negotiating a three day workweek

how i did it, why i did it, how it's going, and where it's headed

Quick Overlay update: I finished my seventh code livestream … It’s coming to life!

Hey everyone,

Last June, I asked my boss if I could work three days a week while retaining my full-time salary.

After a few months of finishing up ongoing projects, it finally happened. My work calendar started to look like this on Thursdays and Fridays:

How I Did It

I. I tried it out first.

Before asking my boss, I wanted to prove to myself that a shortened workweek was possible. What did I need to do differently to get my work done in less time?

There’s a lot of existing literature on this. I ended up trying out many of the ideas popularized by Cal Newport in his wonderful book Deep Work.

1. I reserved 9am-11am for the most challenging work I had to do on a given day.

2. I checked my email only twice a day: once around 11am and again around 4pm.

3. I paused all notifications in Slack and kept my phone on Do Not Disturb.

4. I asked clients and teammates if we could limit meetings to early afternoons on Mondays, Tuesdays, or Wednesdays.

5. I chose the two most challenging things I needed to get done in a given day. If I got those done, I didn’t immediately jump to a third hard thing. That could wait for tomorrow.

In short, I had to learn how to say No, a lot. I didn’t always succeed in asserting my boundaries. Or even following these rules.

But putting these tactics into practice vastly freed up my schedule. I had two uninterrupted chunks of time almost every day. I discovered that by Thursday and Friday, I barely needed to do any work at all.

II. I leveled up.

In order to truly work less, I needed to work on the most important thing, day after day.

Figuring out what was most important became a skill I had to develop. Through trial and error, I noted four necessary sub-skills:

1. Defining Success — what exactly are we trying to accomplish?

2. Decision-Making under Uncertainty — what are we most scared of going wrong? How do we address risk?

3. Communicating Usefully — what does everyone involved need to understand?

4. Executing — how do we actually do the work?

These four combined require a lot of focus, creativity, organization, and teamwork.

Again, a lot of great work has already been done here. So I chose a few writers whose perspectives most resonated with me, and then I studied them and put them into practice:

• Deep Work: Rules For Focused Success in a Distracted World

• Perennial Seller: The Art of Making and Marketing Work That Lasts

• Shape Up: Stop Running in Circles and Ship Work That Matters

• Marc Andreessen’s Guide to Personal Productivity

III. I talked to my manager.

I have monthly 1-on-1 calls with my manager Brian to chat about how things are going. Once I proved out the shorter workweek to myself, I brought the idea up with Brian. He loved it.

Having someone else on the team who was intrigued and supportive of what I wanted to do really helped. I no longer felt like I was doing something shady or off limits. Plus, telling Brian was a good rehearsal for telling my boss.

IV. I made the request via email.

This isn’t a perfect email. But it had three components that I believe worked to my advantage:

1. I made a clear ask that was short and scannable.

2. I framed it as a negotiable experiment.

3. The founders already had a lot of trust in me.

I continue to be shocked by how effective short and direct emails are. “Make it very easy for someone to help you” is the name of the game.

The first version of this email was much longer. I had several paragraphs explaining my reasoning and preemptively defending my proposal.

But all that prose would only matter if they said No. And I was pretty confident they would say Yes, or at the very least Let’s Chat.

One of the founders responded to my email later that day. He would discuss with his co-founder and get back to me before the weekend.

He responded on Friday afternoon:

I think we can make this work :) Let’s chat next week.

We then scheduled a Zoom call, talked logistics, and agreed to give it a shot.

It took a couple months to truly shift to the three-day workweek. I had to get better at asserting boundaries and not feeling guilty for my new hours. But it finally happened, and I’m 3 months into this new arrangement.

Why I Did It

I drafted a longer explanation, but the short version is this:

My self-worth should not be so strongly tied to how I make money. Yet I had spent the best hours of every day for the past decade fashioning beautiful golden cuffs and tightening them year by year around my wrists and ankles. What is it all for?

This observation has churned through my mind for the past while. I finally developed the nerve and the skills to try a different approach.

How It’s Going

All of humanity's problems stem from man's inability to sit quietly in a room alone.

Blaise Pascal

Here’s a sampling of how I have spent my Thursdays and Fridays:

1. I drove to the beach a few times

2. I spent entire days reading and writing and roaming around Brooklyn

3. I started grabbing impromptu coffee and meals with close friends

4. I deepened my meditation practice

5. I studied jazz piano with Noah Kellman

6. I continued my coaching sessions with Justin

7. I picked up tennis again

8. I decided to start working on what is becoming Overlay (!)

And here are some of the challenges I’m discovering with this new schedule:

• The more effective I’m getting at work, the more people want my time. So I’m becoming more protective of my schedule.

• I have to be okay with not “killing it” at work all the time. Performing at 75% capacity rather than 90+% is tough for an overachieving perfectionist.

• I spend less time distracting myself with work. So my mind fills this void with a root fear: the fear of insignificance. As a result, a change. The heroes of my twenties were titans of industry and rebellious musicians. I still admire their chutzpah. But now my heroes are the people whose lives we glazed over in grade school: Buddha, Diogenes, Carl Jung, etc.

• Career uncertainty. Do I still want to work in tech? I sorely miss the community and service dimension of life. I miss being on my feet, using my body more, working alongside other people.

• Resentment of homo economicus — I have been trained to be a productive worker bee in the technology industry. What would I do differently if making a lucrative salary wasn’t such a force? Who am I beneath all the choices I’ve made to afford my current lifestyle?

Much to ponder… Thanks for reading. Hope you found this rundown useful.

Ammar