The Odyssey
The mad [personal] search for productivity.
A few years ago, just after my daughter was born, I embarked on what I thought was the appropriate life-hacking adventure: I would increase my productivity. I had just started a doctoral program, and the logic seemed clear: if I had less time, I needed to make more of it. Hearing what felt like the clarion call of our generation, I became one of the many to have explored and, if we’re honest, spent too many of our could be working hours learning to work smarter.
I didn’t really know where to start, so I let the internet guide me to time management classics: namely the Get Things Done (GTD) system of David Allen. He was, and is, the consummate professional when it comes to creating systems for your work and life — a compartmentalized and highly regimented system to keep all your juggled balls in the air. The guidebook seemed simple, of course. It just had lots of steps. And like so many of these endeavors (as I would come to learn), it started with a commitment to clearing out — dutifully picking through the detritus of your daily life to see what, if anything, should be kept, trashed, or better organized.
This step had a totalitarian logic: everything needed to be accounted for and, where appropriate, recorded. And I was committed. I mean, I thought I was. I had (well, still have) both a digital copy and a hard copy of his book, the latter right here beside my desk. I even have a sun-dyed pink post-it on page 139 with the words “Start Here Tomorrow” (the book is 317 pages long, for the record).
Even more impressive? Apparently, I made it to that same part of the book twice.
The benefits of being a full-throated GTD-er were laudable. Many brilliant and —dare I say efficient — professionals are card-carrying members of Allen’s still-growing club. There are conferences and seminars — webinars and organizational seances and resorts. The very system of chart everything, put it in your inbox, review and organize, and schedule your days has also been encoded in the architecture of uncountable productivity apps. Everywhere I turned, GTD was there. Reminding me, I had things to do.
Don’t get me wrong. I found parts of his approach valuable, like Allen’s Triggers List, which is part of his “Mind Sweep” process of personal housekeeping, where you conjure up everything that could be using mental bandwidth. That triggers list included every idea, project, appointment, chore, piece of software or hardware, bill, tax form, staffing question, planning detail, vacation dream, relationship weakness, prospective or overlooked hobby, wardrobe deficit, training need, volunteer opportunity, communication commitment, upcoming celebration, pet vaccination, legal query, maintenance memo, health appointment… You get it. All you had to do was work through, one by one, and write down anything you could extract from your mind.
According to Allen, each of these potential “to-dos” should be written on its own page, post-it, or index card. Once you had filled out as many as you could, you submitted each of these items to a filtering process: ending up with things you can do immediately, things you can “calendar,” things you should do next, and then those things that sadly get tucked away into the Someday/Maybe file.
The process was intuitive(-ish). It has its own internal logic. And for those sweet seconds, after you’d worked through the steps, it felt oh-so-satisfying. It was, however, considerable work before you did any work. And, as I’d come to discover, the energy of achievement wore off too soon, leaving me, well, listless, as I turned to my to-dos.
So I stopped.
Perhaps what I needed wasn’t a system to collate and organize everything. I just needed a system to get the meaningful work done. I knew what I had on my plate. After all, I’d filled out countless notebooks with different To-Do lists. I even tried the Bullet Journal approach — time-consuming and tricky for a multiple-notebook scribbler like me — and a detour through The Artist’s Way, which I’d hoped might spark some lost creativity. Long story short: lists weren’t the problem. I just needed to find a way to complete them.
Enter Cal Newport. I imagined Cal as a wise elder sage. Until I realized he was actually a computer scientist not much older than me. But you don’t have to be old to be wise. And Newport’s contribution, Deep Work, was, indeed, wise. It featured vignettes of the productively prolific (albeit only males — which is cause for concern) who, through dramatic exits from their regular lives, or some hybrid division of mental labor, were able to find the intense periods of concentration and focus required to do the hard thing: those tasks for which brute-force brilliance is required and can only be rendered with deep engagement.
I think I listened to the audiobook first — while running because I wanted to get the most out of my hours; efficient, right? — and found myself yearning to hole up in some lakeside cabin-like Carl Jung and think rich thoughts, transcribe sharp insights, and get my goddamn work done.
Newport introduced me to time-blocking — a kind of scaffolding for your working hours — intended to minimize the distracting ephemera of our modern lives (notification-happy mobile devices, endlessly updating inboxes, fruitless meetings, or unnecessary commitments). Newport suggested that if you could invert your thinking about organizing your time — like scheduling time to be distracted — you could avoid having your days hijacked and could, yes, get shit done.
