Ask the Expert: How do I ask for the High Holidays off?

What's the best way to approach my boss?


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Question: I’m at my first job out of college, and I’ve been working there for about two months. Now the High Holidays are coming up, and I’m nervous about talking to my boss about all the days I have to take off. Someone in the office suggested I ask that the days can be not counted as vacation, but I’m not sure how to do that. Even if I take them as vacation, I’m concerned she’ll think I’m slacking off if I take so many days in one month. What’s the best way to ask my boss for High Holiday (and Sukkot) days off?

–Craig, Madison

expertAnswer: Congrats on your job, Craig! I know how nerve-wracking it can be to ask your boss for something when you don’t feel like you’ve developed a reputation for yourself yet. But if you’re able to handle the situation responsibly, the High Holidays are actually a time when you have an opportunity to prove yourself as a conscientious worker.

Obviously, this answer depends on what the policy for personal and vacation days is at your office. If someone at the office thinks you might be able to get the days off without dipping into your vacation then it’s probably worth it to at least ask. Of course, it also depends a lot on what kind of person your boss is, and what kind of interactions you’ve had with her in the past. If you know she worries people aren’t productive enough, or that people are leaving too early in the evenings, or coming in too late in the mornings, it’s a good idea to keep these things in mind as you plan how you’re going to address the issue. But assuming you don’t know your boss that well, there are still some basics you can and should cover.

First, provide straightforward information. Say, “You probably know I’m Jewish, and the High Holidays are coming up in a few weeks.” Mention the exact dates you’ll need to have off, and explain that you’ll be at services during those days (if you have plans that don’t involve services you can just say you’ll be observing the holiday). If you’re asking for the first days of Sukkot, as well as Shemini Atzeret and Simchat Torah, you can expect to have to explain those holidays a little. Initially, give only the basic information, but offer to give as much more as your boss wants, and I personally recommend telling your boss she can find out more right here at

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