Philosophy · 27 January 2016 · Ian Malpass

On Sabbaticals

Sabbaticals - a long(er) term paid break from work - used to be the preserve of academia. But, more and more companies are choosing to offer sabbaticals to their longer-serving employees. It’s a tremendous benefit for employees (and, as I’ll argue below, a great benefit for employers too).

I’m fortunate to have worked for Etsy for over six years now, and when they updated their policy to allow a six week sabbatical after five years (it had been seven), I started planning mine.

I took my sabbatical in July and August of 2015. It was fun, relaxing, and not what I expected. After I came back, I had a few conversations with people about it, and I thought it was worth writing down the things I’ve thought about sabbaticals - why they exist, how to get the most out of one, what to do on your return, etc. (This post is an edited and more general version of the email I sent to others considering their sabbatical at Etsy.)

Everyone’s situations - at home and at work - are different, and our sabbaticals will be equally unique. As such, the following is just a list of things I feel are important, having taken mine.

Why do we have sabbaticals?

Thinking about how to take a good sabbatical, I fell first to thinking about why we have sabbaticals in the first place. Are they for us to learn new skills? See new sights? Have adventures? Sit in our underwear in the dark binging on Netflix and popcorn? Yes, any and all of the above. But, fundamentally, I would argue that the main reason we have a sabbatical is so that we can be extremely not at work.

When you leave work, you start ramping down your “at work” mind and before you get to work you start ramping it back up again. During the work week we never really fully ramp down before we ramp up. At the weekend, we might get close. If we take a week off, we’ll probably be fully away from work for a few days in the middle. I’d argue that two weeks is the minimum time to take off to actually get a proper mental break from work. (Note: the dire state of vacation time allotted to employees at many US companies may well preclude this. I’ll admit my privilege in having a good amount of vacation time available to me in general.)

Even so, we’re often left with anxieties about work: Did I leave everything in a good state? What if I left a bug lying around? These mentally drag us back to work. The common habit of checking work mail during evenings, weekend, and vacations compounds this problem0.

A sabbatical is different. A sabbatical forces you to properly relinquish your grip on your job. This is super important for your employer. (It’s also super important for you, but it’s important to recognise that providing sabbaticals is not pure business altruism.) After a number of years at a company, it is super easy to become The Person Who Knows About The Thing, whatever The Thing is. You become a single point of failure because any time The Thing comes up, you’re the one who deals with it. Maybe you can get away with that over a week’s vacation (maybe even two) but a sabbatical forces you to make sure that other people know about The Thing too. This is important because while we take sabbaticals in a very planned, deliberate way, fate can force you to take an unscheduled one through the medium of a critical illness, or an unexpected bus while crossing the road.

First principle: If you think you can’t take a sabbatical, you need to take your sabbatical.

Corollary: You probably should be taking more, longer vacations too.

Tactics vs strategy

When I say that a sabbatical is a break from work, I’m not saying you shouldn’t think about work. I think you should think differently about work.

Part of never ramping down on the day-to-day work is that you often don’t have space to think about the long term - both for yourself and for your job, your team, and the company at large. We tend to think tactically about how to solve the immediate problems at hand, and trust that the longer-term strategic thinking is done by other people. It often is, but that’s underselling yourself. Your company hires very smart, very thoughtful people (yes, you) who care about the company’s mission and the people they serve. After a few years, you’ve seen things (good and bad) and thought things and got a sense of how the arc of the company’s story is curving. Those thoughts are often jumbling around and wanting to settle into some coherent insight, but can’t because you’re so busy doing the day job. Sabbaticals are a chance to clear away the day job and let those thoughts clarify.

I did say thinking about the long term for yourself, too, though. You’ve spent a goodly chunk of time at this company. Are you happy? Are you being stretched? Doing what you want? Is there some itch you want to scratch? Something worrying you that you’re missing? Paying attention to yourself and what you need is really, really important too, and having space to think about it (rather than just getting to the point where you throw up your hands and quit in order to make a change) is super important.

