A productive creative

I recently reflected on my productivity and discovered, to my horror, that I’m doing pretty badly! I used to be very organized and do lots of creative, important work consistently every day for months on end. Somehow, I had lost that in the past 3-5 years.

Doing what comes naturally is a lousy method for doing open-ended, highly uncertain things with no short-term feedback, like finding product-market fit. It is all too easy to lose yourself into doing nothing for days on end while still feeling like you’re making progress.

After discovering this issue, I made a small change: using Pomodoros. That means doing almost all work in 25-minute chunks with 5-minute breaks between them, using a timer to tell you when a chunk/break is over, and taking it seriously.

Even though the Pomodoro is a simple technique, it forces several useful work patterns.

Timeboxing. Even the most annoying task is approachable when you decide to do it for a maximum of 25 minutes (total, or at a time). I’ve started using smaller timeboxes as well, like setting a 5-minute timer to “find potential engineer referrals for company X in my CRM.” Artificial timeboxes help babble a lot while pruning less — which is great for divergent thinking.

Focus bursts. I often used to work an hour or two straight and end up fatigued and unable to focus on the next task. With Pomodoros, work happens in intense bursts, with refreshing breaks between, so I’m doing my best work most of the work-time. Being graded on the top 1% of your work, not the top 80%, this is definitely a positive.

Intentions. I write down an intention for each Pomodoro, with the help of Complice, my daily planning app. That reinforces the focus: whenever you find yourself lost halfway through the 25 minutes, you review the intention to get back on track.

Working off-caffeine. On caffeine, I tend to be narrowly focused on a task, which works great for executing in a known direction. But choosing a good direction seems easier off caffeine, as I’ve discovered having been drinking decaf for the last two months. Off caffeine, 25 minutes seems to be about the right chunk of time I can keep my undisturbed focus on one thing.

Chores. Five-minute breaks are great for knocking out tasks that don’t require or deserve much focus. During breaks, I tend to walk around the house and let my head clear a bit. Doing so, I naturally complete small tasks without spending much willpower: tidying up, shaving, putting away dishes, starting laundry, responding to friends’ messages, etc.

Coordination. Sometimes you want to coordinate with people in the same room: significant other, colleagues, etc. I wear a cap during focus time and take it off for breaks. This lets me focus deeply while giving others a simple cue for when they can disturb me. It’s also a good physical reminder of the current context — a thinking cap.

Here are a few examples of tasks I’ve worked on — I was happy with the outcome in each case:

• 1 pomo: create journey map for <product>
• 8 pomo: build Google Slides prototype of <product>
• 2 pomo: reach out & schedule tomorrow’s user interviews
• 1 pomo: do a convergent thinking exercise
• 1 pomo: try out Vercel serverless functions with neural nets
• 1 pomo: pronunciation exercises in ELSA
• 2 pomo: write into Substack