How to Maintain Your Freelancing Hustle Over the Holidays

One of the things that’s so great about freelancing is the flexibility. It’s just you, and your schedule is (pretty much) your own. You can choose to structure your projects and your workdays however you please. But, when the holidays roll around, suddenly the concept of being a one-man band isn’t quite as appealing.

Sure, you want to take some time off for some festive fun and relaxation. But, without careful planning and preparation, you’ll likely find yourself buried under piles of work—rather than piles of holiday cheer. So, what can you do in order to be able to take some well-deserved time off without sacrificing your professional reputation or too much of your income?

Well, it’s really not too complicated. It just involves some foresight and coordination. Have no fear, my fellow freelancers. Here are five tips that will help you keep up (and maybe even relax!) over the holidays.

Communicate Early

People always say that “communication is key”—and for good reason! Particularly when you’re a freelancer and working remotely, you need to be sure to clearly articulate your thoughts, needs, and plans.

It’s no secret that employees tend to take pretty significant time off during the holidays. So, ensure ahead of time that you have all of the important details and instructions you need for any projects you’re currently working on. You don’t want to be left hanging in the balance and missing a deadline simply because you couldn’t get those need-to-know details from a client that’s enjoying a holiday break on the ski slopes. Sit down, take a look at your upcoming projects, and ensure that you have everything you need now. It’ll save you some stress and a headache.

Additionally, if you’re planning on staying away from your work and computer for some time, make sure to communicate that to your clients so that they know you won’t be at their beck and call over the holidays. Think of it like requesting vacation days from a traditional 9 to 5 job. Your clients need to be in the loop on your plans.

Work Ahead

Taking some time off around the holidays sounds wonderful, doesn’t it? But, you should be prepared for the fact that your period of festive relaxation is likely going to be prefaced with some long nights and early mornings.

Before the holidays arrive, really hustle to work ahead on the projects you currently have sitting in the hopper, so they aren’t hanging over your head. This will remove some stress from your plate, and will also allow you not to feel guilty for indulging in eggnog and family time when you have a backlog of projects you should be working on. Really, feeling caught up is the greatest holiday gift of them all.

Right before the holiday season is also a great time to communicate with your clients about any projects or needs they anticipate for the upcoming new year. While it might seem counterintuitive to ask for more work when you already feel overwhelmed, it’s something you definitely want to consider.

The beginning of the year is a notoriously slow time for freelancers, as organizations are preoccupied with coordinating and working with their own new budgets and plans. So, any projects you can get to tide you over and carry you through that lull will definitely help both your bank account and your sanity. You don’t need to start on those projects immediately. But, knowing that you have some work in the pipeline will help you ease into the new year without worrying about how you’ll make any money.


I can’t say enough about the importance of prioritizing your tasks. But, if you’re a freelancer who’s used to juggling a multitude of projects, clients, and deadlines, you’re likely already a believer in the magic of effective prioritization.

This tactic is especially beneficial during a busy time. So, if your plate is piled high with work you want to power through before the holidays, take a breath and use some time to prioritize your tasks and assignments.

Where should you start? Well, I like to jot down a big list of all of the projects I need to be working on. Once I have all of those scribbled out, I go through and write the deadline next to each of them. Then, I’ll number them according to that end date. That way, I can work through my list in a strategic way that ensures I’m meeting my deadlines.

It seems basic, but it’s incredibly effective. And, even if you can’t conquer that entire to-do list, at least you can enjoy some holiday cheer without feeling like you’re neglecting something that’s due tomorrow.

Set Goals and Strategize

Alright, so you’re busy with a ton of different projects and assignments. But, that doesn’t mean you want to completely miss the forest for the trees.

A new year is fast approaching, so you need to also keep the big picture of your business in mind. It’s important to take some time and reflect on how your business did in the past year. Are there things you could improve? What things did you do really well? What are some goals you should set for the upcoming year?

You might feel like you can’t take time away from billable hours in order to strategize. But, believe me when I tell you it’s worth it. Strategic planning is crucial for any successful business—including your own. So, take the time to not only set goals and strategies for the work you need to do right now, but also for everything you plan to do in the upcoming year.


You’re tired, stressed, and crabby. You’ve spent so much time in front of your computer that your hands are cramped and your eyeballs feel like they just might roll out of your head. You’re wondering why you ever decided to do this for a career—what were you thinking?!

Trust me, every freelancer has been there. And, feeling overwhelmed and overworked is never fun. But, being that freelancing is known for being an unsteady career path, you should actually feel grateful for the fact that you’re eyeball deep in work—even if it is putting a damper on your holiday joy.

Luckily, there’s something you can do that will give you the best of both worlds. What? Send out a cheery, handwritten holiday card to every one of your past and current clients! Not only will this allow you to incorporate a holiday-related touch into your work day (heck, you can even play some holiday music while you do it!), but it’s also a great way to network with all of your clients.

Sharing well-wishes and maintaining those important connections with a thoughtful card will help ensure that you face these same busy circumstances when the holidays come around next year. Because, like I said, you’re actually really lucky to be in this situation.

Typically, your flexible schedule is one of the perks you love most about being a freelancer. But, when the holiday season arrives, balancing everything can definitely be a struggle. However, it’s not impossible! Use this tips (and, if you’re smart, start using them right now!) to strike a balance between business success and holiday cheer. After all, nobody likes a Scrooge.


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