The Automation Paradox is that the better our machines get, the more we struggle when they fail.

When heading out for a hike in the woods, it's tempting to skip the map and compass and rely on our phones and apps for navigation. Yet when we encounter no signal or lose power, we can find ourselves in a sticky situation. Or perhaps, like me, you've come to rely on popping your destination into the satnav or Google Maps whenever you get in the car and have nearly forgotten the ability to navigate without it.

These situations illustrate the paradox of automation, where the more sophisticated and automated our machines and technologies become, the more bewildered we find ourselves when they inevitably fail. Or: the smarter the machines get, the dumber we might get.

In his book Messy, Tim Harford suggests three strands to the paradox as our machines get more sophisticated:

Automation covers up our mistakes, hiding our incompetence, meaning we may not learn to correct ourselves—consider autocorrect cleaning up our typos as we go.

When we rely on automation, we get less practice for our skills, so even highly skilled individuals may find their expertise diminishing—perhaps you've found yourself using your phone calculator for a trivial calculation.

When the easy scenarios are taken care of, failures may occur in complex or unpredictable ways that we may find especially difficult to recover from—like a subtle but persistent failure in the steering of a passenger plane, recovering from a skid on an icy road, or when you're deeply lost in the wilderness.

More sophisticated technology can even make it useless or more dangerous when it fails. Older cars used to be reparable forever. Now, if your vehicle fails, it's likely to need plugging in at the dealership to figure out what's up. How many electronic devices are thrown away because somewhere inside, some tiny loose connection or component makes the whole thing worthless? Were pilots and flight crews better prepared and able to improvise before the autopilot became ubiquitous?

I often wish our devices would fail more like an escalator or an electric toothbrush. If an escalator fails, you can still walk up it. If your electric toothbrush dies, you can still use it to brush your teeth. These could be called Technology-Enhanced Products, perhaps. But when most of our devices die, they're often rendered worthless.

Automation and sophisticated machines help me so much. I did use Grammarly to help check this post. I use Google Maps nearly every time I put in my destination to home, and I often use a calculator to check my maths. But I do pay attention to grammar corrections, bring a paper map when I can, and keep trying to do the maths in my head.

But as Tim Harford explains it, we still face "the paradox of automation: the better the machines get, the more bewildered we are when the machines fail."

The Dunning-Kruger effect (send me proof of purchase of Big Ideas Little Pictures, and I'll send the sketch to you)

Tolkein-style landscape inspired by the excellent Lord of Maps.

The Automation Paradox

Public commitment pledges are a surprisingly effective and free way to help you reach your goals. A public commitment pledge is simply writing what you will or won't do, perhaps something you know you find hard, signing it and displaying it publicly.

In her excellent book, How to Change, Katy Milkman describes how the simple intervention of a public commitment pledge in doctors' offices significantly reduced prescriptions of unnecessary antibiotics—just through a poster on the wall. Commitment pledges are a form of what Katy calls a soft commitment device (of Odysseus fame). This strategy helps us stick to our commitments even when tempted to go astray.

Pledges may work through our desire for consistency and create cognitive dissonance when considering going against the pledge. The benefits of what we desire to do, say "eat cookies," are pitted against the potential guilt or discomfort we'd feel by going against what we said we'd do, not "eat cookies." You don't want to let yourself down. The pledge gives us a greater chance of sticking to our actions and a defence against our present bias.

Is there something you wish you'd do more of or less of? A simple public commitment pledge could help you on your way.

Other free ways to help you achieve your goals: Temptation bundling, The Fresh Start Effect, commitment device, Nine-enders, Implementation intentions

Public commitment pledge

Rose, thorn, bud is a simple tool for reflection for yourself or your team. The basic idea is to look back at a recent project or how things are going and consider each aspect of a rose:

Rose: what are the successes? What's gone well?

Thorn: what are the challenges? What could we do better?

Bud: what are opportunities with potential? What could we explore or try?

If running as a team retro activity or retrospective, you might spend a few minutes individually adding thoughts for each prompt, then talk through each of the thoughts in Rose, Thorn and Bud.

