How to make the holidays work (and be your own best boss)

By Brittany Taylor

Work + Life

How to make the holidays work (and be your own best boss)

12 lessons for boosting productivity, nixing procrastination, and eliminating poor scheduling problems for freelancers, creative entrepreneurs, and side-hustlers

by Brittany Taylor

published November 1, 2017

updated June 5, 2018

Elf on a Shelf has been chillin’ at my local target for weeks now. While I curled my lip at his cocky little face pre-Halloween, I’ve gotta admit that the creeper has a point: It’s time to start thinking about making the holidays work—and how to cram client work, business planning, sleep, and lunch breaks into a schedule that’s already popping with party invites and online shopping binges.

I’ve worked in retail and journalism. I know how much it sucks to work on a holiday, whether it’s by choice or not. I know how depressing it is when you’re watching friends post snaps from ugly sweater parties while you’re stuck answering emails that are only emergencies in the mind of your bag-o’-nuts boss. I know the self-loathing that comes when you put off client work because you wanted to savor that mug of cocoa…and suddenly you’re in crunch time on New Year’s Eve.

This year, I'm going to do better. And this year, you can, too.


This post skews towards western, commercialized Christian traditions. But making holidays work isn't just a Christmas thing. Take these best practices and apply them to any holiday that’s a Big Freaking Deal in your country or culture.

12 must-do's for making the holidays work for your business and your life

Whether you’re a solopreneur, a boss with underlings of your own, a freelancer, a 9-to-5-er, a side-hustler, or some other hard-at-work unicorn, here are my tried-it, sucked-at, and learned-my-lesson best practices for the holiday season.

#1. Communicate the holiday work schedule as far in advance as possible

Some businesses can close for a week or two. Some can’t. Some shutter one year and stay open the next on the whim of a CEO. Some need coverage without overtime. Some need coverage, but will let you work from home. Some need you to be on call. Some want you out the door and not even thinking about work until after the ball drops in Times Square.

When it comes to holiday work schedules, there is no norm. That’s why you need to decide what your schedule will be and spread the word.

This is especially true if you have employees, contractors, subcontractors, or anyone you pay to work for you. These people need to know what your deal is so that they can figure out what their deal is. Let them do that ASAP by giving them the gift of a heads up. If you haven’t explicitly said, “We’re closed the week between December 25 and January 1!” do that now, then come back and read the rest of this post.

No, really. Go do it. The Elf on a Shelf and I will wait.

#2. Set boundaries around the work you’ll be doing during the holidays

You can’t expect clients, coworkers, or managers to respect your boundaries when you don’t tell them explicitly what those boundaries are. You don’t have to be a brat about it either. A quick FYI email will do the trick.

Think: “I’ll have X, Y, and Z completed the Monday before the office closes so that we’ll have the rest of the week to discuss and revise, and I’ll be available on a limited basis by email through Saturday night. Between Christmas Eve and New Year’s, though, I’ll have zero chance to check email or my office voicemail, so I’ll respond to inquiries that come in that week when I return to the office in January.”

This is also a handy thing to put in your out-of-office response, even if you’ve already told the entire world that you’re going to be incommunicado.

#3. Be the one who brings up the holiday conversation first

Clients and employees should never have to ask you about what to expect around the holiday season. You should always broach the issue first—and if you are asked in April about what’s coming in December, be ready with a “I haven’t sat down with a calendar just yet, be we usually close the week of Christmas.”

For those who work with you and for you, think about every aspect of the season. Answer questions including: Are you giving gifts? Will there be a holiday party? Are there holiday bonuses? Will there be paid days off? Will the office be adopting a family or asking for charitable contributions or anything some people might want to make personal plans for?

#4. Build time into your schedule for the stuff you usually do at the last minute

Everything you must accomplish between now and Thanksgiving or now and Christmas Eve or now and New Year’s is something that should go on your to-do list and your schedule. Don’t let trivial activities that aren’t necessarily money-makers or deadline-havers sit on your mental back-burner and turn you into a frenetic, tinsel-tossing idiot. Write that shit down, yo.

Case in point: If you always send out holiday cards to your vendors, that’s not an activity you should frantically squeeze in around client projects, it’s one you should plan for. Can you do it while watching A Christmas Carol? Sure. But put the silly cards on the calendar—and do it now, so that they have a chance to arrive before Santa does.

The same holds true for creating themed playlists, ordering catering for the holiday party, decorating the office, wrapping gifts for coworkers, and writing your auto-responder.

#5. Remind, remind, remind

A one-and-done email is like holiday Russian roulette. Will your boss remember you’re leaving a day early? Will your client send in receivables by the deadline? Eh, maybe. But if you sent that one email about your schedule or your boundaries or you closed-for-business dates a month ahead of time, you’re leaving the door wide open for panic to waltz right in and wreck your wrapping party.

Don’t do that. Opt for over-reminding rather than under-reminding. There are scads of email program tools and extensions that will let you write and schedule these reminders ahead of time, so that you don’t have to worry about sending them ever again.

