Timeboxing for Resilience

A few years ago, coming out of a conference in Madrid, I was rushing into a cab with a colleague and friend of mine, not realizing my backpack was partially open. A laminated sheet with a bunch of odd symbols fell out, luckily inside the cab. My friend picked up the sheet, and saw something like this:

He asked what it was, and I told him it was my timeboxing reference card. He wanted to know more. But this wasn’t a casual inquiry. He wanted to get certified as a Thought Leader level Architect, and just couldn’t find time to prepare his package. Some time earlier he had asked me to be his mentor, but had not begun the process.

He was overwhelmed with tons of work, and thought of giving up. He even wondered if it was a self-imposed and somewhat unnecessary goal. After all, he was already making good money and was very good at what he did, so why should he let this ambition take over his life, especially valuable time away from his family?

Seen this way, it made sense; the constant mental switching between unfinished tasks, new tasks, customer deliverables, requests from his boss, and time owed to his family was strangling the time he had left to focus on his goal.

I told him that he probably had more time than he thought, and that he just needed to organize it better. I challenged him with this thought: although his immediate goal was his package, later in life, he might want to spend time on other goals or on a fulfilling hobby. His responsibilities in the future could also be absorbing a lot of his time, so would he use the same logic then? I piqued his interest.

With more than enough time to arrive at the airport, I decided to share some of my own struggles with him, at least enough to put my words and the odd sheet he saw into context.

During my days as an undergraduate in Computer Science — decades ago — I was struggling to learn a particular concept in Assembly Language for the IBM PC. I couldn’t fully understand how overlapping memory segments worked and how they enabled the Intel 8088 chip to reference a whopping one megabyte of memory with 20-bit addresses. The topic isn’t difficult (makes me smile in retrospect), but I was stuck. I had a general understanding, but still felt extremely uncomfortable, limping along without fully grasping the concept. I even lost sleep over it (yep, a little crazy). Assembly language was one of my passions, and I wanted to master the topic, but this particular concept kept stumping me. Whenever I found the time and had enough energy, I would pull a late night to try to get the topic under my belt, but my attempts were futile.

I felt discouraged, but didn’t give up. One day I decided to do two things:

1. Daily, for one uninterrupted hour, I would read about memory segmentation on Intel chips. My plan was to stick to this, even if I had to read the same page every day. Notice the emphasis on “uninterrupted” At that time, I was a full time student at Fordham University in New York, had a job in the city, and faced additional challenges with a sick family member. Between studying, working, and commuting, my day was packed, and tasks were easily interrupted. Feeling overwhelmed was my daily dose.

2. Because this topic was consuming a lot of my thoughts, I decided that, after completing my daily hour, I would not think about it again for the rest of the day, and I would be at peace with that.

To remind myself, I created a mnemonic on my planner titled MASM1. MASM stood for Microsoft Assembler and the 1 reminded me that this was a one hour deal. I used MASM instead of, say, MEMSEG for memory segmentation because learning assembly language was my long term goal; understanding memory segmentation was just part of it. I planned to continue sharpening my assembly language skills daily, beyond the immediate problem.

Rather than setting fixed times in my schedule, which would have never worked for me, my commitment was simply to have the MASM1 symbol written down every day on my planner, from Monday through Friday. On some days this meant completing the task at midnight, and that was fine with me. I later improved on this.

There was one rule: I could only write the mnemonic on my planner once the task was completed. Seeing a day without the MASM1 symbol would be a constant reminder that I needed to complete the task, while the joy of being able to write it gave me a sense of victory — the feeling of a day well spent.

In just a few days of focus and consistency, I finally understood memory segmentation and the mental torture was over. More importantly, the experience was an eye-opener. Unwittingly, I had discovered timeboxing — allocating a fixed time period called a timebox to perform a particular task and then stopping once the time was up. For me, this was “the” way to get things done in a consistent and, might I add, more civil manner.

That year, I kept implementing MASM1 and eventually started adding new mnemonics to my agenda: Ex1 for exercise, C1 for C programming, FREE1 for “me” time, PR1/2 for prayer time, and Sleep7 to force myself to get enough rest. Some of these I did every other day or twice a week.

My colleague had heard about timeboxing, but still didn’t buy it, mainly because of too many distractions and the thought that timeboxing wouldn’t give him enough time to complete things. As I suspected, he hadn’t really tried, so I encouraged him to give it a shot and keep close track of his timeboxes, which, in my case, were the symbols on my planner.

