Recently, I converted all of my (very old) academic writing from outdated document formats (WordStar and Microsoft Word 6) to more future-proof formats: either Markdown or OpenDocument format (.odt). While I did not re-read every essay I ever wrote for school during this process, I did notice something in my files that surprised me: From my junior year of high school to my final semester of grad school, I created outlines—full sentence outlines¹—for all of my papers that were over a few pages in length. I had forgotten that I used that type of outline for more than two important projects in my academic career: my first English thesis project and my last.

My first English thesis project, wherein I learned about the sentence outline

I was first taught (i.e., forced to use) a sentence outline in high school. It was a requirement of my grade 10 English thesis project, which was a 10-page research and literary criticism paper. At the time, I understood how to create high-level outlines pretty well, but could not understand why I would create an outline that contained full sentences of the essay I was trying to write. I figured that if I could write a sentence outline for an essay, I could just as easily (or more easily) write the essay itself. In grade 10, that is precisely what I did: I wrote the essay and then split apart every paragraph and every sentence into a hierarchical outline. In doing so, I learned almost nothing.

My last English thesis project, wherein I mastered the sentence outline

For my final English thesis project, my senior honors thesis in English at Brandeis University, I resorted to a sentence outline to solve my writer’s block. It was a year-long, independent study project, and my thesis advisor—who mostly told me that despite my anxiety I was doing fine—was not terribly helpful or available. Understandably, I lacked direction. I had no idea how to write a big, scary, and academically significant 80-100 page essay. When I sat down to write, I would either produce a jumbled mess of thoughts and quotations that did not fit together, or I would compose a coherent paragraph that I could not connect to anything else I wrote. As my senior year went by, I felt as if I was falling further and further behind my brilliant, thesis-writing peers. Counterintuitively (or understandably, depending on how you look at it), this feeling of dread led me to procrastinate instead of write.

In the early spring, I realized that if I created an outline, I could work on my big, scary thesis essay without actually writing it. To that end, I split the work that had been going nowhere into two Word documents: (1) a simple, high-level outline that consisted of just a few headings at the start; and (2) an unorganized junk drawer of ideas and quotations from my source material. Outlining quickly became a productive form of procrastination for me. Instead of writing my essay, I would pluck out ideas from my junk-drawer document and drop them into the outline. From there, I would change these ideas, move them around, flesh them out, add to them, or delete them, all without committing to their precise wording or location. Because these ideas were all sentences or block quotes, my outline necessarily became a sentence outline.

Using keyboard shortcuts I no longer remember, I collapsed sections and paragraphs of my thesis outline and moved them up and down to organize my ideas, and I shifted individual sentences up and down to make my arguments clearer and easier to understand. Because I was avoiding the writing phase of my project, I avoided gluing my sentences together with logical-, narrative-, or stylistic flow until I felt sure they were in the right place in the document and in the right order in their paragraph. Doing so took some time to get used to, but granted me a feeling of tremendous freedom as I worked out the essay’s high-level structure and the fleshed out the arguments I was advancing within it.

I didn’t realize until I was finalizing my thesis—when my outline was a 100-page outline full of section headings, topic sentences, and body sentences organized into paragraph-level nodes—that I was doing exactly what I was supposed to do. I had organized my research and my findings in a format that was incredibly flexible, and I was constantly revising it and shaping it into something coherent. By accident, I had finally learned why a sentence outline is useful: It explodes an essay into individual thoughts that are physically separate² and logically atomic³. Doing so makes it easier to evaluate each one independently and—with a good word processor—to quickly group, ungroup, reorder, and move them into place.

In the end, I never wrote my thesis paper. Instead, over the course of a few months, I wrote a sentence outline. I converted it to a manuscript only a day or two before I turned in the final draft. My only edits to it, in manuscript form, were related to applying Word styles to the various paragraphs and adding a title page. The final draft must have been pretty good because it was awarded the Doris Brewer Cohen Award for best senior honors undergraduate thesis in the humanities at Brandeis University.