A separate but no less important step is often to capture actions from the reflection—what you'll do as a result. If you're conducting retros regularly, consider revisiting actions from previous sessions.

I like "rose, thorn, bud" as it's beautiful to consider that a rose contains such different facets, like so many things.

I've come across many retro and reflection activities that are variations of these three prompts: "What went well?", "What didn't go well?" and "What else?" A few to mention:

The sailboat retro: Goal/vision, Rocks, Wind, Anchor — a nice feature for a team is that this activity places you all in the same boat

Strengths, Weaknesses, Opportunities, Threats (SWOT)

A reader suggested a fourth aspect of the rose analogy to reflect on as its leaves or roots: what are the unnoticed or behind-the-scenes things that contribute to the rose's success?

I've come to consider that it doesn't matter too much what activity you choose to get a discussion going. What matters most is regular reflection, hearing all the voices in a team, and making progress together. One teammate ran an excellent retro by us all finishing early and heading to the pub.

I didn't intend it, but some of the products and prints for rose, thorn, bud out to be some of the nicest I have.

Also see: Information radiator, MoSCoW prioritisation, RACI, How to peel a Post-it so it doesn't fall down, the upward spiral

Rose, Thorn, Bud

Too many interesting articles to read? Too many places to visit? Too many projects to work on? Too many podcasts to listen to? Too many interesting things to learn? Try thinking of each as rivers, not buckets.

Oliver Burkeman shared a beautiful and powerful metaphor to reframe the bucket list of everything we want to do but can't possibly get done. There's an endless stream of books to read, programs to watch, and things you may want to get done. Instead of a bucket list to get through, try thinking of it as a river where attractive options drift by. Rather than feeling pressure to clear out the bucket or tick off all the items, instead, you can choose from the river what interests you in the knowledge that more will always come along.

This reframing resonated with me when I considered everything I wanted to read or the emails in my inbox. When you have too many emails, you find you answer the ones that really need answering. There will always be more. Growing up with a scarcity mindset regarding photos, I used to carefully trim each photo I didn't want after a weekend away or travelling. It was a revelation to me to consider selecting the ones I liked instead of worrying about removing every one that I didn't. 

Maybe you do have to get through everything at work, but this mindset doesn't need to apply to your personal life.

Don't beat yourself up. It's impossible to keep up with everything. Consider thinking of areas of your life like rivers, not buckets.

Oliver explains rivers not buckets in "Treat your to-read pile like a river". Or listen to Oliver reading the short essay in the Waking Up app.

Also see: The four pillars of too much, Lifetime reads, Tsundoku

Rivers and buckets

Feedback is how we get better. It's how we find out what we couldn't see ourselves. But there are many reasons why it's more challenging to gather than we might hope.

You might have a design prototype, a book or article draft, a new practice you want your team to adopt, or a project you've been working on. Feedback will make it better, but it's easy to feel anxious.

You might want to avoid having to talk to people. Maybe you're worried about what others think—perhaps they won't like it. Maybe you'll have to start over. Maybe you'll hear what you know deep down. Maybe you might see that others could do it better than you, that it shouldn't be you that's doing it. Maybe you'll find out that you're a failure.

If we care about achieving the best outcome, we can dispel most of these fears with a few moments of reflection—of course, I'm not a failure for trying!—but it doesn't mean they feel any less real at the time. As is often the case, action can be the solution, and gathering feedback is, in my experience, usually energising and confidence-building—now you can see what will make your project fly.

Jane Austen was known to read her novels aloud to her family for both evening entertainment (pre-Netflix) and to help revise and hone her writing.

Remember, the first draft is always perfect.

Don't take things personally or yourself too seriously.

Don't get attached to one option—attach yourself instead to a great outcome.

To avoid sunk costs clouding your judgment, seek feedback before you're too invested.

Share multiple options when you can. It makes it easier for others to give comparative feedback and reduces the chances of taking it personally.

Remember how valuable good feedback has been in the past.

Consider who to gather feedback from. Sometimes complete strangers can help (who cares if they don't like it?), and other times a friendly face can ease you into it.

