how do I give notice to my boss if they're on vacation?

A reader writes:

I am planning to go back to school a month from now, to up-skill and ultimately career switch. Originally, I intended to provide my boss 2.5 weeks of notice before starting my program. However, I just found out this morning that my boss will be on a month-long vacation starting mid next week, which happens to coincide with my entire notice period. Now my original plans to resign are at significant risk as I do not want to burn bridges with my current team and employer. Here are the issues:

1. How do I give notice to my boss if they are on vacation?
2. Even if my boss finds out that I will be leaving while they’re on vacation, they cannot do anything to plan for the transition during their time off.
3. Unlike finding a new job, I cannot simply negotiate a later start date with the educational institution I plan to go back to school for. Start dates for classes are far less flexible than new jobs.
4. I may be blindsiding my boss if I announce my resignation. As we do not have a close relationship (we get along but on a very transactional level), I am not comfortable with informing them about my educational plans until I plan to provide my notice. The reason is that I’m afraid I will be pushed out or added to the dreaded layoff list once they learn that I’m no longer interested in my current position. I still need a paycheck until I resign.

What I plan to do is to talk to my program advisor for the school I plan to enroll into to see if I can be transferred to a later cohort, which is two months after the original one I enrolled in. This way, I can give notice after my boss returns. Although this isn’t the optimal choice for me, I am prepared to change my plans if the risks of my current situation are too big. Please advise on how I can navigate this sticky situation.

Don’t change your plans! You can still resign at the time you planned to.

If your boss is on vacation, you can give your resignation to their boss, or to HR if you have it. It’s true that your boss won’t be able to do anything to plan for the transition while they’re out, but that’s just how it goes sometimes. It’s inconvenient, but it’s definitely not something you should change your school enrollment over.

Side note: Some managers would prefer to hear the news while they’re out. (I used to be one of those, and I now realize how very unhealthy that was.) You don’t need to decide if this is the case for your boss. The person who you give your resignation to in their absence can make that call if they want to.

When you resign, you can say, “I realize this timing is really bad with Alex out. I’ll make sure to leave thorough documentation on where all my projects stand, and given the circumstances I can be available for a call or two once Alex is back if there are things they need to wrap up with me directly.” You don’t have offer that last bit, but if you generally have good will toward them, it can be a good thing to offer.

In a different set of circumstances — where you didn’t worry you’d be pushed out earlier than you want to leave — it might make sense to give your notice now, before your boss leaves for vacation. But you’re not required to risk losing several weeks of income just to make things easier for your employer (and if they want people to do that, they need to build a culture where people know it’s safe to).