How To Prep For A Successful Vacation


Animated character hanging out of a bus window waving goodbye. Caption reads How to be vacation ready

How To Prep For A Successful Vacation


Click on the pic above to watch this video on YouTube or click play below to listen to the Podcast version



How do you go on vacation without your clients all leaving you? How do you go away without spending your entire time on your phone or laptop trying to keep everything together?

Here are my big lessons on how to prep for a successful vacation (even when you’re indispensable) and come back feeling refreshed and happy instead of rushed and anxious!


  • 00:00 Introduction
  • 00:30 What does a “successful vacation” even look like?
  • 00:51 How to book in advance
  • 01:46 Building in buffer days
  • 02:20 Gather your documents in one place
  • 04:21 Tell everybody and set boundaries
  • 06:51 Remind everybody… OFTEN!
  • 07:22 Set your “out of office”
  • 09:24 How to use the buffer days
  • 12:15 Summary of the main steps


The transcript is below if you would prefer to read this yourself instead of watching the video!


Hi! Welcome back or welcome to Sidekick COO. I’m Sandra B your sidekick COO and today we’re gonna be talking a little bit about “how the heck do you even take a successful vacation?” 

As a business owner, taking a vacation can be very, very difficult, especially if you have clients and trying to balance the workload can be problematic. 

Here are a few tips for how to prep for a successful vacation (even when you’re indispensable)

So first of all, what is a successful vacation? 

To me, a successful vacation is one where I don’t have my laptop with me, my phone is on “do not disturb” and I am not doing any work. I am away and nobody’s gonna be contacting me. So to me, that is a successful vacation. 

The ways that I make sure that I have a successful vacation is first I book it really far in advance. All of my vacations tend to be booked six to eight months in advance at the minimum. That way I can:

  1. make sure that everybody knows about it
  2. plan for it in advance. 

If I already know that I’m gonna be taking a vacation in quarter three of 2023 when I’m planning for the work in the my 90-day sprints, I can look ahead and see anything that I was planning on doing that month that I might wanna do extra in the month before (or the couple months before) to accommodate the time off. It just helps me plan better to make sure that we still manage to stay on track to meet our goals, but I also get to take time off.

All of my time off gets booked pretty far in advance. I very rarely take just a random vacation. When I do book my vacation, I always add a day to the beginning and to the end of the vacation period. 

If I’m going away for five days, everybody is told I’m going away for seven days. If I’m going away for seven days, then everybody is told that I’m going away for nine days. Those days are technically days off. They are part of my vacation, but I call them “buffer days”. I have those buffer days because it just helps to make sure that I am relaxed for my vacation and relaxed when I come back from my vacation. 

The next thing I do is I create a Google Doc and I use that Google Doc to keep track of all of my flight information, my hotel reservations, and to create a running list of anything that I have to do beforehand or anything that I want to pack or to make sure I bring. So, for anything that I might forget, I just make sure that I have that list there. 

I also connect with a family member. When we used to have pets, it would be to take care of our pets. Now that we don’t have pets, it’s to take care of my plants. So always contacting my sister or my niece to come in and water the plants while I’m away and just get that kind of locked in. 

I then also connect with our neighbors to let them know and make sure that they’d be okay to bring in our mail while we’re away, especially if we’re gonna be away for multiple days. That’s just to set it all up but of course, we would remind them about it closer to the time.

That Google doc then gets set to be available in offline mode cuz I want to be able to access it regardless of where I am and whether or not I have service. Then I set a shortcut to that document on my phone and make sure that whoever I’m traveling with has a copy of that document.

I also make sure that someone here has a copy of that document. So whether that’s going to be my sister, my assistant, or my child, whoever I know is going to be around and available on the off chance that I need access to it and can’t access it on my phone for some reason, they’ll be able to send me details if needed. So just as a backup, they have it there. I don’t think I’ve ever had to contact anybody to give it to me, but it’s there. 

I also make sure to take pictures of my passport and have those on my phone, but also I have them in a folder that somebody has access to just in case I lose my passport and I need a picture of it sent to me. I can have that. 

I then add a shortcut for the Google Doc onto my phone. ???? I think I said that already.

Then I notify everybody.