The size of my colleague’s final goal, his certification package, which back then was a 40–50 page report of demonstrated accomplishments, was discouraging him from taking small consistent steps toward his goal. He went back and forth between thinking he was an underperformer to looking at his certification as superfluous, despite knowing it would help his career. I advised him to dismiss those thoughts and just consistently work on his package, even if it was just for 20 minutes a day. Surely he could find the time. “Don’t worry about the deadline,” I advised him. If he was consistent and still missed the deadline for that year, so be it; he would be more than ready to present his package the following year, and would have the satisfaction that he spent his time wisely.

I added that I knew guys who said they would work on their packages — with the best intentions, no doubt — only to find that a couple of years later they hadn’t started.

I recommended these three simple steps:

1. Prepare a reference card with the symbols that will guide your daily activities. As you learn more about how you work, tweak it accordingly.
2. For each symbol, use a number to remind you of the time involved. Make sure your numbers add up to a full day minus some extra buffer time. I like to use a superscript font for the numbers.
3. Keep the card inside your planner, as a reference of what you need to complete that day, and then write the mnemonics on your planner only as you complete them.

I then added some additional tips:

1. Start small and stick to the allotted time. You can always add additional mnemonics later.
2. Prioritize and plan ahead. Create the most important mnemonics first.
3. Resist the temptation to exceed your planned time, just to finish a task that day. Of course, use common sense. If you’re a student, for example, and your paper is due tomorrow, finish it. Your teacher may not like that you stopped working to follow the higher cause of timeboxing.
4. Record your symbols and review progress daily
5. Double-dip your tasks when necessary to not go crazy. For example, my Org2 symbol meant I had to spend two hours of my day organizing things and catching up. This could mean taking care of bills, catching up on emails, helping my children with homework, etc. If I spent all that time helping my son with his science project, for example, I could also count that as family time, especially if he told me the night before that his project was due tomorrow.
6. At least one of your symbols should mean the equivalent of “Free Time.” You’re not a machine. Leave enough buffer time for yourself and between tasks to regroup.
7. Get creative, and add mnemonics for atomic habits too. If you love sweets, and want to stop eating them between meals or altogether, why not add a symbol to remind you of this in your daily plan?
8. Treat yourself to a full rest day during the week.

I also identified some anti-patterns:

1. Don’t start your day without first pausing to look at what’s ahead, even if it’s just from your bed. For me, prayer in the morning works best. If you don’t pray, take some time to think about the quality of your life, your health, your relationships, the goodness in others, etc. Read an inspiring book.
2. Remember that your time is limited. Don’t pack your day with so much to do that you can’t recover from short interruptions.
3. Don’t feel you have to make every day identical. That’s what the reference card is for — to remind you of which symbols you need to have in your planner for that day.
4. Don’t try to make up for goals not reached in a day. If you missed an hour of exercise, for example, don’t try to do two the next time. You’ll just burn yourself out. Having some days with missing icons may bother you, especially if you are compulsive about a “perfect record,” but following this rule will eventually teach you to avoid time wasters and focus on your daily goals. Don’t lose sight of the bigger picture, which is to establish good habits for managing your time, not to have a perfect report card.

“Finally,” I told him, “the real benefit to timeboxing is resilience.” Many times, when school, work, and my personal life were too overwhelming, timeboxing meant “living” in the midst of the craziness. Exercising and getting enough sleep, as well as spending time doing something that I loved was important and refreshing enough to help keep me going. I also felt better knowing that I was intentionally using my time consistently. The rest would just have to fall in place. To each day its own evil.

“Don’t lose hope,” I insisted. In the end, one of the craziest years of my life became one of the most productive at the time, and my knowledge of assembly language and C paid off in ways I couldn’t have imagined. Years later, I was hired by IBM to do OS/2 Kernel debugging, which required heavy knowledge of C and assembly language.

By the time we reached the airport, my friend was visibly inspired and full of hope. I reminded him not to get discouraged if he found it difficult at first.

The hardest part of many things is getting started, and timeboxing takes practice, discipline, and willpower. Experts say it takes at least 21 days to create a new habit, so try really hard not to miss a single day at first, even if you fall short of meeting your goals. Just keep going, and guard against time-wasters, laziness, and perhaps your own natural resistance to continue.

A few days later, my friend called to say that he had started timeboxing and had carved out 30 minutes daily to work on his package (his mnemonic was CertPkg30m, by the way). He did so consistently, and completed his package that year, successfully becoming a Thought Leader level architect. I was elated.

Timeboxing is king. Over the years, I’ve experimented with different approaches to time management, some more sophisticated than others, but this simple way of timeboxing has been the indisputable champ for me; whenever I apply it, I am the most productive, resilient, and happy version of myself.