The Ultimate Pre-Vacay Checklist

June 6, 2018

Reading Time: 4 minutes


“It’s summertime and the living is easy.”


Whatever fool uttered that statement must have been a solo, traveling millionaire with no responsibilities. 

What part of shutting down your work life for several days and unplugging is actually easy?

You’re racing until the very last minute to finish up a few projects, fire off a few emails and scribble some instructions for a coworker should anything come up. (And of course it comes up, because Jennifer has her own work to deal with, much less take on your mess.) But you assure everyone that you’re taking your phone and your laptop with you so you can be available if anyone needs you.

Gee. That sounds real easy.

And then you arrive at your destination. You’re still worrying about an upcoming presentation. You jump every time your phone pings, worried that an account is collapsing. Or your boss decided to add another event and needs a full logistical plan the day you return from the office. So you curse at the horrible WiFi at your vacation spot and spend almost half of your vacation in a coffee shop, proving your worth to your boss and your team while missing out that rest and relaxation you were hoping for.

Vacation hopes, dashed.

I’ve been there. Years ago, I even holed up in my room for several hours on a trip to Vero Beach, Florida to hammer out a speech for my government official boss. Super fun, lemme tell ya. I’ve taken my calligraphy supplies and 3-in-1 copy/scan/printer to 30A because a bride wanted MORE edits to her invitation monogram, and I didn’t have a limit on drafts clearly defined in the contract. (Lesson learned.) You better believe that loading a printer into the SUV next to my beach bag got some weird looks from my in-laws.

It took me a number of less than stellar trips to figure out a better way, and I want to pass that on to you.


Set boundaries.
Unfortunately if you’re leaving for Cabo next week, it’s a little late for this step. But if you’ve got some time, start identifying some of your pain points and begin setting healthy boundaries for yourself. If you have a client that always calls with an “emergency” at 8PM on weeknights, start training them to expect a response from you the next morning. If your work involves open-ended client projects, consider limits you can set via your contract language. Setting boundaries and expectations far in advance not only helps you become healthier and less stressed – but it makes hitting pause on your projects just a little bit easier.

Build your bench.
You already know how I feel about delegation. It’s tough, I agree – especially when your projects are your passion. If you work with a team, it’s time to start looking around for folks who can take on your responsibilities if need be. And before you remind me of the business maxim “Be Irreplaceable” just remember that if you’re the only person in your organization that can do what you do – you might find that you’re not getting promoted because there’s no one else internally who can readily move into your role. If you want to enjoy that piña colada on the beach instead of in front of your laptop, start delegating and training your team members now.


Share your vacation dates with your team members.

This should be a no-brainer, but it can be easy for your departure date to slip up on you, so give advance notice.

Identify an emergency contact for each of your projects.
If you have a partner on an account, or a co-chair of your non-profit committee, now is the time to ask them to serve as your emergency contact in the event that something comes up while you’re off the grid.

Look ahead
It’s easy to get SO excited about your trip to Key West that you completely forget to consider deadlines and project benchmarks due the week you return with your tan and a Facebook album full of vacay pics. Plan ahead and start tackling any projects now in order to ease your workload once you’re back in the saddle. 


Update your team on the status of your projects. 
Whether via email or in a team meeting, give brief description of any major issues to look out for while you’re out. Help them understand what constitutes an actual emergency, and what really isn’t a big deal.

Notify your clients/external partners of your upcoming time out of the office.
Bonus points: Introduce them to and connect them via email to the emergency contact. 


Set a detailed “Out of Office” auto-responder message or voicemail. Make sure to include

  • the dates you’ll be out of the office

  • Your emergency contact

  • Whether or not you will have access to email or plan to respond while you’re away

Feel free to copy/paste this one for future use:

Hello there,

I will be out of the office on vacation beginning Tuesday, June 5 and will return on Wednesday, June 13th. While I am away, I will have limited access to email and will respond as soon as I am able.

If this is an emergency, please contact Suzy Smith at 504.504.5044 Ext. 504 or via email at

Anna Dearmon Kornick

Turn Off Email Notifications on Your Phone 
Seriously. Just do it. You’ll thank me. No one needs the increased anxiety that comes with wondering if every beep or red number is a J. Crew sales email or a work catastrophe while you’re in line for Space Mountain at the Magic Kingdom. You might realize that you don’t need those notifications at all!

Bon voyage! Happy trails! And don’t forget to wear sunscreen!

What will it take you to get from chaos to calm?

Leave a Reply

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

Hey Anna! I'm looking for an episode about...

Hey Anna! I'm looking for an episode about...