Emma: I think the inability to truly go on a vacation, to turn off work completely, is a sign of immaturity.
Is that too harsh?
Andy: It’s not harsh! It’s a totally loving explanation. Your work brain hasn’t grown enough to know how to turn off. I remember going on vacation to New York early in my career — the same week I got a promotion, in fact — and I kept getting +ed into all these emails. I remember sitting on a stoop in Chinatown, crying while scrolling through my phone. There was just no way to answer them all.
I can confirm: I wasn’t mature enough to put my phone away and say, “Now isn’t time for emails. Now is time for dumplings.”
Emma: Looking back, I think I was “always available” because I was kind of obsessed with working. I would tell myself that it was expected of me, or that my team needed me, or that I was just showing how good of a boss and employee I was by being engaged with my job even though I was three hours in the future on an island off the coast of Maine. But there is no way my lingering presence in Slack was actually necessary for business to keep propelling forward.
Andy: Yep, same for me. My identity was: I am a good boss and employee. I didn’t want to go a half-day, let alone 7–10 days, without that reminder. Honestly, I didn’t know how to find my identity and worth in other ways. It’s easy to avoid acknowledging that reality by saying it’s work’s fault that I can’t stop for a few days. But that’s just the cover story.
Emma: Go on vacation! Have an identity crisis!
Andy: Perfect advice.
Emma: Unfortunately, here’s what not turning off during vacation really shows: Your team isn’t equipped to function without your supervision. You don’t have even one person on your team whose judgement you trust. You aren’t able to plan ahead for your absence.
If any of that is true, then yeah, I can see not wanting to unplug.
But it also means you’ve got some unbelievably gnarly problems on your team. So gnarly, in fact, that a week of letting them run unchecked while you’re off camping probably isn’t going to make them that much worse.
Andy: It’ll probably make them better! Someone will step up, solve some problem you’re standing in the way of, shine light on something hidden. Either way, you personally holding the hull of the torpedoed ship together with your splayed body is not the answer.
Emma: When I finally finally learned that not truly going on vacation is micromanage-y and condescending and sends up all the wrong signals, leaving work behind was so much easier for me and my ego to swallow.
It also helps me let go when I think about how annoyed I get when my boss suddenly *pings* me from their trip to Greece. It’s not helpful. It’s an immediate stress inducer: Wait, I thought mom and dad weren’t getting home until tomorrow!
A First-Timer’s Guide to Going on Vacation
If you’ve never felt able to go on a real vacation before, or always find yourself compelled to just “hop on real quick to check in” while you wait for the rest of your family to finish getting ready to go to the beach, your work is fourfold.
1. Confirm going offline with your boss
This is a little different than asking for permission. That’s an important distinction, especially if you have a boss that tends to do a lot of work while they are on vacation, if your boss emails a lot over the holidays, or you have a hunch they expect you to be available even when you’re out of the office. That kind of boss may not be as mature as you are about vacations. Don’t follow their lead. They are developmentally behind you and just don’t know it yet.
When you tell your boss that you’ll be out of pocket (have you heard that one before?) you’ll want to confirm: that you won’t be answering, but this person will be answering, and this other person is the backup in case of emergencies. Do not offer yourself as any of those roles.
Here’s a sample conversation:
“I’ll be out of office and cell range until the 10th. Katie will be writing the weekly report and Amy will be running the scrums. In case of more specific issues, I’ve listed all the backup contacts in my out-of-office reply.”
2. Trust that your team knows what to do without you
You need to be able to walk away from your desk knowing that the work that needs to be done will be done right. If you don’t have that trust, you need to build it. This takes time — for any vacation longer than a week, we’re talking about a month(!) or so of work.
If you’ve been practicing delegating, you’ve already got a lot of this prep work done. If you haven’t been practicing, try these four things:
1. Make a list of everything that will need to get done, or that might come up, while you’re gone.
2. Evaluate who you can delegate to. Look at your team, but don’t forget you can also delegate laterally to co-managers or even upwards to your boss.
3. Make a list of everything you can imagine going wrong. Create solutions for each of those things. Is it a document that outlines contingencies? A template email? A folder full of examples of what you’ve done in different scenarios? Is it moving a meeting to before you leave or after you get back?
4. Ask the people who will be covering for you what they are worried about. Work together to build plans for each of these scenarios. Sometimes that will be doing dry runs. Maybe that means giving someone your login information, or even your computer password, so they can access all your documents if necessary.
3. Make it really hard to access work while you’re away
These are going to make you roll your eyes. But they are the kind of dramatic steps necessary for certain people to unplug. (You know who you are. If it makes you feel any better, in our experience the anxiety of not knowing what’s going on at the office lessens a lot after the first 48 hours.)
• Vacation somewhere without cell service or WiFi.
• Delete all of your work apps from your phone.
• Block your boss’ cell from texts or calls. You can unblock it when you get back.
• Change your email password to something you don’t remember and leave it written down at home.
• Tell your vacation mates that you’re not going to check in on work, and make up some consequence that’ll matter to you if you mess up. Maybe it’s an increasingly large fine for every slip up — say $5, then $50, then $500.
• Get a flip phone for vacation so you’d have to T9 your way through trying to work. Mwahahaha.
4. Don’t regret it
Block off the day (or days!) you return from vacation so you can wade through the backlog of emails and catch up.
As you’re catching up, you may find that projects got kicked off without you, that plans were made, that you’re behind and have been left out of important stuff. Or, you may find that people used your absence against you — to do lower-quality work, for example, or to say you’d approved things you sure are shit didn’t approve. You may feel tempted to blame yourself and your dumb vacation: I should have been here. Resist! That’s your immature brain talking.
You can ask your boss to be included if you need to be included. Shine the light on any bad behavior. Go talk to that person’s manager: I wanted to share that while I was on vacation, Jerry pushed through a sales package I’d previously rejected by lying and claiming I’d approved it.
But you should also relish the fact that your team got things done without you. That you didn’t make everything come to a standstill so you could go ride a gondola somewhere.
Then move on.
Good Boss Achievement Stickers: OOO Edition