Remember the spectrum policy to focus on the good in an idea.

Feedback fear

Sharpen the saw is a metaphor and story to remind us to refresh and recharge ourselves.

When you're deep in, it may feel like you have no time to pause. No time to take a break, there's too much to get done. Perhaps no time to stop and think about how you're working. No time to step back and improve your processes or work on your tools. Maybe even no time to look after yourself, to recharge, to reflect, to take a walk.

As the metaphor goes, you may feel you have no time to stop and sharpen the saw. Until you do it, and then you may realise you have no time to not stop and sharpen the saw.

Sharpen the saw is habit 7 of Stephen Covey's classic The 7 Habits of Highly Effective People

Sharpen the saw

Extrinsic motivation is the carrot or the stick — when the motivation for doing something is an IF/THEN reward or punishment. We use extrinsic motivation all the time like paying people to come into work, or issuing speeding fines to make people slow down. It can work well for simple problems, basic compliance, and short-term results.

However, when you need long-term behaviour change, when creativity is needed, or you're tackling complex problems, external rewards and the threat of punishments can even decrease performance and productivity. Rewards only go so far if you want to inspire a hit album, create the next Oscar-winning film, or create a breakthrough product. That is, for most of the important work we do in our lives, including I believe parenting, using extrinsic motivators of rewards or punishments is likely to be far less effective than tapping into intrinsic motivation — motivation that comes from inside ourselves.

I like Dan Pink's Autonomy, Mastery and Purpose framework for intrinsic motivation. His TED talk on the Puzzle of Motivation is also a fun and interesting watch.

Extrinsic motivation

A hybrid meeting is when some participants are in-person, using shared equipment, and some are remote using their own. Generally speaking, hybrid meetings have a number of disadvantages you may have experienced and are best avoided if possible. Perhaps you've been on a call where everyone's laughing about something except the people joining remotely who have no idea what's going on. It can be pretty rubbish.

For the in-person participants, it's easy to chat with the people in the room, but with just one person controlling the screen it can be hard to see details of any docs that are shared, and it's difficult to see the remote participants as clearly as those in the room. Those not driving also can't scan through docs at their own pace, or share a screen, or collaborate on a document. It's like having just one person with access to the whiteboard.

The remote participants have it worse. Because the camera is likely not as good for the in-person participants the people are smaller and it's hard to see expressions or track who's talking. Some may be off-picture. Without seeing expressions, and with a delay even a tiny bit longer than being in-person it's much harder to find when to join in a conversation. The sound quality ƒrom the room will often also make it harder to hear some of the participants and because the shared mic won't be on mute there'll be background noise.

Taken together these disadvantages make hybrid meetings best avoided where possible.

Where possible, for the in-person meeting have everyone use their own equipment, joining the call on their own laptop so their video is clear and if not using headsets buy a high-quality speaker.

Thanks to GitLab whose list — hybrid calls are annoying — made the disadvantages much clearer to me and led to better meetings at work.

Hybrid meetings

Yak shaving describes how when setting out to do something, you found you had to first do something else, which needed you to finish this other thing, and so on until you found yourself shaving a yak, or equally unrelated activity, to do the first thing you set out to do.

It's pretty frequent in life — tidying your room? — and particularly resonates in software development, where when tackling one thing, you often find yourself fixing something else, which needs you to fix something else, and so on. Here's the ever brilliant xkcd on fixing problems.

Yak shaving features, lovingly polished, in my book Big Ideas Little Pictures.

Here's a brilliant 40s clip of Hal changing a lightbulb from Malcolm in the Middle, classic yak shaving

Early yak shaving features in the song There's a Hole in My Bucket in which fixing a bucket requires straw, which requires a knife to cut it, but the knife needs sharpening, which needs a stone, which is too dry and needs wetting with water, which needs fetching...with a bucket

The first I found of yak shaving was a short article on productivity in the first issue of Make magazine by Danny O'Brien and Merlin Mann.

Yak in the style of Alison Green and Adam Stower's excellent children's book, What can you Stack on the Back of a Yak?

