How much mess do you embrace in business? Should you be embracing a more Messy business?

Is it possible to take the ideas in books like Deep Work (my review) too far? Can you lock yourself away to focus on the work at hand and miss out on your best creativity?

This is the central thesis of Messy by Tim Harford.

The argument of this book is that we often succumb to the temptation of a tidy-minded approach when we would be better served by embracing a degree of mess.

He contends that we stop digging in to things, we stop being creative, when things line up ‘just so’. If we embraced a bit more mess in our work and lives, we’d generate better ideas. If we addressed the messy issues in our life instead of letting them lie fallow, we’d have stronger relationships. Just not neater ones.

We prioritize neat over effective.

I’m sure that’s not what you intend. It’s certainly not what I intend as I embrace focus in my life, but do we fall in to that trap?

Lets dig in to Messy to find out.

Harford addresses a different aspect of how messiness can help us in each chapter. Starting by addressing how embracing a bit more unknown can help our creativity and carrying it through collaboration, our workplaces, and ending with automation.

Chapter 1: Creativity

If you rely on transit to get places stop and think about what a strike would do to your commute? I bet that thought stresses you out. Back in 2014 there was a strike by the workers of the British underground. While it threw much in to chaos, a number of commuters actually got benefit from it. As they looked for new routes to their work about 1 in 20 stuck with the route after the strike.

Would they have started to look for a new route if there wasn’t a strike? Likely not, we love to stick with whatever we are currently doing because it’s easy and working. Presumably the new route they stuck with has some benefit and they only found it because of the mess of the strike.

What about in your work. Do disruptions help you? When things go wrong does it help you find a better option?

Messy disruptions will be the most powerful when combined with creative skill. The disruption puts and artist, scientist, or engineer in unpromising territory – a deep valley rather than a familiar hilltop. But then expertise kicks in and finds a way to move upward again: The climb finishes at a new peak, perhaps lower than the old one, but perhaps unexpectedly higher.

One fault in this first chapter is that it seems to make the assumption that it’s talking to masters not apprentices. When your starting out and ‘mess’ gets tossed up in your face you have no basis to even come up with a new idea or way around the mess. It’s a problem and you don’t have the information yet to evaluate the possible great options that come out of it.

Only as someone with experience do you have that experience. I fear that many the apprentice will read the book and assume that they should embrace the mess on their way to mastery when really what they need to do is put their head down and get the experience they need.

Distractable brains can also be seen as brains that have an innate tendency to make those useful random leaps.

Harford cites Brian Eno who takes an interview to his music room. He does this because there is a hugely distracting conversation happening outside during the interview. His room is a jumble of instruments and inspiration. What’s missed in the book is that all the mess is tied to making music. There isn’t a phone constantly sending social media notifications and lots of other things that distract from the creative task. In fact, he went there because it was a place of focus. He pulled himself out of the distraction of the street.

Eno’s music room is all geared towards a master getting the most focus in his music.

Don’t be one that confuses the ‘mess’ of creativity with the distraction of not doing the work you need to do.

Chapter 2: Collaboration

Is the best way to collaborate to interact far and wide, spread you ideas as it were. Or should you be ‘locked away’ with a few team members intensely focused on producing something of value.?

Turns out, it’s a bit of both.

Most tasks require a combination of bonding and bridging: flashes of inspiration to identify the right approach, and long effort characterized by selfless teamwork. To put it in to practice

Getting the diverse ideas of a large group is a great way to get a project going in a creative way, but then you need to sit down and do the work.

Harford cites a great study to show you us the importance of bridging. Given a jury of white and black people judging cases of black or white people in crime you get a much more ‘just’ verdict if the jury is mixed race. If it’s all white people the sentencing is harsh but with black people on the jury it’s a much more moderate decision. The presence of black people on the jury causes the white people to evaluate their ideas of justice harder and make a different decision.

There are a number of other examples that lead us to the conclusion that when our ideal get challenged by those ‘outside’ our group we come up with much better ideas.

This goes counter to the great HR push to make sure that people ‘fit our culture’. We know that this is often code for ‘people like me’ and given the research presented in Messy, we know that if you’re going for a solid culture mesh all the time, you’re going to be giving up on many great ideas that would come if you embraced challenge.

Chapter 3: Workplaces

Ugh cubicles suck. Who wants to have their work environment dictated all the time. In Messy, Harford talks about one company that even dictated if you were allowed to have a pen on the top of your desk. In theory this ‘tidy’ work place meant that you could work free of distraction.

Instead it turns out we like to build our own productive environment.

People flourish when they control their own space.

As you build a team or office that means you need to empower people to decorate the office. They should be able to put the transformers they collect on their desk. In this control, you’ll get the happiest most effective workers.

No it may not look as pretty as the renderings you were provided with, but your goal isn’t pretty. Your goal is to get work done well.

Chapter 4 Improvisation & Chapter 5 Winning

I’ll tackle these chapters together because I think they were the weakest. Chapter 4 told us not to stick to a script. Be willing to roll with the punches like Martin Luther King who’s famous “I have a dream” speech was not really what was prepared.

