Ask Ashley: How do I set my vacation up for success?

Learn 5 strategies to follow in the weeks leading up to a vacation to set it (and your return!) up for success.

Ask Ashley: How do I set my vacation up for success?
Photo by Tim Gouw on Unsplash

Welcome to the Ask Ashley advice column! On the second Wednesday of every month, I answer a question from my subscribers, consulting clients, or social media followers on their biggest productivity challenges.

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Dear Ashley,

I have a vacation coming up in a few weeks and I am SO EXCITED, but I want to make sure I can enjoy my time away without worrying about work piling up and coming back to a disaster. I need a plan so that I can take a true break and recharge… but it feels overwhelming! I don’t want to spend another vacation checking my phone and thinking about all the things that aren’t getting done.

How do I let go and set my vacation up for success?

- Ball of Vacation Anxiety

Dear Ball of Vacation Anxiety,

Yay for vacations!!

I love this question because a “vacation” spent checking email and worrying about work defeats the purpose of a vacation…but it can be so hard to avoid falling into that trap!

Vacations often come with a feeling similar to FOMO (the Fear Of Missing Out). It’s the feeling that things are going to break, screech to a halt, not be done properly, or an opportunity/client/money will be missed.

The result: working on vacation! Boooooo.


While it’s possible that one (or more) of those things might happen, some intentional planning ahead of will reduce their likelihood. Beyond that, there is an opportunity to take a step back to clearly articulate the true consequences of those things happening.

There is tremendous value in giving your mind and body a break from work, even when you enjoy what you do. Whether it’s a staycation to hang out in your own backyard, or traversing South America on a rusty motorcycle, being able to disconnect and truly engage with the people around you is incredibly valuable for your overall well-being.

A change of routine and scenery gives an opportunity to recharge, shift gears, relax, learn new things, and encourages other ways of thinking. In fact, this year I started taking a semi-annual retreat/vacation to help me reset, push outside my comfort zone, and breathe new life into my writing.

Besides, life is too short to worry about work all the time, and you deserve to enjoy your vacation!

Almost all of the photos related to the search term "vacation" were of people on a beach. I decided that I wanted one of a lot of cheese. My kind of vacation. (Photo by Kate Hliznitsova on Unsplash)

How to set a vacation up for success

The following are 5 strategies to follow in the weeks leading up to a vacation to set it (and your return!) up for success.

1. Divide tasks and commitments into pre and post-vacation lists

Review your task list and calendar of commitments in the 1-2 weeks leading to your vacation and in the 1-2 weeks after. Identify what absolutely has to be done before you go, and what can wait until you get back.

As you divide the tasks and commitments, something to anticipate is the common combination of the pre-vacation crescendo of work and the decrescendo of motivation. As in, you will try to jam a monumental amount of work into the week before you leave, but the desire to work and get a lot done decreases as you get closer to your time off.

Keep that decrease in motivation in mind as you work through the following processes and prioritize your tasks.

2. For each of the pre and post-vacation lists, go through the “4Ds Process”

The 4D Process is reviewing each item on each list and asking if it can be Declined/Deleted, Delegated, Deferred…or if it just has to be Done.


Is there anything on the pre or post-vacation lists that can be removed entirely?

For example, perhaps there is an event that you committed to before you booked your vacation time that can be declined. Or maybe there is a recurring meeting in the first few days back that can wait until the week following instead.

This comes down to good, old-fashioned, obligation elimination. There is no better way to keep your schedule under control before and after vacation than by removing commitments where possible.


If you can’t decline or delete something, is there anything on the pre or post-vacation lists that can be delegated to someone else?

Obviously, this depends on your role and if there IS anyone else, but consider things like:

  • Is there a meeting you can ask a colleague to attend on your behalf?
  • Is there a task you can assign to a team member that might be a good learning opportunity for them?
  • Is there someone who can take on oversight of any of a project while you are gone to help keep them moving forward?
  • Is there a process that you do that you could document and ask someone else to take care of?

Sometimes delegation feels like more work than doing something yourself but it can be a huge weight off if it’s an option and allows you to let go while you’re away. It might even be something you can leave on someone elses’ plate going forward!


