Falling In Love With Structure & Discipline

(Software, Google Calendar, and one of those giant novelty checks.)

Have you ever really wanted to accomplish something and realized that you just simply haven’t made time for it? And then, to your excitement, your brilliant, innovative mind decided you could just block off some real-estate on your Google Calendar? How easy! Once I put this 90-minute block on my calendar, it will be impossible to schedule over it! How brilliant!

And then, I ask, how does it end? Do you spend that 90 minutes entrenched in your work? Did you already have your coffee brewed, your Spotify “Chill Mix” playing, and your cursor blinking while you cracked your knuckles and looked at the computer screen with determination? Did you fall into your chair with a satisfied grin and take a deep breath just before starting the plunge into a hypnotic state of deep work?

Hell no. That almost never happens. It’s not the calendar’s fault and it’s not the process’ fault — not entirely.

There are two things at play here: structure and discipline. I’d like to break these down in a way that you might not be used to, so stick with me here. There are examples. There are graphs. This is going to be a fun post.

Your Calendar Will Whisper Sweet, Sweet Lies To You

The calendar represents the structure that can be so helpful in getting things done. The discipline is the habit, not the act, the habit, that enables us to leverage the structure we’ve created for ourselves.

Let’s be clear about something, I’m using this example because I’ve done this plenty of times. I’ve carved out the time and then skipped it. I’ve made the space and then pushed it back. I’ve taken the first steps and then quit before really getting warmed up. This isn’t about judgment, this is about unpacking some of the mechanics of long-term, high-output work.

Together Forever

In order to see results, both structure and discipline have to be firing simultaneously and with the same vigor. Structure with no discipline leads to a bunch of calendar events with no action and a ton of shame and disappointment. In fact, when we do this, we reinforce the idea that we can’t trust ourselves with projects and it’s easier to slip into depressive bouts.

Every time you fail to make something happen, it’s like someone showing up at your door with one of those huge novelty checks and balloons, only the check is for $0 and the guy kicks you in the knee, twists his evil mustache, laughs a diabolical laugh, and then speeds away in his unmarked 1977 Chevy Express. And there you are, standing there, with a bruised knee, a bruised ego, and a giant piece of useless cardboard. Happens all the time.

Discipline

Discipline with no structure means that we can accidentally over-work without proper rest or over-work in the wrong direction. Discipline, all by itself, can also lead to bureaucracy, which is a system of constraints that inhibit growth. It’s like a plant that’s too big for the pot. It will strangle itself.

Discipline, if done correctly, will unlock new growth.

Consider the daily practice of an instrument. I practice drills on my guitar, not because they sound good or they’re fun to play — they’re boring and miserable — but I do them because I like suffering. No, that’s not why, I practice drills because they enable me to then play freely and however I want when I’m finished. Proper discipline creates freedom. Say it with me: “discipline creates the freedoms!”

If we think about discipline, at its core, it’s really just about following through on the structure we’ve set. If you hear the word discipline and think it means “punishment,” like I did for many years, you’ve got it wrong. And you’re probably Catholic. Are you Catholic? Delete that thought. Let’s unlearn and relearn together, here.

For the most part, punishment doesn’t work for modern humans. It only works in certain scenarios and has some serious limitations. Just to over-clarify, I’m defining what’s known in psychology (specifically behaviorism) as “positive punishment.” In other words: “I’m inflicting this specific pain on someone so they won’t want to behave that way again.” We do this to others, but we can also do this to ourselves. The best example is smacking the snout of a dog who just did something bad. It works better if it’s immediate. It works better if it’s consistent. (Cheney & Pierce, 2004).

The greatest drawback of positive punishment is that it fails to teach the replacement behavior. Plus, punishment can create unproductive and damaging emotional reactions such as passivity, fear, anxiety, or hostility (Skinner, 1974; as cited in Cheney & Pierce, 2004). It’s nasty. This is what happens when you use the dark side of the force. Don’t say I didn’t warn ya. But still, for some reason, punishment is seen as more acceptable than other forms of behavior management, like positive reinforcement, because “people believe they are free to choose to behave in responsible ways to avoid punishment” (Maag, 2001).

