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A Step-By-Step System for Checking Out of Work to Take a Vacation

March 12, 2020

I’m Kelly Nolan.
I'm an attorney who'd been decently organized through law school but got quickly overwhelmed as a actual attorney. After nothing else worked for me, I created this system – and kept on practicing law. Years later, I found out others were interested in learning it, so that's what I do now! Let's get this realistic system in your hands so you can start living a life that feels more calm, doable, and that lights you up.
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I used to work with an attorney who basically refused to take vacations. In his eyes, the stress and work leading up to them and the work avalanche that hit on reentry just weren’t worth it. 

While it’s an extreme position, most of us, to some degree, know what he’s talking about.

So, how do we actually take vacations in a way that’s enjoyable and minimizes the stress associated with the pre- and post-vacation work surges? 

And is it best to totally disconnect, keep a toe in throughout your vacation, or plan to work a bit each day?

While there aren’t right or wrong answers to these questions (industry, personality, and time of year affect what’s right for you), there are ways you can minimize your stress and maximize your enjoyment of your vacation and reentry. 

Here are 9 steps to planning and preparing for a vacation you can actually enjoy.

All steps may not be relevant to you – e.g., perhaps the Murphy’s Law Memo is overkill in your line of work. Pick and choose what feels right, and then come up with a system to use for each long vacation you go on going forward.

And, because you know I love calendaring everything, there’s a cheat sheet of things to calendar as soon as you put a vacation on your books at the end of this article.

Step 1: Strategically Time Your Vacation & Take Advantage of Buffer Days

In terms of planning when you’ll actually take your vacation, there are a couple of things you can do to help out Future You.

Return to Quiet Weeks

First, the following advice from Ellen Ginman, a senior director at a hospital in Boston, blew my strategy-loving brain:

“Pick weeks away right before or right after ‘quiet weeks’ – i.e., my husband and I love to go on vacation the last week in June so the week back at work is Fourth of July week and is typically much quieter and much easier to ease back into.”

Brilliant!

PERSONAL BUFFER DAYS

Second, if you can, seriously consider tacking on an extra vacation day at home before and after your trip. Use the “before” day to pack, clean up the house, and wrap up personal tasks (e.g., sending off a kid’s tuition check) before you leave. This alleviates the stress when you’re wrapping up work because you’re not trying to wrap up work, your personal life and pack at the same time.

(Side note: if you’re leaving kids with someone else for this vacation, start making your document of instructions, healthcare authorization stuff, etc. weeks before – and calendar time to do it. That could be a whole other article, but just flagging it for now!)

Use the “after” day to give yourself breathing room to unpack, do laundry, and put the house back together. This lets you return to work feeling calm and collected – and return home to a peaceful, clean home after your first day back. 

(Also, speaking of the return, bonus tip: I order Instacart to be delivered an hour or so after we land from a trip so we have milk, eggs, lunch fixings, etc. the next morning. I can’t tell you how wonderful it is.)

WORK BUFFER DAYS

Third, I love this smart tip I hadn’t thought of before: tell your clients and other external work-related people (e.g., opposing counsel, vendors) that you’re out of the office a day earlier and return a day later than you actually do. 

As Amy Phillips, an attorney, explains, she uses work “buffer days” to bookend the vacation. As she explains, on those days, 

“I’m fully present at work so it’s not a day off at all, and I’m there for my team members, but as far as the rest of the work world is concerned, I’m still (or already) out of town. I have my out of office email response on and my team is able to tell people I’m not available. It allows me to process allllllll the communication that took place while I was out, meet with my assistant and have any other internal meetings I need, spend some quality time with my calendar, and ease back into work without having to deal with too many people yet.”

Alright, now that your trip is booked and buffer days (work and personal) are in place, let’s turn to the next step.

(Side note: if you love practical strategies like these, consider joining my eight-week time management program. It teaches you my whole realistic time management system designed for professional working women.)

Step 2: Communicate with your team. A lot. 

Communicate. Communicate. And communicate with your team some more. 

As Sara, a business owner, says, “over communication prior to vacation is best when it comes to taking time off.”