In grad school and beyond

I went to business school after college, and did not have to write nearly as many long papers to earn my M.B.A. as I did to earn my undergraduate English degree. Despite the small number of major papers I wrote, and despite not remembering the writing process I followed for them, I discovered that I wrote sentence outlines for each one.

After grad school, almost all of my long-form writing has been technical writing for work. While I do not have any old drafts lying around, I recall using outlines extensively to plan and structure my work, but I never again used sentence outlines to draft and perfect it. One reason for that may be that I used different software to write with: mostly plaintext editors, rarely Word (not until I had a first draft nearly completed), and never a dedicated outliner like OmniOutliner. Another reason is that much of my technical writing had to fit into pre-existing document templates that already consisted of many short sections laid out in a specific, required order.

After discovering my longer-than-remembered history of using sentence outlines, and reminiscing about the senior honors thesis project on which I mastered the use of them, I now wonder if I should go back to using them for my larger writing projects.

I have been doing fairly well at work this month, but I feel kind of terrible about it. I feel like I am falling short in terms of productivity every day. Part of it is that I have been spending a lot more time managing than doing. I am keeping abreast of what my team needs, at the expense of getting my own tasks completed.

I probably won’t be able to prioritize my tasks as well as I would like to for the next two of three months. To regain some feeling of control, however, I will go back to a technique that I have often employed when I am unsure of myself: starting each work day with a journal entry in which I list my priorities for the day.

The poet often sits upon the edge of reason, testing the waters of both sides with both his hyperactive poet-senses and his nightmarishly sluggish normal-senses. Treading both sides for a time, he realizes both of these seas are just as cold and just as briny, but the one just beyond reason is far deeper. With this, he dives in, drinking deep, closing his eyes beneath the surface, coughing up the salt when he bobs up for air.

The internal battle begins between the all-knowing and the not-caring, between divulging too many secrets and sharing too little of what he knows; it promises to rend him in two. This is the curse of the poet. And that of the saint. To see so much, and know so little, and yet grasp an understanding far beyond the rest of the world.

At his worst, the poet sits high up above the world and showers his insight down upon it. At his best, he sits high above the world and pulls the rest of it up to him.

A big success is made up of many smaller ones. A coworker reminded me of that today, and I really needed to hear it.

Modernity is a thin veneer over thousands of years of baser and humbler human history. Almost everything we take for granted today—like electricity, telecommunications, antibiotics, vaccines, knowledge of the internals of the atom, an understanding of DNA, the discovery of plate tectonics, limited space travel, microchips, complex computer modeling, the internet, and so on—was invented or discovered within the span of two or three lifetimes.

When I was a little kid, some of the things I was taught in science class had only been discovered or agreed upon within the past twenty years. A lot more things, such as nuclear energy and weapons, had been invented or discovered in the prior fifty years. As a six-year-old first-grader in the 1980s, fifty years ago may as well have been five-hundred; I couldn’t understand how new everything was around me. For instance, I didn’t realize that my dad had been born before the atomic bomb had been invented. Just today I learned that he was born even before helicopters, which he helped manufacture throughout most of his career, were invented.

It is absolutely astonishing to be alive at such a time, when the past hundred years or so invented nearly everything around us, and we expect new scientific discoveries and new inventions practically every week. It is also very troubling that humans, after only such a short time enjoying the fruits of our ingenuity, seem to be unable to focus on and solve the climate crisis that modernity caused. I fear that thousands of years of baser and humbler human history could return to us at some point in the future if we do not learn to work together to preserve our planet.

When I first started work as a systems analyst I knew nothing about business and nothing specific about systems, but I knew a lot about language. I realized early on in my career that technical and non-technical people approach problems so differently that they are, in many cases, not even speaking the same language. In meetings between the business team and the IT team, I would always either start the meeting, or steer the meeting toward, defining common terms for both sides to use to talk about the problem. It is a tactic I still employ a lot to this day, especially when people seem confused about what the problem is or when the conversation isn’t going anywhere.

