The Procrastinator’s Guide to Starting Fresh: A New Year Paradox

Welcome back to the Wednesday Weekly Reader, where I invite you to explore books on a myriad of topics – reading that will challenge how you think and live. 

This week, as we stand at the threshold of a new year filled with resolutions and fresh starts, I’m turning to two books that will make you reconsider everything you think you know about procrastination: John Perry’s The Art of Procrastination and Andrew Santella’s Soon: An Overdue History of Procrastination. Both authors argue, from different angles, that our cultural anxiety about delay might be misplaced. 

At this point I need to pause and give special thanks to my youngest son Aaron, who in his senior year in college pointed me to The Art of Procrastination. After he bought the book, read it, and wrote a paper on procrastination – all done the day it was due – he gave it to me to read.

Through it, I was introduced to the concept of horizontal organization. I enjoyed learning about, and practicing, Structured Procrastination, To-Do Lists, Procrastination as Perfectionism, and other strategies for the serial procrastinator.

Over the holidays, we were reminded of that apt demonstration of procrastination, and it inspired me to visit this timely topic.


It’s the first full week of January, that glorious window when the world feels scrubbed clean and anything seems possible. You’ve made your resolutions, bought the planner, downloaded the productivity app. This year will be different. This year, you won’t procrastinate.

But what if I told you that your procrastination isn’t the problem you think it is? What if the real issue isn’t that you delay, but that you’ve been thinking about delay all wrong?

The Paradox of the Productive Procrastinator

Stanford philosopher John Perry noticed something peculiar about himself: despite being a chronic procrastinator who avoided grading papers and other pressing tasks, he maintained a reputation as someone who got things done. This observation became the foundation for what he calls “structured procrastination” – the art of accomplishing tasks by avoiding other tasks.

The insight is both amusing and profound. Procrastinators aren’t lazy – they’re just doing the wrong things at the right time. Perry explains that procrastinators seldom do absolutely nothing; instead, they engage in marginally useful activities like organizing files or sharpening pencils, precisely because these tasks help them avoid something more important.

This month, before you beat yourself up for not immediately tackling that major project, consider this: you’re probably getting plenty done. Just not what you think you should be doing.

What History’s Greatest Delayers Teach Us

Andrew Santella’s exploration of procrastination reveals that many eminent historical figures produced great work while putting off tasks they were supposed to complete. Charles Darwin spent twenty years describing barnacles and writing about coral reefs before finally publishing his theory of natural selection. Leonardo da Vinci delayed completing commissioned paintings. These weren’t failures of character – they were human beings wrestling with complex motivations.

Santella suggests that the knottiness of human motivations means we all have lists of things we should do, yet we find reasons not to do them. This isn’t a bug in our psychology; it might be a feature. Sometimes delay allows ideas to percolate. Sometimes avoidance is our mind’s way of signaling that we need to reconsider our priorities.

Santella questions our devotion to what he calls “the cult of efficiency,” suggesting that paying attention to our procrastination means asking whether the things the world wants us to do are really worth doing.

That’s a radical thought for January, when we’re conditioned to optimize and maximize. But perhaps the most important question isn’t “How do I stop procrastinating?” but rather “What am I avoiding, and why?”

The Perfectionism Trap

Perry argues that many procrastinators are actually perfectionists – not because they do things perfectly, but because they fantasize about doing new tasks perfectly. You receive an assignment and immediately imagine producing something Hemingway could have written. You set the bar impossibly high, then look at it and think, “I’m not going to try to jump over that.”

Here’s the liberating truth: procrastination can give you permission to lower the bar. As the deadline approaches, you realize you won’t achieve perfection, so you sit down and produce something perfectly adequate instead. And here’s the secret—perfectly adequate usually does the job.

This new year, instead of vowing to do everything perfectly, try vowing to do things adequately. “Adequate” sounds uninspiring, but it’s the enemy of paralysis. An adequate workout is better than no workout. An adequate first draft is better than a blank page. An adequate conversation with a friend is better than avoiding them because you don’t have time for a “proper” visit.