Logistically, here’s what to do: 

Calendar your trip in your work calendar – e.g., “Kelly Out of Office” – from the start of your vacation to the end. Note: Don’t include your work buffer days (as you’ll be in the office), but do include your personal ones (you want colleagues to think you’re not accessible even though you’re still in town). Make sense?

Then, invite all relevant people so it’s on all of their calendars.

In addition, send an email to all relevant people as soon as you know what your dates are, informing them of your vacation, how long it’ll be, how accessible you’ll be (if at all), and request that anything that requires your involvement be brought to your attention by a date about one week before you leave. If you’ll draft a Murphy’s Law Memo (see Step 4 below), give them a heads up that it’ll be coming as that’ll assure them you have a game plan for your cases/projects while you’re gone. 

As one virtual-friend-through-social Kelsey Janet, shared,  

“I start to set up expectations early, like two weeks out. I tell them that I’m starting to block time for before and after to make sure that I take care of what I need to because I won’t be available during my time off. I set those boundaries super firm. The key is to KEEP them. If you don’t, people will take advantage of that and they won’t believe you next time. It also prompts them to put in requests and add time to my calendar for things they need earlier. It’s helped me.”

I love this! Not only is she blocking her activities on her calendar (which you know I love), she’s reminding others that her calendar/time is limited in terms of what she can get done before she leaves. This incentivizes them to really start thinking through what they need from her now. It strikes a great balance of demonstrating a willingness to work with colleagues to set them up for success before she leaves – and setting boundaries. Brava.

In addition, remind colleagues of your trip 1-2 weeks beforehand. People weirdly aren’t as excited about your vacation as you are, so they’ve probably forgotten 😉 Remind them about your accessibility or lack thereof and your request to have anything they need from you brought to your attention by your listed date.

Step 3: Make important clients aware of your vacation

In addition to keeping your team happy and prepared, you want to make sure your clients and any important vendors also aren’t surprised by your trip. 

As Sara, the businessowner, shared, “I also let all existing customers know well in advance that I’d be out, and I let them know exactly what to expect if they contacted me while I’m away. For new customers or leads, I establish someone as a backup. In [the corporate world,] it was a co-worker that could handle urgent requests. As a business owner, I empower my assistant to communicate certain things on my behalf while I’m on vacation.”

I recommend sending emails to your clients about two weeks before your trip. In the email, list out your vacation dates, how accessible you’ll be, who to contact in which scenarios, and potentially a request that anything requiring your attention be sent to you by a date about a week before your trip (or shift all these dates earlier if that makes more sense for you!). Send a reminder a week before to those more demanding clients (you know who they are). 

Heads up: This is a great task to delegate to an assistant if you have the option.

(p.s. don’t forget – you can get a cheat sheet of these dates at the end to help make all of these things happen.)

Step 4: Draft your “Murphy’s Law Memo” 

When I practiced law, before any big vacation (e.g., missing more than 3 days of work), I’d draft up a memo or email (depending on length) about all my cases.  

I thought of these memos as my Murphy’s Law Memos – if someone had all the information, they wouldn’t need it. But you can bet your bottom if they didn’t have the info, they’d need it. And I’d get called on my vacation.

My goal: no calls/interruptions on my vacation.

So: memo.

In short, the Murphy’s Law Memo is a “here’s the important information you may need if a fire hits while I’m gone” memo. 

Note: This isn’t fancy (it’s mostly bullet points) and, so long as you chip away at it early and consistently (as I explain below), it really shouldn’t be a big headache. 

CALENDAR TIME TO DRAFT IT

To make sure you create an effective Murphy’s Law Memo, calendar time (about 45 minutes) about two weeks before your trip to start drafting your Murphy’s Law Memo. Anything earlier and things may become outdated. On the flip side, you’ll likely discover things you want to do (e.g., emails you want to send) before you leave during the process of creating this memo, so it’s nice to give yourself time. 

In addition, calendar time to update the memo whenever makes sense to you (e.g., 8 days before your trip for 30 minutes, 5 days before for 30 minutes, 3 days before for 30 minutes, 1 day before for 60 minutes). You don’t want to have to stay late just to work on this memo/fill everyone in.