At some point, everyone wishes to be seen and heard. Giving people the attention and consideration they deserve takes focus, patience, and a commitment to preserving their dignity.

Sometimes the person wanting to be seen and heard is a victim; other times that person is a bully. It can be very difficult to see and hear them both.

The worst part of memory is its selectiveness. I can remember, in excruciating detail, every embarrassing moment, every incidence of social awkwardness, every chance I should have taken but didn’t, every blunder or pratfall, every mistake on an important exam, every poorly written paper, every taunt hurled at me, and every dressing down I ever received. I wish I could say that I remember all the successes and great things in my life just as vividly, but it simply is not true.

From what I gather, the way my mind works is entirely normal. I wonder if all it takes to remember all the winning moments in life just as well as the embarrassing ones is to make the effort to do so. For some reason—human nature, I always figured—it feels much harder to celebrate the wins than to mull over the losses.

One thing I never planned for in adulthood is developing a strong preference for trailing punctuation to remain outside of quotation marks¹ unless the period, comma, or other punctuation mark itself is being quoted. I wonder if the people I work with, who read my emails and technical writing every day, think I don’t know how quotations marks are supposed to work in American English². No one has ever called me out on it. Either they don’t know that trailing punctuation is supposed to go inside quotation marks in most cases, they don’t care about it, or they don’t notice it at all.

When I find myself struggling to be creative or productive, I always think of a story I read in Annie Dillard’s The Writing Life. It was about a rower who was pulled out to sea one evening by the ocean tide. He rowed and rowed all night and kept being pulled farther and father from land by the ebbing tide. In the morning, however, the direction of the tide reversed, and he was pushed back to the shore to safety.

I remember this story so vividly because I had to write a very short essay about the book in my A.P. English class. We had to answer three specific questions about the book in one paragraph each. The teacher stressed how important it was for this assignment to be brief; only one page and three paragraphs.

I chose to answer the last question by writing about the story of the rower. Unfortunately, my explanation of the rower’s story stretched to two whole paragraphs, making my essay far longer than the one-page limit. At that time in my life, I had no idea how to pare down my writing even if it meant cutting parts of it I liked. I agonized over how to cut it down, but decided, uneasily, to turn it in as it was, despite it exceeding the one-page limit.

Happily, my overlong essay was a big success. I may have I understood the story of the rower better than even the teacher did, because the day after I turned it in he began the class but projecting my essay—all two pages of it—onto the classroom’s pull-down screen, and asking the whole class to read it. He seemed genuinely touched by it, too.

This evening I pulled the essay out of my archives to reproduce below. The last two paragraphs are about the rower. I think about the ideas expressed in them on a weekly basis to this day.

An Approach to The Writing Life by Annie Dillard (20th century [1980s])

Michael Descy

AP English

10/26/95

A main theme of Annie Dillard’s The Writing Life is the importance of overcoming all the difficulties faced in the fulfillment of one’s dreams. The life of a writer can be dark and lonely, demanding much introspection and many late nights alone with an unruly manuscript. The writing process itself is difficult beyond most people’s conceptions. It is so harrowing, so haphazard, and so time consuming that most people that have one burning idea for a particular novel or story are never able to actually follow through its capitalization. Most never really even start, and the few who do often form such an attachment to their work, because it was so hard for them to accomplish, they will not allow themselves to alter it in any way, even to tie up loose ends or discard the beginnings of dropped themes and plot turns. Thus, their piece is never perfected; their dream is left to waste. Despite all these trials, however, writing is a very rewarding activity. Writing is like a passion eating at you, an aching, a hunger that can kill if not satiated. Only persistence, slogging through the murk and endless toil of the process, will enable one to fulfill his dream.