Yak shaving

One of the simplest and most effective behaviours that you can try to help you level-up is to keep creating forcing functions for yourself. A forcing function is an external stimulus that makes you get to where you want to be. Signing up for an event so that you are forced to get yourself in shape, offering to give a talk so that you learn your material, inviting people to a dinner party so you get your house in order, paying for a personal trainer to make you turn up every week — all useful forcing functions to get you from where you are to where you want to be. Forcing functions play, very effectively, on our fear of letting ourselves down to make ourselves do what we want us to do.

Another useful sense of forcing function is a way to help people make fewer mistakes, like putting your passport on the door handle so you can't forget it before your flight.

Forcing function

In Manager Time a day is neatly sliced up into hourly chunks according to the calendar. Meeting someone is as easy as finding a free slot that coincides. You don’t have to worry too much about what you’ll be doing next as your calendar will tell you.

In Maker Time a day is an open book to get something hard and meaningful done. Even thinking when a meeting might be and remembering to go can distract from getting on with making. Long, uninterrupted chunks of time, not sliced and diced by meetings on the hour are ideal to make progress on hard problems and tackle something new. Even a single meeting in the middle of an afternoon can disrupt that long meaningful chunk into two that make it harder to tackle something big as you have to context switch and pick up where you left off.

Most modern offices operate on Manager Time. It’s great for meetings but comes at a cost for getting meaningful work done. If you’re a maker you may associate with the feeling that to get some real work done you feel you need to do it at the weekend, or in an evening after everyone’s gone home, when you’ll be free of interruptions.

If you’re a manager, consider your makers when you schedule your next meeting.

If you haven’t already, you should read the original article Maker’s Schedule, Manager’s Schedule, by Paul Graham from whom this excellent observation is from.

Manager time, maker time

Sometimes we’re smart enough to know that we’ll have trouble doing something we want to get done. That might be going to the gym, finishing that essay instead of goofing around, quitting smoking, doing your taxes, or, if you happen to be Odysseus, listening to the sirens’ song without going crazy and diving in the water or driving your boat to be crashed on to the rocks.

In these cases, you can try a commitment device: a voluntary restriction to help maintain our future self-control. In Odysseus’s case he instructed his men to fill their ears with wax and to bind him the mast and told them if he asked them to let him go then they were to bind him tighter. In this way, he managed to listen to the sirens’ song without ending up at the bottom of the sea.

Other commitment device’s may be more mundane, such as publicly announcing to your friends that you’re going to do something, paying a bunch of money to sign up for something upfront, or handing a $20 bill to a friend with instructions not to give it back until you’ve done what you’re supposed to.

Here are some nice examples of commitment devices.

Commitment device

The more transparent your workplace the less transparent your employees. In an age of trackers, wearables, online monitoring, workplace chat and always-on devices it turns out that not only does a more transparent workplace actually drive people to more secretive behaviours, but that adding a little more privacy actually may improve productivity also.

Very simply, the transparency paradox is the idea that increasingly transparent, open, observable workplaces can create less transparent employees.

See Harvard prof Ethan Bernstein’s The Transparency Paradox study (pdf) or I learned about it from the Freakonomics podcast: Yes, the Open Office Is Terrible — But It Doesn’t Have to Be.

The transparency paradox

The Peter Principle (book) states that “every employee tends to rise to his level of incompetence.”

Someone who is good at their job is likely to get promoted. However, the promoted position will likely require different skills. If they’re good, they may get promoted again, but if not, they will stay. At some point, each employee in an organisation will be incompetent at their position.

I like this short take on the Peter Principle by Tim Harford.

The Peter Principle is a specific case, the case of people, of the Generalised Peter Principle which states that "Anything that works will be used in progressively more challenging situations until it fails." See rule number 1 of indoor games.

The Peter Principle was an observation originally meant as satire. Laurence Peter later wrote a book called The Peter Principle: Why things always go wrong.

