Break Yourself: How to Vacation as a Solo Attorney

As a business consultant to solo and small firm lawyers for the past decade, Jared Correia has helped lawyers deal with many law practice … issues. In his column, “Law Practice Confidential,” he will be answering real questions from real lawyers. To send Jared an anonymous question, use the form at the bottom of this post.

Q: I work really hard, like most attorneys. But, I’m starting to feel like I’m burning myself out. I’m doing well financially, but I have to work all the time to do it. I’m comfortable working a lot. I just need a break sometimes. I haven’t gone on a real vacation in three years. I’m starting to feel like it’s impossible for a solo lawyer to take a vacation. Can you help?

—NWA, Hendersonville

A: Well, mid-summer is probably a good time to be dreaming of a vacation so let’s make those dreams a reality.

This is a common problem, especially for solo attorneys, on whom the weight of an entire business falls. If you’re a solo lawyer who’s also the primary breadwinner for your family, it makes it even harder to divest yourself from your business, even for a short period of time. Beyond the question of whether it’s possible (it is), the psychological toll it takes for a solo to intentionally ignore business matters, even for a day, is often what closes the book on the notion of a vacation before it even opens. The primary concern that most solo lawyers have is that something important will come up and that they won’t be able to respond to it in time. Fortunately, there are ways to manage that. There are also changes you can make to your business which would make it possible for your company to move forward—even when you’re not physically present to advance the ball.

Move to the Cloud

Yes, just like Jimmy Buffett, you too can be eating dairy-covered meat in a tropical location in large part because you can bring your business with you.

If the main reason you’re afraid to leave your business otherwise unattended for a week or so is that you’re worried about leaving your systems behind, there’s an easy way around that: start leveraging cloud software. Local applications reside on specific devices. If that specific device, for you, is a desktop, you’re not bringing it on vacation. Maybe you don’t want to bring your laptop, but would you be comfortable taking along a tablet or smartphone? The trick is to get to a point where you’re device-agnostic. If you’re using cloud software, it does not matter what device you use: you can access your software (and the data that resides on it) anywhere you have a secure internet connection. If you no longer have to worry about being in your office to access your systems, but could access them anywhere, that “anywhere” could be Maui.

Any of your favorite software systems will likely have cloud-based versions or alternatives.  Business software (like Microsoft Office), law practice management software and accounting software (like QuickBooks), are all accessible via the cloud, including mobile versions for use on smartphones or tablets. If you’re worried about missing something, imagine instead a scenario where you listen to a client’s frantic message on your smartphone, log into your case management system to get updated on the matter, access the problem, solve the problem, notify the client of the solution via a quick call or email and then order another mai tai. That option is well within reach.

However, if you truly want to unplug, do it. The risk of the above scenario is that you could also use cloud software as an excuse to work regular hours during your vacation. Don’t fall into that workaholic trap. Instead, truly unplug and only respond to emergencies.

Schedule Your Free Time

You can also free up time to take regular vacations if you become more rigid about how you manage your calendar. Most solo lawyers are bogged down by administrative work. They have no one to help them with that, though things like virtual receptionist and secretarial services and scheduling apps like Calendly can help. But, if you’re a true solo, you’re likely managing your own calendar at some level. So, step one to taking a vacation is actualizing it.

Book the trip and start informing your clients that you’ll be away. The sooner you do both of those things the more time you will have to arrange/rearrange your schedule. Block out your vacation time on your calendar, and don’t schedule anything for those days. This will help you to avoid temptation. If you’re open and up front with your clients and colleagues, you can create a free week for yourself. But, remember that weeks off don’t just happen—you have to arrange for them in advance.

Get a Substitute

When you complete your malpractice insurance application, you’re asked to list a backup attorney—someone who can cover for you in the event you’re not available. This arrangement is very important to malpractice providers, for obvious reasons. What you probably did was pick a colleague’s name at random and write it down. You probably didn’t even tell the person you picked. It is a small percentage of lawyers who formalize backup attorney arrangement, but if you want to go on a true vacation, you should be one of them.

Think of it as your own personal, mutual vacation club: a solo backs you up when you want to go away, you back up that solo when they want to go away. You can develop a formal contract, respecting what that arrangement entails. And you should definitely share your system passwords with your backup attorney because that is where all your data lives. Having a competent person who can jump in if a local issue arises while you are on vacation is a necessity.

Formalizing that arrangement in some fashion has a direct impact on its effectiveness. Most lawyers and law firms and malpractice insurers think of backup attorneys in cases of disaster, like death or disability, but, if you’re intent on ramping up your vacation time, you should think of backup attorneys in terms of convenience. Using a backup attorney to babysit your practice does not foreclose your ability to check up on things. If your law practice is cloud-accessible, you can monitor it from anywhere, while your backup attorney is ready to respond to local exigencies.

When you use a backup attorney for a vacation, you’re delegating an aspect of practice management to someone else so that you can unwind. If you’re the kind of solo who employs staff or virtual personnel, there’s much more that you can delegate.

Your secretary can help you to arrange your calendar in advance of a vacation and can assist in scheduling matters while you are away. Your paralegal can create first drafts of documents that you can review while you’re out or when you get back in. Your bookkeeper can make sure the financial wheels keep turning, that approved billing is being sent out and that outstanding billing is being collected. If you’ve virtually staffed up correctly and delegated appropriately, the basic functions of your law firm should be able to go on without you. The best type of solo practice is a staffed one that you don’t necessarily have to be there on a daily basis to manage.  If you’ve established that groundwork, going on a vacation should be the least of your concerns.

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Originally published 2017-07-18. Republished 2017-08-25.


  1. Avatar Chris Cantrall says:

    Great topic. I love to travel, and so a big part of the appeal of the cloud for me is that I can travel so much more because my work is always there. On the downside, it means I can never fully remove myself without effort, but on the upside, it means I can go on a monthlong vacation and work as needed.

  2. Avatar Brendan Chard says:

    A strategy I’ve picked up over the years is to leverage the email out-of-office responder before I leave to automatically notify clients that I’ll be out of the office soon and to bring things to my attention now rather than later.

    Another one is that when I do set my out-of-office message for my actual vacation, I only put down my return date, and I usually put it down one day later than my actual return. Client’s don’t need to know how long you are gone, only when you’ll be back. And, giving yourself a buffer day really helps to unpack, ease back into work and cherry-pick the most important things to respond to.

  3. Avatar Debra Carpenter says:

    I work for an answering service that does business with a lot of solo attorneys. One of the most common reasons given for signup: “I’m going on vacation next week and need someone to handle my calls.” Don’t forget that an answering service can handle calls while you take some time off. It can allow you to truly disconnect while you’re away!

  4. Avatar The truth says:

    Get teamviewer and make sure you have support staff that is good with staying in touch with you and the clients.

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