Putting this into simple workplace terms, this is known as the “carrot or the stick” method. It’s intended to incentivize good behavior and disincentivize bad behavior but that’s not the whole truth of the consequences. It typically just means that people work just hard enough to get the carrot (and not to their fullest potential) or just hard enough to avoid the stick. What a well-intentioned and terrible limitation!

There’s no infinite upside. There’s no fulfillment of potential. Just a sad ebb and flow between the upper limit of the carrot and the lower limit of the stick. It’s more suffocating than the time you were stuck in the middle seat in the back of the car between Aunt Bess and Uncle Rico on a 100 degree July drive while they were both smoking unfiltered cigarettes. Not fun.

Okay, end rant about punishment. Let’s go back to discipline.

Basically, the punchline is that discipline is the route to self-mastery. Self-mastery is the sharp tool that helps us achieve our goals.

Structure

Structure is less focused on the self and more focused on taking actions to control the world around you. It’s about setting yourself up for success. For instance, I love having a morning routine. I love having a minimalist, capsule wardrobe. I love keeping everything in the same place. I love setting up the systems and environment around me as much as I can.

Rather than just your calendar, think of structure as the sequence of situations you put yourself in throughout the day. Instead of getting ambushed by urgencies like emails and meetings, you have the opportunity to set up the battlefield however you want.

Over doin’ it.

Okay, quick time out for a caveat. One of the places that I and others struggle is over-structuring. When every minute of every day is accounted for, it doesn’t allow flexibility to adapt to the problems that life undoubtedly throws at us.

The best example of this is flight delays. For several years, I traveled 100–150 days per year. I was always flying. Only just a few months of this, anyone can easily tell that flights in the morning tend to fly as scheduled. Flights in the afternoon and evening tend to be more vulnerable to delays.

One of my favorite places for statistics, FiveThirtyEight, breaks this down. In his analysis, FiveThirtyEight states that flights departing between 6 AM and 8 AM are about the same, with very few delays. Flights after are more and more likely to see delays.

Just to be super clear about the data, the Bureau of Transportation Statistics also states that there are 5 main types of delays: aviation system delays, severe weather delays, late-arriving aircraft, security delays and carrier delays (such as those caused by mechanical or crew problems).

Here’s the breakdown by each type. As you can see, factors like weather and system errors don’t come close to the same level of impact as a plain ol’ late flight — in other words: life happens.

This works just like your Google Calendar. If you have meetings stacked up back to back to back, and you are 15 minutes late for your first one, you run the risk of never catching up and being late for every remaining meeting throughout the day.

To avoid over-structuring my day and becoming too rigid to adapt to problems, it might be helpful to schedule more flexible blocks of time as the day goes on. This would put you in a position where you have the resources to fight the problem that you are more likely to face — it’s you setting up the battlefield before the fight instead of walking into the ambush.

A Lesson From Software

A few years ago, I was managing a software team. They were brilliant and dedicated but they asked for some operational help. I asked them about their typical day and when they felt most productive. The answers I got formed a pattern. Most developers said they were most productive in the morning and dreaded long meetings where they couldn’t work on their part of the project. They also expressed the understanding that meetings were necessary for communication, but the interruptions were really the painful part.

So, what did we do? We added just a little bit of structure. In the mornings, we scheduled 4-hour “flow” blocks. This was slated to be uninterrupted, headphones on, head down, keyboard clackin’ time. They loved it. We also held a team meeting after lunchtime when everyone was feeling more ready to interact socially and discuss challenges after already feeling somewhat accomplished.

The key here was that we weren’t really managing our time. We were managing our energy. When did the team feel the most ready to code? When did the team feel most ready to interact with others? Nothing brilliant here. Just listening and taking action.

The other part of this that worked well was that huge 4-hour “flow” blocks gave developers the freedom to work however they wanted during that time. If they wanted to take a coffee break, they could. If they wanted to take a walk and clear their head, they could. They could do whatever they needed to do to be brilliant without worrying about the next meeting. Energy management. Not time management. Frameworks that served the team, not rigid obligations that made everyone a slave to their calendar.