THE MEMO’S CONTENTS

In terms of the actual memo contents, again, this doesn’t have to be fancy. 

List out all your active cases, projects, clients or however you organize your work.

Quickly summarize the details of each project – e.g., for a litigator, each case’s court, case number, judge, opposing counsel names, and the underlying facts (1-3 sentences); for others, perhaps the project name, client, contact info.

Then, quickly write out in bullet points the case/project status, what the next 1-3 steps are, important upcoming deadline, where relevant binders/documents are, and basically any other information someone would need to jump in if an urgent issue arose. 

Note: As you draft this up, make sure you look at your calendar not just through your vacation, but also through about a month after the vacation. Clients, for example, may start looking ahead that far during your vacation and have questions. Better to get ahead of those questions/deadlines now!

(Side Note: As you create this memo, you’re going to think of things you need to do before or after your trip. As you do, list them out – and then calendar when you’ll do them before or after. Just make sure to build in wiggle room, especially for those tasks you plan to do on your return, as things are sure to crop up between now and then.)

Now, if someone had to cover an actual event for me while I was gone (e.g., a hearing, phone call), I’d list that in the memo (e.g., “James covering [xyz] hearing on [date] at [specific courthouse] before Judge [Smith]”). I’d also schedule a meeting about 4 days before I left with that person in advance, give them a debrief of the case, and hand off any binders/documents they may need. (Update: instead of a meeting, record a Loom video so they could rewatch it again if necessary!)

In addition, consider including any login information others may need and be clear how they can contact you if there is a true emergency – and define what an emergency is.  

CIRCULATE THE MEMO

Calendar when you’ll circulate the memo (e.g., 12pm or 4pm on the day you leave). In my lawyer days, I also considered meeting certain partners in person to assure them everything was covered. That said, even if you meet in person, I highly recommend putting everything in writing. Writing will help you be clear on the game plan, and we can’t expect colleagues to remember or even find their notes about your conversation if a fire hits five days later. Put it all in writing, send it to their email inbox, and you can rest assured they – and everyone else you sent it to – is set.

While this memo requires work we’d all rather not do (and work I typically didn’t bill for … double womp womp), it is super helpful in making you take a step back and evaluate your projects, check in on deadlines, demonstrate to your colleagues/bosses that you have everything covered to by partners, etc.

It also helps you strut into your vacation feeling solid about where you’re leaving everything, know you’ve reduced the number of interruptions you’ll get on vacation, and smooth your reentry preemptively by leaving things in good shape

Step 5: The Out of Office Message

Calendar a reminder to set up your out of office email responder and voicemail at the end of your last day in the office. In both, state you’re out of town, when you’ll return, and when the person contacting you can expect a response. State who they should contact if they need help before then.

If you’re able and want to go hardcore in an impressive way, consider the approach of my friend David Gardner, founder of ColorJar, one of Chicago’s top-rated brand consulting and design firms, and host of the amazing podcast, The Big Jump. In his words, to “avoid the post-vacation inbox avalanche,” state, 

“I’m traveling off the grid and will be deleting all emails received until [DATE]. If you need something now contact my colleague at xy*@co******.com or email me again when I’m back. If it’s urgent and important, text me.”

Dannnnggg. And effective!

Step 6: Be nice to Future You

Leave time (you know me – calendar it!) to tidy up your desk for your return. You know that Future You returning from her vacation with a fresh cup of coffee in hand would much prefer to return to a sparkling desk than one where chaos exploded right before she dashed out the door.

Plus, it’ll help you make sure you dealt with everything before you leave and help you clearly see what others put on your desk while you were gone.

Step 7: If you feel solid you left everything in good shape, ignore the snide comments & enjoy that vacation!

No matter how much we prepare, there are going to be some people who are jealous, insecure, or for some reason think it’s funny to give you crap for – gasp – taking a break with your family, friends, or by yourself.

All you can control is what you can control, so here’s my advice: prepare to whatever extent makes you feel solid that you’ve done all you can to ease the effect your trip has on them, and then just ignore them. 

