A Year Of Working 6pm to 2am

What would you do if you woke up with a blank calendar?

I spent all of 2021 working 6pm to 2am. I was visiting my family in Madrid whilst working PST hours for a Bay Area company.

Covid (remember that thing?) was still raging in 2021. Armed with almost no cooking skills, a burning desire to not pay $2,000 / month in Bay Area rent, and permission from my boss, I decided to fly across the Atlantic and move back home.

Lunch break became dinner break. My morning shower was replaced by an evening shower post gym session.

And speaking of the gym: it was empty. No one goes to the gym at 3pm.

As a proud night owl, I looked forward to this adventure. Working at night in the past had meant the ability to focus for long periods of time and be uninterrupted.

My 9ams were about to be replaced by 6pms. I was excited.

But what would happen when I’d have to take a call at 1am? Would I take it from bed? Would I manage to contribute in a meaningful way?

Over the next few months, I got my answers and much more.


Waking up every single day at noon sounds like every 12 year old’s fantasy and for the first 3 months, it was pretty fantastic for even a 24 year old.

In a usual 9 to 5 gig, work comes first and then you plan your life around that. But when you’re working night hours, you get to put all the other stuff first.

Except socializing: as you can imagine, that takes a huge backseat when you’re pretty much unavailable in the evenings. But because this was during the heat of the pandemic, I ignored this aspect of my life completely (which in hindsight sounds pretty crazy).

In any case, having the whole day to myself meant being able to:

And this stayed true for pretty much the whole year.

Having a solid 6-7 hours after waking up to myself meant that I was able to spend a lot more time exploring ideas and hobbies I couldn’t back whilst working a normal schedule.

But waking up at noon everyday ironically got pretty tiring.

I found that regardless of how many hours of sleep I got, waking up at noon made me feel like a complete loser. The world was out and about, buzzing, having already completed 3 hours of work, and here I was about to brush my teeth.

You might be doing the math in your head and trying to figure how I’d wake up at noon if I finished working at 2am. And no, I don’t get 10 hours of sleep.

Here’s the thing: when you work late hours, it’s really hard to switch off.

Switching off

I’d clock off around 2am, but my brain would be awake till 4.

Seriously, I’ve never had sleep problems in my life but I found it impossible to quiet my brain down and fall asleep at a reasonable time.

I would get tons of good ideas about work right before dozing off and then I’d jolt back awake. This was something I hadn’t considered before moving. I’d expected to be able to clock off immediately at 2am and then wake up around 9-10am.

Maybe this was just me, though. One of my clients mentioned that she also worked PST hours from Luxembourg and she found that she effectively had two days combined into one (since she was able to wake up at a reasonable time despite going to bed late).

I’m not sure how she did it.

Being able to do my best work

I initially thought that working in the evenings would mean fewer distractions.

This is true, except when your evenings are also when your coworkers are working! Writing this out I feel stupid but I never thought about this and so the emails didn’t stop and I didn’t really gain any focus time.

One thing I was right about, though, was that the dreaded 9am PST meeting turned into a much more productive and useful 6pm meeting.

At 6pm, I was sharp, ready to contribute, and found that I could pay attention for the entirety of the meeting. This would carry on till 10pm, after which I’d find it much harder to concentrate.

Speaking of meetings, I noticed something interesting.

Scheduling less meetings

My coworkers knew I was working late and most of the time, no one would book a meeting with me after 11pm.

This was surprising because I hadn’t actually told anyone not to book my calendar afternoon PST time. It was almost as if people naturally just felt uncomfortable making me sit through a meeting on mobile measurement attribution (I worked in Adtech) super late.

Could a similar approach be applied to my life now that I work normal hours again?

For example, would letting everyone know about potential obligations around 5pm limit afternoon meetings? Would knowledge of me working on things outside of work like volunteering or taking classes make them value my time differently?

The Slippery Slope of Remote Work

I made a mistake of conflating the ability to work remotely from a different country as almost an escape route from my day job.

The physical distance and time offset between my job and actual location convinced my brain that I was effectively “quitting” it and that I was now embarking on a new adventure.

This would have been fine if I had actually, well, quit the job, but some indecision eventually turned into a year of deliberation and that turned into this article.

I’ve noticed something similar with friends that view remote work as the antidote to working a job they dislike. If they’re able to find shortcuts and spend only two hours per day working, they’ve managed to “hack” the system.

Or maybe remote work gives them the freedom to travel around so much that the fact they actually hate their job gets buried under the shiny new town or monument they’re exploring.

Remote work can make it much easier to tolerate a job you dislike. You can slack off, avoid responsibility, invest time in other things during the day – but therein lies the danger!

It pushes back what should be your number one priority: to find work you enjoy.

I feel like if you wouldn’t do the job sitting in an office, you probably shouldn’t do it working remotely. No, I don’t think everyone should love their job, but you need to find it interesting enough to get better at, want to take on more responsibility, and keep progressing.


Moving to Madrid also gave me this amazing feeling of keeping my options open. Suddenly, it felt like I didn’t need to choose.

I was earning a Bay Area salary without being locked into a 12 month lease in San Francisco. I was working a fulltime job whilst having the whole day to try other things. I was on an H1B visa whilst living in Europe.

I was everywhere, all at once, and this made me feel very secure. It meant that I could postpone important decisions like where to take my career next or where to move almost indefinitely.

But when you keep postponing important decisions, you reach a phase called decision impotence.

Decision impotence is what happens when all your brain power is being used moving back and forth between decisions, but not taking action. “I’m thinking about it” is the land of safety and means we never really have to pull the trigger.

I kept “thinking about it” for over a year until I realized that by keeping all my options open, I wasn’t really pursuing any of them.

And that led to me starting a new job and moving back to San Francisco.

It’s funny, I traveled halfway across the world just to move back on the same street as my old house.

Now I’m back to the 9-5 grind and I’m loving it.

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