A dominant tone of the work can be described as enthusiastic. Dillard is intense as she explains the writing process. She describes writing in exhilarating terms, comparing it to playing tennis, lion taming, and stunt flying. Her metaphors are powerful, zesty. She shows your work as a line of words pulsing through your bloodstream and shooting across the universe. She tells us committing a vision to paper is a futile fight with the jealous, tyrannical page, the forces of time and matter working against you. Her chapters are choppy, broken down into many vignettes and tiny observations. There is a break on almost every page. They are so frequent each seems to be a gasp of breath between her quickly blurted images.

A strong scene that feels as though it will provide a good doorway for thoughtful attention to an important aspect of the work is the story of Ferrar Burn, which her painter friend, Paul Glenn, told her. One evening, years ago, Ferrar Burn caught sight of an eight-foot log of Alaska cedar floating out in the channel by his house. It was high tide, the water slack, so he rowed out, tied the log to his little eight-foot pram, and proceeded to tow it in. The tide turned, however, catching him, pulling him farther and farther out to sea. But Burn kept rowing against the tide, stubbornly, obstinately towards his house. He strained against it all night to little avail. When the tide finally changed the next morning, it finally pushed the still-rowing Ferrar Burn back home.

This scene connects very well to the aforementioned theme. Through persistence against terrible odds, the rower Burn was finally able to succeed. Had he given up, stopped rowing, he would have drifted so far out to sea that the tide change which eventually pulled him back in would not have helped him. A writer too must pull against opposing forces to accomplish his or her goal. There is much about the process that pushes people away. Most would just assume go along with the tide, take the easy route, and be led far away from their dream. But the few with the dogged insistence to stick with their craft, pull through their troubles, and never lose sight of their objectives are able to ride out the tough times and sail swiftly and smoothly through the good times. These few are steeply rewarded in the end. Their prize: accomplishment of a dream.

I have been having trouble lately coming up with something to say each day on my blog. I am feeling somewhat uninspired. This lack of spark probably stems from spending many hours this past week (far more than usual) writing software. The many hours spent programming have taxed my brain so much that the acts of writing, doing chores, or doing my other day-job work have felt exhausting and unrewarding for the past few days.

The reason I have a blog is that I want to write every day, even when it feels impossible to put anything down, even when I feel I have nothing to say, and even if nobody else reads it. My goal is to practice explaining my ideas and opinions, developing ideas, and telling stories. Doing it every day is important to me because I have given up my creative endeavors too easily in the past. Stories seem impossible to end. A good song seems impossible to write. A buggy app seems impossible to fix. No one really cares about the things I create anyway, so why bother finishing them?

I have a different mindset now. A blog is never “finished” so I can’t fail at completing it. Conversely, a blog post is very short, so it is easy to finish. More importantly, it no longer matters to me if anyone else reads it. If someone does read one of my posts and leaves me a comment on Micro.blog, I am very flattered, but it doesn’t really matter. The blog is a kata. Practicing the forms is key. Nothing matters more.

Back in 2006, I bought a Nintendo DS and was fanatical about the game Brain Age: Train Your Brain in Minutes a Day. It was a game that promised to make you mentally sharper, as long as you did solved simple cognitive training puzzles every day.

For several months I played it daily, for five minutes or so, before I watched TV or played a more conventional video game. I told everybody about it. My best friend was a fan, too. After several weeks, I became blazingly fast at most of its puzzles, which included performing simple arithmetic, memorization, and doing a Stroop Color and Word Test. (The Stroop test was the hardest for me, due in no small part to my red/green color-blindness.) At the time, I thought that the daily training was making me smarter. Aside from being able to calculate restaurant tips more quickly, however, I noticed no other intellectual gains.

After some time, I stopped playing Brain Age—at least the brain training part. I had read that it didn’t really improve your cognitive abilities, and had come to the same conclusion myself by that point. Despite that conclusion, I still believe that playing games can make you smarter. That’s why I picked up Sudoku (which was included in Brain Age), the New York Times crossword puzzle, and, more recently, chess. I also do computer programming as a hobby, which is a little like playing a game against the compiler sometimes.

