Taking Vacation – Without Losing Your Mind

Beach, originally uploaded to Flickr by anda (:.

2017 Update: We still stand by this advice on how to prepare for vacation without losing your mind— links have also been updated below.

How can you take all of the vacation time to which you’re entitled — without falling behind on work and stressing yourself out? Reader K has a great question:

I’m a prosecutor so one of my benefits is a lot of vacation tine. “Nice Girls Don’t Get Rich”recommends taking it, so I do. I wind up working so many hours in preparation for vacation I am exhausted, grouchy, and usually sick when I leave. Then I spend the first part of my trip recovering. How do other readers get prepared to be out of the office without going crazy?

Sing it, sister — I totally know how that goes. We’ve polled readers to see how much vacation time you’ve taken, and had an open thread about how to prepare for vacations long ago, but I thought it might be worth revisiting.  (Pictured.)

Some suggestions:

  • Plan, plan, plan.  Know what’s due before you leave, when you’re gone, and when you return.  Prioritize things based on the schedule, but also based on how much work you can get done, if needed, while on the plane or (heaven forbid) the vacation itself.  For example: that fact-based project with a zillion binders? Get that one done at the office.  That article you’re writing — for which the research is done but the article is heavily in need of editing? — that’s a great project for the plane, if it comes to that.
  • Let other people know that your planned vacation time is coming soon.  This depends a lot on the dynamics of the office — I’ve done everything from emailing my superiors (and subordinates) to let them know it was coming up a week or two ahead of time, to leaving a travel guidebook on my office desk (as a silent reminder).
  • Leave your office well-prepared.  If you’re working on three or four different projects, leave a pile for each on your desk so that if a question comes up in your absence, your coworkers have at least a fighting chance of finding the answer themselves.  Also, I’ve always left a printed sheet with my itinerary, my hotel information, my cell number (and my traveling companions’ numbers), and anything else pertinent.  You may want to even “schedule” a time each vacation day to answer emails and voicemails, so other people know when they can expect a response.

Readers, how do you prepare for vacations?

Picture below via Flickr.



  1. Young Consultant :

    I am one of those right out of school, mon-thurs traveling consultants. While I technically get a good amount of vacation days (around 25), I am struggling to know when it is ok to take them, and really how to ask my boss. Many of my peers and supervisors have taken a week or more off during the project, so I know it is not standard to only take vacations between projects. However, I just feel like I don’t know how to know when it is appropriate to take vacation and how to ask. I don’t want to end up that person who dosen’t take a day their first two years! How did you all figure this topic out?

    • While I’m not a consultant, I do my best to schedule time off after major deadlines and at seaonally-appropriate times to take vacation (holidays, etc.) I mostly took a lot of long weekend vacations my first couple years.

    • Is there a reason why you can’t ask? Don’t be so timid! If there is no formal HR policy outlining a supervisor’s approval, send an email to your supervisor. Something like, “I am planning on taking vacation on 10/15-10/23.” or “I am requesting approval for vacation on 10/15-10/23. I will be back on Monday 10/26.”

    • Seconding Godzilla, that’s what I did, I’m in my first year too. I think about a month and a half beforehand (when I was looking at prices, etc.) I sent an email asking if there was any problem with me taking X week off. And as my first real vacation from work, it was the greatest thing ever.

      • I’m in consulting and a recent grad also. Just ask! Maybe ask a peer that has been working longer than you have. Your manager can’t get mad at you ask ahead of time.

    • If you have your eye on certain dates, let them know ASAP, but if not, then just ask HR or your boss the same thig you did here, but without the insecurity. Just say you’re really enjoying x project, but you’re also aware that there are vacation days you should take; when and how should they be scheduled?

    • When I was new to consulting (I have since left! Whooo!), I planned far in advance, and with some flexibility. I usually shot my manager an email in like, March, saying “I’m looking to take some time off at the end of the summer. Right now I’m looking at August 5th-10th. Do you see any issues with those dates?” Then, if there is a legit reason why those dates won’t work, your manager doesn’t feel like an @ss for raining on your parade and can simply suggest you go earlier/later in the summer.

      This may be office-specific, but I always shoot out an outlook meeting for when I’ll be on vacation– as soon as I know. Right now I have one sitting out there for Feb. So nobody can say “I had no idea you’d be out of the office!”

    • I would recommend talking with your project manager as well. Give them a heads up you are planning on taking some vacation – that way they will have time to find a backfill for you or let other team members know that you will be out. As someone who has been in consulting a little over 5 years and does the mon-thurs. travel you NEED to take your vacation. If you don’t you will get burned out quickly!!

