail the scope of work, cost, exclusions, and the length of the project.

To create these estimates consider using intuitive tools that let you create estimates in a matter of minutes with one-click templates and many built-in features.

Once you’ve sent your estimate, don’t assume your clients will read it. Follow-up with a phone call – or if you can’t – an email to discuss it to make sure you’re on the same page before you start the project. Or, use online tools – such as FreshBooks, that let you collaborate and discuss the estimate through built-in discussion features.

With estimates, it’s far less likely that you’ll have disagreements about price. And in the rare case that you do, feel comfortable with that conversation knowing that you can justify what they may regard as “surprise” extra charges by referencing your estimate.

4. You Can Build Upfront Deposits into Your Invoices

As a rule, I charge a 50% upfront deposit with any new client. Of course, I am flexible and do sometimes waive this deposit if they’re a reputable company that pays staff (A quick Google search can help you determine this). I also discard that deposit over time as I learn to trust that the client will pay me on time.

Of course, this is how I choose to approach deposits and I understand you may take a different view altogether. Maybe you charge a lower deposit?

Regardless, I like deposits because they reduce the chance of non-payment. If the client is happy to pay that 50% upfront they’ll be more likely to pay the balance. For me, this means there’s no stress and discomfort in having to chase them for payment.

It also ensures that I have a steady stream of cash flowing in and a positive cash flow. That’s not to mention that clients are more likely to be vested in the project if they have to fork out upfront cash. And, for projects that require considerable client input, this is an absolute godsend.

To ensure that clients are aware of, and make these deposits I use invoicing software that lets me specify the deposit amount and allows them to pay me directly from the invoice. This avoids the back and forth emails of telling clients how they should pay me the deposit.

5. You Can Send Recurring Invoices

Do you offer maintenance plans for products? Do you bill for a fixed number of working hours? Do you provide monthly service packages? Then you’re the ideal candidate for recurring invoices.

Recurring invoices are invoices that you send out on a regular schedule and ensure that clients pay you on time. They work because they encourage clients to fall into a regular payment routine.

Think of it like this: Do you question your phone, rent, and cable debit order that goes off each month? No, you don’t because It’s a regular bill that you have to pay.

By sending recurring invoices and cultivating these good habits, you’ll spend less time chasing payments and avoid uncomfortable money discussions.

With the right invoicing tools, sending these recurring invoices is a breeze. You can set when and at what intervals the invoice sends. Beyond helping you avoid awkward money conversations, they ensure you don’t have to create a new invoice each time.


Talking about money isn’t easy, I get it. It’s something I struggled with and continue to work on in my own business. I’d love to tell you that you can build a thriving business by avoiding these conversations. But I would be doing you a disservice because these discussions are unavoidable.

However, with the right tools, they can be more manageable. These tools will help you:

  • Automate late payment reminders and remove the anxiety of having to chase payment
  • Set late payment fees to avoid reminders altogether
  • Create simple project estimates quickly so that clients don’t receive surprise costs
  • Charge Upfront deposits and make it easy to pay from an invoice
  • Send recurring invoices so you can cultivate good payment habits

The one tool that comes to mind in helping you do all the above is FreshBooks. FreshBooks is business accounting software designed for small service-based businesses like yourself.

Not only does it make money conversations more manageable by putting processes on autopilot, but it also makes billing painless and ensures you spend more time doing what you love and less time on accounting. Sign-up for a free 30-day trial and conquer those awkward money conversations.

about the author

Freelancer & FreshBooks Customer Nick Darlington is a FreshBooks customer and small business owner who's been running a writing business for close to 4 years now from his home in sunny South Africa. When he’s not sharing his knowledge and experience about how to successfully run, manage, and grow a small service business, he’s helping aspiring and established writers succeed at WriteWorldwide.