Practical Strategies for Working With Your Nature

So how do we harness procrastination instead of fighting it? Here are approaches drawn from both Perry and Santella’s insights:

  • Embrace Structured Procrastination. Keep a list with seemingly important tasks at the top. You probably won’t do those tasks, but you’ll accomplish the items below them while avoiding the top priorities. The trick? Put things on your list that seem urgent but aren’t actually critical. Let yourself delay those while getting real work done.
  • Question the Cult of Efficiency. Not everything on your to-do list deserves to be done. Before you procrastinate, ask yourself: Is this task genuinely important, or is it something imposed by external expectations? Some procrastination is wisdom in disguise.
  • Lower Your Standards (Strategically). Perfectionism paralyzes. When you notice yourself avoiding a task, ask: “What would an imperfect but acceptable version of this look like?” Then aim for that. You can always improve it later.
  • Use Procrastination as Information. If you’re consistently avoiding something, investigate why. Are you scared? Uncertain? Is the task actually important to you, or are you doing it because you think you should? Your resistance might be telling you something valuable.
  • Maintain Multiple Projects. Procrastinators need options. When you have several meaningful projects active simultaneously, you can productively procrastinate on one by working on another. This is far better than having only one priority that you’ll avoid by doing nothing of consequence.
  • Accept Yourself. Perry’s colleague suggested that happy people often take an inventory of their flaws, adopt a code of values that treats these things as virtues, and admire themselves for living up to it. There’s wisdom in this tongue-in-cheek observation. Stop fighting your nature and start working with it.

A New Year Without Guilt

As you move through these early days of January, carrying your fresh resolutions and good intentions, I invite you to consider a different approach. Instead of declaring war on your procrastinating self, try understanding that self with compassion and curiosity.

You are not broken because you delay. You are human. And humans are complicated creatures with competing desires, protective instincts, and creative needs that don’t always align with productivity culture’s demands.

This year, when you find yourself cleaning out your inbox instead of writing that proposal, or researching new productivity systems instead of using the one you have, pause. Notice what you’re doing without judgment. Ask what you’re avoiding and why. Consider whether the thing you’re avoiding actually matters.

And then – here’s the truly revolutionary part – do something else from your list. Move. Create. Connect. Just don’t do nothing, and don’t waste your energy feeling guilty about not doing the “right” thing.

Because here’s what Perry and Santella both understood: procrastinators aren’t lazy people who need to be fixed. They’re active people who need to be understood. And sometimes the path forward isn’t through better discipline, but through better self-knowledge.

This January, instead of resolving to stop procrastinating, resolve to procrastinate with intention. Understand your delays. Use them. Learn from them. And give yourself permission to be imperfectly productive.

After all, you’ve probably been getting more done than you realize. You just need to give yourself credit for it.

Now, if you’ll excuse me, I should probably get to that other thing I’ve been putting off. Or maybe I’ll do something else first. And that’s perfectly fine.


Part of a regular series on 27gen, entitled Wednesday Weekly Reader.

During my elementary school years one of the things I looked forward to the most was the delivery of “My Weekly Reader,” a weekly educational magazine designed for children and containing news-based current events.

It became a regular part of my love for reading, and helped develop my curiosity about the world around us.

The Love-Hate Confessions of a Horizontal Organizer

or, the domino effect of renovation in action.

A few years ago, my wife and I replaced our antique brass bed with a new bed. That led to a minor redecorating of our bedroom, which led to a major effort to simplify life in our house. As parents of four, but being empty nesters, we decided to reduce our furniture footprint, change our room use around, and redecorate our house – to be accomplished over several years.

After a few trips to Goodwill and Restore to donate furniture and other items, we had a working kitchen with plenty of space for 3 chefs at a time (we’re a foodie family), a small home office tucked away to one side, and an island for casual eating for 3. The family room lost the media center, replaced by a wall-mounted screen and sound system. The fireplace wall’s built-in side book shelves were cleaned up, organized, and looked great. Free standing bookshelves were rearranged, relocated, or removed. New furniture was chosen and delivered to create a simple, clean look. A complete redesign of the room-facing fireplace wall brought a new focal point to the entire room. The original dining room – our computer room and my office for 17 years – was returned to a dining room furnished with art from several Charleston trips, along with a custom-built dining room seating ten. One of the front bedrooms – our daughter’s – became known as the Disney Princess room, decorated with Disney art, a “magic mirror,” other Disney features, and a Lego Disney Castle, all just waiting for our grandchildren to visit. The other front bedroom – our youngest son’s – became Anita’s office, but also a guest room, courtesy of a Murphy bed mounted to one wall. The front bathroom was remodeled with a new designer vanity and tile flooring. The entire downstairs ceilings were stripped of that awful 90’s popcorn ceiling, smooth-coated with plaster, and painted. All of the downstairs rooms were painted in shades of grey. My office was relocated upstairs to what was originally a bedroom for two of our sons, and also fulfills a guest bedroom role.

