4 ways to plan ahead for a less stressful holiday season

The holiday season is a perfect storm for stress. Often, there are a lot of things that need to happen in a short period of time. There are family obligations. You have to address year-end issues at work. Plus, you probably have to buy a few gifts, and—if you’re like me—you’re never sure how well those gifts will go over.

So, what can you do to minimize the stress that often comes with the holidays?

Start as early as you can

You might need to save this tip for next year, but get an early jump on thinking about the holiday season. Part of what causes stress around the holidays is that you know there are things that need to be done, but they feel overwhelming. In fact, a big reason why people don’t plan ahead is that they don’t want to peek into the abyss. But, you generally feel better about situations when you know exactly what needs to be done. So, procrastination in your holiday planning only makes things worse.

If you have to travel, lay out the dates sooner rather than later. Get to work on thinking through the work obligations you may have. Maintain a list of gifts you need to buy for others. Write it all down so that your brain doesn’t think it has to keep track of everything for you.

Map out your work

Think through the structures you use to plan your work. Many people have a daily calendar and a running list of tasks that need to be done. But, you may not take the extra step of figuring out exactly when key things are going to get completed. And that is generally fine. As long as your work gets done, you don’t necessarily need to micromanage your schedule.

Around the holidays, though, there are often several deadlines that may hit all at once. If so, it can be useful to set up a calendar that lays out all those deadlines and then plays Tetris with your schedule to ensure that all the steps leading up to those deadlines can be completed in time. That way, you’re not spending that last week of work hustling to take care of several weeks’ worth of work at the last second.

Of course, if you run your own business or have to hustle to find work, the holidays are stressful for the opposite reason. Lots of people stop hiring (or making big business decisions) in December. You may have to do a lot of work in the summer and early fall to make sure you’re busy in December and January. Plan your spending each year with the assumption that December and January may be slow so that you don’t add money worries to the other stressors.

Seek flexibility

Holiday travel sucks. Everyone is trying to get somewhere at exactly the same time. That makes the airports and roads crowded. Fares are higher. Tempers are shorter.

If you have to travel to see family, work with your boss to see if you can work remotely for a few days before and after any winter holiday break you may get. If you can time your travel to avoid the biggest crowds, you’ll be happier, and you might even be more productive.

If you’re the boss, consider offering some flexibility around remote work around the holidays. A little good will goes a long way. Also, it is often your employees who make the least who are given the least flexibility around the holidays. That adds extra expense to the lives of people who can least afford it. Your flexibility becomes a gift with real value.

When in doubt, ask

Finally, a word about gifts. It’s easy to get bent out of shape when having to buy gifts for others, as it’s hard to know whether you’re getting the right thing. It turns out, there are two things you can do to ease the gift-giving process.

First, if you’re buying things for colleagues at work, it really is the thought that counts. More than anything else, it is nice to know that people at work are thinking about you. So, anything you get for someone will have the desired impact. (That said, before buying food for someone, check on their allergies or dietary restrictions.)

Second, if you have people you’re really trying to impress with a gift, it never hurts to ask what they want. Most people (even long-married couples) have difficulty predicting what someone else wants. That’s why the folks who are most likely to give a gift someone else wants are the people who ask about the things people like to get. It may seem cheesy, but there are lots of things that people might want that they are reluctant to buy for themselves, but would be happy to get as a gift from someone else.