If you can’t delete it and you can’t delegate it, is there anything that can be deferred to later?

Look at due dates and meetings in the weeks leading up to the vacation and for the few weeks after and ask: Are any of them flexible? What can be pushed back a few weeks?

Deferring tasks or commitments is a way to do intentional expectation management. It’s a lot easier to communicate a shift in timelines on a project weeks before it is expected to be complete than it is to need an extension days before because you stuffed too many things into the week you return.


Once you’ve gone through the lists of pre and post-vacation tasks and commitments through the lens of Decline/Delete, Delegate, and Defer, you have a list of things that need to be DONE

Now, do another pass of prioritizing what needs to be done before you go, and what can be taken care of when you get back from vacation.

Working through the 4Ds is kind of like creating a map forward for yourself. Remember when we had those...on paper?! (Photo by KAL VISUALS on Unsplash)

3. Time block the DO list for the week leading into the vacation AND the week you get back from vacation

Y’all know how much I love time-blocking.

Time block the remaining tasks in your calendar for the weeks before and after your vacation to get a realistic view of the ACTUAL available time. Creating a visual in your calendar will help make sure you don’t over-commit because you can see how the tasks fit into the schedule.

For detailed steps on how to do time-blocking, check out my article, Time-Blocking and Imagining Your Ideal Week.

4. Protect the week leading into the vacation AND the week you get back from vacation

When I say protect them, I mean to be intentional about what you agree to do in each of them by setting expectations. Ideally, don’t take on any new commitments during these weeks. Instead, give yourself space to avoid the pre-vacation work crescendo and a runway to ease back into the swing of things upon your return.

I always think of this as making sure Present Ashley makes good life choices that don’t give Future Ashley terrible regret.😁

A few ways to protect your future self:

Don’t jam every meeting or request you can’t take during your vacation into the week you get back.

Again, try to ease into coming back to work. If you get a meeting invite that is supposed to happen over your vacation, consider how far it can be pushed back. Does it have to happen as soon as you get back? Most things can wait an extra week or two.

The point here is to not waste all that good vacation recharge time by coming back to 25 meetings and a 152 item to-do list because you set unrealistic expectations for what could be done the week you come back.

Set reasonable expectations for email responses and inquiries post-vacation with a clear out-of-office reply.

An out-of-office reply needs to communicate:

  1. How long you are gone for
  2. When a response can be expected
  3. Who the person can contact about their issue instead of you
  4. If there are any circumstances under which you will respond

Something to consider is to not set the expectation that you will respond to all emails the day you get back in the office. Instead, say you will reply by the end of the week or at least a few days later. That way, the day you return doesn’t feel like drinking from a firehose.

For email specifically, I have a whole article specifically on how to get your email under control post-vacation.

5. Set boundaries around what circumstances you are willing to be contacted on your vacation (if any)

Depending on your role, you might not be able to completely disconnect, but it is incredibly important to set really clear boundaries with clients, colleagues, and employees around what circumstances you are willing to be contacted while you are away.

Otherwise, they will email, phone, and or text, which pulls you back into thinking about (or even doing) work, when you are trying to disconnect.

Think about what would have to happen for it to be ok for your vacation to be interrupted. Then communicate those situations, along with how to best contact you ONLY if those situations occur.

May your vacation involve whatever you like as much as I like reading in the sun. (Photo by Link Hoang on Unsplash)

The world will not end if you are unavailable for a few days or weeks

It’s both humbling and freeing to check yourself a bit and remember that, while you are important and your work is important, being away for a few days or weeks is not going to break the world. Even if you did none of the strategies I listed above…it would probably be ok.

You are allowed (and should!) go on vacation without work hanging over every movement. Turn the phone off, leave the laptop behind, and step away. You can (and will!) have a successful vacation by being intentional about how you prioritize your tasks and commitments, setting clear expectations and boundaries for yourself and the people around you, and then allowing yourself this time away!

Do you have a question about how to manage your time differently or anything else related to productivity and intention? I would love to hear it!

Shoot me an email to be featured in a future Ask Ashley or Book a Free Consultation to talk about it!