The Peter Principle

It’s easy to think “it’s just a few minutes.” But as the number of people that you hold up increases, the true cost of being late scales rapidly. Being 10 mins late to a meeting with 10 others is 100 minutes. Holding the door for 20s on a train of 600 people is over 3 hours of time collectively. Unless your time is worth a lot more than everyone else’s it’s worth thinking twice before holding the door to a train or not taking the start of a meeting seriously. I think, at the end of the day, it’s really about respect.

The cost of being late

A streak — achieving something on a schedule without missing a slot —  has a remarkable pull over us when it comes to helping us get things done. As Seth Godin points out, streaks turn an activity into a game. And while we may have started out with the intention simply of completing the activity, our continued motivation can transfer to simply be the motivation of keeping the streak going.

If you’re into streaks or want to give them a try to achieve something yourself, you might like the Streaks app (which is how I knew I’d done 2 years without missing), Austin Kleon’s 30-day challenge, or the simple power of one-a-day.

Streaks can also have a dark side: if you break the chain you can think it’s not worth getting started again. For that reason, I like James Clear’s advice to never miss twice.

The power of streaks

The Pomodoro technique, or Pomodoro method, is a super simple method to help you get your tasks done. Named after a pomodoro (tomato) kitchen timer, the essence of it involves considering in advance how many pomodoros you might need for what you want to get done, setting your timer for, normally, 25 minutes and then focusing on your task until the time’s up. Then take a 5-minute break. That’s one pomodoro. After you’ve done four pomodoros take a longer break, of about 30 minutes.

Protect your pomodoro from distractions — make sure that you spend the full 25 minutes on your task. If people want things let them know you’ll get back to them after your pomodoro.

Properly break in your breaks — no sneaky working.

It’s flexible, not rigid. If you need longer or shorter times, that’s OK. It’s about what helps you focus.

You only need a timer, but there are a number of simple apps that can help if you want to try it too, like this nice one with a bear: Bear Focus Timer.

The Pomodoro Technique ® was created and named by Francesco Cirillo.

If you like the Pomodoro Technique, you might also like the other sketches of my toolkit for life in my book Big Ideas Little Pictures, which even has a lovely review from Bill Gates.

The Pomodoro Technique ®

These are a super useful trick to increase the chances of action, be it your own others. Essentially, a vague intention of “I plan to do that,” is much less likely to be followed-through on than if you get specific. It takes out the ambiguity of when and where you’ll do something because that’s already decided. For example, asking voters simple questions like how they’ll get to the polling station has been shown to increase turnout on the day. You can use this to your own advantage too — get specific with yourself to help you get things done, be it how and when you’ll workout, or when you’ll study or whatever.

Here’s a simple template for implementation intentions you could try:

I learned this, and many more tips, from James Clear’s book Atomic Habits, all about how to create good habits and break ones.

Implementation intentions

The Doorstep Mile is a brilliant Norwegian concept for how the hardest part of a journey can be just getting out of the door.

So, sometimes, as Seth Godin would say, the most important thing is just to start — start small, start now, step by step, day by day, and you can give yourself the chance to make something amazing.

Got something you’ve been meaning to start? Maybe today’s the day?

When I created this sketch, it was my 104th in consecutive weeks — 2 years of weekly sketches without missing — and sketchplanation number 583 in total. And I can tell you that it didn’t start glamorously, and they weren’t high quality or even interesting, but I did start. Sketch by sketch. Week by week.

More sketches about starting and getting started.

The doorstep mile

UPDATE: Since releasing this sketch, which is a fair summary of Kamal Meattle's TED talk, it's been made clear that, though plants do improve air the improvement doesn't compare with a simple change like opening the window. The original "plants improve air quality" study was done by NASA in an environment wholly unlike having a few plants in your living room. Listen to James Wong explain the situation in the Sketchplanations botany podcast.

In his 4 min TED talk, Kamal Meattle explains how to grow your own fresh air inside with just 3 common house plants. The areca palm works hard during the day, the mother-in-law’s tongue during the night, and the money plant cleans out volatile chemicals. He transformed the air inside a New Delhi office park by filling it with these three plants with seemingly some wonderful health and productivity benefits.

Though plants are undoubtedly lovely to add to your office and home, see the update above for the caution around it.

