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Difficult Conversations

November 1, 2025

Dear Advy,

There don’t seem to be enough hours in the day, and I’ve already had to cancel two vacations in order to meet my goals. How do I talk to my firm about this without harming my standing?

Sincerely,
Difficult Conversations


Dear Difficult Conversations,

Your letter raises two distinct, though connected, issues:

  1. Is skipping vacations (or other personal time outside of work) a good idea?
  1. How do I talk to my superiors in the firm, who seem to answer Question 1 with “Yes, yes it’s always a good idea to deny yourself personal time!”?

The flippant answer to your letter is to say that there are always the same number of hours each day, with the possible exception of the days when we spring forward and fall back due to Daylight Savings Time. That’s not very helpful.

Before dealing with those two questions, though, I notice you mention that you have skipped vacations to meet your goals. Whose goals, are they? If these are goals imposed on you by someone else, do you agree with these goals? Are these goals you mention realistic goals or are they impossible to meet?

Among the key skills lawyers must develop for our work is the ability to assess goals critically. We usually do that on behalf of - and in consultation with - our clients, not for ourselves. Is the client’s goal of a victory in court (or some other legal goal) realistic? What kind of time, money and other resources would it require to meet that goal, and does the client have the means to reach it? Should these goals be revised to consider the costs and the risks associated with pursuing them?

You would do well to apply the same skill that benefits your clients to your own situation. One of the costs of these goals you mention is your long-term mental health and probably physical health. They create a risk of deteriorating productivity, a shortened career, and, frankly, a miserable life. More on that below. Should these goals (regardless of whose goals they are) be revised to consider those costs and risks?

Only you can answer those questions. However, the good news is that you don’t have to tackle them by yourself. You can get expert help in doing this assessment of your goals - for free - from your local lawyers’ assistance program.  Many lawyer assistance programs also have peer support and even coaching programs to help you work through the costs versus the benefits of these goals you mention.

On to the two questions built into your letter.

There is hard data supporting the conclusion that when skipping vacations becomes a pattern, you open yourself up to a significant and accelerated risk of burnout and more serious mental health disorders. In fact, taking vacations is important enough that it made the list of final recommendations of the 2022 National Study on the Health and Wellness Determinants of Legal Professionals in Canada.  Don’t take my word for it. You can direct your employer (and yourself) to Page 390 of the study:

Professionals should also take a REAL vacation. Professionals must adopt practices that allow them to truly disconnect from work and take proper vacation time (e.g., delegating files, organizing time differently). Vacations are critical to protecting mental health. It is important that professionals take real vacations every year and as needed so they can disconnect completely.

Taking real downtime may seem difficult but it is a critical investment in your own well-being over the long term. Now, I’d guess you already know that. After all, you took the time to write into an advice column about well-being. My sense is that it’s the second question that is really bothering you.

How then do you persuade your firm that you should be allowed to take vacations and other needed time to recharge your batteries? You’ve signed your letter “difficult conversations”. That suggests that you anticipate having this discussion with your firm will be difficult. Fair enough. The first step in having a successful difficult conversation is to understand that it will be a difficult conversation. The second step is taking a deliberate, planned approach to how you conduct this conversation.

Again, I’d recommend taking the skills you spent years honing and applying them to this task. You’re a lawyer. No matter what area of law you practice in, you are in the persuasion business. A difficult conversation, like the one you anticipate having, is an exercise in persuasion. It takes a lot of time and money to develop the skills you have. Put them to use for your ultimate client – you.

Here are some points you learned in becoming an advocate for your clients that you can adapt and apply to this conversation:

  1. Define Your Persuasion Audience – Who do you need to speak to? No, really, who do you actually need to speak to in the firm about your need to take vacations?

Odds are the firm has a formal structure related to taking vacations (clearing the time with the office manager or human resources department) but it is the informal barriers to taking a vacation that are stopping you from following through with them. Is the demand you perceive to forego your vacations coming directly from clients? Is it coming from partners or other lawyers in the firm? Are you concerned that your peers or competitors would swoop in during your absence to scoop up the choice work?

Make a list of all the people/groups of people who have acted as a barrier in the past to your taking vacations and keep that audience in mind when you prepare your case.

  1. Assess How Your Audience Thinks – If you were appearing in court, you would likely assess your case based on how a judge would see the strengths and weaknesses of it. If you were in mediation or even in a board meeting, you would structure your case based on how the other people around the boardroom table would understand it. Your message will have limited appeal if it is tailored to the needs of the wrong audience. If, as you prepare your argument, you find yourself straying away from presenting it to meet the mindset of your persuasion audience, stop and refocus your efforts on what you need this audience to hear in order to come to the conclusion you are aiming for.

Assuming your audience is the partners in your firm, what do the partners worry about that they look to you to help resolve? Probably these partners worry about bringing in enough revenue to pay the rent, keep the office lights on, and earn some kind of profit. I’ll give you some specific points to deliver to that kind of audience below, but you know better than I ever will what appeals and doesn’t appeal to your audience.

  1. Marshall the Facts and “Law” – When was the last time you took a vacation? How long was it? Did you interrupt it to finish a brief or attend a video call? What effect is skipping vacations and other personal time having on you and your ability to contribute to the firm? Does the firm have a vacation policy? Do the firm’s recruitment materials use words like “balance” or “building a practice”? Does the firm’s real-life practice measure up to its own hype? Be prepared to give your audience the facts it needs to come to the right conclusion.
  1. Deal Squarely with the Problem Facts and “Law” – The best cases consider the weaknesses inherent in their argument. If you were defending someone for shoplifting, you should probably deal head-on with the security video showing your client lifting the product off the shelf and walking out the door.

