How to Prep for Vacation (Plus a FREE checklist!)

One of the biggest benefits of freelancing is the flexibility of work hours it brings. You can generally decide where and when you work. Of course, being able to work any time and any where doesn’t mean you should work all the time. Freelancers deserve a vacation as much as anyone else.

If you want to stand out in your career, it’s important to be professional and reliable at all times, even when you’re taking time off. It can be hard to plan for vacation when you freelance. You need to make sure you have enough money in the bank to take time off. You need to make sure you’ve finished all the work that would normally be due while you’re relaxing on the beach. You need to get past that mental script telling you that you don’t have time or money to take a vacation.

Trust me. You deserve a vacation. Taking time off will help you recharge. You’ll be more energized and creative when you return to your business, and you’ll reduce your risk of burning out. But everyone deserves some time off from work. If you have a good work/life balance, your vacation should be a true vacation, without checking your email every five minutes.

If you’re ready to take that long-awaited vacation, here’s how to prep your business so you can truly relax.
So how can you remain reliable? The key is an effective “Out of Office” auto-responder, which automatically gets sent to whoever emails you after you activate it. You might think this is obvious, and if so, good for you — you already have great professional etiquette. Unfortunately, there are people still behind. If you are one of these people, and you take time off without setting an out of office, you’re making everyone who emails you think you’re ignoring them. In the age of immediate communication, this will aggravate people and make you seem unreliable.

There are two types of auto responders:

  • “Out of Office” reply – for when you’re on vacation, medical leave, have a family emergency, etc.
  • “Slow to Respond” reply – for when you’re at a work-related event or will be replying to emails throughout your vacation.


Vacation Prep Checklist

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Prep Your Clients
Give each client advance notice of your break. I usually tell my clients about a month in advance. This gives them time to think about what they might need when I’m gone and plan for my absence. If you have a client who seems stressed out that you are taking vacation, address their fears. How are you going to make sure their needs are taken care of while you’re away? I usually tell clients that I’ll have all the work I’m doing for them turned in a week before I leave, so we’ll have plenty of time for revisions. If you work for an agency, suggest someone who can act as your backup if anything goes awry while you’re away. You may also want to remind your client the week before you leave that you’ll be gone. A quick email to remind them is probably all you need.


Clear Your Calendar
In order to truly relax on your vacation, make sure you’ve turned in all the work that’s due. You don’t want a looming deadline to cast a shadow over your vacation. We’ve all seen that person perched on the end of a lounge chair at the resort pool frantically typing into a iPhone. Don’t be that person. Plus, as you’ll see in the next section, things don’t always go as planned when you’re on vacation. You might assume you’ll be able to do a few quick revisions and submit work while you’re away, but if the Internet connection is bad, you forget your computer charger, or some other crazy thing happens, you’ll be stressed and waste some of your precious vacation time trying to fix it. You may have to work extra hours in the weeks before your vacation. That’s normal, even people who work in a traditional workplace have to do this. Try to be as organized and focused as possible, and remember that after all this work madness is over you get to relax.


Plan for Emergencies
In reality, stuff happens. I’ve been in hotels where the Internet connection is so slow I couldn’t load gmail. I’ve misplaced my laptop charger, making it impossible to retrieve work from a dead laptop. If you plan on doing any work when you’re on vacation, including checking your work email, then plan for emergencies. Build some work time into your vacation schedule so you don’t have to rush to finish something. Bring an extra phone, laptop, or tablet charger (and keep it in your carry-on luggage). Save important files on a flash drive and keep it in a different location than your work device. Research where the nearest Internet cafe is BEFORE you arrive or bring your own wifi hotspot.

If nothing goes wrong, you’ll be pleasantly surprised. If something does go wrong, you’ll be prepared.

You might also want to create a buffer of one or two days for yourself for after you get home. Your flight may be delayed, so you could get home a day late, or If you’ve just driven 12 hours home, you might need a day to unpack and clean up the car. Plus, sitting is the last thing you’ll probably want to do after an epic road trip.

Don’t plan on working immediately after you get back from vacation. Give yourself some time to transition back into work mode. Preparing for vacation is always a lot of work, and it’s even more work when you own your own business. A vacation is worth the extra preparation, though. You’ll be amazed at how relaxed and ready for work you are after you’ve taken a break.


How to Write an “Out of Office” Reply
Keep your “Out of Office” reply short and simple. Here’s a sample “Out of Office” message you can use:

Subject line – Out of office:

Thanks for your email. I am out of the office until [DATE]. I will reply to your email after I return.
If you need more immediate assistance, please email John Doe (

Short, sweet, and professional. Notice the non-committal phrases, too:

  • You’ll reply “after” you return, not “when” you return. Don’t commit yourself to reply THE DAY you return. You might come back to hundreds of emails — give yourself time to catch up.
  • “More” immediate assistance, not “immediate assistance.” Don’t commit your colleagues to reply immediately. They’re already going above and beyond to help you out when you’re away. Instead, they’ll be able to provide assistance “more immediately” than your return date.

Here are things you should not include in your Out of Office message:

  • Why you’re out. Don’t brag about your tropical getaway. Don’t relinquish details of your medical mishaps. Don’t confess you have a family emergency. It’s really none of anyone’s business why you’re unavailable — people just need to know that you are unavailable.
  • When your first day out was. Many people say, “I will be out of the office from [DATE LEFT] to [DATE GETTING BACK]. If someone is receiving this Out of Office message, you are already out of the office. There’s no need to reveal how long your vacation is. This will just give Competitive Cathy ammo to hold against you.
  • Where you’re going. Again, there’s no need to brag. Also, if a perfect stranger emails you, they’ll also receive your Out of Office. Just like you shouldn’t tell the world on social media that you’re away from your home, you shouldn’t via email either. Don’t call me paranoid — my neighbors got burglarized just last year when they left for a long weekend. It happens.
  • Excuses. Don’t say you will not have access to wifi. Don’t say that you need to sleep off an illness. Again, it’s nobody’s business why you’re out. Just let them know that you’re out.

How to Write a “Slow to Respond” Message
A “Slow to Respond” message is what you should use if you go on a business trip, have a team offsite, or any other occasion in which you’re still working, you’re just not going to be able to reply to your email as reliably as usual. Do not use a “Slow to Respond” when you’re on vacation. Take a vacation. But it’s essential to remember the “Slow to Respond” when you will, for whatever reason, be working but slower to respond. Here’s an example “Slow to Respond” message you can use:

Subject line – Slow to Respond:

Thanks for your email. I am at [EVENT NAME] until [DATE] and may be slow to reply until then.
If you need more immediate assistance, please email John Doe (

Again, short and sweet, much like the Out of Office. In this case, it’s good to say where you are in case whoever emails you is there, too. It might be a good opportunity to connect at the event itself.

Instructions for Setting Up Auto-responders
If your not sure at how to set up your email auto-responder, instructions for technically setting up this auto-responder will depend on which email client you use. Here are the instructions for some of the more popular email clients: