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How to Take a Vacation from Your Corporate or Biglaw Job

The Guilt of Taking a Vacation – Get Over It


Ahhh, vacations. The most glorious time.  And also one of the most confusing and stress-inducing aspects of a demanding job like that of a Biglaw associate.  For starters, like most things in Biglaw, you can never please everyone.  That applies to vacation time too, especially when it comes to the more junior associates.

People have different views on whether junior associates or employees “deserve” vacations.  A common sentiment from the more senior attorneys at law firms is that, because junior associates have only been working for a short amount of time, they should wait until they have been around longer (some like to grumble – “put in twenty years like me and then come back and ask about taking two weeks off!”) before they plan a trip.

Needless to say, Biglaw is a confusing place when it comes to vacations and I imagine other corporate environments are similar. There are going to be policies in place and messaging from the firm, whether it be via firm communications, the HR department, your group leaders, or even the people you work directly with – that say that the firm values vacation time and that all associates should take it. And then there is the reality of how taking a vacation feels. The feeling is: guilt.

You will feel like you are abandoning the rest of your team every time you step away. A  feeling of guilt will probably linger during your vacation, no matter what you do. Even if you covered for somebody the month before when she was on her well-deserved vacation, you are going to feel guilty when you casually check your email and see that she was sending documents and emails out on your deal up until 4am the night before.

Clearly she was slammed with work and you cannot do much about it while you are away, but you cannot help but be stressed that she is up so late on account of your vacation.

I worked with a partner who only took one real two-week vacation (for his honeymoon) during his fifteen year and counting Biglaw career, and he wore this as a badge of honor.  Knowing this, even if he never told anyone directly that they couldn’t take a vacation (in fact he encouraged taking vacations and would cover for associates when they were out on vacation), created a certain vibe around the office.

It was a culture in which everyone felt guilty and badly about taking the vacation, even if it was deserved and totally needed so that they could recharge and come back to the office refreshed and better able to handle the stresses and demands of the job.

Unfortunately I do not have the perfect solution for getting over this vacation guilt.  But maybe it’s not such a bad thing that I can’t offer a step-by-step solution.  Because maybe it’s not that complicated. Just get over the guilt and take the time away – you deserve the vacation.

Planning for Your Vacation


Once you have decided that you are going to take a vacation, commit to it and book the trip no matter what.  Then begin planning for it as far ahead as possible. Here are a couple of tips I learned along the way to help give yourself as relaxing of a vacation as possible:

1. Before your trip, spend as much time planning it as you can and as you want.


Various studies have shown that part of the fun of taking a trip is the anticipation of it.  When you are so stressed and busy that you do not let yourself spend any time planning or thinking about your trip (maybe you have even outsourced the trip planning) you do not get the full benefit of the vacation.

Part of the enjoyment of a vacation is the anticipation of all the awesome things you are going to experience, so if you are super stressed leading up to it, you lose some of that magic.

Build some time into your schedule to pick your destination, research the sights, learn about the culture and the food (maybe even book some tours and make some restaurant reservations ahead of time) and generally learn a bit about the place.

2. Take a day off at the beginning and the end of your trip.


This is a key strategy that I did not learn until the end of my Biglaw career and it is a lifesaver. Let’s say you booked a trip to Italy for eight days – well then you should take ten calendar days off of work. If your flight leaves on Wednesday, take off Tuesday.

And if you get back on the following Wednesday, do not tell your team you will be available to work the second you land on Wednesday evening. Tell them that you are getting back on Thursday and will be available Friday (even better if you can extend your vacation to Friday and then have the weekend free to regroup).

My main point is that you should give yourself a buffer at the beginning and at the end of your trip for two reasons. At the beginning of the trip, you are going to be scrambling to prepare your team for your absence and things will inevitably come up that you have to deal with.

I cannot tell you the number of times I was going on vacation, leaving the following morning at 6am, and I was stuck at the office until 2am trying to wrap up as much as possible. If I had given myself the buffer day, I would have avoided a sleepless start to my vacation.

Not to mention the stress levels of trying to deal with things at work while at the same time worrying about how you are going to get your laundry done and suitcase packed all by 6am the next morning.

You do not have to lie to your team, but you do not have to share your exact flight schedules either. It should not matter if you are taking that last day off to be in Italy or to be in your apartment doing laundry, packing, and generally resting up so you can enjoy your well-deserved vacation.

At the end of the trip, the buffer is just as, if not more, important.  You need time to come out of vacation-mode and get back into job-mode and that simply cannot be done immediately.  When you set foot in the office after being away for more than a few days, it will be almost impossible to avoid the situation where your boss, even if he is well-meaning, welcomes you back with a huge pile of new work that he has been saving for you.

In his eyes, you were just gone for ten days and are refreshed and ready to go, whereas in reality you probably traveled all day and night the day before and are jet-lagged and your brain wants to do anything but think about a new deal.

Give yourself a break and take a day off to be in your apartment. If urgent things come up of course you can answer them, but by this time your team has survived a week or so without you so anything can probably wait another day.

Do your laundry, buy some groceries, get a good night’s sleep, and mentally prepare yourself for the next morning when your boss will be oh so happy to see you. The transition will go so much better if you plan a bit!

Reminder: Take the Vacation.


The bottom line is that taking vacations from your Biglaw or other demanding corporate job can be tricky. But I encourage you to push through any barriers or guilt you might be facing and take your vacations, making sure to enjoy both the pre- and post-trip planning process and experiences.

Trust me, if you do take your vacations the right way, you’ll make for an even better employee and a more pleasant co-worker to have around once you’re back!

When was the last vacation you took? Did you come back refreshed and ready to go, or were you more tired than when you left? Hopefully these tips will help you have a better and more relaxing vacation the next time around.

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