Resolution Review #4: Trying Structured Procrastination

Resolution Review #4: Trying Structured Procrastination

"Groundhog Day Resolution Review #4 2015" This post is several days late, but ya know what? That’s OK! This past month I’ve been practicing elements of John Perry’s Structured Procrastination, and I’m feeling more relaxed about meeting personal deadlines such as this. Less anxiety means less stress, and less stress creates a free flowing mind! I think I’ve been more productive than I have in a while, albeit not in a rigorous sense. It’s all pretty groovy.

In this month’s Groundhog Day Resolution Update, I want to talk about a different model of being productive, which involves embracing my imperfect procrastinating butt and redefining what productivity means in this context.

Accepting Procrastination

One of the key insights behind structured procrastination is recognizing the essential characteristic of a procrastinator is not to do what’s important, AND that this is not something that can be fixed with the wave of a hand. And really, it’s not the most awful of traits either. As Perry points out, a structured procrastinator can be quite productive because of all the other things they accomplish in the act of avoiding the “important” work.

This idea resonates with me quite a lot. As much as I wish I wasn’t a procrastinator, my history suggests that I have always been this way. When I was in the first grade, my grades were terrible because whenever I got an assignment from the teacher, I would just stuff it into the back of my desk. I didn’t realize that it was something “important” until my parents asked me about school, and I told them what I was doing without any sense of having done something wrong. Ok, maybe that’s just anyone being a first grader, but as school life went on, I found homework and lectures very tedious and arbitrary. Whenever I learned something, it was because my attention was hijacked by curiosity, or I had become enthralled with helping my friends do something super-cool as an attention-worthy challenge. I suppose I inadvertently had the time to learn by minimizing my effort on homework assignments, spending the rest of the time exploring computers and trying to understand how they worked. At times I would be enthralled by a a writing assignment that involved creating systems. College and graduate school largely provided me with the opportunity to access more information than I had before, and my grades were good in classes that I found useful and terrible everywhere else. In graduate school, I did come to appreciate the value of discipline and hard work because I respected the people around me, but did poorly in replicating it. In the workplace, I eventually found that I could shore up my management skills, after not being very good at it, by learning to see what really was inside the hearts of people and then applying my technical understanding to making it real. It’s served me fairly well in a rather eclectic journey from an English Major aspirant to Computer Engineering student to Computer Graphics art student through Video Games, Graphic Design, and now…whatever it is I’m doing. I guess the word I’m looking for is, “unemployable” ;)

But I digress. For all the advancement I’ve made, I still innately resist doing what ‘should’ be done.. The response is wickedly visceral, immediate and unstoppable. My brain feels choked of oxygen, and lethargy swiftly casts the pallor of death over the day…unless I choose to do something else. If I’m not mindful of it, then I’m merely distracted, but if I am then it’s a battle between demons. I’ve occasionally come up with ways of tricking myself into being productive, which compensates for that initial wave of negativity, but these tricks only work once. After that, my brain quickly evolves an immunity to them. I have over the course of my life discovered the sure-fire ways to rouse me to action, but the conditions that make it possible require external resources that are not always available to me; more on that later.

This month, rather than try for the umpteenth time to “fix” the response, I’ve decided to embrace it and see what happens. Procrastinators, after all, are REALLY GOOD at finding OTHER work to do; if that work can still be useful, then one can be productive accidentally on-purpose. The alternative is to keep trying what I did from April to May: reduce the number of responsibilities I have down to the absolute minimum, so I have no choice but to work on them. Apparently this is a rookie mistake; as John Perry says in his structured procrastination essay:

Procrastinators often follow exactly the wrong tack. They try to minimize their commitments, assuming that if they have only a few things to do, they will quit procrastinating and get them done. But this goes contrary to the basic nature of the procrastinator and destroys his most important source of motivation. The few tasks on his list will be by definition the most important, and the only way to avoid doing them will be to do nothing. This is a way to become a couch potato, not an effective human being.

Ouch. That is TOTALLY what happened to me.

Part of “embracing procrastination” is the willingness to shed any guilt, shame, or regrets that I might have about it. There is something about my brain that resists the command to do what I am “supposed to do”, even when it’s ME that’s setting the goals. It’s automatic, immediate, and powerful. And that’s how I am. It is OK. Breathe! Accept!