How to grow your own fresh air

The sweet spot for flow and mastery where the task is not too easy, not too hard — it’s just right. 

Also, just the right spot for learning similar to Vygotsky’s zone of proximal development. In that model when you’re out of your comfort zone, and not in your anxiety zone you’re in the learning zone.

And yet another way of looking at it, still without as catchy a name as Goldilocks tasks, is getting the right match of challenge to your skills to avoid anxiety and boredom to be in flow.

 I learned the name from Dan Pink’s excellent book Drive.

Goldilocks tasks

Shares information passively, with the neat effect that having a good one in an office can go a long way to getting people on the same page without explicitly calling meetings or sending out updates to do so. Handy to also have a good space in front of it for talking, discussing and generally collaborating. A common term in agile development, originally I believe from Alistair Cockburn of Thoughtworks. To quote from his article, of many possible:

- Is large and easily visible to the casual, interested observer
- Is understood at a glance
- Changes periodically, so that it is worth visiting
- Is easily kept up to date”

Information radiator

The simple fact that the start of something, pretty much anything, means we’re more likely to try something new. Be it your birthday, your next house, a new day or a new country, these turn out to be great mental triggers for us to get started.

For more, you could do much worse than listen to Katherine Milkman, an assistant professor at The Wharton School of the University of Pennsylvania, on the Freaknomics podcast: When Willpower Isn’t Enough.

The fresh start effect

More value will likely be found through analogy than the shipping situation. Watch out for barnacles on your project. One by itself is nothing, but enough of them can cost you.

Watch out for barnacles

Some activities, no matter how much time you spend on them, just keep coming back. These include cleaning, ironing, washing up and watching the news. There’ll always be more tomorrow. If I can, I try to spend time, first, on activities that have a lasting impact, even in a small way. Better to be tired tidying the kitchen than too tired to start that project you care about. If possible, forget about news entirely. I have consistently found that when we’ve been out of touch traveling for some weeks, the world has carried on plenty well enough without me.

Unfortunately, you still have to do the others sometimes, just try not to let them push out the other things. As you can imagine, this leads to a delicate household balance.

Spend time on activities with long-term value first

How to get into flow at work? Match challenge with skills.

When your work is too hard for your skill you experience anxiety.

When your skill is too high for the work you experience boredom.

When your skill is matched with the challenge of the work then you can experience flow.

This simple framework comes from the deep insights of the work of Mihaly Csikszentmihalyi and his book Good Business.

Match challenge with skills for flow at work

How to peel a Post-it™ so it doesn’t fall down: pull flat and straight.

This is helpful if a) you use Post-Its™ a lot, and b) you need them to stay up and don’t want them raining to the ground.

Typically, people pull Post-Its™ by starting from a corner and pulling it off diagonally. This leaves one corner itching to peel away from the wall. Once it starts peeling, it will dry out, and the rest will follow.

Believe it or not, on a rainy day, I even recorded a video about how to pull a post-it so it doesn’t fall down. And we did do some tests.

I learned this technique while at Jump Associates, where we used a lot of Post-Its™, and who, I believe, learned it from some people at 3M, manufacturers of the Post-it™.

This sketch, lovingly polished, is one of many featured in my book Big Ideas Little Pictures

Peel a Post-it so it doesn’t fall down

OK, so this seems like the most complex yet, but I find myself doing this small and rapid series of key strokes many times a day and it saves a whole lot of fiddling.

Update: Several people have helpfully pointed out to me that you can do this better and more easily simply with Control + shift + v on PC and Command + Alt + Shift + V on Mac. More time saved!

Remove text formatting

A few minutes of writing each day or a sketch can end up as a book (like Big Ideas Little Pictures)

One piece of litter from each of us ends up as a trash heap, or a small souvenir taken with you can mean nothing is left for anyone.

Thanks to Seth Godin for sharing the simple power of one a day. Sketchplanations was founded on this principle.

Enough molehills make a mountain

Arrange kitchen storage to minimise excess travel

Something I try to keep in mind whenever I set to thinking and run out of space. As much as possible, find tools that don’t limit your thinking.

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Category: productivity