enterprise it in the hour of the wolf

While there are plenty of different descriptions to be found on the internet, the more common descriptions place it as being between midnight and dawn, and more likely, from about 02.00 or 03.00 onwards. It’s a time attributed to not being able to get back to sleep well, of when supernatural forces come out to play, and all the worries of the world come crowding in.

Back when I was in presales, the hour of the wolf was an insomnia-thing, and yes, it was most likely to be the time for me when all the worries of the world came crowding in.

I’m not by any means the first person who has to work in the hour of the wolf. My father was a train driver (or, “locomotive engineer” if you want to be formal about it), and he was a true shift worker. It really didn’t matter what hour of the day or night, he’d at some point have to get up at that time, get ready, then head off and drive a (usually freight) train.

More recently I’ve had my fair share of experience with other shift workers too — the doctors and nurses who staff emergency departments and hospitals 24x7. People I’d always admired for their tenacity. And having experienced it a couple of times now first hand, it was sobering to see just how professional someone can be on insufficient sleep at 03.00 when their body is wired to not want to be in that state.

I started my own journey in the hour of the wolf at the start of 2022 when I joined a product management team in a global company. With people I routinely work with in all mainland USA time zones, chunks of Canada, China, India, Israel, Ireland and Poland (just to name a few), I’ve had to learn new hours of working. It’s not quite what you’d call shift work (in that there are hours I won’t touch), but it’s reasonably and consistently offensive to the notion of a circadian rhythm.

To be fully transparent, while I expected I would have to do some meetings outside of my regular hours, I perhaps didn’t expect just how many such events would happen. But as I reflect back on the last few weeks with work times regularly starting at 02.00, 02.30, 03.00 and yes, even a couple of 01.30 starts, I’m reminded again there’s a bit of an art to being able to do these sorts of hours while still remaining compos mentis – and doing more than just turning up. (As a recent example, last week my Tuesday to Friday had meetings starting at 03.00, 03.00, 01.30 and 02.30 respectively). I’d estimate that at least 20% of my meetings take place before 6am. To put that in perspective, I did 1,315 meetings in 2023, 1,120 meetings in 2024, and so far 2025 is on very much on track to be my host hectic yet.

Oh the early morning alarms I have. Credit: Bigstock.

So what are my techniques for dealing with working in the hour of the wolf? The body is, for the most part, naturally disinclined to be up and participating in enterprise IT with heavy thinking at that time of the day, so if you ever find yourself in it, how do I recommend coping with it? Here’s a list, in no particular order.

know when to disconnect

OK, this probably is the most important lesson of all. Regardless of whether you’re starting at a normal time and working until late, or like me, starting at an abnormally early time, you have to disconnect at the end of it and give yourself a break until the next day starts. My Tuesday-Fridays are typically long: 2am to 4pm, 3am to 5pm — so when I finish at the end of my day I have a very limited window where I check email or messages.

A meeting request for 3am comes in at 7pm? Too bad. I don’t see it. That’s not about whether I'm dedicated to the company or not — that's about me recognising my health is also important. I’m in bed by 8pm most nights. I’m not checking email that late in my day when I’ve been up so long. To help me with that disconnection, I have a separate phone for work — and my personal phone has absolutely no connection to work whatsoever. So when my phone is left on my desk, it’s not bothering me.

uncompromisingly define your earliest start times

I say earliest start times because there should be at least two: one for normal circumstances, and one for exceptional circumstances. There may even be an in-between time — for start times you’ll do regularly, but not weekly (e.g., monthly or fortnightly). But don’t yield on those times. It’s not a case of “give an inch, take a mile” – more simply it’s that you should expect people in other time zones will not always remember or be aware of the implications of the meeting time they’re sending you.

So for me, my normal earliest start time is 3am. My occasional start window is 2am/2.30am. And in exceptional circumstances I’ll consider the 1am to 2am window. But it has to be exceptional — and at that point, those afternoon meeting availabilities disappear because...

...you cannot burn the candle at both ends

It gets said often enough that sometimes it seems like noise in our busy lives, but it’s the absolute truth. Or put it this way: you’re damaging yourself, and wasting your time if you turn up to a meeting so tired that you can’t function properly, and you (a) bring no value to it and (b) get no value from it.

be prepared

You can’t do these hours if you’re unprepared for them. That means either having the setup for them, or getting ready for them in advance. When I rented in a smaller apartment in Melbourne, that meant having a thermos of cold water and a thermos of hot coffee prepared before bed so that they’d be available for me in the morning. Eventually, that pivoted to just a thermos of cold water and a small pod coffee machine on my bedside table.

Now I live in a more spacious house, I have a dedicated room for my home office, and have a bar fridge and the coffee machine in my office. But even so, there’s still a level of prep that has to be done. When I know I have an early start the next day (which is most days, to be fair), that also involves things like having my free slots recorded (so my husband and I can coordinate breakfast and morning walks), having a fresh coffee cup ready in my office, etc. It all sounds almost inconsequential, but if you’re not organised, it takes longer to get ready. As it is, I can set my alarm for half an hour before my first meeting and have time for a shower, coffee and waking up sufficiently.

take notes

In my first job, back in 1996, one of the senior people in my team who was involved in our hiring talked about a night out on the town with some of her colleagues before having to conduct interviews at 8am the next morning. On just a few hours sleep, she watched her colleague furiously writing notes through the entire interview. When she asked him what he was notating during the meeting, her showed her a pad that just had written constantly, “I must not fall asleep.”

Now, “I must not fall asleep” is not the notes I’d recommend taking, but my general technique for being in a meeting is that when I’m not talking, I’m taking notes. Doubly so when the meeting happens during the hour of the wolf. It’s a simple, effective technique for staying focused and not letting the mind drift — because trust me, at 2am or 3am in the morning, the mind wants to drift. Also, if you’re not used to taking notes, remember — it’s a habit, and like all habits it takes a while to develop. (So don’t be too hard on yourself if your notes are pretty basic to start with.)

remember, it’s jetlag

If you’re thinking of going into working these sorts of hours, the best way I can describe it is: jetlag. Yes, that means I’m effectively jetlagged multiple days a week. If you’ve experienced jetlag (particularly of the Australia to US/back again variety), you’ve got a good idea of what it feels like for me multiple days of every week.

don’t take it personally

Meetings are going to get scheduled at midnight while you’re asleep for 2am and you’ll sometimes log in to see messages from people asking why you’re not in the meeting. Meetings that you're setting an alarm for are sometimes going to get cancelled 15 minutes before they’re due to start, meaning you’ve got up and showered and swilled that coffee for nothing.

It's not fun. It's arguably infuriating. But it’s not personal. And remember, some folks just don’t get time zones.

set a limit

Have a number in your mind on how long you can last doing this sort of work. Don’t assume you can do it forever. Down that path lies very dangerous health situations.

be kind to yourself

Taking everything else I’ve said above: there are going to be days when you are so tired that you’re not your exceptional best. But remember this: none of us can work at our peak 100% of the time. Sometimes, particularly those times when you’ve had a week of 4-5 hours sleep every night, your exceptional is still being there, taking notes, answering questions, making decisions. Cut yourself some slack.

Disclaimer: All content is the work of the individual and is in no way affiliated with or representative of any employer, past or present.