Make things messier to achieve your goals

Make things messier to achieve your goals

The June pick from the Recharted Territory reading list was “Messy: The Power of Disorder to Transform our Lives” by Tim Harford. In the book, the author shares a lot of examples of when a “clean and tidy” approach to life and business may not be as beneficial as a messy one.

It’s around the time for mid-year reviews. We’re starting to reflect on the past six months and thinking about where we’d like to go in the next six. Did you execute your plan as originally outlined? Have you achieved your goals? Did your office look Pinterest perfect along the way?

Maybe more messiness would help.

I pulled out four insights from the book that seemed especially interesting for people improving complex systems and leading teams.

They cover how we can…

  1. Leverage messiness to come up with new ideas and perform better than we thought possible,
  2. Foster high-performing teams,
  3. Empower team members, and
  4. Design better products and systems.


1. Mix in some random shocks with your hill-climbing

Harford shares a couple of examples where creatives, scientists, students, and commuters who were put in a messy situation, like dealing with disruptions or a new environment, were able to achieve breakthroughs and stairstep growth.

He equates our typical “tidy” approach to advancement in work via focus, study, and practice to a “hill-climbing” method. Ambitious to “move up the ladder” in any pursuit, we aim for continuous progress in a positive direction. But what if you were on the wrong hill in the first place? What if there’s a higher or better one out there?

Focus and practice can help with local, incremental improvements. However, adding in random shocks can help us get unstuck, or make creative leaps when solving a problem or creating something new. The random disruption can be uncomfortable at first and we might initially perform worse, but we could also end up with a more creative solution or optimal approach.

“It’s human nature to want to improve, and this means that we tend to be instinctive hill-climbers. Whether we’re trying to master a hobby, learn a language, write an essay, or build a business, it’s natural to want every change to be a change for the better. But like the problem-solving algorithms, it’s easy to get stuck if we insist that we will never go downhill.”

– Tim Harford

Harford mentions a study at Harvard that suggested some of the most creative people were also less likely to filter out distractions and focus their attention in a busy environment. Prolific scientists and creators are also likely to be working on multiple projects at once. Multiple and varying sources of information meant they were able to make new connections between stimuli that other people might think were “irrelevant.” Of course, the most successful people were also able to apply focus and honed skills to research the topic and execute on their ideas. Messy disruptions can help us be more creative, while focus can help us execute on and improve those ideas.

Application to daily life

Disruptions and distractions can be helpful but they can also prevent us from executing once we’ve formed an idea. In another great book “The Accidental Creative,” author Todd Henry advises that we consume information the same way we approach our diet. That means focusing on quality stimuli. He suggests creating a Stimulus Queue and a study plan that covers information you might need in the future for upcoming projects, what you’re curious about, and knowledge gaps that would be good for you to fill. Don’t forget to add “random shocks” to you queue, by collecting random prompts or putting together a list of resources, places, activities, or events that are completely different from what you normally encounter.

If you’re working with a team, you could create a shared list or make a physical resource library in your team’s war room. 3M encourages people to spend time doing things that don’t involve “hands on keyboards” because they know that sometimes the breakthroughs happen when you’re doing or looking at something else. Switching up your work environment and adding in some breaks for physical activity can also help.

Besides taking in stimuli on a regular basis, the next step is to capture those creative synapses to turn the messiness into value. I’m a fan of always keeping a notebook around or a text document for those random flashes of insight. Regularly reviewing notes is great for times when you’re stuck on a current problem. Keeping your notes and stimuli for each project in separate notebooks, documents, or physical boxes (like choreographer Twyla Tharp does) can be helpful to mentally deal with multiple projects at once. For teams, I think wiki spaces or physical rooms are the best for this. If you have everything stored in folders and documents it can be more difficult to remember what’s there and foster random connections.


2. Pursue goal harmony over team harmony

High-performing teams get along. Right?

Harford mentions that sociologists have defined two ways that people work together: “bonding social capital” and “bridging social capital.” Bonding social capital happens within a team that has isolated itself from the outside world to focus and build internal trust and efficiency. That’s great for hill-climbing when the goal is relatively clear and the team just needs to minimize distractions and get things done. Bridging social capital helps spread ideas across networks and disciplines, sharing among groups that normally wouldn’t associate with each other, and facilitating random shocks that help people get unstuck and generate new insights.

