How to ACTUALLY Rest on Vacation

As spring break approaches, it's the perfect time to start planning not just where you'll unwind, but how you'll truly disconnect to recharge.

You might fly first class, you might stay in a 5-star hotel, but in our always-on world, being fully offline is the real luxury of vacation.

Here’s a step-by-step guide to ensure you can leave work behind with peace of mind, fully relax, and recover. Whether it's delegating responsibilities, unplugging from all digital leashes, or setting yourself up for a smooth return, I want to help you master the art of truly restful vacations.

Step #1 :: Ensure your Teammates & Stakeholders get What They Need & Close All Loops

A primary source of stress on vacation is dropping the ball for teammates and stakeholders, so let's get ahead of that. Remind this group a week out that you're going on vacation, and ask them to request anything they need from you at least three days before you leave. You are showing them empathy that their priorities are important, and giving them confidence that their needs will be met even with you going on vacation.

Time-block your calendar for the last three days before you leave for vacation to support other people's needs. Close all loops before you leave. Ensure there is nothing dependent on you or your memory while you're away.

Step #2 :: Find Someone to Be Your Vacation Shield

Consistent with our fear of dropping the ball, is our worry that if we don’t keep an eye on our email/Slack/Teams/Text messages, the balls WILL drop. A Vacation Shield solves this.

This person needs to fully cover for you while you're gone, including responding to any messages that might come your way (and you in turn can return the favor when they head out of town). Notify your teammates and stakeholders that this person is covering for you, put it in an email auto-responder, add it to your voicemail, put in your Slack/Teams away message. You don’t want anyone trying to reach out to you directly, only through your Vacation Shield.

You can then confidently avoid your email/Slack/Teams/Text messages, knowing that if it’s truly urgent, your Vacation Shield will call you, otherwise you are free to be on vacation.

Side note: buy your Vacation Shield something nice on vacation. They are giving you a great gift by doing this for you.

Step #3 :: Time-block Your Calendar for Re-entry Activities BEFORE You Leave

72% of workers don’t even go on vacation just to avoid post vacation stress and anxiety. This step directly addresses this.

Time-block your calendar for the first two days back in the office BEFORE you leave. Focus on re-entry meetings with your key team members and stakeholders, ample time to clear your email/Slack/Teams/Test Messages. The goal is to get you back up to speed quickly like you never left, without setting heavy expectations for deliverables on your future self.

Knowing you have a good plan will reduce or eliminate your anxiety as you approach the end of your vacation, and give your key team members and stakeholders confidence that you’re back in the game and ready to support their needs.

Step #4 :: Log Out of EVERYTHING  

If any work thing can ping you, it will pull you out of vacation emotionally. You’ve done the work to close all loops, there’s no reason for you to check your work accounts while you’re away, and your Vacation Shield is there to handle anything for you anyway.

As you leave, turn off your devices or log out of all work accounts. Only answer the phone if it's your Vacation Shield, who knows to only call you if the sky is falling.

Step #5 :: Vacation the Way you Want to Vacation

You’ve done the work to create mental freedom on this vacation, now it’s time to enjoy it. Choose a life-giving schedule and activities that are going to fill you up, and drink it in deeply.

Step #6 :: Have a Day at Home to Reset Before You Go Back to Work 

A big idea of Time Boss is just doing one thing at a time, and it’s challenging to do this if you’ve got a stack of laundry, and piled up chores or errands. They will impact your ability to be fully present as you reenter work.

Give yourself a day at home before you get back to work. Do your laundry, run your errands, check the mail, clean your bathroom, be fully reset and ready to dive back in.

Step #7 :: Do What Your Time Boss Planned For You For Re-entry

You did the work before you left to make it a smooth re-entry. Simply run the plan your Time Boss created for you!

After you complete your reentry meetings with your key team members and stakeholders and process all your inboxes, you’ll have a clear picture of work priorities, and are ready to run a Weekly Planning Meeting to flesh out your schedule.

Restful Vacations Are Part of an Effective Time Operating System

The ability to rest well on vacation flows naturally from a thoughtful Weekly Operating System that protects your priorities and allows you to rest and recover, such as Time Boss. If you don’t have a Weekly Operating System you trust, check out the recording of the The Time Boss Weekly Operating System Masterclass. In 90 minutes, you’ll learn the Operating System that is helping so many people make massive progress without impacting their mental health.

One more thing: If you’re ready to dive into the deep end of the pool, jump into the next Time Boss Cohort with 4 other leaders looking to permanently adopt the Time Boss model. The next cohort launches March 4th and has 3 spots left!  Here you’ll also find an employer reimbursement request form to more easily secure your spot.