#6. Build padding into your schedule for last-minute projects and problems

You can communicate your deadlines until you’re blue in the face, but sometimes, shit happens. Sometimes, shit takes longer than you thought it would. And when it does, the least frustrating option is to have foreseen the possibility of shit happening and to have time built into your schedule to deal with it.

After all, the worst that happens is everything goes swimmingly and you have 2 hours free to watch another Hallmark original.

#7. Ask yourself “is this really necessary?”

If I had a nickel for every brilliant-but-elaborate marketing plan I’ve concocted to coordinate with a certain holiday, I wouldn’t be wondering where my present-buying budget was coming from this year. We all have ideas that are far larger than our schedules and abilities allow, and yeah, sometimes we let ourselves get caught up in them—and that’s OK. But the holiday season is not one of those times.

The holiday season is when you want to prune. After all, you’ve got a lot of balls in the air right now, and if you want to catch most of them, you’ve gotta trim the fat. Do you need to test 10 different CRMs the week before Thanksgiving? Is it necessary to publish a post a day on your blog while a large part of your audience is busy devouring leftover turkey sandwiches and throwing back mulled cider?

Walk through every item on your to-do list and decide if it’s a must-do, nice-to-do, or don’t-even-bother. Then, build your schedule based on these priorities.

#8. Create a contingency plan

Have you ever walked up to a cash wrap only to be told that the computer system just froze? Somehow, life is always breaking whenever you really need it to work. The holiday season isn’t any different, and planning accordingly now will be a life saver, if (and when) your life (and your work) actually need saving.

Make like a parent with that list of numbers on the refrigerator and create a list of people you can call during a holiday season if/when crisis. Server goes down? Figure out who your point person will be. Need to call in back-up staff? Assign on-call days and hours. Double-booked? Check in with a sub-contractor who’s down for working holiday hours, just in case.

#9. Work ahead

I have written so many posts while promising my coworkers I’d be ready to go in just one more minute. And you know what? They’ve done the same to me while I was tapping my toe, ready to set the alarm and lock the door.

Save yourself from the frantic keyboard-tapping and start working ahead now rather than later. Does it suck to have to do more work consistently for a month or two? Yeah, it really does. But that suckiness pales in comparison to the insanity that strikes when you leave it all the week-of. Swallow your moaning and do a little bit at a time. And take my word for it: It’s better this way.

#10. Allow fun things to be priorities, too

The eternal grind makes for bitter bosses and resentful employees, especially when there are so many events and activities to look forward to that have absolutely nothing to do with work.

Let yourself enjoy those things! Before the season gets into full swing, make a list of the activities you absolutely want to take part in, the parties you want to attend, the gatherings you want to throw, the family and friends you want to hang out with, and the downtime you need to be cozy and festive and 100 percent alone.

Then, schedule that shiz, too, and while you’re partaking, remind yourself that this is important self-care and it doesn’t include checking your email or worrying about tomorrow’s work load. Be in the moment so that you get the most out of this holiday season.

#11. Stick to what you said you were going to do

Respectful bosses, colleagues, and clients, will leave you the F alone during the holidays. But not all humans are respectful people. Remember this, though: Just because someone asks you to do something doesn’t mean you have to do it. And if you do decide to do it, you don’t have to do it on their terms; you can absolutely do it on yours.

When you let people walk all over your boundaries, they realize that your boundaries are more like suggestions and less like absolutes. Accepting a call on Saturday even when you don’t technically work on the weekends trains your clients to expect you to answer their calls 24/7.

In some industries and businesses, this is just reality. Sometimes, emergencies do happen, and sometimes, you do need to be available even when you’d rather be staring at fairy lights. For many of us, though, shutting down for a week isn’t the end of the world for any party involved, and you won’t lose your job or your client if you push back with a polite “no.”

#12. Don’t just disappear

The biggest N-O of them all is to disappear off the face of the Earth with zero warning. It’s one thing to set up an out-of-office response that lets folks know you’re off the grid and when you’ll be plugging back in. It’s another thing entirely to slip out the backdoor and leave people hanging while you’re enjoying an extending vacay. The first thing is A-OK. The second thing is a major Don’t with a Capital D.

If you’re an employee or if you communicate to the world at large almost entirely through email, you can stick with just the auto-responder. If, however, you’re a small business owner like me and you communicate with various audiences on various platforms, post a note on each of those platforms that lets folks know, A., that you’re gone, B., when you’ll be back, and C., how they can reach you in a true emergency. Think: email, social media, and the contact page on your website or storefront.


Running behind schedule? No worries. Get the guide to writing a holiday-themed blog post at the last minute.

About me

Brittany Taylor

My name is Brittany, but my friends and clients call me "Britt." Online small business owners hire me to create content strategies and write their blog posts, email newsletters, and social media updates. I work with bosses around the world from the marshes of Charleston, S.C.


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