Ok! Having accepted myself, this is a good time to remember that there ARE ways around my procrastination. There are basically three conditions that have to be met:

C1. I am in charge of the project, and I have made a promise to deliver by a certain date. C2. I am communicating face-to-face with people on a daily basis, and they are equally invested in the work as I am.
C3. Someone really DOES need something from me, and they are at risk of experiencing some form of pain if I do not deliver as promised.

I’ve found that all three of these conditions MUST BE PRESENT for me to initiate action quickly and without delay. Unfortunately for my personal projects, the conditions are all external motivators, and are not generally available when I want them. If I try to apply them in the personal context, this is what goes through my head:

  • Regarding C1: When I’m in charge of my own project, I feel I can break the promise to myself because no one is getting hurt. And it wasn’t really a promise, right? More of a fuzzy goal?
  • Regarding C2: Communicating with myself isn’t that interesting, though it’s a useful proxy. I write a LOT when I’m doing work, often in a journal form, because the conversational flow keeps my mind somewhat engaged and writing is really easy for me. However, communication with other people is energizing, while writing for myself depletes energy in exchange for clarity. It is a limited resource.
  • Regarding C3: Many of my personal projects are not immediate “needs”, falling instead into the “would be nice to have” category. Even the ones that I know will bring me money, resources, opportunity. It’s just too abstract to feel immediate and compelling to me.

So these conditions are not going to be useful in tackling my current work, with the exception of my paying project where I can collaborate in real-time with my colleagues over regular Skype meetings. That leaves structured procrastination as a strategem.

Applied Structured Productivity

The key behind structured procrastination, as I understand it, is to arrange to be productive when you are procrastinating. For that to happen, I need to change my definitions.

Here’s a standard definition of productivity that I pulled out of my butt:

Productivity is producing the results you have set as a goal in a timely, efficient, and predictable manner.

Sounds so rational and wonderful! Too bad I can’t have it. Instead, let’s try:

Productivity is producing useful, tangible results that have value now or in the future.

The difference between the definitions is the elimination of timeliness and predictability. That doesn’t necessarily mean that the procrastinator is UNRELIABLE, though I’m sure some people would disagree with that. If one defines “reliable” as “producing something when they promise it”, then the procrastinator can be reliable if they never promise or never commit to delivering something by a particular time! It’s called “being impeccable with your word”. Though it sounds weaselly, I figure so long as one has produced something of value in the past that is STILL paying-off, it’s OK. One of my favorite authors, Douglas Adams, was a terrible procrastinator from what I’ve read, but he did OK. That’s really what I want, a kind of “fruit orchard” model of productivity, where one walks among trees of all generations and types every day, seeing what’s about to drop and feeding what seems to need feeding. This is a pleasurable alternative to the “factory assembly line” model that we hold up as an example of progress. Another author, Neal Stephenson, summed it up as “making stuff up and cashing checks”. YEAH!

The Process of Effective Procrastination

To kick off the process, I made a list of starting insights, hypotheses and principles.

  • GIVEN: I automatically resist what I am “supposed” to do (important tasks) if there is no compelling social context for it.
  • GIVEN: When I am resisting important tasks, I procrastinate by doing something else interesting.
  • INSIGHT 01: (from John Perry) If I reduce my set of available activities to only the important tasks, the only recourse is to sit on the couch and do nothing productive (this insight is from the Structured Procrastination essay)
  • HYPOTHESIS 01: Given Insight 1, if I increase the number of projects and people I am involved with, would more opportunities to create arise because there are more tasks to avoid?

Seems plausible.

  • INSIGHT 02: I often procrastinate by satisfying my curiosity. I’ll call these secondary tasks, and keep track of what they were.
  • HYPOTHESIS 02: Perhaps the secondary tasks will actually add-up into something that resembles productivity.

Also plausible. I was ready to give it a try, but also wanted to keep track of what I did. Perry notes in his book that he likes to celebrate things that get done, no matter how small. Upon reflection, this is something I like too. It may be that my desire to have a great team is less about competence than it is about having people to celebrate with. Since I don’t have people around to help me with this, I had to look for another solution.

