How to Take a Vacation

Some lawyers are good at taking vacations. Some aren’t. You know who you are.

If you’re reading this from a mountaintop villa or an oceanfront condo, then you don’t need my help with taking time off.

If you’re reading this in the courthouse or in your office, then you’re the person I’m talking to today.

Vacation seems like a good idea. We know we should. We all get it. Downtime results in more productive uptime.

You understand that the machine can’t run 24/7/365 without some maintenance. You appreciate the importance of time off.


  • The judge says you’ve got to be there.
  • The client won’t let anyone else handle it.
  • The associates will screw things up.
  • The money doesn’t come in if you don’t show up.
  • You’re just getting started, and you need to get this thing running better.
  • (Fill in the blank…we’ve each got a good story).

So you decide to hold off on planning a trip. You figure you’ll make it happen when an opening pops up in your schedule. You’ll wait for a lull, and then you’ll jump on it and go.

And you’re right. There’s a lull. It happens. Things slow down for a couple of weeks. You’ve got this big opening in your schedule.

Quick Quiz

When you have an unexpected opening in your calendar, you:

A. Take a week off and enjoy it.
B. Use the week to catch up.
C. Spend the week worrying about revenue and how to end the lull.

If you answered “A,” then you’re probably off your meds. Come on, I know you’re doing “B” and “C,” and you know it too. Very few of us jump up and head out on vacation when we see the opportunity. That’s just not how we roll.

The only way your vacation is going to happen is to plan it in advance. You’ve got to take action in order to get going. Very few of us take spontaneous vacations. Most of us simply can’t make that happen as a result of our schedules or our families.

Your Vacation Action Plan

If you want a great vacation, then here’s your action plan.

1. Calendar it.

Now is the time to book something for this summer. You’ve got big blank weeks on your calendar. They won’t be blank for long. Block off a week or two or three. That’s the only way you’re going to actually make this happen.

2. Book the hotel.

Go ahead and find a place to stay. I’m a huge fan of Airbnb and use it all the time to book apartments in residential neighborhoods. I’ve used it all over the world and just left a great Hong Kong apartment I found on the service. Go ahead and book a place now before the good places are filled up. I suspect, between the value of the US dollar and the recent events in Paris, that you’ll find amazing prices in France this summer. Can you say crepes? There are so many awesome places to visit.

3. Arrange coverage.

Now is the time to arrange office coverage if you’re a solo and will need help while you’re gone. It’s dramatically easier to get another lawyer to commit to help if you ask six months out rather than six days before you leave. Most of us will agree to do pretty much anything if you ask us way in advance. Now is the time to lock down a deal with another lawyer to cover your business.

4. Tell everyone.

Tell your friends and family that you’re going. That helps to lock you in so you won’t wiggle out. It also starts your excited anticipation for the trip. Vacations benefit you twice. First, you get to enjoy the anticipation for months in advance—it’s fun. Then you get to actually go on the trip. Put the word out so you can’t change your mind, and that way you’ll let others join in your excitement.

5. Start shopping for plane tickets.

The best way to get a deal on plane tickets is to know what’s reasonable so you’re comfortable buying when you come across a good price. Set up price alerts on Hopper so you’ll know when a good deal comes up. Use Google Explore to find great destinations at good prices.

6. Buy your seats.

Book tickets around two or three months ahead of your departure date (for domestic) and maybe four months ahead for an international flight. Hopper will tell you when the time is right.

7. Go.

Things will likely happen in the weeks before your trip that cause you to question the wisdom of going away. Don’t talk yourself out of the trip. All of us know lawyers who “postpone” their trip forever. They’ve got their reasons for canceling, and it happens every time they schedule a trip. Don’t let that happen to you.

8. Stay.

So many lawyers come home early. They start checking their e-mail and find that things are developing. They get anxious. They start to feel stressed, out of control, and pressured to return. They end up on the phone calling clients, and they decide that it would be better to return a day or two or three early. Don’t let that happen. You may need to disconnect if you lack the ability to relax while continuing to check on things. Don’t come home early. If you’re tempted to come back, then you’re the one who needs to stay even longer.

Your Next Steps

It’s easy to read this article and get back to work. It’s harder to open your calendar, block off a few weeks, and alert those who need to know. Do it now. This is not one of those things that’ll happen if you don’t force it. There’s no client or judge pestering you to take a vacation. You’ve got to drive it yourself, and now is the perfect time to make it happen.

[ While I have you here, I wanted to remind you that you can get the latest articles delivered do your inbox. Just one email per week. Sign up here. ]

If you’re good at taking vacation, then you’re already packing your bags. If you’re not, and I’m looking at you right now, then it’s time to act. You need this. You deserve this. You’ll do a better job for your clients, your family, and yourself if you take some time away. Go.

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