A lot of this thinking can be subconscious. You don’t have to go and sit at the top of a mountain and think about your job for weeks (I mean, you totally can if you want) but making space for strategic thinking in amongst sabbatical activities, and doing some deliberate thinking about it towards the end is useful.

Second principle: Day-to-day work pushes us to think tactically; sabbaticals push us to think strategically. Both are valuable.

Safe disconnection

To achieve this state of unworkness - to realise the benefits to yourself and to your company - you need to disconnect. This can feel really weird. (It can also feel really nice.)

Primarily, I mean disconnecting from email (and IRC, GChat, Slack, etc.). This is the constant drip-feed of work (or worklike stuff) that pulls you back in. If you see something that you can help with, the compulsion to actually go and help is hard to resist, and then you’re screwed.

What you need is trust that everything will be OK in your absence. There are two parts to this: doing your best to hand off everything that’s normally on your plate, and doing your best to make sure that the unexpected will be handled cleanly.

How you deal with those two is largely down to the sort of work you have, but for the latter I would recommend the following out-of-office reply1:

I’m currently on sabbatical and won’t be checking my email until [return date]. Jane Manager - - should be able to handle anything I’d normally deal with. If you specifically need me urgently for some reason, Jane knows how to get in touch with me.

You clearly set expectations - “I’m not going to be reading your email” - and a mechanism for resolving problems. And you provide an escape hatch: if the world is ending and only you can help, your manager has your personal email/phone/batsignal/whatever and can call on you. And they won’t do it. You’ve already done the work to make sure you’re not a single point of failure before you leave. You work with good people. But knowing that escape hatch is there lets you relax knowing that if the worst does come to the worst you can be summoned. (Note that you don’t put your personal email on your out-of-office reply - this only works if you make sure you have a gatekeeper.)

Third principle: Do the work to gain confidence that you can be away, and then trust that that the mechanisms you put in place are good.

Corollary: If you don’t trust your manager, your company has larger problems they need to solve.

On being surplus to requirements

One of the things I kind of struggled with before I went on sabbatical was the idea that I wasn’t actually… necessary. And if my team and the company could do without me for six weeks, then maybe they didn’t need me at all.

This plays into a workplace anti-pattern I tend to think of as “heroism”. You’re the one who swoops in and saves the day. You clean up the messes. You do the reviews that spot the problems that would have been catastrophic. You have the Good Ideas. All of this is absolutely terrible for the company (and for you, long term). Again, the single point of failure. Other people on your team need to step up, and need space to step up. That’s how the company grows and evolves.

Just because you’re not irreplaceable doesn’t mean you’re not valuable. Your perspective, experience, skills, and love of a good pun make you valuable, and those aren’t predicated on you saving the day all the time. In fact saving the day all the time is probably stopping you from applying all those skills to more important problems.

Extended time away lets you come back to work having shed an old, constricting skin. Your team grew more capable in your absence, and you have new freedoms to now make it even better.

Fourth principle: Just because your team can function without you, doesn’t mean they want to.

When to go

This depends on your company’s policy, but in most cases there is no requirement to take your sabbatical the moment you qualify for it. Dates will be constrained by various logistical requirements. Want to spend your sabbatical with your kids? You’re probably limited to school vacation times. Want to go on a grand tour of New England? You might want to do it in the autumn to get the best leaves. Want to do a particular class that’s only offered once a year? You get the idea. Similarly, it is unlikely to be ideal for a product manager to go waltzing off in the middle of a critical project, for a support person to head off into the sunset during your busiest time of the year, etc.

Balancing the work and personal constraints may be tricky, so start talking to your manager early. I know of some people who are planning their sabbaticals at least a year in advance due to time constraints. The earlier you talk, the easier it is to factor your disappearance into project plans.

