4 min read

I love December. Things slow down, feel more casual, and I can look forward to the year ahead.

Now, two years ago, December was nerve-wracking. I miscalculated my cash flow, and was slowly bleeding cash while I waited to start the next Unreal Collective Accelerator cohort in January.

It seems like people fall squarely into one of two camps in December:

  1. The impenetrable “Out Of Office until January” Autoresponder
  2. Let’s get this done NOW before the first of the year frenzy

When you’re running low on cash in December, and clients aren’t getting back to you, it can be tough.

But that doesn’t mean you should give up. December can actually be a great time to line up some new projects or partnerships for the new year.

For me, sitting on the other side of the equation after a good year and thinking ahead, I have different challenges this year. And one of those problems is taxes.

Let me explain why…

I pay quarterly taxes based upon the income projections that my accountant and I come up with for the coming year. Those quarterly tax projections ideally will be strong enough tax withholdings that I still manage to get some small refund come tax season.

But since I’ve had a better year than projected, that means I haven’t been withholding the appropriate amount for quarterly taxes. And instead of receiving a refund this coming tax season, I’ll probably be writing a check.

Taxes are a GOOD thing. It means you’re doing well. You wouldn’t pay taxes if you’re not making money, and I’m proud to pay taxes and do my part. But there truly is a lot of value in having a tax strategy.*

*of course, I’m not a CPA, so it’s worth talking to your accountant if you’re in this situation.

Here’s why this is an opportunity for you as a freelancer

What I’m describing to you is a bit of a cash surplus. So if I’m already anticipating or considering any expenses related to my business, incurring them before the end of the fiscal year is a good idea for me – that will lower my tax burden.

Last year around tax time, I invested in coaching and a live event I wanted to attend. They were big expenses, but I had the cash and they really brought down my taxable/net income. So it made sense to do take those expenses on in 2019.

Who are your clients?

If they are individuals, smaller organizations, or small businesses – they may be in a similar situation. If they’ve had a better year than they were expecting, they may be in the market to spend some of that money in December 2019 as opposed to January 2020.

You should give them that opportunity.

Reach out to your clients and let them know that you’re booking now for the first quarter of 2020. This is a win-win for everyone:

  • It gives you some predictability and security booking into the new year
  • It shows clients that you are in-demand and they need to think about booking you sooner than later
  • It gives the client the opportunity to book an expected 2020 expense on their 2019 books

Don’t overthink this. Just reach out to your past, existing, or potential clients and let them know that they can pre-book you now for 2020.

Hey [client],

I hope you’re enjoying the end of the year! I was thinking about you and the work we did together (get specific) in [month]. I wanted to let you know that I’m grateful for the opportunity and the work we do together.

I’m looking ahead to 2020 and wanted to touch base with you sooner than later. I’ve had a great year, and I’m already booking my calendar into January and February.

Are you available to catch up over the phone and talk about your plans for next year? Some of my clients like to pre-book Q1 2020 and put the expense on their books for 2019. If that sounds like a good idea for you too, let’s talk about it!


It’s not pushy. It’s not salesy. It’s genuinely thoughtful and sincere.

I spent just this week catching up with past clients and friends, and it turned into more work for the first quarter of next year than I anticipated.

Of course, some people will pass, and that’s OK. You’re just making the offer – that’s all!

If you talk with them and they seem like a good fit, let them know that it sounds like a good idea to YOU, and they’ll probably agree with you.

Worst case, you’ve just put yourself top of mind again – even if that doesn’t pay off for weeks or months. There is a mad rush for time on peoples’ calendar in January, and you’re definitely putting yourself at the top of the list.

Even if you’re just starting, December doesn’t have to be a slow month. Start some conversations!