deformed hands reaching out of purgatory
Photo by Yaopey Yong on Unsplash

The Art of Procrastination

Maria Massei-Rosato
Better Humans
Published in
9 min readApr 1, 2022

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As far back as I can remember I have been a procrastinator. Not many people know this about me. Probably because what I present to the world is a woman who can get stuff done. My cousins and I have a dream of writing a television series together, Surviving the Cousins. To get started, we crafted character descriptions for each other. This is the one my cousin wrote for me:

Maria believes her day has 36 hours with a typical day including: 2-hours of writing, a family bike outing, a trip to a museum, and then when her family is ready to crash, she suggests a kayak ride which doesn’t surprise her husband anymore ever since she dragged him 3,300 miles across the country by bicycle.

In high school I read books assigned in English just a few days before the assignment was due. In college I would study late into the night, David Letterman playing on a Panasonic 10.5” television, humongous textbooks open to chapters I would be tested on in the morning. Whenever I had a thought that this was crazy and I should have started studying sooner, I would reassure my procrastinator mind that cramming made the information stick in my head. I have no objective proof of this since I never tried to study for a test a week or two beforehand.

My daughter is a procrastinator too. She waits until the very last minute to complete her high school assignments. It will be 10:00 pm and she will dance with headphones on, watch a few episodes of a Netflix series, and make herself crepes from scratch before she’ll sit down to start and finish a report that is due at midnight. I don’t police this. She knows what has to get done and her procrastination works for her — she’s a straight-A student. But it isn’t always pretty. Just after a melt-down, minutes before a midnight deadline, she said “the problem is that I am a procrastinator and a perfectionist.” She nailed it. I took the opportunity to say “Good that you recognize this. How about letting one of them go?” And she said, “Nah, it works for me.” The wisdom of a child.

Purgatory Diversion

I am not sure I would have ever been able to articulate this at her age, and I only realized I am exactly both of these after she said it. When I shared this with my cousin — the same one who wrote my character description — she reminded me that Dante describes procrastination as one of the sins punished in purgatory. That didn’t sound good.

In my career at the NY Fed, I procrastinated my way through the most complex and creative work. When a teammate would ask, “How’s that paper coming along?” I’d reply, “Great.” even though I hadn’t started it yet. When my boss would ask, “How’s that presentation coming along for the president?” I would reply, “Slides are almost there,” when really I would only have a very rough draft.

My colleagues never guessed because I always delivered the goods. And they never suspected because there were so many other non-complex, non-creative tasks that I would complete ahead of time. This is because I am wired to execute. Give me a problem to solve and I’ll solve it. I never really understood the difference between my two modes of operation. Easy stuff — just do it. Complex, thorny, creative problem-solving — start at the very last moment. But then I was introduced to concepts and skills that explained the why behind my actions.

The Aha Moment

It started five years ago with an executive education course. I was in a rut. I felt I hadn’t learned anything new in the last few years and that’s a huge disappointment for someone who thrives on continuous learning. I had all the technical skills I would ever need. I was adept at communicating both in writing and in-person; I had worked at networking and building relationships in and outside of the organization. I was a good manager, coach, and mentor, so what was left? I started a random search. Well, not so random. I decided on exploring the executive education courses on the east coast. Not long into my search I stumbled upon Leading & Building a Culture of Innovation offered by the Harvard Business School (HBS). Yes! This was it. Not only was I trying to build a culture of innovation with my team and with others in our organization, but I had that feeling of knowing — I knew this was where I had to be.

Each day we learned a framework or concept and then we broke up into small groups to practice it. We designed and built a physical model with constraints. I don’t recall the exact instructions, but it was something like: an object needs to travel 3 feet and then drop from a height of six inches in less than two minutes. I do recall we failed, and so did everyone else with the exception of one team. I’m convinced they had been front-loaded with engineers. In another breakout we designed life in outer-space, all the components of what makes a successful society and who should travel there to create it: scientists, doctors, botanists, teachers, politicians, etc. The politicians were left behind.

The concepts behind these exercises, adaptive leadership and design thinking, were like magnets to me. Adaptive leadership is a model created by Ron Heifetz and Marty Linsky that embraces change, experimentation, and innovation, and one that can mobilize a group to handle tough, adaptive challenges. And so what is an adaptive challenge? It’s a challenge that is high in ambiguity and sometimes high in conflict. It’s a challenge to which no known solution exists, and the skill-set to solve it isn’t already in your bailiwick. It’s a challenge that tempts the desire to reduce conflict and/or create less ambiguity. Lightbulb on! How many times had I struggled to solve a problem and realized that either I didn’t have the skills or information to solve it, or I sought to reduce conflict and ambiguity without fully extracting the learnings? Or, and most often this happened too late, solved for the wrong problem?

When I’m attracted to concepts, I want to share them. So I set out to recreate an experience like the HBS program for my organization. I worked with Maurizio Travaglini and his team of Architects of Group Genius to develop a lab experience inside the NY Fed. It was called Dare to Do New, and it was a phenomenal success. The participants had their own lightbulb moments. Our executive sponsor even admitted to everyone in the room, some of whom worked for him, that he had spent much of his career solving adaptive challenges with technical skills.

