The Freelancer’s Guide to Taking Time Off – The Startup – Medium


It’s time to put a stop to working vacations

When was the last time you took a vacation?

I don’t mean a working vacation, where you travel but you’re still tied to your laptop or stuck on the phone with a client. I mean a REAL vacation, where you leave work behind for days and give yourself time and space to relax and recharge.

If you can’t remember the last time you did this, or if you haven’t since becoming a freelancer, then this post is for you. And you, my friend, desperately need a vacation.

According to Business Insider, the average American worker now takes less time off than a Medieval peasant … and I’m willing to bet that we freelancers take even less time than the average American worker.

Long-term, that kind of schedule wreaks havoc on your productivity, your health (both physical and mental), and eventually, your client relationships. Not giving yourself time off can lead to fatigue, lost motivation, and burnout.

It also makes you a terrible boss, even if you are your only employee.

As a former boss once told me, there’s a reason every sport has a halftime. Taking a break gives you a chance to clear your head, rest your body, and come back with a fresh perspective on things.

But that can be hard to do when you’re the only person in your business. It’s not easy to let go, even if only for a day or two, and when you do, it can be hard to get back into the rhythm of things without missing major deadlines.

I’ve been freelancing full time for a year and a half now, and though I still haven’t managed to take a completely unplugged vacation, I have figured out some tricks to taking time off in small chunks. Here are the best ones.

Consider vacation and sick days when you calculate your rate

One of the main drawbacks to freelancing is that there’s no paid time off. So when you set your rates, you need to build in some downtime to allow yourself to recharge.

Start by deciding how many vacation days you’ll give yourself. At the very least, you should give yourself 2–3 weeks per year, which puts you on par with most entry-level benefits. If you love to travel, have family who live out of state, or have a boatload of weddings to attend in the near future, you may want to allow yourself more time.

Next, give yourself sick days, because believe me, you WILL need them.

I usually calculate about 5 sick days per year simply because that’s what my last full-time job before I went freelance allowed. If you have a chronic condition that frequently makes it difficult to work, you should probably allow yourself more time.

And if you really want to do yourself a favor, you’ll build in a few mental health days as well.

Now add up all of that time and subtract it from the 52 weeks in a year. That result is the number of weeks you can reasonably expect to work, and that’s what you’ll use to calculate your hourly rate.

Start planning far in advance

Taking time off regularly gives you something to look forward to and helps prevent burnout — which is WAY more devastating to your business as a freelancer or solopreneur than it is when you’re a traditional employee. So when you sit down at the end of the year to plan out the next one, go ahead and start thinking about when you’ll take your vacations.

This year I knew I needed to travel from New Jersey to California in June for my sister’s graduation, and I knew that I wouldn’t need to travel as much this holiday season as in previous years since my fiancé and I now live near one set of parents and siblings. And now that we’re on the east coast, I knew I’d want some time to meet up with friends in nearby cities and explore places I’d never gotten to visit before.

Keeping those things in mind helped me think more strategically about how much work I took on each month. It even influenced my marketing strategy for the year because I knew I could count on my dad for some updated branding photos when I visited in June.

Maybe you don’t have a family event to attend, but there’s a conference later in the year that you’d love to finally go to. Think about what events are coming up, where you’d like to visit, and what your business goals are, and plan your vacations around those.

Cover your shift

For most of us freelancers, the price of a good vacation is spending the weeks leading up to it working overtime to get stuff done in advance.

That’s a decent solution if the work you do is regular, recurring, and predictable. But if you mainly work on retainer or on one-off projects, you may not be able to double up on future tasks.

This is where it comes in handy to have a solid network of freelancer friends in your field of expertise that you can outsource to if needed. In a pinch, they can take over your projects while you’re out of office and handle any client emergencies that come up.

You might also consider hiring a virtual assistant to keep up with administrative tasks for the week or two you’ll be gone especially if your vacation overlaps your regular invoice date.

If you’re not in a position to outsource yet, you may need to accept the fact that you’ll just have a lower income that month and try to take on extra projects earlier in the year to make up for it.

Let your clients know early

While researching this piece, I discovered — via two very informal polls, one on my Twitter page and one in my Facebook group for freelancers — that quite a few of us worry our clients will be upset that we’re unavailable when we take vacations.

Though I’ve never personally experienced this, there are a few ways to keep them happy in your absence.

First of all, as soon as you know which days you’ll be out of office, you should let your clients know. If you sign any new clients between then and your vacation, tell them, too. And if your time off coincides with any deadlines, talk to those clients individually about how you’ll make sure they still get their work on time.