How can we balance the benefits of both types of social capital? Researchers studying video game creation found that having cohesive, longer-term teams that worked with other tight-knit teams with a different background produced the most original games. However, the less cohesion you have, the more likely the team is to fall apart, so these networks of teams can be difficult to maintain over time.

Unified teams are longer-lived and the urge for cohesion is strong but it can also be problematic. To maintain a friendly atmosphere, some people may avoid sharing doubts or concerns.

However, just one person with a different perspective or voice of dissent is enough to spark a conversation among the rest. The need to explain or justify your decision to a stranger or someone with a different viewpoint forces people to more critically examine their own position.

“People think harder when they fear their views may be challenged by outsiders.”

– Tim Harford

Harford shares some studies that suggested we tend to stick with people we know or who seem more like us, leading to greater comfort but not necessarily better decisions. We might feel like we’re achieving better results because the experience felt more fluid. He asserts that a messier team dynamic with conflict and different points of view can be good for the team if you have a shared mission. Leaders promoting goal harmony over team harmony are more likely to encourage teams to question assumptions and have important debates.

Application to daily life

How are you supporting both bonding and bridging social capital? If you have multiple teams working on a project, who’s actively working to connect those teams? Who’s encouraging interactions, sharing information, and building cross-team trust by being an “insider” on more than one team? Many scaled agile projects struggle if they’re missing key bridging roles.

Are your teams prioritizing team harmony over goal harmony? Are team members even clear on what the goal is? Ask each member individually to see what they think and if they’re not in sync, try a visioning or process modeling exercise. Externalizing the goal helps shift focus from social dynamics to an objective problem to solve.


3. Prioritize team member empowerment over visual tidiness

Harford shares an interesting study that tested how work environments impact productivity and morale. Specifically whether the amount of decorations and if you had control over how those decorations were arranged would make a difference. There were four test cases, (a) a “lean” office with only the essentials, (b) an “enriched” office with a few decorations, (c) an “empowered” office where participants could rearrange the items as they wanted and even remove them, and (d) an enriched space where the participant first designed it the way they wanted and were then forced to work in a space that was reverted back to the original setup. The best case turned out to be when workers had some control over the environment, and the worst was when the environment was dictated to them after a promise of autonomy.

While a messy desk might be less appealing to an external observer, the space could actually be very motivating and organized to the person who designed it. Since tidiness in many scenarios doesn’t necessarily create better outcomes (although sometimes it does in the case of manufacturing and safety) managers should focus on creating flexible environments and fewer rules.

“The office is a highly personal tool shop, often the home of the soul… this fact may sound simple, but it eludes most architects, office designers, and thousands of regulations writers in hundreds of giant corporations.”

– T George Harris, journalist

Application to daily life

Let people decorate the war room, personalize their work area, and pick their own team name. Provide modular furniture, budgets, and a minimal approval process (if anything) because the faster and easier it is to make changes, the better. The productive and morale-building value of empowerment usually trumps any aesthetic value of office tidiness.


4. Create confusing situations on purpose

For people designing products or physical spaces that impact people’s behaviors, automation can cause some issues. One of which is the “paradox of automation.” When automation replaces simple actions and corrects common errors, humans are often less prepared to take over when things go wrong.

This can be dangerous because (a) automatically correcting for small errors can hide operator incompetence, (b) humans are left with fewer opportunities to practice, which erodes their skills and (c) when the machine fails, it tends to fail in unusual ways that require a highly-skilled human operator.

“Automation will routinely tidy up ordinary messes, but occasionally create an extraordinary mess.”

– Tim Harford

Harford shares some stories where people purposefully designed systems to be messier, which ended up with safer outcomes. Messiness and confusing situations keep us alert because we don’t always know what’s coming or what to do. We need to continually observe, orient, decide, and act. It forces us to pay attention, improv, and practice multiple skills instead of becoming passive.

Application to daily life

Consider adding diversions or opportunities to apply skills to keep humans manning machines alert. Also be sure to account for the probability of some false positives or false negatives because it can be easy to overtrust the results of automation. While the outliers may be unusual, they will happen, so we need processes to handle them.


Tidiness has its advantages but maybe we need to appreciate and foster a messier life. I encourage you to check out this book if you haven’t already to learn about more benefits of messiness.

How will you embrace some messiness to achieve your goals? 

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