Plan ahead for a stress-free holiday season

small business prepare for holidays

I can’t believe it’s almost December. In just over a month retail businesses will be completely swamped...and my business will be a ghost town.

If you are in the world of retail, where everyone pays you before they leave the can safely skip this post. This information is for those of us who provide services and who spend time chasing down payments throughout the year.

This is a very tricky time of year. The holidays usually demand a large monetary sacrifice, so we want to bring in as much money as possible. We also roll into December completely exhausted, and want nothing more than to take some time off.

I made a big mistake for many years. I like to be able to take time off with a clear conscience. That means I like to wrap up as many projects as possible before I go. I also wanted to do a big burst of work so I could send out a few last minute invoices to cover the extra costs. I would give myself a deadline like the 15th. Then, in an unsettling display of mania I would work day and night to get project after project wrapped up. By the time I was clicking send on my invoices, my hands would be gnarled claws, shaking and twitching from the caffeine overdose. It was not a pretty sight, but I got it done!

Guess what happened next? Nothing. And do we know why? Because who pays for invoices a week before Christmas? Nobody, that’s who.

What lessons can you take from my failures?

Know your clients.

If you’re counting on some last minute revenue to help cover your holidays, you need to know if this is possible. If you work with clients who typically pay in Net 30 or Net 45, don’t send out an invoice on December 15th and expect to see any funds before the New Year.

Also, if your bigger clients are taking time off, make sure you wrap things up and invoice them at least a week before they leave. I don’t know your clients, but any mail I get after December 15th that isn’t a package or a Christmas card is getting ignored until after the holidays.

Tackle your receivables.

Take a minute to review your outstanding invoices. This is something you should review on the 1st of every month, but do it as early as possible this time.

Reach out to all your clients with past-due balances right away. If any of them are working with a limited budget, you’re going to want to be the first person they hear from.

Finally, here are two more tips. One for this year, and one for the future.


If you’ve done your work and followed up on your receivables...there’s not much more you can do. Make the most with what you’ve got and really enjoy the time off. Running your own business means holidays are rare. If you get a chance to take a few days off this year enjoy every minute of it.

Learn from your mistakes.

Take some time in the New Year to review 2014 thoroughly. As it pertains to this post, review your cash flow for November/December. If possible, pull up similar reports for 2013 and 2012. Are there any obvious patterns? Did cash flow stop on a certain date? Did your clients pay less or slower than usual? Take these facts into consideration when budgeting for the 2015 holiday season.

What about you?

How do you handle the holidays? Do you take time off? Do you have a hard time collecting payments? Let me know in the comments.