Then Harford tells us to be careful and cites many of the recent US political gaffes. Unfortunately that’s about where he ends. There is little guidance about when to choose the script or to wing it.

We just have to guess.

Chapter 5 used lots of war examples. German generals who went off script and over extended their troops to take some advantage over the British in Word War 2. Donald Trump always being random and forcing the other candidates to respond to him.

Again, there is little direction on when to do this or how to do it effectively. Hardford cites a bunch of people that did it successfully but doesn’t really answer the counter point of all the others that tried it and failed spectacularly.

With a bit more direction on how to decide between messy and random and planning, these chapters would be much stronger.

Chapter 6 Incentives

We all want to reward good behaviour so that we get more of it. The question is, are we rewarding for the right behaviour? What other consequences can come from the standard we set.

Think back to the recent Volkswagon emissions issue. They performed well in the automated test done at the predictable locations but if you strapped the emission testing equipment to the car and drove around you got a different result.

Because the tests were predictable they were gamed, and this wasn’t the first time. Major truck manufacturers were caught doing the same thing years ago.

There are many other examples provided and one main guidance. We need to make sure that the metrics we put in place don’t have the bad result of people only performing well on the metric to the detriment of everything else.

You should have many metrics and then choose one randomly to test. The lack of standardization ensures that you will get the best overall result.

Chapter 7 Automation

Automation oh how I love thee. By making my call calendar run by Calendly and using Zapier to connect to Zoom I can send a single link to someone that wants to talk with me and I end up with a single link to click to connect for a phone call.

This is a great thing for me, but automation can have dire consequences.

Harford tells us the story of an ill-fated flight that 99.9% of the time ran on autopilot. This meant that when things went bad and the auto-pilot needed human intervention the humans weren’t used to flying without help and crashed the plane.

Because they had almost no practice flying in the basic situations they made bad decision after bad decision and killed hundreds.

The rarer the exception gets, as with fly-by-wire, the less gracefully we are likely to deal with it. We will assume that the computer is always right, and when someone says the computer made a mistake, we will assume they are wrong.

It also extends to things as mundane as the phone numbers we can no longer remember because we store them in our phones.

This problem has a name: the paradox of automation. It applies to a wide variety of contexts, from the operators of a nuclear power station to the crew of a cruise ship to the simple fact that we can’t remember phone numbers anymore because we have them all stored in our cell phones and that we struggle with mental arithmetic because we’re surrounded by electronic calculators. The better the automatic systems, the more out-of-practice human operators will be, and the more unusual will be the situations they face.

For us it means we need to introduce times of challenge. I do this with my kids on canoe trips where we practice flipping the canoe, we take a short paddle from camp with no gear in the boat. Then we intentionally flip the canoe and practice getting everyone back in. Sometimes we do this when there is a bit of rain and wind coming in so that we are used to these less than ideal circumstances. We practice when the conditions are less than optimal so that when we are forced to be out in the bad weather we are ready to deal with it.

Chapter 8: Resilience

While we’re past the days of segregated neighbourhoods by law (or because you just didn’t sell a house to ‘those’ people) we still are in a world with a surprising lack of diversity.

We all feel more comfortable when the people around us are ‘like us’. This goes is very similar to the research cited in chapter 2 with the trials. When we have all of our neighbours share our views, we are never challenged. We sit safely in our confirmation bias.

Far from a more secure safe neighbourhood, we will have a more robust neigbourhood culture if we embrace diversity. That means apartments beside houses beside townhouses. That means no clustering of similarly priced homes and apartments on the same streets. We need to break them up so that people of many incomes can live in close proximity.

This will help us be more resilient. It will help the community feeling in our neighbourhood. It will help our children be more resilient when they encounter struggles.

Chapter 9 Life

How many times does this conversation play at a networking event?

You: Hey how are you?
Them: Busy, and you?
You: Busy.
Them: great
Both: awkward silence

Do you really get to build a deeper relationship with that person you wanted to connect with? Not in any fashion at all, but in theory that’s the goal of a networking event. To build the trust with a possible client so that they feel safe purchasing from you. Yet we repeat this terrible conversation over and over and wonder why no one purchases from us.

Instead ask questions they don’t expect. Maybe:

Where was your last vacation?
Did you miss any business goals this year?
What was the hardest thing this year?
What’s the big dream you’re working on currently?

Here we may actually get real questions answered and build some real trust with the person across from us. Both of those things are the point so instead of valuing comfort, value effectiveness and change the script you use at a networking event.


Overall, Messy is a good read. I think that a few chapters are weak, specifically 4 and 5, but they weren’t terrible.

The big takeaway from the book is that you need to embrace lots of diverse stimuli if you want to be resilient and creative. The danger is that you embrace this fully and always go for diverse stimuli instead of taking some and then going back to the place where you can focus and actually do the creative work all these stimuli are supposed to spark.

If you were interested in Deep Work, then Messy provides a decent counterpoint. It provides the diverse thinking to help you balance your deep work with the creativity you hope to have.

Get Messy on Amazon.

photo by: kalexanderson