I let my team know that I’m gonna be away. I let all my clients know that I’m gonna be away. I put my vacation into my client’s calendars so that they have it on their calendar. In most cases, anywhere where I’m like in somebody’s business day to day, (there’s like two or three people that that might apply to) I’ll put my vacation in their calendar so that they can see it and know that I’m away. It’s just a nice reminder for them. 

I then also make sure that I take the time to set the expectation with them as to whether or not I am gonna be available. If I’m gonna be taking an actual vacation, I let them know I am not available after that. Part of our planning is to confirm with our clients anything that needs to be done. We tend to work in quarterly sprints for most people so this is already kind of baked into the process anyway and we always look a couple of quarters ahead to account for anything like this.

But for anybody that we’re not actually working in their business on a day-to-day basis, or we’re not doing quarterly sprints with them, then we would just connect with them just to see what they might have coming up that we need to plan for. I try and make it clear to my clients that only things that are planned for are going to get done, which means any last minute things that come to their mind are likely not gonna be accommodated.

I’m just trying to set the expectations and make sure that everybody is accommodated as best as I can with the time that I have. When we’re having these conversations, when we talk to clients about getting work done, we do try and accommodate as much as possible, but there’s something about going on vacation where as soon as people hear that we’re gonna be away or not available, all of a sudden there’s a bunch of extra things that come to mind that they all of a sudden wanna have done before I go away. 

I don’t know what that phenomenon is, but it seems to be pretty consistent that I will not hear about things and then all of a sudden, the idea of me being away, brings things to the forefront. 

So we’ll go over all of these ideas they have for getting anything done before I leave and we’ll just decide what is and is not possible to have done before I go depending on how close to wrap-up time we are. But again, typically anything that’s last minute that we haven’t previously discussed is not gonna get done. I make sure to communicate to my clients all of that information, all of the boundaries, all the time off and make sure that they understand what will and will not be done before I leave.

I’ll then remind everybody, my team and my clients, a month before my vacation that I am going to be away. I’ll also try and remind them the week of and usually the day before I leave. Most of my vacations I tend to have from a Thursday to the next week or so. Basically, Friday is the first day off with usually Saturdays being my travel days. It’s not always the case, but that’s what I try and do. So it’ll mean usually like on Monday I’m reminding them and then on Thursday, I’m reminding them. 

After that’s all taken care of, I make sure that I set my out of office. I usually schedule that pretty far in advance cuz we use Google Workspace. So you can actually set it as soon as you book it.  I can set it in advance but because I book so far in advance, I’ll usually set it the week that I’m gonna be off. I’ll have a task in my project management tool just to remind me to set my out of office usually the day before I leave. And that out of office includes those buffer dates that I’m talking about. So if I’m traveling on a Saturday, that means I have Friday off as my buffer day and my out of office would start the Friday morning. 

When I’m traveling on vacation, I make sure to not take my laptop with me. I try not to take my iPad with me either, even though I like having it to watch movies on while on the plane,

especially if we’re on a longer flight, I’ll try not to bring it just because the temptation will be there to check in and do work. So I really don’t want that temptation. I will typically leave it at home. I make sure that all of my notifications are turned off. I make sure that my assistant has my cell phone number and that they understand what is and is not an emergency.

The only way to contact me when I’m on vacation is through text messages. 

They can try calling me but they usually will have to leave a message. I don’t often answer phone calls. So sending me a text message is really the only way to get ahold of me if there’s an emergency. And all of my clients are given my assistant’s contact information, so they’re told not to contact me directly. Typically they all have my cell phone number anyway and they do know that they can contact me if it’s like a true emergency, blah blah blah. But I mean I’m not saving lives in my business so…

I don’t know that I’ve ever really had a true emergency so really, they’re not contacting me. But if there’s ever any, if there’s anything that comes up and they need an answer, they can contact my assistant and then my assistant can choose to contact me if they feel it’s an emergency and that they need an answer for.

So part of having a successful vacation is making sure that there’s really only one or two people that can ever contact me while I’m on vacation and everybody else knows to funnel through them. 

Now getting back to those buffer days.

So, the day before and the day after, those technically are working days so they’re not a vacation. They’re not lounging on the beach, but they’re prep days. 