Also in the category of structure, falls things like how and when you wind down. A few years ago, I was traveling a lot for work and moving through different time zones. I couldn’t always go to bed or wake up at the same time. This was challenging, especially because I’ve always been someone who has benefitted from a morning routine.

What I could do, though, was create a ritual of behaviors at these times to let my body and brain know it was time to sleep. Exercise and writing worked best in the morning and reading or meditating worked best in the evening. By having these tools ready to go at the right times, we are setting ourselves up for success instead of just hoping that we’ll be energetic or ready for sleep at the right times. Even though the time of day I performed these habits was somewhat inconsistent, the habits themselves were the familiar muscle memory I needed to shift gears into the next type of activity or thinking.

Don’t be a hero.

I have seen this pattern of heroism in many work cultures. You know what I mean. Something goes wrong, the project is late, and someone needs to pull extra hours to reconcile. This would happen all the time when I worked in the events industry. Events are inherently time-based, which means it always feels like everything is urgent all the time. It can be exhausting.

The dangerous part of this is that it can work the first few times. You stay late, you make things happen, and your work culture will most likely reward the behavior — remember behaviorism from the example above? It’s the same concept here. The first hit is free. Stimulus, behavior, reward. Problem at work, work overtime, get a solid “atta boy” from leadership. This is called a behavioral feedback loop and it’s the exact same neurological conditioning used to train a dog to sit or poop outside.

So, what do our brains do? They repeat the loop. Before you know it, you’re in a chronic pattern of swooping in and saving projects instead of diagnosing operational errors and empowering other team members.

If you need heroism to save your project or your schedule, something went wrong with your systems. Systems are in place to provide protection from old problems and help prevent possible new ones. If you’re chronically saving the day, you have an operations problem, not a sudden or emergent problem.

In a Harvard Business Review article titled “Productivity Is About Your Systems, Not Your People,” author Dan Markovitz cites:

“As legendary statistician and management consultant W. Edwards Deming argued in his book Out of the Crisis, 94% of most problems and possibilities for improvement belong to the system, not the individual.

I would argue that most productivity improvements belong there as well. Personal solutions can be useful, but the most effective antidote to low productivity and inefficiency must be implemented at the system level, not the individual level.”

The Elephant In The Room.

There’s this lie that if you do all these things, work and life will fluidly dance together in a glorious midnight tango of romantic productivity where they hover an inch above the ground and hum in some kind of telepathic orgasm. But you know better.

Tell me if you’ve heard this one:

“We identify issues, we discuss them, we crush them. Our organization doesn’t have chronic issues because we’re on top of them before they start.”

If you’ve heard this, then congratulations, you’re part of a team with delusional leadership! That’s right folks, please step right up and take your golden trophy. That’s right, now step along quickly because we need to give these out to everybody.

Chronic issues happen. Sometimes they’re obvious. Sometimes they’re not. It’s not that they can’t or won’t be solved eventually, it’s just that no one’s perfect. Yes, yes, I know this is obvious, but I still think it needs to be said. I have accidentally written with fervor in my posts and left little room for hedge or (in some cases) reality. Having reasonable expectations is half the battle — probably more.

Anyway, there’s a lot to think about in this post. Discipline and structure work together but they are absolutely separate concepts. Without each other, neither one works as well. In fact, without each other, they can go dangerously awry.

You may have more or less flexibility to do these things depending on your work, lifestyle, or personal schedule. Just because you can’t get up at 5 AM like a navy seal every day doesn’t mean that you can’t have any structural components in your day. Sometimes, a loose framework is better for some personalities anyway. Mileage may vary. I’m not telling you what to do, I’m not your dad.

Ultimately, it’s up to you how you want to set up the battlefield each day. You can’t control everything, but it’s worth thinking about where that line is. It’s worth the long, slogging path to developing discipline (it’s a skill, not a trait) and combining it with structure to become some kind of Captain Planet super mutant force for good.

TL;DR: Discipline takes practice but it unlocks new capabilities. Structure is best used as loose guidelines not rigid obligations. Using discipline and structure together amplifies their impact on your life. You can do it.

I hope this post was useful and FUN!

If you’re liking this new approach, write me back and let me know. If you think I should tone it down and go back to less rambly, more straightforward posts, I want to hear from you, too.

Thanks for reading.