5 hexagons with the following phrases: empathize, define, ideate, prototype, test
Stanford d.school Design Thinking process

The Masquerade

Where does design thinking fit in all of this? The design thinking process (empathize, define, ideate, prototype, and experiment) is crucial to solving adaptive challenges. This design thinking is not to be confused with the Agile process applied to software development. While they are both set on the foundation of design thinking, the process I am describing applies more broadly to creative problem-solving.

It may sound counter-intuitive to slow down, mull over, iterate, and step back to ensure the right questions are asked before any action is taken. It’s this lack of action that can masquerade as procrastination, not the kind punishable in purgatory. It’s the kind that creates space for deep thinking to happen to truly understand the nature of the complex problem, to live with the discomfort of conflict and ambiguity, and to avoid applying technical skills to solve an adaptive challenge.

Cal Newport, professor and computer scientist, wouldn’t call it procrastination. Cal, the author of Deep Work, says that great work demands concentration and intensity in a distraction-free state. That means no multitasking, no checking emails or answering Slack pings. And besides, there is no such thing as multi-tasking. Really! I lived my life under the illusion that I was a multi-tasking expert, knocking things off my to-do list with precision and speed. My son, a freshman in college at the time, burst this bubble when he started a conversation with “Mom, you know there is no such thing as multitasking.” I shot back quickly — of course there was — I spend my whole day multi-tasking. He proceeded to tell me his university professor declared that the brain can only work on one thing at a time. And I had two thoughts: Is this really what I’m paying for? And, do these cushy academic professors understand the nature of the corporate world and how we must multi-task to survive?

But my son was right. Amishi Jha, cognitive neuroscientist says it best:

Multitasking is an absolute myth. Our mind cannot pay attention to more than one thing at one time. While multitasking we are only doing task switching. It wears us out more than anything else. The fatigue makes you less able to handle your emotional state. It degrades the capacity you need to handle your stress.

And if this wasn’t bad enough, I learned sustained rapid switching from one task to another can permanently impair our ability to do deep work. Psychologist Daniel Goleman says,

Attention works much like a muscle — use it poorly and it can wither; work it well and it grows.

This realization was a low moment in my career. What if I was working in a way that was permanently impairing my ability to think deep? Had I really spent much of my time and energy in a space that stifled my ability to be creative? I took solace in the fact that in my writing life I was practicing deep thinking. It’s how I wrote a memoir and a screenplay based on the memoir and that’s how I intend to develop that television series with my cousins. But it never occurred to me that this would be important in my day-to-day job of running a start-up program in our 100+-year-old institution. So I decided to test this out. I blocked time to work on thorny issues with just a marker, a whiteboard, and some music.

Several old alarm clocks on a self
Photo by Ahmad Ossayli on Unsplash

Wait, Like Kafka

So what happened? I got better at understanding the nature of the problem I was trying to solve. I sometimes spent hours just asking questions, pondering the ecosystem of the challenge, coming up with ways in which to test my hypotheses. It was important to detach from technology for this deep thinking to happen. As someone in the technology space, this was difficult to accept.

Once I experienced the power firsthand I decided to try it on my graduate students too. I approached the subject of going no-tech on the first day of class. There were a few loud gasps and worried looks because of course they all had their laptops and phones on their desks, taking notes or searching a term I used. I sent them home with Cal Newport reading material and at the next class they all agreed to give it a try. Guess what? It was a total success — even I didn’t use technology — I taught the old-fashioned way: I wrote on whiteboards, used hard copies of articles that we could work through together, and organized workshop-style exercises without the use of a laptop or projector.

So what is my advice on deep thinking and procrastination? Do it when you have a complex challenge. Set aside time for it. You don’t need your organization to bless this rule, a la Google. You can find this time. Believe me. It is there if you look. Block your calendar each week for 2–3 hours (at least). Go to a new space, not your home office or your cubicle or pod. Get outside or find an indoor space that’s conducive to creativity — high ceilings, lots of light, green landscape or live plants. Maybe play music, softly, without lyrics. Take a journal and a pencil or pen. Use a whiteboard with markers, or Post-its. Don’t pack your laptop and place your phone in airplane mode hidden inside a bag. Even seeing it will be distracting. Do all this as preparation and then WAIT. Yes, this also seems counter-intuitive, but the art of procrastination requires this time to be set aside. It is not to be confused with waiting for a muse. The distinction is preparing the mental and physical space for your mind to take you places you would not have been able to go if you had stayed with the mentality of do, do, do. Franz Kafka, the author that brought us Metamorphosis, said it best:

Remain sitting at your table and listen. Do not even listen, simply wait, be quiet, still and solitary. The world will freely offer itself to you to be unmasked, it has no choice, it will roll in ecstasy at your feet.

So there are advantages to procrastinating. I am a procrastinator, my daughter is a procrastinator…and I sure hope we won’t end up in purgatory.

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Author, screenwriter, and believer. I write about the intersection of my life as mother, executive, educator, and innovator. https://mariamasseirosato.com