Giving your clients an early heads up helps them book their projects around your absence and plan for any gaps in coverage that need to be filled. It’s best to do this in writing so they can easily refer back to the dates as needed. I keep a list of all of my clients in Mailchimp so that it’s easy to email my whole roster in one fell swoop instead of sending copies of the same email over and over again.

Here’s a template you can use:

Hey there, [NAME]!

I wanted to let you know that I’ll be on vacation in [LOCATION] from [DATE] through [DATE]. It’s still weeks and weeks away, yes, but I thought you should have these dates in advance for your own planning.

If you have any questions, feel free to reply to this email with them. I’ll also touch base again closer to when I’ll be gone.

Have a great day!



You should also remind them of your upcoming vacation the week before and ask if there are any last-minute things they need taken care of. They may have forgotten about your plans even though you told them early on, and they’ll appreciate the chance to touch base before you go.

This is a prime opportunity to let them know your availability while you’re gone. Will this be an unplugged vacation, or will you be checking emails periodically? Will you answer phone calls? What should they do if they have an emergency related to the work you do for them?

Feel free to use the following template:

Hey there, [NAME]!

I’m popping into your inbox to remind you that I’ll be on vacation in [LOCATION] from [DATE] through [DATE]. While I’ll still check my messages periodically — I’m a millennial and it’s 2018, after all — I won’t be working on any client projects during that time.

However, my assistant [NAME] will be available should you encounter any [SERVICE] emergencies. You can reach them at [EMAIL] or [PHONE].

Is there anything we haven’t yet discussed that you’d like me to tackle before heading out of town? If so, please reply to this email and let me know. Otherwise, you can expect to receive your projects by the previously agreed-upon deadline.

Have a great day!



If you’ve taken all of these steps to communicate with your clients and they’re still upset that you’re going on vacation, then you have a problem. And that problem is them, not you. Everybody takes time off — yes, even your clients. You’ve earned this vacation by hustling your butt off, and if they can’t see that, then you may need to reconsider your relationship with that client.

Pre-schedule your own marketing

On top of your client work, you also need to consider how you’ll continue to market your business while you’re on vacation.

If you publish blog or podcast content regularly, you’ll need to create and pre-schedule at least enough posts or episodes to cover your absence, if not also your first week back.

The same goes for your social media — schedule enough posts that you won’t have to worry about it while you’re gone. You can use a tool like Hootsuite or CoSchedule to share new content, or use RecurPost to keep your evergreen content circulating.

I usually schedule all of my vacation social media posts while on the plane to my destination. A chunk of uninterrupted time to work on my own business always feels like such a treat, and I get to write off the in-flight wifi bill as a business expense.

But regardless of when you choose to do it, taking some time to schedule your marketing so that you don’t completely lose momentum while you’re gone.

Set an auto responder in your email

A day or two before you go out of town, set up an email auto-responder.

Since you’ve already given your clients the important details, this message is really for anyone else who might try to get ahold of you, like new leads or connections. As such, it can be a little bit more vague, like the following template:

Hey there, friend!

I’m on vacation in [LOCATION] from [DATE] through [DATE] and am not responding to messages during this period.

If you’re a client with a [SERVICE] emergency, please refer to my previous email for how to get ahold of me or my assistant. Otherwise, you can expect to hear from me by [DATE].

Thanks for your patience, and I look forward to connecting with you when I’m back in the office.



If you really want to unplug and relax, you may even want to pause your inbox for part or all of your vacation. Gmail now has this feature built into its system (you can find the button right below the “Compose” option), and if you’re the type who just can’t leave your email alone, this might be the push you need to let go and take your mind off work.

Give yourself extra time

Here’s a brilliant life hack I learned from Chris Ronzio over at Trainual: Build an extra day into your vacation specifically for catching up on things once you get back.

Nobody wants to dive right into the daily grind on their first day back. You need time to unpack and do laundry. You may have jet lag and need to catch up on sleep. You’ll definitely need time to go through your emails and build a plan of attack for getting through the work that piled up while you were gone.

That extra day at home without the pressures of client demands is a lifesaver, and if you haven’t tried it yet, I highly recommend you do so.

Another way to get back into things faster is to plan out your first week back before you even set foot out the door. Chances are you already know what your priorities will be, and having a plan in place can help keep you from feeling overwhelmed by everything you have to do.

It’s also a good idea to block out the last day before you leave. Use this time to tie up any loose ends on your own without having to constantly jump on a call with a client. You’ll feel better knowing that everything is taken care of beforehand, and hopefully, you’ll be able to start your vacation with a clear mind.

Still not sure how to pull the plug and take some time off from your freelance business? You just might benefit from a personalized freelance coaching session. In our call, we’ll talk about exactly what’s holding you back from taking time off, and work together to craft a plan that helps you feel comfortable going on vacation.

Ready to talk? Book a session here:

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +385,976 people.

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