I was completely happy to be out of sight from the main floor, and relocated my work there. Since Auxano had been founded as a digital company in 2004, most of my work took place there.

Therein lies the problem.

My vocational title at Auxano is Vision Room Curator and Digital Engagement Leader, which is a really cool title, but functionally I read, research, and write – a lot of all three. Which involves books – lots of them (even in the digital reader age). And project files (I’m trying to go digital, but it’s taking awhile). More books, as in book towers – one for each of the 7+ years of SUMS Remix. And visual learning objects – lots of Disney items including a Sorcerer Mickey hat and Mickey hands; gas station memorabilia; Starbucks cups and barista training materials; pirate gear and props, etc. – all related to projects I’m currently working on and/or keeping updated. Then there’s special family photos, challenge coins and patches of my Air Force son’s career, and did I mention personal books?

My name is Bob, and I’m a horizontal organizer.

I like the things I am working on spread out on a surface in front of me, where they can beckon me to continue working on them. Efficiency experts and time management gurus live in a world of vertical file management and a digital, paperless world, but me – not so much.

As a horizontal organizer, I am at a situational disadvantage. The whole world is set up to help keep vertically organized people on top of things. On the other hand, all my work is on top of things – my desk, the tops of filing cabinets, bookshelves, the nearby futon (I’m getting better, Anita – I really am!), and the floor.

As you have no doubt heard, a messy desk spread thick with paper and stacked high with books is the sign of a genius at work.

At least that’s what I tell myself.

The relocation of my office from the main level of our home to the second floor has had many benefits, not the least of which is increased domestic tranquility – a phrase not exclusively limited to governmental issues by any means. Because of my tendencies towards horizontal organization – actually, more like a full-out embrace – my working office is out of sight, but not out of mind – the office must also remain a guest room (but give me a couple hours notice, please, to ahem – rearrange things).

Anita has gently, but, firmly, been suggesting for several years now something to the tune of “that mess office needs some work.” As with much of life, it was put off some, and then some more.

At this point I need to pause and give special thanks to my youngest son Aaron, who in his senior year in college pointed me to the book The Art of Procrastination, by John Perry. After he bought the book, read it, and wrote a paper on procrastination the day it was due, he gave it to me to read.

Through it, I was introduced to the concept of horizontal organization. I enjoyed learning about, and practicing, Structured Procrastination, To-Do Lists, Procrastination as Perfectionism, and other strategies for the serial procrastinator.

With that under my belt, I became aware of another book with a similar topic: Soon: An Overdue History of Procrastination, from Leonardo and Darwin to You and Me. Author Andrew Santella explores a diverse group of individuals, from Charles Darwin to Leonardo Da Vinci to Frank Lloyd Wright, to ask why so many of our greatest inventors, artists, and scientists have led double lives as committed procrastinators. Here’s a couple of quotes:

In the process of trying to avoid one task, I was in fact completing many other tasks. Even procrastinators can become task-oriented, when the task they are oriented to is procrastinating.

Procrastination is really a kind of time travel, an attempt to manipulate time by transferring activities from the concrete past to an abstract future.

As noted in last week’s Friday post, Anita had had enough. In the genuine spirit of a combination birthday and Father’s Day gift, she said we would be redecorating my office. And, by the way, something had to be done about those books.

You saw the panoramic shot; that was then, this was next:

The entire office was crated, cataloged, and moved to first the garage, and then a storage unit. If you’re counting, that’s 42 crates as pictured above, plus another dozen or so boxes of various sizes.

Finally, a blank canvas:

Next week: The Big Reveal