I play all these games to stave off what I fear is inevitable in my old age: mental decline. It think it is inevitable because I watched it happen to my father. At the tail end of his career (he worked until age 75), his mind started slipping away, little by little. I thought it was because he no longer had challenging work to do. Eventually, he developed dementia, and it became clear that the cause was medical in nature.

I realize now that I played Brain Age at the very start of his decline. Perhaps it was the trigger. I also realize that I still want there to be something I can do—mentally, that is—so that I don’t end up with the same fate.

Digital media is a miracle. It is infinitely reproducible with no loss of quality. The internet and all the devices we have make sharing digital media less expensive, on a marginal basis, than was possible via any other technology that came before it. We have invented a way to make some resources—like art and entertainment—effectively unlimited and nearly free.

We take it for granted now, and moneyed interests are busy trying to dismantle it with blockchains as I write this, but I think we should all step back sometime and consider how incredible and wonderful it is. The miracle of digital media isn’t that it can be made finite; it is that it is infinite. We should embrace that miracle rather than try to replace it with something mundane.

I advised a colleague today to research web3, because I think it may be the most interesting InsurTech technology of the year. I don’t think that glomming cryptocurrency and smart contracts onto the web is a good use of technology at all. The idea is especially dubious, and that is the reason it is interesting to me. I honestly think that web3, along with the cryptocurrencies that make it possible, are based on a long con.

Web3 appears to be something to make cryptocurrencies, which are useless—except as a speculative asset or a way to pay the criminals who ransomware-attacked you—useful. Web3 will require you to have a digital wallet to pay for and log into any website with a web3-type paywall. The rest of web3 is just another name for smart contracts, which—as far as I can tell—are an interesting idea that has not caught on very well in real-world applications.

Perhaps the scope of both my research and my imagination is too narrow, but I don’t think web3 is going anywhere outside the venture capital community, at least not for a very long time.

“That which can be asserted without evidence can be dismissed without evidence.” —Christopher Hitchens

I don’t get nervous speaking in front of people. I never have. The main reason is that I firmly believe that the audience wants you to succeed. And, if you don’t succeed, the audience will generally forgive you. Just show them respect at every step, and things will go fine.

I love how Matt Birchler compares crypto to BitTorrent in his latest blog post, “Maybe It’s Just a Product Nobody Wants”:

I don’t think crypto is going to disappear, by the way. I think it will always have a place in the world, but much like bittorrent before it, it was new & exciting, people tried to use it for basically everything, and then it settled into being used for, well, nothing for most people. Blockchains likely have a more prominent future, but there’s a lot of spaghetti being thrown at walls right now, and I think very little of it will stick because it’s not actually making better products.

I’m a crypto skeptic who thinks a lot about blockchain for work-related reasons. I dislike blockchain technologies because I think that, in the real world, they would fail to eliminate trusted intermediaries in financial transactions. Establishing trust without intermediaries is the whole point of blockchain.

I believe people and businesses are too risk-averse to do away with intermediaries like governments (who offer useful things like a legal system and deposit insurance) and the technology providers, agents, and brokers who make business work today. If crypto really takes off, and the old intermediaries are pushed out, I think that new intermediaries will pop up to fill in the gaps left behind. That future—blockchain with trusted intermediaries—is no better than what we have now, and is in many ways worse.

I wonder what specifically happened this week to make “web3” a topic on every tech news site and every tech podcast I listen to.

The elliptical machine and the treadmill stand proudly in my basement like dusty monuments from a forgotten age.

Stephen Sondheim died today. The world has lost a titan. My wife and I were lucky enough to see him sit for a long interview at Mason Gross School of the Arts at Rutgers a few years ago. He was sharp and witty and gracious, and we learned a lot. It is no surprise when an old man dies, but our minds are spinning nonetheless. At least he was able to live a long, productive life.

