How to Take Your Work on Vacation (Yes, You’ll Have To)

When was the last time you took a real vacation?

I’m not talking about seeing your family during holidays, or that weekend you drove two hours to see your niece get married.

I’m talking like sitting on a tropical island, fruity cocktail in hand, completely disconnected from your work life kind of vacation.

You’re probably laughing right now, because most freelancers don’t think they have the luxury of taking time off like this.

After all, freelancers only earn money when we’re doing actual billable work—it’s not like we have paid vacation days and sick leave pay from an employer. Every day we don’t work is a day we don’t generate revenue, or income. And we sure know the bills will keep on coming even if we’re not earning money.

So is it really possible to take a vacation as a freelancer?

Grab a beach chair and stick with me. Your dreams of rest and relaxation are totally going to become a reality after you follow the tips in today’s post.

Have a Cushion of Benjamins

Let’s get the financials out of the way.

Besides saving money for your vacation, set aside a small fund for when you return back home and don’t have steady work coming in immediately.

If you manage to save at least one rent payment, enough money for groceries and electricity, plus some extra ‘just-in-case’ cash, you won’t feel so anxious about being away.

This will also give you enough time to start accepting work again from current and new clients.

Create a Vacation Timeline

While it’s going to be tempting to create a huge countdown calendar for your trip to paradise, creating a work timeline will be much more helpful.

First, pick a date you want to get away.

Keep in mind that it’s never the “right time” to go on vacation. But there’s a reason employers are required to give their employees vacation time: to keep their sanity.

You need some time away to recharge and relax.

But if you don’t want to take work with you, or feel the dreaded work monkey on your back when you’re at the beach, you’ll have to create a timeline you can stick to.

One month before your departure, send each of your clients an email with the following three pieces of information:

Your Vacation Start/End Dates

When I give clients my vacation dates, I add a two day buffer zone. This means I’ll have those days to get work done or readjust back to the real world while still flying under the radar of clients.

Don’t tell them this.


Assure each client about your time frame for completing their outstanding work. Will you be finished before you leave, or work during your time off to still meet your agreed-upon deadline? (I recommend the former).

Also use your upcoming out-of-office dates as a way to push clients to get you content (or other deliverables your work depends on).

Keeping clients in the loop about your work schedule makes for happy clients who typically won’t mind your vacation. In reality, you’re taking this time away to recharge your inspiration tank and serve them better.

For more on the balancing act between clients and vacation, take a listen to this excellent chat with Jennifer Bourn and Brian Bourn on Episode 77 of

The Last Day You Will Accept New Projects

Sometimes your email will inspire your clients to think about projects they want you to work on. Choose a date to let clients know when you will not be accepting new work, so you don’t take on too much when you’re trying to wind down for your time off.

Don’t flat out deny the opportunity if one should arise; mention that you’d love to work on the project when you return if it doesn’t fit into your hectic vacation schedule.

For those of you who communicate your “next availability” on your project or contact pages, be sure to update that date as well.

How Clients Will be Able to Reach You (If They Can)

If you’re going to truly disconnect, let your clients know that they will not be able to reach you while you’re away.

However, you may have clients who rely on you for help 24/7. If you want to include a clause in your email that makes room for emergency contact, give your clients the best way to reach you and the times you’ll be checking your phone/email/apps, so they’re not left to fend for themselves.

You never want to abandon a stressed out client; this will certainly discourage repeat business and referrals and we freelancers operate on a strong need for both of those.

You could decide to work on an 80/20 system.

This means you’ll be unplugged 80% of your vacation time and only spend 20% checking emails and doing light fixes. Set aside a specific time each day to work this 20% before you leave, so you can schedule vacation activities comfortably around this.

How to Handle Last-Minute Projects

What happens if a client offers you work that needs to be completed before or during your vacation?

As writer Ann Friedman puts it, “If they agree to increase my pay rate, only then do I move my vacation.”

Treat these last-minute orders as an “urgent delivery” that demand a higher premium.

If your client holds off on the project until you return, you’ll still have your dream vacation to look forward to just as you planned.

But if your client bites and you’re willing to work during your time off, kudos on getting the extra money! Here’s how to work on vacation without missing out on the fun.

How to Work on Vacation the Stress-Free Way

According to one survey, close to 60% of U.S. employees work while they’re on vacation.

And 35% of millennials reported that they “worked every day of their vacations, and felt less productive when they returned.”


If you can’t get all your work done before you leave (highly recommended!), here are a few tips to make working easy while you’re away:

Take Advantage of Time Differences

While traveling to different time zones sometimes means the dreaded jet lag that comes after, you should make time differences work for you.

If you live on the east coast of the U.S., for example, and you’re taking a trip to San Francisco, you’ll be three hours ahead of your usual workload.

If you normally wake up around 7 in the morning, keep your routine on the west coast and wake up at “7 a.m.” while away.

This is an easy way to sneak in work while everyone in your destination city is sleeping (it’s only 4 a.m. afterall!). Sure you’ll be up early, but you won’t have to take time away from all those vacation activities if you finish before they start.

Plus, this will still keep you on track for your normal deadlines as you’ll be ‘working’ in the same time zone as when you were home.

If you really want to get ahead of your work game while on vacation, choose a destination on the opposite time schedule as your hometown—you’ll be half a day ahead!

Let a New Locale Inspire You

Working on vacation sometimes doesn’t feel like working if you set the scene right.

Instead of sitting in your hotel room frantically typing away, bring your laptop outside to the patio area, or hang out in one of the far seats of the lobby bar during off-times. Honestly, I can think of worse situations than needing to complete your work while in a hammock on the beach.

The point is, immersing yourself in your destination while still doing work may actually help you work faster to get back to the fun.

Don’t Spend Too Much Time on Social Media

If you regularly post three blogs every week and tweet something hilarious to your followers everyday, make sure to set up these posts before you leave and put them on a schedule so they go out while you’re away.

Your tribe may not even know you’re gone unless you post jealousy-inducing Instagram pics of your vacation.

I know it can be a scary thought to take a week off to totally unplug and disconnect from your work life, but you can do it with a little planning and a lot of dedication.

Communicating with your clients about your time off is critical to them being on board (and sticking with you). Meet your agreed-upon deadlines and turn in work before you leave for vacation to stay in their good graces.

If you have to work while you’re away, immerse yourself in the scenery of your destination while you work and you’ll never feel like you’re missing out.

Leave a Comment

Your email address will not be published. Required fields are marked *

Carrie Dils uses Accessibility Checker to monitor our website's accessibility.