Similarly, your argument for the right to have personal time including vacation time will be stronger if you deal with the so-called “bad facts” of your case clearly. Did you get a bad performance review recently? Did a client complain about your handling of a file? These are problems that you can help solve by taking some vacation time. You are at your sharpest and most productive when you have the chance to recuperate. Take the things someone might raise as objections to your request and either turn them into reasons to accept your theory of the case or at least neutralize them.

  1. Read the Room – When the time comes to present your case, always keep your eyes and ears on whomever is making the decision and adjust based on what you see and hear.

There is a very good chance that your firm’s partners do want you to take vacation. The problem is a co-ordination problem or what social scientists call a “common knowledge” problem. One partner does not know what kinds of demands other partners are and are not placing on you. Similarly, clients do not know how much their own needs for your time and attention compete with other clients’ needs. If pressed, none of these people would say you should never take a vacation. They would say they had no idea you were not taking a vacation because of them.

Individually, none of the members of this audience knows that their own actions are preventing you from taking the vacations you need. Indeed, it is entirely possible that their individual demands on you don’t prevent you from taking vacations. What prevents you from taking vacations is the aggregation of those demands. The more widely distributed the people who are making demands on you are, the less likely any one of them understands what their aggregate demands are doing to your ability to serve their needs, not to mention have a happy life.

Pay attention to what your audience is communicating back to you about your message. If the source of the problem is, as I’m guessing, a deficiency of common knowledge, your audience may express surprise that you are not taking vacations because of them. If you detect that reaction, make sure you provide the information your audience needs to develop common knowledge about how you manage your expectations to allow you some time for yourself. Of course, if the audience is clients, you must do that while respecting each client’s right to confidentiality.

Whatever the audience’s reaction, adjust your message to deal with that reaction. By the way, one of the most effective ways of gauging what your audience thinks is to ask. It can be scary to ask someone what aspect of your request they are struggling with, just as it’s scary to ask a judge the same thing. However, the feedback you get is invaluable to tailoring your message and ensuring you are as persuasive as possible.

  1. Leave Them with a Call to Action – Every argument you present in court ends with – and often begins with – a statement of what you want the judge to do. Make sure you do the same for your own persuasion audience in this case. If you need to take at least 2 weeks off this quarter, say so. If you’re unclear about your need to unplug from work, your audience won’t know what to do with all the facts and arguments you’ve given them. Be as specific as you can be about what your needs are. Give them something to act on.
  1. Understand Your Plan B – The reality is that sometimes your persuasion does not work. If you were going to court, you would understand and communicate what your client’s appeal rights are. If you were negotiating a settlement, you would determine what you should do if the discussion appears to be leading you nowhere.

In negotiation theory, this is called assessing your B.A.T.N.A. That acronym stands for “Best Alternative to a Negotiated Agreement”. It is a realistic plan for what you could do if you can’t get what you need through this negotiation. For a lengthier explanation of how to use BATNA in your career and life, you can find more in a previous letter to this column.

If your audience – whether it’s partners in the firm, your peers, your clients, a combination of those groups or someone else entirely – continues to make taking a vacation impossible, assess whether you can and should continue to serve that audience.

Remember that you do no one any favours by denying your own needs to the extent that you burn out and become incapable of meeting their needs. Yes, cue the cliché metaphor of the speech you hear when you board an airplane:In case of cabin depressurization, you must put on your own air mask before you help someone else with their mask. That metaphor has become a cliché for a good reason. It is actually true, even though we often forget it, that we cannot be a help to others when we neglect our own needs.

So, if your firm really does demand that you shorten your own life and career by taking no time for yourself, what options do you have to earn a living in a way that does not take away everything you live for? I suspect it’s highly unlikely that the firm really does have this attitude, but it still helps to assess your BATNA.

Taking time away from your practice has benefits beyond just helping you feel better. While your own well-being is the most critical thing for you to protect and enhance, your firm’s decision-makers might be persuaded to support your needs if it realizes there’s something in it for them too.

Going away and arranging for someone else to be able to step into your shoes temporarily on a file is an excellent opportunity for putting your file into a condition where it is possible for someone else to step into your shoes. Put memos on the file. Gather your notes from phone calls into one place. Take stock of where things are to be able to delegate responsibility to someone else. All these things and many other steps you take to prepare to go away help you detect gaps in the file. Is there a deadline coming up? Is there an aspect of the law or of the evidence you have put off examining as much as you should? These and other questions you wrestle with in preparing to take a vacation have the side benefit of making you a better lawyer. Having someone else’s eyes on the file can also help you identify problems and opportunities that you may not have seen yourself.

The Honourable George R. Strathy, Former Chief Justice of Ontario, gave the keynote address at the November 2023 CBA National Conference on Well-Being. Much of his address was about the kinds of specific steps legal professionals can take to enable them to take time away from the office that I’m talking about here. If you need to cite higher authority than a humble advice columnist, consider listening to his presentation.

You have every right to have some time for yourself balanced against the demands of your job. I hope this has helped to give you some ideas for how to win the most important case of all: Your happiness.

Be well,

Advy