Starting My Work Day at 5 am is (Maybe) the Best Decision I’ve Made This Year

Many of the best experiences in life are totally unplanned.

I remember one of my last days in high school when the entire grade 12 class (all boys) hopped over the fence of the neighboring girls’ boarding school in the middle of the night and went streaking.

I made a wrong turn and — with nothing but running shoes on — stumbled upon a legion of young girls staring out of their dorm windows. Totally unplanned, 100 percent memorable.

*Yes, I’m well aware that this story is a little odd for a post about work, but hey, at least you found out something new about me!*

Whether it’s random high school moments, a spontaneous weekend adventure or a serendipitous encounter, we’ve all experienced the beauty of stumbling into something awesome.

Stumbling into a 5-am start

I work for an incredible company, with teammates scattered around the globe.

Most of us tend to work 9–5ish hours, and up until a few months ago I did, too. My schedule was pretty standard:

• Start work at 8 am
• Lunch at 12:30 pm — head home to eat and put my three boys down for their nap
• Back at work for 1:30 pm
• Finish at 4:30 pm

But a few weeks ago, this all changed.

I’m part of a three-person team, and recently we got the chance to build a new online product. But, before we could begin, we first needed to complete a five-day design sprint to validate the idea.

The other guys on my team live in Europe (I’m just outside Toronto, Canada) so I woke up early for those five days to spend as much time as possible together. It was a stellar experience to have Zoom (video call) running for the entire day as we brainstormed, built prototypes and gathered user feedback.

As the project advanced past the sprint, I no longer needed to be up early but I felt an urge to keep doing it. I’d stumbled upon a remarkable discovery:

I love starting work at 5 am!

My new daily rhythm

Here’s what my day looks like with this new schedule:

• Wake up at 4:30 am
• Team sync at 5 am
• Work until 11 am
• Break from 11 am to 3 pm
• Work 3–4:30 pm

The key part of this new rhythm is the middle section. From 11 am to 3 pm, I’m free to do whatever I want!

During this break, I typically hang out with my wife and kids until 1 pm, put my two older boys down for their nap, then head to the gym for an hour. I’m back by around 2:30 pm, at which time I grab a quick shower and meal then jump back in to work.

It’s so trippy to take a four-hour mid-day break but still smash out a full day of work.

The other added benefit is how this schedule affects my evenings.

I need to be sleeping by about 9:30 pm to feel fresh in the morning. Generally, I’m not doing anything super valuable late at night, so I find that most of my time awake is spent on activities that mean a lot to me (e.g. hanging out with my family & friends, fitness, reading, work).

Of course, I will stay up late if we’re we have people over or if there’s something I want to watch live, but I’m usually in bed a little after 9 pm.

The power of choice

I’m aware that most people don’t enjoy the same freedoms as I do at my company— the choice to work where and when I want. However, my new-found love for 4:30 am wake-ups isn’t just about when I start my day.

As I reflect on why this new rhythm makes me feel so great, I realize that they’re something deeper, something beneath the long mid-day break and the pride of waking up early.

It’s about the ability to choose.

In her book, The Art of Choosing, Sheena Iyengar describes an experiment where people were given chips to use at a casino. They were presented with two options for where to use their chips:

1. At a roulette table with one wheel.
2. At a roulette table with two wheels.

All the wheels were identical. So, which table did people prefer?

The table with two wheels.

Why? Because on that table, they could pick the wheel they wanted to play on, and that allowed them to feel more in control of their bet.

This experiment illustrates what many people really want— to feel like they’re in control of what they’re doing.

I’m incredibly grateful to enjoy this privilege.