My wife teaches a public speaking course, and from time to time we talk about what examples of public speaking would be good for her students to watch. While we go through the usual speeches by luminaries such as President Kennedy and Martin Luther King, and also pick apart the speeches of politicians of our day, I always argue that, if you want to learn public speaking, you could do a lot worse than viewing and analyzing Steve Jobs’s many famous product launches. So much has been made of Steve Jobs’s keynotes that there is a Wikipedia page dedicated to them: Stevenote. He was a mesmerizing presenter.

I still think about how he unveiled the iPhone, which everyone in the audience at the time expected and knew would be a cell phone, but had no idea would be, well, the iPhone. He knew what the audience expected, and faked them out through the first half of his presentation about it. He said “Today, we’re introducing three revolutionary products” which upended the audience’s expectations. He repeated what those devices were—“An iPod, a Phone, and an Internet communicator”—as icons for those three things spun around on the big screen behind him, until the audience was laughing. Then he said, “are you getting it?” and people cheered as they realized that he was talking about a single product.

The thing that is amazing, re-watching the presentation, is that it is full of jokes, like the image of an iPod with a telephone rotary dial instead of a click wheel. It’s also amazing how Steve Jobs was able to sound so natural, even though he never ad-libs and never flubs a word. He extremely well rehearsed, and he made what he did look easy.

I like to think that he was genuinely excited about what he presented, and that is a key factor I have tried to bring to my own presentations. I’m not able to present anything as fascinating as the iPhone to my peers, but I have the creative freedom to come up with my own ideas when I made a presentation, and I can certainly be excited about them. The way I see it is that I present ideas, not just facts. Ideas are propulsive in ways that facts are not. Connecting ideas together is exciting—at least if done in such a way that you can keep the audience interested. Humor and surprise are effective tools to do so, as Steve Jobs so often demonstrated.

Two reasons:

1. Culture. The Puritan work ethic is one of the foundations of our culture, and has been since colonial times. Work is righteous and cleansing to the soul. Of course this is nonsensical, but it is baked into the culture. People are brought up hearing that our ancestors pulled themselves up by their bootstraps (itself a nonsensical idea if you think about it), and that when times get tough we should do the same rather than reach out to others for assistance. This idea can be termed rugged individualism.
2. Economic uncertainty. The US have a poor social safety net, and about half of all voters consistently vote to strip more and more of it away. I have it pretty good, economically speaking, but I feel like I am only a few months away from losing my house if my wife or I lose our jobs and can’t replace it incomes and our health insurance right away. Also, income inequality is such that there is always someone vastly richer than you to compare yourself to. That drives a lot of people to work harder, even though a lot of the very rich inherited their wealth (seed money at least) and/or the connections needed to grow it.

In college, one of my humanities professors, Prof. Klein, told me that genius is being able to look at the same things everybody else does but see something different. She told me a story to illustrate:

One time she had company at her house—a friend and her kids—and they needed to find a place for three little kids to sleep for the night. There was only one bed, but it was a queen-sized bed, which she thought would only suit up to two people. The friend, however, knew right away that it would work. The friend realized that, because kids are short and small, they could be fit onto the bed, just not in the normal, expected way. The friend put three pillows on one side of the bed, arranged down the long way. Then she adjusted the sheet and blanket so they opened up on the side of the bed where she had put the pillows. Then the three kids slept in that bed, arranged sideways, and had plenty of room.

I always appreciated the simplicity of this story.

One of the disheartening but more interesting things you learn in business school is that most of the growth in the stock market can be attributed to inflation. That’s why I’m not that excited that my retirement portfolio has been growing quickly lately as the stock markets keep reaching new highs. I know that there’s a catch. Those dollars aren’t worth as much, and that’s part of the reason that markets are rising.

The New Jersey governor’s election is certainly a nail-biter! Maybe Phil Murphy will pull out a win after all. I can’t help thinking, though, that there is no good reason any statewide election should be this close.