My Trello setup has worked well in the past, so I resurrected it (it had laid dormant for about a year), and reorganized it. Instead of using a “left-to-right task progression” approach, it’s now arranged roughly by “importance” (split into a number of sublists), “priority”, and “what got done”

Current Trello List for Procrastinators On first glance, this might just look like a medium-sized todo list, but it’s not. It is a guilt-free memory board. Remember what I said about embracing procrastination and dropping shame and guilt? I WAS NOT KIDDING.

Here’s some details on how I’m using it:

  • I’m treating it as a way to remember things I wanted or might do someday without shame, guilt, or other forms of self-recrimination. It doesn’t do me any good to think that way. If I thought of it as a to-do list, I would curl up in a ball and cry.

  • Likewise, the prioritized list is there to remind me what I “should” be doing, but procrastinatory forces will push me toward one of the other lists. This is structured procrastination applied.

  • Finally, if something pops into my mind and I do something that’s not on any list, I add it to the DONE column and add a + in front of it. This is also structured procrastination, which recognizes that we like to feel we’ve accomplished something and celebrate it.

So how did it work in practice?

If the theory holds, the “should do” list should create a repelling force that drives my attention onto one of the receiving sublists. Here’s the “should do” list for reference again:

  • My Video Game Project
  • Creating more Stationery Products
  • My Living Room Cafe Project
  • Billable Work

It’s fascinating that as I look at this list that I KNOW are ALL COOL projects, I still feel my brain rejecting the very idea of working on them just because they’re things I “should” do. This reaction is so dumb, but yet it’s there. And as you might expect, I hardly worked on them. In hindsight, the work that DID progress (living room cafe project, billable work) happened because I happened to make face-to-face contact with the people directly involved. Personal interaction drives my work, apparently.

So let’s look at everything else. Thanks to the Trello board, I can look back at my past four weeks of what “got done”, which results in the following:

MAINTENANCE DONE: Major car repairs, rebuild and mirror Windows 8.1 workstation, backup system image for easy restore, setup iTunes libraries, upgrade virtual machines for code development, get snow tires swapped, brought the garden hose to the second floor deck, cleaned up cat litter area, break down boxes in bases and take to dump, started gym, paid medical and printing bills.

LIVING ROOM CAFE PROGRESS: Went to the flooring center three times, checking out samples overnight. Picked floor sample, worked through estimate, consolidated money, booked the work and made down payment. Researched furniture. Acquired packing boxing. Started packing boxes of books to clear living room for pending installation.

CURIOSITIES RESEARCHED: bed desks, compact grills, current standing desks, Medium as a writing channel, Alain de Botton and the nature of Fulfilling Work, buying ISBN numbers, small hatchbacks, AI steering behaviors, contact lens monovision selection, magnetic screen doors, spicy noodles, Scoville heat ratings, control systems (PID), Apple II FPGAs, Tuft & Needle mattresses, Roost 2.0 laptop stand, NoFilmSchool website, Gregory Ciotti, sub-irrigation planter updates, Enjin templating. Wrote some notes on mmorpg design, using Git, and designed a character sheet.

BOOKS READ: Read “The Art of Procrastination”, started “The Art of Asking”.

FOOD EXPERIENCES PURSUED: Marinated three kinds of chicken, tried Momofuku soft-boiled eggs, got into Samyang Spicy Hot Chicken noodle challenge, tried three kinds of cinnamon tea.

MEDIA CONSUMED: Saw “Age of Ultron”, “Mad Max Fury Road”. Watched “The Blacklist”, “Agents of Shield”, and “Community”.

IMPROVEMENTS BOUGHT: New book ends in bulk for new shelf organization, mini charcoal chimney starter, chinese scooter repair manual, Game AI textbook 2nd edition, “Don’t Make Me Think” 3rd Edition, Harney & Sons Cinnamon Sunset tea from Target, magnet screen doors (returned 1), bought bulk packages of samyang spicy chicken noodles

WORK DONE: Forked Project 1401 (game project) into phase 3 of STEP project, wrote technical design document for phase 3, researched AI behaviors, met with researchers over Skype, build Isotyop prototype page for web client.

COMMUNED WITH: Joined digital independent group, increased participation in online game chat room, Arts Council monthly board meeting, Website Committee monthly board meeting, processed photos from local arts events, interview for Alpha Efficiency, reconnect with old friend, had a picnic, two-day video shoot for musician friend, joined online game fansite as moderator, built proof-of-concept fansite.

