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A Freelancer’s Guide for Going Back to Work After a Vacation

Oct 23, 2020
(updated: Feb 14, 2023)
Max 5 min read

One of the many perks of living the freelance life is that you can take as many days off as you want. That is, you can take as many days off as you can afford while still being able to pay your bills. 

The truth of the matter is that we freelancers tend to take fewer days off than others, though. In fact, in a 2019 survey, 92% of freelancers said that they never take a vacation that’s truly work-free.

Part of the reason is that we’re all flying solo so there’s no one to cover for us on our days off. We overwork ourselves before the vacation to prepare and then our first day back to work after vacation is a frantic attempt to catch up. It’s time to stop the madness. Try these five steps for going back to work after the holidays or a vacation.

1. Go In with an Open Schedule

Personally, I’m a time management fanatic. At the end of every workday, I have a clear schedule for the next day of which tasks I’m going to handle and when. Your first day back to work after a holiday is a day to skip this and let go of any and all expectations for productivity.

Don’t schedule any meetings for that day. Don’t commit to any deliverables for that day either. Consider it to be a planning day to get back into the swing of things and give yourself the space to think.

2. Tackle the Inbox First

Especially if you’ve taken more than a few days off, your voicemail and email inboxes may as well be Mount Everest. Those messages will dictate your to-do list and goals for the week ahead, though, so they’re the first thing you should tackle on your first day back.

Simply go through one-by-one and take notes on each message as it comes. Keep a running list of notes and to-do items as you do this, but don’t respond to any messages or take action on anything until you’ve cleared out your inboxes. Sometimes a client may request something in one email and then call you later to change their request, so your first trip through the inbox is just a fact-finding mission.

3. Assess All Your Works in Progress 

Depending on the services you provide, you probably have projects at various stages of the pipeline for multiple clients at any time. For instance, if you’re a freelance web designer, you might have mock-ups for one project that are waiting for the client’s review while you work on creating a different client’s designs, and you’re waiting on a third client to respond to your project proposal. To keep it all straight, you should have a task manager or some system to keep track of each project in the pipeline.

Now that you’re going back to work after a holiday, it’s time to get a fresh perspective on your pipeline. Review each project’s stage in the process and determine what you need to prioritize, what you need to follow up with clients about, and so on. This sets the stage for the next step in your day.

4. Create a Plan Moving Forward 

This is where it all comes together. With your current task manager and your inbox notes, create a clear list of tasks and priorities moving forward. Put those to-dos from your inbox notes into your task manager. Create a priority list and block your time for the following day or for the rest of the day, depending on how long the first three steps have taken you. This is your time to get your mind back in the game and re-orient yourself for a productive week ahead.

5. Reach Out to Your Clients

Now that you have a grasp on all your tasks and projects, it’s time to reach out to all your active clients. Let them know that you’re now back in town and you’re getting back to work after your vacation. It’s also a good time to let them know what you’ll be working on for their project in the days ahead or to remind them about anything they need to send you. 

Has a few purposes. First, it helps you get back on the same page with your client and ensures that you’re all on the same page. Not only will it boost your client relationship because your client will love the clarity, but it makes for a more organized and simpler project.

Second, that email sets the precedent that you’ll notify your clients when you’re available after you’ve taken time off, even if you told them when you’d be back before the trip. This makes it less likely for clients to unintentionally contact you while you’re on future vacations because they know that if you haven’t reached out, you aren’t back yet.

Your Plan for Going Back to Work After the Holidays

For freelancers and employees alike, the first day of going back to work after the holidays is always stressful. You feel mentally disorganized and you have no idea what chaos your inbox may be holding. The five steps above can turn that first day into a productive one that makes you feel at peace and in control so you can get back to doing what you do best.

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