Getting comfortable with getting paid


Hi Friend,

I remember the first invoice I created as a business owner...

It was for some marketing materials I designed for a shop down the street from my shop and it was called “Jeannie’s Gift Box + Hair Braiding.”

Jeannie was a blast to be neighbors with. Her joy lit up her entire shop full of bedazzled handbags, colorful scarves, and lotions.

It always smelled of incense and coconut-vanilla candles that had been burning for hours. She was so happy to finally have business cards and fliers for her dream business.

I made her invoice in a Word doc on a Monday, wrote it, reread it 400 times, asked myself if it was professional enough, and then sat on it for TWO WEEKS before I brought it to her. I could only take cash or check back then. (It was like 2009, okay?)

AHHH! The work was done… why did it take me so long to bring it over there?

At the time, asking someone for money still felt weird to me, even though I’d earned it. It was my first time running a business on my own. Creating an invoice meant I TOO had to take myself seriously.

I’ve learned now that when I feel that discomfort, it means I'm leveling up as a business owner. Things changed for my business when I started treating myself like the CEO.

But it took me years to get more comfortable with getting paid.

I wish I knew then that getting paid is by far not the awkward part of running a business.

I remind folks all the time that no one has the same money story, baggage, mindset, privilege, or difficulties that you do, and you don’t need to assume that they do when sending an invoice.

But the systems I’ve built in my business take the “thinking part” out of getting paid and help me stay consistent, and it's a frequent topic with coaching clients, so I wanted to share with you too.


How I stopped being weird about getting paid.

1) I created multiple offers (a pricing ladder)

Some of these offers were more accessible, from lower-priced items to higher-priced ones.

  • Client wants coaching? Choose from a 1-time call or an 8-month package.
  • Client wants something community-based? Join my mastermind.
  • Client only has $15 to spend? Grab a PDF workbook from me or one of my free resources.
  • Small business client that needs social media help? Purchase social media management or classes from me.

Having offers and prices I felt confident in let me meet people where they were, instead of letting them decide what it was worth.

2) I realized that certain business systems, like contracts, proposals, and invoices, are relationship keepers and builders.

I think it was my lawyer friend Ashley who said, “Contracts are relationship-keepers,” and I loved that.

Efficiency and clarity = respect. The longer you wait to propose, contract, or invoice, the more the request feels like an interruption instead of a natural next step. I’ve learned it’s best to build a Standard Operating Procedure for contracts and invoicing that you use every time.

Be timely so your client remembers exactly why they’re paying you, and you’re not carrying an open loop in your head.

3) I learned to make it as easy as possible.

Getting paid quickly is about clarity and ease. When you have clear terms, a professional invoice, a reliable system, and an easy way to pay, it makes the process so smooth.

4) I made my progress trackable.

Tracking my profitability and expenses, and being able to see it all at a glance, can be really motivating. I love seeing a monthly view from last year to this year, or checking out what months tend to feel slow and which months seem to be more successful on a year-to-year basis.


I actually got to talk about this exact thing recently, when I spoke at FreshBooks’ Small Talk Chicago event about building your Client Experience alongside your Personal Brand. It was such a special room full of solopreneurs, all running a business of one.

FreshBooks makes invoicing, payments, and balancing your books feel simple and powerful.

The reason I point clients toward FreshBooks when they ask is that it is so dang easy to use, and they have great customer service for small business questions.

You can send professional invoices with built-in payment options like Buy Now Pay Later, so clients can pay their own way and you’re not waiting on a check in the mail.

Receipts get scanned and categorized automatically, your bank connects straight in, and the dashboard gives you a monthly view, at-a-glance read on the business I mentioned above, without you having to build any of it yourself.

Right now they’re running a promotion where new customers get the FreshBooks Lite plan for $1 a month for the first 12 months, and they asked me to share it with you. (Literally $12 for the whole year, insane)

Quick disclosure: I earn a very small commission if you sign up through my link. I am VERY PICKY and only partner with brands I already point my clients toward. FreshBooks is one of them.

Get FreshBooks for $1/month

… I think about Jeannie sometimes. I don’t think she owns a shop anymore, but she was such a graceful first client when I was a fresh college student just starting out owning a business.

I hope she is enjoying life. I will light a coconut-vanilla candle for her. Do you remember your first invoice? Reply and tell me about it!

Talk soon,

Lauren V. Davis

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