Fifth principle: There is rarely a good time to leave work for an extended period of time - don’t let this stop you.

What to do

I think most people who are given the opportunity to go on sabbatical struggle to work out what we want to do with the time. It’s an unusual, valuable gift, and we feel a responsibility to use it well.

The good news is that, based on what I’ve described above, it doesn’t actually matter what you do. Anything you choose to do is just icing on the cake.

There is also an element of uncertainty in planning many sabbaticals - if you’re planning far enough ahead, the unexpected may pop up and change everything. I ended up selling my house and moving a week before my sabbatical started, so suddenly had “sort out the new house” as a project I could not have anticipated. I had also planned to do some projects that ended up being impossible due to unforeseen events. Be ready and willing to adapt your plans2.

Sixth principle: Allow room for serendipity, the unexpected, and exploration.

Before you go

Sabbaticals should be largely free from work-worry, so do the work to avoid the worry up front. Perhaps more importantly, though, plan your return with your manager. A lot of worry during sabbaticals is about “what will it be like when I come back?” so having set a plan before you leave can alleviate a lot of this concern. What will you be working on? Who will you be working with? What deadlines will you have? Make sure that you have a good sense of all this, and that your manager is aware of (and shares) your expectations. It may not be possible to set up a specific project for your return, but making sure your manager will explicitly have something ready for you is important.

Set up a debrief meeting for when you get back so that you can get up to speed quickly.

This forward planning will make for less worry, and a much better sabbatical (and return). Then set your out-of-office reply and leave with a clear conscience!

Seventh principle: Plan for your return before you leave, to avoid worry.

When you return

Most work environments are fast-paced, and things can change a lot even during a few weeks away. Moreover, you may well have changed in six weeks.

Everything might be just fine and dandy on your return. That’s great!

Equally, it may feel a bit weird when you come back. This is also OK and perfectly normal. I found that peer support was invaluable in managing my return3 - talking to people I trust (including, but not solely, my manager) about what I was feeling, what changes I wanted to make, etc. Allow time for that, and embrace it as a positive aspect of going on sabbatical.

Eighth principle: The sabbatical process doesn’t end after six weeks.

A sabbatical doesn’t mean quitting

Sometimes people quit after going on sabbatical. There, I said it.

People also don’t quit (I came back!). You don’t have to be unhappy or dissatisfied with work to go on sabbatical, nor should going be viewed as a precursor to leaving completely. Some people may realise they want to make changes in their work while they’re away, and for some of them that might mean doing something completely different, but that’s a very individual choice. There may be some degree of correlation between quitting and sabbaticals, but I’d argue that there is no causation there.

I certainly came back having missed everyone I worked with, and while there were things I wanted to change, my time away reaffirmed to me just how much I love Etsy, its people, what it stands for, who it serves, and the impact it can have in the world.

Ninth principle: You don’t have to be unhappy or frustrated in your work to go on sabbatical.

That’s it

That’s a lot of stuff. I’m amazed you’ve got this far. Hopefully these principles are useful for those of you thinking about sabbaticals. They may even be useful for managers with staff with impending sabbaticals, or for companies thinking about implementing or updating a sabbatical program.

One thing I’d emphasise is that many of them apply to taking “regular” vacations too. The ability to disconnect from work is, in my opinion, one of the most valuable skills you can acquire.

Tenth principle: If you’re going to enumerate principles, try to come up with a round number.


0: To be clear, I’m not criticising or trying to shame people who check their work email outside of work hours. There are reasons why that happens (I often do it myself). But, we should be clear about the trade-offs we’re making and the implications of them, and the reasons why we’re doing things.

1: I’d recommend this for vacations too, for what it’s worth.

2: My parents were visiting us during the start of my sabbatical, and as a result one of my favourite sabbatical memories proved to be spending a week with my dad fixing up the dock at my new house. I could not have planned this, but will treasure it.

3: In truth, I had a bit of a Mid-Career Freakout….