The day before my vacation is the day for me to: 

  • wrap up all of the loose ends that might be hanging over my head
  • make sure that my inbox is at inbox zero
  • double check that my out of office is on everywhere
  • make sure that I have all the information I need to have
  • make sure that I’m all packed 

All of those last minute things like…

  • double checking all of my projects and making sure I’ve set any statuses that need to be set and I’ve provided any updates to anybody that needs updates

Just handling any urgent stuff that was left over so that there’s nothing waiting. And really I check in with each of my team members as well to make sure that they’re not waiting on me for anything, for any work that they have to be doing while I’m away. So just making sure that they’re all okay and they’re not gonna be stuck while I’m gone.

I don’t typically check in with my clients on my buffer day. As far as my clients are aware, even though most of them know that I do take this buffer day, they know that that is a day off like it’s marked in their calendar that I am away and I don’t check in with them because there is a tendency, again, if they know that I’m gonna be away, if I check in, they will find things for me to do even though they’re not actually urgent things, they are almost always things that can wait and because we do so much prep in advance our clients, my clients really should already have all that taken care of. 

So I check in with them like during that week leading up to my vacation but that buffer day where I’m just like finalizing everything, I don’t check in with them. And then that buffer day when I’m back from vacation, so the day after my travel day, that buffer day is there on the off chance that my flight ever gets canceled and I do have to stay overnight cause that did happen once. I already have that day booked off and nobody’s expecting me. So I’m all good there. 

Then also I can use that day to just kind of like ease myself back into work. I can make sure that I’m unpacked, my suitcase is away, and my laundry is all done, and get everything back in order. I can start by processing.

  • going through and getting my inbox back down to like ‘inbox zero’ 
  • checking in with all my projects and checking in on all the statuses 
  • then like my action plan for the day!  you know, the first day back what do I need to do?

Just kind of reviewing what I need to hit the ground running on (if anything) or what am I gonna prioritize this week. So that’s what the buffer day is for. I do tend to work that day, but it’s not usually a full day of work. It’s really just to catch up and prep myself for coming back to work in, you know, full force the next day.

That is how to be vacation ready. It’s how I prep for a successful vacation.

So to recap:

  1. it’s booking things in advance
  2. making sure I have a place where I can easily access all of the important information that I might need on my trip.
  3. Making sure that everybody is aware of the vacation time and what my boundaries are. 
  4. Prepping the work, making sure that I’m preparing for that time off. 

So if we have any big projects coming up or projects happening during that time that we account for that missing time, I try and get a little bit more done before I leave or plan to catch up when I get back. And it’s just about staggering work and doing a little bit extra. It’s not usually about working longer hours or anything like that. 

Though sometimes I will do that, I try not to make it about working extra hours. It’s more about maybe taking less meetings leading up to the vacation and making sure that I have the time to actually like implement the things I need to and then confirming the goals with clients. 

After all of that…

  1. is reminding everybody about the vacation leading up to it. So a reminder the month before, the week of, and the day before.
  2. Making sure I schedule that out of office and that everybody knows to go through my assistant if they need to get ahold of me for anything urgent and making sure that everybody understands what urgent means cuz some people do not.
  3. Having those buffer days

Buffer days where I can really kind of like just make sure that I’m good to go, finalize anything,  and then come back and kind of ease myself into the working week. 

So that’s it!

If you’ve enjoyed this video or if you know somebody who needs to take a vacation and really needs to know how to do one well, please don’t forget to share this with them and make sure you like and subscribe while you’re at it.

Together we thrive. 

Have a great one.

Meet your host

Sandra Booker, Founder of Changemaker Inc. (home to Sidekick COO and The VA Studio) and creator of Scale Society and The Advisory Board, is a mentor, Fractional COO  and growth strategist. She specializes in helping overworked, overwhelmed, multi-hatted entrepreneurs become the CEOs of sustainably scalable, and powerfully profitable businesses. 

After helping local businesses thrive, and receiving accolades in her community (like the 40 Under 40 award) Sandra turned her attention to the world of online service providers, and her clients include familiar names like Chanti Zak, Tarzan Kay, and Laura Belgray.

In her (efficiently used) spare time, she teaches others how to build and grow their own 6-figure virtual assistant practices and is on a mission to create a million jobs by helping her clients and students scale their businesses.

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