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The holiday season should be a time of happiness and joy, but for many freelancers the holiday season brings with it some freelancing dilemmas.

If you’ve freelanced through a holiday season before, you may already be asking yourself, “what am I going to do about the holidays this year?” That’s right. It’s that time of the year! We’ve reached another year-end. (I hope your freelancing business did well this year.)

I’ve written about this topic before, but these problems are real, so the topic is worth revisiting.

Even freelancers who don’t normally celebrate at this time of the year are affected by the year-end activities. In this post, I’ll discuss seven dilemmas that freelancers face during the holiday season.

Dilemma #1. Should I Send a Gift to My Clients?

Many business gurus will advise freelancers to send out holiday gifts or cards to their strongest clients as a way of saying “thank-you” for their business during the year. In fact, gifts can be a good strategy and may serve to keep your name in front of a client.

What’s the problem, you might ask? Well, there are two main problems that freelancers face with sending out gifts.

• The first problem is that not everyone celebrates holidays during this time and some may even be offended by said holidays. Many freelancers may not even be aware of their client’s feelings about the holidays. In most cases, however, a gift tied to the end of the year and not to a specific celebration won’t be offensive to anyone.
• The second problem is finding the right item to send to a client. It’s important to send something that fits within your budget. A client gift should be something the client can really use as opposed to something cheap that happens to have your business name printed on it. Choosing the right client gift can be particularly challenging because most freelancers have at least one client that they have never met face to face.

Dilemma #2. Should I Work on the Holiday?

Another freelancing holiday dilemma concerns taking time off.

Many freelancers desire to take off time during the holidays to be with friends and family, but for some the holidays can be a busy time of work. Some companies will assign projects to freelancers during this time so that their regular staff can take a break.

If you’ve decided to take some time off during the holidays, how do you break it to your clients? If you’ve decided to work through the holidays, how do you break it to your friends and family?

Plus, if you do take time off at the end of the year your income will likely be affected, which brings me to the next freelancing holiday dilemma…

Dilemma #3. What About Lack of Income?

Freelancers are paid when they work. When a freelancer doesn’t work, they don’t get paid. It’s just that simple.

If you haven’t been saving all year for a year-end vacation, a holiday break may seem out of reach. However, you still may be able to take on extra projects so that you can take off later. Also, remember that many retail stores hire extra part-time staff during the holiday season–you could moonlight on your freelancing with a part-time job.

Also, remember that even if you have decided to work through the holiday, your client may have decided to take it off. Unless you know otherwise, plan for them to be unavailable during this time period.

Dilemma #4. Should I Publish a Post on the Holiday?

Most freelancers have blogs to help promote their services and to establish themselves as experts in their field. (If you don’t have a blog, why not?)

If you’ve been publishing regular posts on your blog all year long, you may wonder whether you should publish a post on the holidays. If you do, will anybody read it?

I can’t tell you whether you should publish on the holidays, but I do think that most of your readers will understand if you don’t. I’ve noticed that many large blogs just put up a greeting at certain times of the year.

Dilemma #5. How Can Avoid Holiday Stress?

Volumes have been written about holiday stress, so I’m not going to go into detail about that here. Social workers and mental health specialists have documented that the holiday season (and the period immediately after the holidays) is one of their busiest times.

If you suspect that your holidays are going to be stressful, you can take some steps to make sure that your business isn’t affected. First of all, be realistic about how much work you can handle. This isn’t the time to overload yourself. Even if you are busy, be sure to take adequate breaks. Finally, don’t hesitate to get professional help to deal with your stress if you feel that you can’t handle it yourself.

Dilemma #6. Am I Really Ready for the Year-End?

The end of the year is an important time for any business. Freelancers should make sure that their record keeping is up to date and that they have supporting documentation for major transactions such as major purchases, and so on.

By this time, you probably have some idea of how much income your freelancing business took in. If you had a particularly good year, did you know that there are some year-end steps you can take right now to reduce your tax liability?

Investing in a retirement account, donating to charity, or accelerating the purchase of a capital asset are all actions that may affect your 2011 tax liability. Check with your accounting professional to determine the best steps for your business to take.

Dilemma #7. Slow-down and Extra Time

Some businesses slow down at the end of the year. Your clients’ businesses may be among them.

If you find yourself with unexpected down time during the holidays, you may be wondering what to do. Of course, you can always spend time with family and friends–but there are also some steps you can take to improve your business.

Use any extra time you have to organize your office and your files. Won’t it be great to start 2012 with everything in order?

Another year-end task you can tackle is to revisit your 2011 goals. How many did you achieve? By evaluating last year’s business goals now you can get a head start on next year’s goals.

Your Turn

Did I miss any freelancing holiday or year-end dilemmas? How do you handle the holidays?

Share your answers in the comments.

Image by judsond

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