  2. I am a huge advocate of taking vacation and making it very clear that I am not available to check email/phone while on vacation. There are times when this is not possible of course, but in most instances you are not indispensable and someone can cover for you while you’re gone. I’ve been lucky that everyone at my firm respects vacation and I’ve never been bothered with emails while away from the office. Don’t make the mistake of replying to non-urgent emails while on vacation, then people automatically assume that you are around.

  3. In addition to Kat’s suggestions, I usually try to draft a quick note on each case/issue that might possibly come up and email them to anyone who might get involved. For example “The Smith case involves (subject), and nothing’s due until X, but client may call about Y.” Just so they’re not entirely lost if something does come up.

  4. This is what I love about medicine. Or my medical community. Right now, my husband’s partner is on a 3 week trip in Africa on safari. We are planning 10 days in Maui in April. We just set our vacation, and the expectation is that the other physicians in town will cover. Due to the nature of medicine, it’s nearly impossible to deal with issues from afar, so its very rare for me to have to do anything on vacation. Any urgent issues get dealt with by the other surgeon in town.

  5. emcsquared :

    I’m a lawyer, so different but still similar issues with vacation – unpredictable deadlines, focus on client service, demanding bosses and colleagues.

    I leave a detailed list of every matter that I’m working on if I’ll be out of the office for a week or more. I give it to my assistant, and it includes a short description of the matter, the status (i.e., letters have been sent, waiting for response), the external contacts who may call about the matter, and the internal contact person who can handle it while I’m away. I find it to be a helpful way of making sure I’m not missing anything, and helpful when I return so I can just pick up where I left off. My assistant likes it because she has something to say when a client calls (“Mrs. Emcsquared is out of town, but Mrs. Jones is aware of this matter – may I forward the call to her?”)

    And I like to set aside a half hour each vacation day to clear out my e-mail. I don’t generally respond outside the firm; I just forward to my internal contact and let them respond. I hate coming back to a full e-mail box. Finally, try not to send any e-mail for 3-5 business hours before you leave town (meaning, if you leave at 6 am, don’t send e-mail after 3 pm the day before). The more e-mail you send, the more you get back…and if you do have to send an e-mail in that window, make sure it’s a complete and organized description of your conclusions and proposals, not just a “let’s talk about this” e-mail.

    And while you’re on vacation – put your phone in the safe and turn off the ringer. Or switch off the e-mail synch function, or disable the e-mail notifications. I did this accidentally once, and have done it intentionally ever since. Truly worthwhile.

    • I’m in a pretty client-facing role now, and I ALWAYS give my clients the heads up that I’ll be out, and contact info for the person that will help them “in case of emergency”. Generally, they know they’ll be happier if they wait until I get back, though, so they don’t bother my #2.

  6. karenpadi :

    I am in an area where we have several small, discreet projects with well-defined due dates and few surprises. Before a vacation, I clear my docket, set up a back-up attorney, let the support staff know, and note anything I think might come up. I share a client calendar with a partner for tracking meetings with the client so I add my vacations on there as soon as I book the tickets.

    I go on vacation where I have no access to reliable and private Internet and no private phone line. It’s getting harder to find but scuba diving destinations are still remote and under-developed enough to convince people that I can’t work. I also have a destination in the woods where there is one phone line (for voice and Internet) shared with 30-80 people and no cell service.

    I act as back-up attorney for many people in the office when they are on vacation and haven’t contacted them on vacation (yet–knock on wood)–even if it means me doing extra non-billable work or pulling an all-nighter to meet a deadline that they were unaware of.

    To those people who think that their vacation can’t inconvenience anyone else: every time I take vacation, one or two issues pop up. Luckily, they are generally minor and easily handled by my back-up and the staff. Sometimes they don’t handle it how I would have, oh well. That’s OK because I will do the same for them when they are on their vacation.

    • I too have a place in the woods where there are more bears than cell phone towers. Just the knowledge that nobody will be able to reach me instantly puts me into relaxed holiday mode. Not to mention how the familiar and beautiful nature soothes my soul. Mountain hiking (off-ski resorts), sailing, trail riding and spelunking would also be good activities for going off the radar.

    • LIveaboards, where the only phone is a satellite phone?

  7. harriet the spy :

    I have yet to put this into practice, but I think this is a good reason to take either very short vacations (like, four-day weekends) or very long vacations (10 days, two weeks.) For a four-day weekend, you can get away with doing very little to prepare. And the preparation for a week-long vacation is just about the same as it would be for a two-week vacation, but you get more bang for your buck.

