Odysseus and Intentionally Inconvenient Design

You perhaps know the famous story of Odysseus and the Sirens.

In Greek mythology, the Sirens were famous for their gorgeous singing. So very beautiful was their signing that any sailor who heard their songs would stop sailing their ships to listen. With no one steering the ship, the ship would crash, and everyone who heard the Sirens’ songs would die.

In the great Greek epic the Odyssey, the hero Odysseus avoided this trap by telling his men to block their ears with wax. And then he ordered his sailors to tie him to the mast so he could hear the Sirens’ songs without doing anything stupid like intentionally crashing the ship so that he could hear more songs.

Lo and behold, it worked. By planning ahead of time to avoid temptation, Odysseus managed to experience what was most beautiful in his voyage home without killing himself.

Given that this was written about 2500 years ago, it’s clear that the human struggle with what we know will tempt us as opposed to what we know is best for us is nothing new.

But I’m of the opinion that the struggle is harder now than it has ever been. That capitalism is an evolutionary process that continues to push the boundaries of what tempts us, and to continue to make it harder to resist. Every new day, we are faced with the most potent new forms of temptation known in human history.

This makes Odysseus-like skills at avoiding temptation more important than ever.


Last year, I was listening to one of my favorite podcasts, 99% Invisible, and I learned about the concept called “unpleasant design.”

According to the show:

Benches in parks, train stations, bus shelters and other public places are meant to offer seating, but only for a limited duration. Many elements of such seats are subtly or overtly restrictive. Arm rests, for instance, indeed provide spaces to rest arms, but they also prevent people from lying down or sitting in anything but a prescribed position. This type of design strategy is sometimes classified as “hostile architecture,” or simply: “unpleasant design.”

Unpleasant design is an intentional structure that’s designed to make you uncomfortable. What a brilliant idea! Using discomfort by design to deter certain behavior.


Given the challenges that I have in keeping attention focused when I want to focus, I have often thought about the idea of tying myself to the mast in designing my own workspaces. To do work, you have to go online. But when you’re online, the entire information age with all of its increasingly well-cultivated attention traps are there to tempt you. It’s not easy for me to get what I need to get done without hearing the Sirens’ song of web temptation and crashing into a rabbit hole of internet distraction.

So I’m constantly working on better ways to filter the internet I need to use from the internet that is taking me away from what I need to do.

What I’ve been working on is a concept I call “intentionally inconvenient design.” It’s stolen from the idea of unpleasant design, and the basic thought process is that I need to be able to search for things. But the internet now proliferates with sites and attractions that make it hard to do just the bare minimum online, which means I tend to spend far longer online than I need to when I go online.

My solution is to make it difficult to go online, particularly to sites that are not designed for productivity.

This is still a work in progress. But here are a few things I have done to improve my own work environment:

  • I use a service called “stay focused” that gives me a nuclear option to block all sites except for certain allowed sites while I am online.
  • I’ve created impossible-to-remember 25-30 character passwords for Twitter and Facebook. I then printed them out and put them in my sock drawer, and I don’t keep them anywhere on my computer or other devices. That way, if I really want to access social media, I can. But it’s not easy. I have to really want to do it or it’s not going to happen.
  • I created a slightly-less challenging password that I must manually input into my computer ever time I want to use an internet browser.
  • I have a sit-stand desk with a ball. I alternate between sitting on a ball that’s tiring to sit on for too long and standing, which is also tiring to do for too long. That way, my work time is more concentrated and intentional.
  • I try to never use the internet while sitting comfortably.
  • I store my iPad in the least convenient place I can, in a closet in the least-used part of my house.
  • I have a 4-year-old iPhone with cracked glass and an internet browser that does not work well. The phone will not be replaced until the “phone” feature stops working.
  • I put all desserts in a crawl space only accessible by a rickety ladder and in a 24-inch stainless steel safe that is protected by padlock.[1]

I appreciate that all of these mechanisms are kind of ridiculous. But as silly as they all seem, I think they help. It’s much easier to go online and let my attention wander rather than doing the things I know will make my life better. And, without prior restraint—true to Zipf’s Principle of Least Effort—that’s what I do. Unless I tie myself to many different metaphorical masts throughout my day, I waste much of my day.

The whole world of information and entertainment is right there, at our fingertips, every minute of every day. That’s gotta be every bit as tempting as the Sirens’ song, right?

[1] This one isn’t true.