None of this was really planned, and on first glance, this looks like quite a lot of stuff. A lot of it was useful research related to projects of personal interest. I learned a bunch of stuff too, becoming passably competent in a range of subjects. More importantly, I didn’t feel terrible about not having done what I was “supposed to”, and this lack of negative feeling makes it more likely that I will do it. I would say that the “unplanned” to “planned” ration is 10:1 or higher.

Although I promised myself that I wouldn’t feel bad about being a procrastinator, I have to admit I feel a little twinge of, “I seem to be able to do so much! Why can’t I just do it on purpose?” I have no answer. It’s not the kind of thing that can be explained away by some smug non-procrastinator waving the “just do it” banner. That might work for them, and God bless them for it because we need people like that. But don’t try to make it seem that it’s any better or any worse. We’re all people with diverse gifts and idiosyncrasies, after all!

With Regards to Groundhog Day Resolutions

Before I close this post, I think it’s worth looking back on my original Groundhog Day Resolutions for 2015. They are quite different from what I’m doing now. Here’s the goals from the beginning of 2015:

Umbrella Goals (rewritten slightly):

G1. Eliminating Time-based Thinking G2. Reduce Possessions and Responsibilities that sap energy G3. Build full-time stationery business by end of year G4. Find will to create and share more G5. Build health and strength

Specific Goals that are on the top of my mind

  • Personal Project 1401 Video Game Project (relates to G4)
  • Paying Project Work (relates to G4)
  • Adding new products to the Stationery Business, particularly the full-size notebook and marketing (relates to G3)
  • Living Room Cafe (relates to G4)
  • Dental and Blood Pressure (relates to G5)

What I think I’ve learned from this past month of “structured procrastination” is that the freedom to work on where my mind takes me is essential to my feeling of well being. In the past, I had thought that Creative Independence was going to be the vehicle to that kind of happiness, which made my goal of building a financial foundation to reduce my need for continuous work (aka the stationery business) a priority. Today, I’m leaning toward the idea that it is the ability to effectively harvest what I produce, even when it’s not what was planned or expected, that might be the long-term solution. If I can live my life like this and not hurt anyone, I think it’s OK. Here are some ideas that might prevent people from getting hurt by my unpredictable productive proclivities:

  • Selling products as opposed to services, for example, is one way to be erratically productive and not inconvenience people.

  • Paying people generously to do the tedious work that I’m not good at following is another way to do it, and I need to take advantage of that option more often.

  • For those times when I do need to work with singular focus, making sure that the three conditions I mentioned earlier are in place. If I know those conditions can’t be met, I shouldn’t take the project.

An unexpected bonus from adopting structured procrastination is that I’ve accidententally completed Groundhog Day Resolution #1: “eliminating time-based thinking”. If you look at the definition I made for productivity, the lack of time references makes that happen. The original reason the goal had come about was because I’d noticed that the time I spent worrying about future efficiency took my attention off the actual DOING of things; the goal was a way to reset my attitude about time. Embracing procrastination seems to another way of doing that.

Possible Problems

The biggest problem with embracing structured procrastination is probably other people’s expectations. Embracing procrastination, or any “character flaw” for that matter, is not popular with the fix-it mentality of mainstream society. It’s a little crazy, creating a credibility problem if I were to advertise my services as a “designer/developer for hire”. However, it’s only a problem if I make my living from doing work for other people who don’t know me; if I shift to a product-based revenue (which is goal G3), that problem goes away.

A more interesting solution to the credibility problem is reframing the structured procrastination approach so it is predictable from another perspective. For example, rather than offer “predictability of time” as my main credibility metric, I could offer “predictability of quality” or “predictability of uniqueness”…something like that. I suspect that the truly great creative agencies, the ones that create great works of design and quality, are using approaches very similar to structured procrastination, and perhaps timelessness as well, as part of their creative process. The creation of original and compelling works doesn’t come from a factory model. With additional study and practice, perhaps I can learn how to build a bridge from where I am now to that place where I’m a creator at the very top of his game, integrating play with purpose, and learning to flow into work that is freeing rather than confining.

