Structure is freeing, not restricting

Tim Casasola
The Startup
Published in
5 min readMay 10, 2020

I’ve always thrived on having structure. When I was a breakdancer in high school, I set a practice schedule. I’ve practiced a 9–5 workday since I was a college student. Today, I do weekly, monthly, and annual reviews.

“Isn’t all this restricting, Tim? Are you ever spontaneous?”

I’ll admit. My way of structuring my life isn’t normal. I think my craving for structure came from realizing as a kid that I didn’t achieve my goals if I didn’t have structure.

However, I believe it’s human nature to thrive in structure. In this essay, I’m going to share some thoughts on how there’s no such thing as a structureless person, how structure is paradoxically freeing, how structures should develop organically, and how negative emotions that come from structure are an opportunity to reflect. Let’s dive in.

There’s no such thing as a structureless person

In The Tyranny of Structurelessness, feminist scholar and activist Jo Freeman critiqued the widespread belief that “structureless” groups formed the women’s liberation movement. She writes:

“Structurelessness” is organizationally impossible. We cannot decide whether to have a structured or structureless group, only whether or not to have a formally structured one.

Structureless is organizationally impossible. The fact that people have different backgrounds, predispositions, and talents forms a structure.

Of course, Freeman is talking about group structure when I’m talking about individual structure. But I think the principle of “structureless is organizationally impossible” applies to individuals as it does groups.

There’s no such thing as a “structureless” person. Someone who doesn’t prefer using a calendar to plan their days isn’t necessarily structureless — their structure doesn’t include a calendar. Someone who’s more spontaneous isn’t “structureless” — their structure is fluid.

We all shower, brush our teeth, eat, and sleep on a regular basis. We all have a structure. And it’s this very structure that frees us.

There is freedom in structure

Structure is a form of a constraint. And constraints free us from anything that gets in the way of our intent.

Constraints are defined as a limitation or restriction, but they aren’t inherently negative. They can be positive. In A Beautiful Constraint, Adam Morgan writes:

“A constraint should be regarded as a stimulus for positive change — we can choose to use it as an impetus to explore something new and arrive at a breakthrough.”

A constraint should be regarded as a stimulus for positive change.

In a way, design is about making constraints useful. The elements on an interface are constraints, intended to help a user meet their goals. Design frees the user from unnecessary decisions and obstacles in the way of their intent.

I like the way Koroush Dini defines “organization.” In Workflow Mastery, he shares:

“Organization is a process of supporting and clearing a path for an intention’s development.”

If you replace the word “organization” with “structure”:

Structure is a process of supporting and clearing a path for an intention’s development.”

Structure clears a path for our intention’s development. Without structure, we’re susceptible to go down paths that don’t support our intention’s development. We get lost in the woods and aren’t sure how to get out.

Good structures emerge organically

However, there is a difference between good structure and bad structure. Let’s start with bad.

Bad structures are…

  • designed to solve anticipated but yet present problems.
  • disconnected from reality.
  • overly complicated.

Here are some common examples:

  • Your New Year’s Resolution is to the gym every day when you currently go the gym once every two weeks
  • You commit to waking up at 5am every day, when you normally wake up at 8:30am
  • An organization creates a thirteen-step approval process to assess the risk of every project
  • An organization implements Scaled Agile Framework to achieve organizational agility
Agility at scale, alright.

Gall’s law states this:

“A complex system that works is invariably found to have evolved from a simple system that worked. A complex system designed from scratch never works and cannot be patched up to make it work. You have to start over, beginning with a working simple system.”

Replace the word “complex system” with structure, and you get this:

A structure designed from scratch never works and cannot be patched up to make it work.

Good structures aren’t determined upfront. They emerge through self-experimentation. They’re in a cycle of noticing, brainstorming, trying, evaluating, and noticing again. They get 1% better every day.

Examples of good structures:

  • For the once-a-week gym goer, they commit to going twice-a-week to the gym for two weeks. After those two weeks, they see if they hit their goal. If they did, they increase to three-times-a-week.
  • For the 8:30am riser, they commit to rising at 8am for a week, then check back on how they did. If they did well, they wake up at 7:30am for the next week. If they didn’t, they try to understand why they’re not waking up earlier (no light when waking up; always hitting snooze).
  • For the organization that’s tempted to implement Scaled Agile Framework, they instead retrospect to understand what’s working well and what isn’t in their way of working and try bite-sized practices.
  • You use notetaking apps like Roam or Obsidian that structure your notes based on the relationships between your thoughts, rather than a pre-determined “file cabinet” hierarchy.

Let structure emerge organically. When it’s imposed from the start, you prematurely constrain what may emerge and artificially compress the nuanced relationships between ideas. –Andy Matuschak

Negative emotion as an opportunity to assess the problem

Structure can stress you out, though.

When I look at my todo list and see a bunch of tasks I haven’t completed, I feel “behind.” I wouldn’t feel behind if I didn’t have a pre-existing structure of capturing my todos.

When I look at my calendar and see a bunch of events all over the place, I feel overwhelmed. I wouldn’t feel overwhelmed if I didn’t have a pre-existing structure of creating appointments.

In both situations, is my structure not serving me?

Perhaps not. I’ve learned that overwhelm and stress is signal to reflect on the problem.

Is the problem that I have too much work in progress? Do I need to cut back on the number of projects I’m taking on?

Is the problem an aspect of my structure itself? Did I “overdo” my structure, rather than let it emerge?

Does the problem have to do with I’m relating to my structure? Am I viewing my schedule as something I have to do or choose to do?

Structure will create unwanted emotions. Let stress or overwhelm tell you “hey, this might be a good opportunity to reflect on what the lesson is here.”

Conclusion

View structure as enabling rather than freeing. There is no such thing as a structureless individual, so we might as well welcome it. Even when it produces unwanted emotions.

Without structure, we’re burdened to figure out how to achieve our goals and do what we intend on. Rid yourself from that burden. Be free.

I originally published this on my personal site.

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Tim Casasola
The Startup

Product & organizational development. Currently at Manhattan Hydraulics. Now writing at theoverlap.substack.com