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After a couple years of running my agency I started to find myself not enjoying the end of the year. Actually, I kinda started to hate it. When this started to happen, I couldn’t really pinpoint why I wasn’t feeling too “festive” during the holiday season, but I clearly see it now. The end of the year is filled with entrepreneurial trauma.

1. Tax Planning Stress

Sometime around mid-November I always had a tax planning meeting with my accountant. This meeting always resulted in “to do list” of items to complete before the end of the year.

“You need to pay $____ more in federal tax.” “You need to pay $____ more in state tax.”

“Anything you think you’ll need to purchase for your business next year, you should buy now.”

This November tax planning meeting triggered a busy rush to adjust business financials by the end of the year. Balancing the financial numbers every day from mid-November through the end of the year was always a bit stressful.

2. Holiday Party Stress

My agency always had a holiday party for our team. In the early years, when we were small, my wife and I would have the party at our home.

“Gotta get the house decorated for the holidays.”

In the later years, when the team was large, we rented a venue and hired entertainment.

“Who should we get for entertainment?”

“Who is going to cater the food?”

“What will the menu be?”

The holiday party planning always brought some stress with it. They sure were fun, but I was always glad when they were over.

Our agency holiday party in 2015 (team members and their +1). These parties got pretty big as the team grew.

3. Gifts and Bonuses Stress

One of my objectives while growing my business was to create a company that I would want to work at. And I would want to work at a company that shares the profits and gives thoughtful gifts.

The first year I did holiday bonuses for my team I thought, “Well, I just gave away as much money as a new Corvette.” But I don’t regret it at all. My team worked hard and deserved to share in the gains of the business. (But that doesn’t change the fact that it was a lot of money going out of our business accounts.)

The agency party in 2011 included iPad 2’s for everyone.

On top of some bonus money, I loved to give gifts. One of the best year end gifts was the year I got everyone on my team a custom bobblehead of themselves. Haha. That was a good one. Who doesn’t want a custom bobblehead?

The 2012 party was the custom bobblehead gift year. It was so fun to surprise the team with these.

Seriously, I loved this party so much. The bobblehead gifts were such a hit. Somehow we missed getting a pic with the bottom three people (including me), but trust me, the likenesses on them was amazing too).

4. Projects Slow Down Stress

At the same time my business was hemorrhaging money on taxes, bonuses, parties and gifts, projects ALWAYS slowed down during the year end holidays. Clients didn’t reply as quickly. New project inquiries trickled (or stopped altogether).

“I’m shelling out tons of money and my business inflow is so slow. Will we survive this?”

“Will we ever get another project?”

Project slow down stress is one of the worst types we feel as creative entrepreneurs. It is even more stressful when the project slow down happens at same time that the business financial reserves are depleting. Welcome to the holiday season as a creative agency owner.

5. The Anxiety of the Upcoming Zero Balance

The end of the year is a great time to assess performance. After all of the money is collected and spent, you can look at a final profit and loss statement. What was the annual income? What were the annual expenses? How much money did you really make? The annual business game is over! What was the final score?

While it is always fun to see the final score of the game at the end of the year, there is some stress knowing that in just a few days the game will start all over again. Both the annual income and expenses go back to zero and you are faced with another 12 months of finding clients, selling your services, executing projects, hiring, firing…tough business decisions to try and win the game again next year. Stress.

Don’t Be Like Mike – Enjoy the Holidays

I WASTED a lot of holiday seasons working through them and worrying about all the stuff in this article. The stress of wondering if it was all going to turn out all right used to overwhelm me. How many times I wished for a crystal ball, because I would have known then what I know now, everything is going to be just fine.

  • This article was written on December 10th. If your business made until this point in the year, it will make it through the end of the year and slide right into the start of next year. Stop worrying about it and enjoy the holiday season.
  • You will have more projects. Clients always slow down during the holidays. Stop worrying about it and enjoy the holiday season.
  • By the middle of January you’ll be so busy with new opportunities you’ll wonder how you’ll get it done. Stop worrying about it and enjoy the holiday season.
  • The holidays are a time for celebration and enjoyment. So enjoy it! Take a little time away from your computer (you’ve earned it). The work will still be there tomorrow. Stop worrying about it and enjoy the holiday season.
  • In MOST of your cases, next year’s business final score will be bigger than this year’s. You’re probably going to have a big and busy year, so enjoy the fact that this year’s game is over. If you’re still in business, YOU WON. And you’ll most likely win even bigger next year. Stop worrying about it and enjoy the holiday season.

P.S. I needed to read this article for my own mental health as much as you needed to read it for yours. I sincerely hope it will help you find at least a few moments (or days) of “less stress” between now and the end of the year.

Michael Janda

I am Michael Janda, an executive level creative leader with more than 25 years of experience in both in-house creative departments and agencies working with some of the greatest brands in the world including Disney, Google, Fox, ABC and NBC. I create books, courses, workshops, lectures and other training materials to help creative entrepreneurs run successful businesses.