  8. Thankfully, in my industry (engineering), there are a lot of people working on the same project so one person going on vacation, even for a month, isn’t *that* big of a deal. Something key is to have an out-of-office email response (or voicemail, if phone is how most people communicate with you) stating that you’re on vacation, will(not) respond before you return and who that person can contact while you’re out.

  9. ah, biglaw. the years where billables are a-plenty and I wouldn’t have to worry about taking time off hurting my hours, it’s that much harder to schedule time away. the years where work is lighter, taking an extra week might mean missing out on your bonus for not making hours (and looking like a slacker compared to your colleagues who did). FOOEY is all I have to say about that.

  10. AnonMouse :

    I have a sort of related question — how do you encourage people to actually BE on vacation while on vacation, rather than just…. ending up working remotely?

    Maybe it’s just my dad being a bad manager, but whenever I go on vacation with my parents, he feels the need to call all three of his assistants every day, separately. (Maybe the clue is that he has three assistants, and still manages to get nothing done. Hmm, lol.) I don’t care if he does email at night when we get back to our hotel/homestay/whatever, but… it seems like he must get some bizarre ego boost from feeling like he’s so busy that he just can’t possibly take a day off, even if he’s out of the country for two weeks.

    (He also doesn’t seem to understand or care that in other countries, it’s accepted that everyone is quiet-ish on public transportation, and he just sits there and yaks up a storm loudly on his cellphone!)

    There has to be some balance! Does anyone else have experience with prodding someone to just have some fun on vacation?

    • harriet the spy :

      Short of going to places with no phone or email service, i don’t think you can. People do what they choose to do. I think that the key question is this: How do you find a way to have fun on vacation with your dad, in light of the fact that he will call his three assistants every day while on public transportation?

  11. E. Parsons :

    For nearly five years, I barely took vacation because I was afraid that something would come up. Now, though, I’ve learned that something always comes up and to just enjoy my time off. I highly recommend it. And I second what everyone has said about prepping support staff and letting other attorneys know.

  12. After many years in the law biz I learned to take the computer on vacation (and /or the phone) and to keep up with clients while on vacation. They appreciate it so much, and love getting communications from Paris or California. I did go incommunicado in Russia and China.

  13. I build an extra day when I return. We fly back in on Saturday so we can adjust to jet lag and do laundry, catch up on email, triage the inbox. If things got so bad on getting things in order before I left, I would consider building an extra day on the start of vacation, plan to take Friday off to adjust people to my time off. Finish things up at home to help transition out. But really, something always happens. People can survive without you. They don’t want to, but they can.

  14. My coworkers and I try to make each others’ vacations a little easier by divvying up each other’s work while we’re out. So, if I were going on vacation next week, I would meet with my two coworkers and split my ongoing projects between them. For each project, they get the latest drafts (or instructions if there is no draft), the client contacts, and I tell the client to contact Coworker Jane with any questions or issues about their matter while I’m gone. When Coworker Jane takes her vacation, I reciprocate. Coworker Jane and I trade cell phone numbers for emergencies, but we rarely use them. This works so well for us that we can generally take an entire week-long vacation w/o a single call from the office. If you can work out this kind of shared-work arrangement with your colleagues, it’s a great way to make sure you don’t have to kill yourself trying to clear the desk entirely but can still really unplug when you take your vacation.

  15. Please address the issue of getting sick as you depart. I caught nasty colds (on LONG flights, I think) on my way to my last two scuba diving vacations and spent most of the time in bed, miserable.

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  17. I’m commenting late on this…

    My preference has always been to make a point of using up my vacation time by taking short 3- or 4-day weekends. There’s almost no preparation required to be out of the office for 1 or 2 days, and very little comes up that can’t wait a day for me to get back. I tend to enjoy the shorter trips more than longer vacations away from home. The only time I take big chunks of vacation time is when I’m planning a big trip abroad, which I certainly don’t do every year.

  18. Boy am I glad to live in Ausralia where we get 20 days/4 weeks of annual (i.e. vacation) leave per year. And I thank my lucky stars that the partners in my team generally subscribe to the view that when you are on holiday there is no email replying or phone call answering. Yes I work in what we call a “top tier” or your “big law” law firm but that is no reason why you should run yourself into the ground or be too scared to take leave. I have somehow managed to accumulate 15 days of sick leave (not sure if you get that in the USA?) and have recently started using a day here or there as a “mental health day” just to relax and not think about work….

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