The Month Ahead

While I’ve enjoyed my month of structured procrastination, I’d like to push myself more on the “should do” tasks. These are, again:

  • The Stationery Business
  • Paying Work
  • The Video Game Project
  • The Living Room Cafe

I’ve found a useful technique is applying a 5-minute timer to see how far I can get on tedious tasks. Since I want to get them done quickly anyway, the 5-minute challenge plays into that desire. 5 minutes creates more of a sense of urgency, and since it’s short I don’t feel like I’m “trapped” as I do even with a fifteen minute timer, which I think of as the first block in a chain of work units. The cool thing is that I know if I just get started, my procrastination symptoms drop away and my curious/rational side takes over. Then, the minutes tend to spool off into hours of productive work.

Failing that, my fallback will be unapologetic structured procrastination. We’ll see how well that works out come July 7!


  1. Doreen 9 years ago

    As usual, I loved your post and perspective. I find I can relate to many of your ADD and procrastination ‘challenges,’ and I learn a lot from you. Thank you for reading through “The Art of Procrastination” for your friends and for sharing your knowledge. I am in a thirteen-month-plus rookie mistake of weaning down my responsibilities to the bare minimum in the hopes of getting my major project done. Alas, Parkinson’s Law is winning again. Although I have taken some baby steps toward finishing my project, you’d think I’d be further along after more than a year of ‘concentrating’ on this job. If I’m lucky, I get one or two small tasks done per month, even tasks as theoretically simple as getting to the bank to deposit checks. The good news is that I keep up with the laundry and dishes…two tasks that have nothing to do with my project! Maybe your five-minute timer will work for me, too. I’ll try it!

    Good luck with your experiment, progress, and bridge-building. You inspire us to keep putting one foot in front of the other, to keep trying to find work-arounds for our idiosyncrasies. Most of all, you make the journey fun! Thanks, Dave!

  2. Amit Patel 9 years ago

    Thanks for writing this up Dave. I’ve been trying to figure out how to deal with my procrastination. I tried reducing the number of things I need to do so that I’ll work on them instead of juggling tasks, but I ended up just not doing much of anything. I think my next step is to make the current project into a secondary project, and move to another primary project. Maybe I’ll make progress on it while procrastinating on the new one. ;-)

  3. Cherry Jeffs 9 years ago

    Smiled and nodded in recognition to lots of what you said, Dave :) You call it ‘structured procrastination’ – I call it ‘natural GTD’. I have a timetable with slots of what I’m going to do but I rarely follow it. I move those slots around as to how I feel following my natural impulses. My last resort is to delete a slot altogether. That means I’ve resigned myself to not doing the thing this week – or sometimes ever. Like you, I eventually get a lot done, it’s just not incredibly linear. I think there’s far too much emphasis on linear productivity. I’m sure many creative people don’t work like that at all. We have to leave space for our imaginations to play!

    There’s a great quote from Lisa Baldwin (zen at play) that I use in my book: “It’s only procrastination if you spit at yourself while you do it.” I think you just figured that out!

  4. Anne 9 years ago

    I think that mindfulness gets lost in the shuffle of “Am I going to make the deadline?!” I’ve been slowing down my life and not adding more responsibilities, but it feels weird. I’m not being more productive. My usual habit is to add as many interesting projects, classes and activities as possible, learn from those, but not necessarily finish any of them. Maybe that’s what works for me? As I get older, I’m becoming less of a procrastinator and more of a forgetter. Like, I’ll forget I have to do something. I guess that’s Creative Procrastination too! Thanks for your thought-provoking post.


  5. John Dance 9 years ago

    Dave, I stumbled over your blog after downloading your excel time tracker template. Thanks for that template by the way, it’s just another attempt from my side to try avoid becoming unemployed and ‘unemployable’ very soon. You explained exactly how I’ve been feeling my entire life so far, and I’ve been struggling with this through school, jobs, and every other activity. The only thing that is really helping right now is having been diagnosed with ADHD and taking a good dose of slow release ritalin/concerta each day. Even that does not make things perfect, but it takes away anxiety and procrastination. I feel like for me, procrastination is just a side effect, and not really what I need to focus on. Once I started my medication, procrastination virtually disappeared, and so did anxiety. When the medicine kicks in, I can focus and work on what I’m supposed to do, and don’t have a problem at all However, I’m still stuck with some issues, where it’s almost impossible to be productive in absence of your 3 Conditions which I fully subscribe to as well. I feel like no amount of medication will replace Dave’s three laws of productivity: accountability, interaction and meaningful work. Thanks again for your template and good luck with everything!