“I’m too busy to go on vacation!” 

Have you ever uttered those words?  Out loud, or in your own head?
But if your vacation days aren’t rolling over, you don’t want to lose those days, do you?  (No, you don’t; that’s like flushing cash down the toilet!)

(Now, you might be wondering why the heck I’m talking about vacation right now, just as the school year has started. But here’s why: you don’t want to be thinking about how to prepare for your vacation in the midst of planning your vacation. You want to have a plan in advance so that you even feel comfortable scheduling that vacation!)

OK, so you plan a vacation.  And yes, you’re excited to take your vacation, but it’s also a little bit stressful.

You’re worried about getting everything done before you leave, and you’re worried about the backlog when you return. 

But, with a little extra prep, and by fostering a little goodwill and setting the right expectations, you can plan to have a stress-free vacation where you can truly disconnect.  (Sound impossible? I promise it’s not.)

Want a playbook for how to set yourself up to actually enjoy that vacation?  Let’s go!

A Few Weeks Before Your Vacation

  • Block off the last day (or afternoon) before your vacation on your work calendar as a prep day so that no one can schedule a meeting.  Use this time to wrap up all loose ends.  
  • Block off the first day you’ll be back on your calendar so no one can schedule meetings.  You’ll use this day to play catch up on emails, Slack, and voicemails, and to get status updates from your team.
  • Find a coworker who will handle emergency issues for you while you’re out.  (And don’t forget to promise to return the favor.)
  • Block out your vacation on your calendar so people know you’ll be gone.
  • Reschedule or remove any meetings or events, work or personal, that occur during your vacation.

The Day Before Your Vacation

  • Send out an email to your manager and relevant colleagues documenting the status of all projects (as described above).  
  • Set up your “out of office” voicemail, email auto-reply, and Slack status message.
  • Set yourself a task for when you return to complete the “Return from Vacation” process (You don’t want to be worried about this on vacation, do you?)

When You Return from Vacation

  • Thank yourself for blocking off the first day for catch-up!
  • Update your voicemail and Slack status and turn off your email auto-responder.
  • Listen to all your voicemails, process all of your email and Slack messages. Use the One Touch Rule
  • Re-prioritize your task list (incorporating the new items).
  • Have a chat with the colleague who was covering for you to get an update on any developments.
  • Let the team know you are back and thank them for covering for you.

Ok, fine, we’ve got work covered.  But what about the other stuff that makes preparing for or returning from a vacation stressful. 

Let’s make a plan for that as well!

Before you go

  • Packing
    • Use a packing list! Make a template that you can use over and over again. (I have templates for solo trips, full family trips, camping trips, etc.)
    • Make that packing list at least a week before you go and then designate a spot in your house to put things you’ll pack.  That way, as you see them around the house, you can drop them there, making packing much less daunting. You can even use the “little by little” strategy I wrote about last week.
    • Then, when you start packing, it’s already ½ way done.
    • Maintain duplicates where possible
      • Toiletries!  If you can swing it financially, buy an extra set of toiletries (deodorant, toothbrush, toothpaste, etc.).  Keep your toiletry kit always stocked so that instead of looking around for the 20-odd things that go in the case, you just pack your already-complete travel toiletry case and you don’t worry about missing something.
      • Cords! I think I’m not alone in saying that we all travel with electronics these days.  Right?  We need cords, chargers, etc.  Heck, we even travel with a travel router these days, and a LONG ethernet cable, just in case. If you can swing it financially, have a travel case ready to go with all the electronic accouterments you may need.

Travel to-do template

  • There are always a bunch of tasks associated with traveling, and they tend to be pretty consistent, things like:
    • Turn off heat/AC
    • Clean out the fridge
    • Hold the mail
    • Lock all the windows
    • Set a travel alert with the credit card companies
    • Etc.
  • Create a template for this, so you never worry that your electricity bill is sky-high while you’re not even there, or that there will be a fridge full of rotting food when you return! 


  • If you use a house cleaner, schedule them for the day before you leave.  There’s nothing like the feeling of coming back to a house that smells like bleach and sliding into clean, crisp sheets that first night back in your own bed.
  • If you don’t use a house cleaner, plan to do whatever level of cleaning feels good to you, but at the very least, make sure there are no dirty dishes left in the sink.
  • Take out the trash, recycling, and compost the night before you leave, or the morning of.  You don’t want to return to the smell of garbage.

When you return

  • Unpacking
    • Make it easy on yourself!  Drop the bags in front of the washing machine and immediately get a load going. Remember, action begets motivation!
    • Over the next day, keep the wash running until all the clothes are clean.

Now it’s your turn!  Tell me your hacks for travel. 

What do you do to ease the stress and burden associated with taking time off, so that you can truly enjoy it!


  • Alexis Haselberger

    Time Management and Productivity Coach

    Alexis Haselberger Coaching and Consulting, Inc

    Alexis Haselberger is a time management and productivity coach who helps people do more and stress less through coaching, workshops and online courses.  Her pragmatic, irreverent, approach helps people easily integrate realistic strategies into their lives so that they can do more of what they want and less of what they don't.  Alexis has taught thousands of individuals to take control of their time and her clients include Google, Lyft, Workday, Capital One, Upwork and more.