As long as you feel confident you’re pulling your weight the rest of the time and being responsible about checking out when you do, confidently rock it! We all need breaks, and you’re smart to take one. It bodes well for your mental health, marriage/relationship, family relationships, and enjoyment of life! So, rest into the confidence that comes from knowing you’re doing what’s right, and enjoy that time off! 

Step 8: When it comes to working/emailing on vacation, know yourself and communicate your plan

There’s no clear answer on whether you should check email/voicemail or not on vacation. It really depends on what will help you be less stressed out and what flies in your industry/company.

When I was practicing law, I preferred checking email once a day on vacation because I wanted to rest assured no fires were going on without my knowledge. It kept me more relaxed to have a five-minute peek at my inbox, scan for fires, and then know all was okay without me. 

That said, since the purpose was just to be assured there were no fires, I love this alternative approach by Cat Mulvihill, a Personal Development Coach & Nutritional Therapy Practitioner, 

“Something that worked well for me in my former job was telling my boss and coworkers that I was deleting work email and calendar [apps] from my phone for the duration of the vacation. That way, I wouldn’t see the number of unread messages piling up (less stress). But, I did tell them if there is a really pressing question that only I can answer, then text me. But I knew that would be unlikely. It worked really well.”

That’s an awesome way to be able to trust that silence = no fires, and I’d definitely give that approach a whirl.

Whatever you decide, consider calendaring time to do it (e.g., 15 minutes each day to check email, 20 minutes every other day). I know that sounds weird, but having an allotted time to do it will allow you to feel comfortable and enjoy NOT checking email/working the rest of the time. And that’s the more important point of all of this!

Step 9: Reentry

As mentioned, hopefully you’re coming back to a day at home without work and then a day at work where only those internally know you’re back. And if you’re really smart and able, hopefully you’re coming back to a slow week in the office.  

Additionally, you’ve hopefully calendared what you intend to work on when you return, so you’re walking back into a clear game plan of what to work on to be effective.

And fingers crossed, you’re walking back into a tidy office that feels fresh.

Lovely!

Conclusion

Alright my friend, hopefully this gives you a system to run through to maximize your enjoyment of vacations and minimize the stress/anxiety it may cause you. 

While I wish I could, I can’t wave a magic wand to let you totally check out of work without the prep work. That said, having a system to help you set yourself up for a stress-free, enjoyable vacation can be magical, too. 

We go over other strategies like this one in my eight-week time management program if this was helpful to you!

And, as promised…

The cheatsheet of things to calendar

Once you have a vacation on the books, spend 10 minutes calendaring the following dates. 

For each calendar entry, just write out generally what to do and copy and paste this article’s url in the calendar entry’s notes section for details. Sound good?

  • Calendar your vacation and, at least for your eyes only, your buffer days – see Steps 1 and 2

  • “Vacation: Email colleagues reminding them of trip” – 1-2 weeks before last day in office

  • “Vacation: Let important clients know I’ll be out of office” – for ~2 weeks before last day (consider reminder 1 week before, as well)

  • “Vacation: Draft Murphy’s Law Memo” – for ~30-45 minutes on each day: ~14, 8, 5, 3 and 1 day before trip (on the last day, consider 60 min instead)

  • “Vacation: Send out Murphy’s Law Memo to relevant, internal people” – likely on your last day (if people have to do real work for you while you’re gone – e.g., attend a heading for you – meet with them beforehand)

  • “Vacation: Set up out of office message and voicemail” – for your last day in the office

  • “Tidy up office” for the last 30 minutes you’ll be in the office

  • Consider calendaring when you’ll check email/work while on vacation, if you will – ONLY so you know you DON’T have to the rest of the time.

  • “Order Instacart for return” – likely in personal calendar; either before you leave scheduled for when you get back or a day before you leave. Also, calendar the delivery window so you remember to modify the delivery if your travel plans change – or at least ask the neighbor to go get the groceries!

  • “Vacation: Do I have everything I need, or do I need to order/buy certain clothes, shoes, gear?” – 2 weeks beforehand; likely in personal calendar

So – what do you think? Have any additional tips? If so, share below!

And if you love practical strategies like these, check out my Bright Method time management program (click here to learn all about it)!

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