Newport really had me with Digital Minimalism, his follow-up book which offered permission to check out of your digital life, too, to reclaim more of your analog existence for deep work — well, as much as one can when you need the internet for work or research. During the pandemic, and specifically under lockdown, this Digital Minimalism program has come under certain duress. After all, you could barely confirm other humans existed without some broadband signal or distracting online anger-rooms of Twitter.
Further still, I was pretty sure Newport was on to something. After all, he was a professor and managed to turn himself from a prolific-academic-journal-article-writer into superhuman-academic-journal-article-plus-self-help-book-writer by streamlining this very system. Epic, right?
I learned a lot of things from Cal. Including my most critical lesson: I am not Cal Newport.
Don’t get me wrong. I think he’s right. I think the human brain works best when left alone (provided all the necessary information for your work is neatly accessible for your brain). I also find a particular kind of meaning-making clarity when I can trigger deadline stress to quicken the synapses. But when I took stock of how much of my own life was consumed with deep work (I was and still am working on a dissertation), my shallow brain sputtered.
Focus is important and novel, perhaps most critically, because it specifies an exceptional state, not the standard operating procedure. Deep work felt like the only kind of work I had to do. So I lost it.
Metaphorically.
I had days with lengthy and useful periods of productivity — moments where I could affirm the Newport philosophy and felt motivated and ready to work. But those were often followed by a kind of hollowed-out ennui that lingered for twice as long.
If Allen’s GTD had me working too hard to prioritize what I should be doing, Newport’s Deep Work had me monomaniacally focused on the work I should be doing. But neither felt sustainable. Or, to put it bluntly, I had a hard time remaining, well, stable.
The winding trail through the dark woods of self-improvement eventually led me to Greg McKeown’s work Essentialism. It sounded like a better fit, provided I could figure out what was essential, of course. McKeown’s philosophy was akin to employing a vigorous life editor. As he points out early, quoting Lin Yutang, “The Wisdom of life consists in the elimination of the non-essentials.”
The Essentialism system had fewer parts and lessons that read like Buddhist mantras. McKeown’s book was even structured in reasonable steps. Essence —> Explore —> Eliminate —> Execute. How hard could it be?
In our super-committed modern world, where the dominant strategy for most is to say “Yes” quickly, Essentialism urges you to slow down, consider, reflect: to live in and of the now. McKeown even offered a helpful explanation of what I’d been doing to date: straddling, which he defined as stubbornly holding on to your current strategy while simultaneously trying to adopt the strategy of a competitor.
Was that why I was helplessly trading through productivity hacks? Maybe the reason I wasn’t successful with GTD or Deep Work and having trouble trying to integrate Essentialism was merely a question of commitment. These are clearly not programs meant to be pursued in parallel.
But by this point, I knew that wasn’t it. I felt what Socrates cautioned us about long ago: Beware the barrenness of a busy life. This time, though, my busyness wasn’t just the work I had to do, but the work I was doing to try and be more effective in getting the work done. More than anything else, I’d lost the plot.
At the heart of McKeown’s work is an urging, not merely to keep going more efficiently but to figure out what’s worth working efficiently on.
So at some overgrown crossroad on this same journey, I found Ryan Holiday and his support for (not to mention life’s commitment) to Stoicism, reading my way through his three-book series, The Obstacle is the Way, Ego is the Enemy, and Stillness is the Key. I completed the last book just hours before taking a vow of silence in a five-day retreat. I really wanted stillness to be the key.
More generally, however, it was hard to dispute the Stoic creed. And, if there is one, it’s likely best boiled down to the apocryphal prayer: Lord, grant me the strength to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference. The Stoic school of thought offers solace in the most hectic moments — when the world feels tilted against us. But I’ll put my cards on the table. I’ve never attended church. I don’t have a god. But if I did, I’m still not sure I’d want it to be Marcus Aurelius.
Look, he was great. He ruled an empire, kept a diary, worked to control the things he could around him, and taught the rest of us — by virtue of these daily scribblings — to be unruffled by everything beyond our capacity to shape. He lived the Stoic life, and, of course, that kind of life carried benefits: if you didn’t take the frustrating parts of your time on earth so seriously, you would presumably find more space and energy to get on, well, getting on. Stoicism was an approach to living that didn’t emphasize being more efficient. It required that you figure out how you could best spend the time you had alive.
In the end, however, what it taught me was that I’d been working backward. Framing my struggle in terms of productivity had the effect of doubling down on a false sense of progress: I could cross things off my list (and did) endlessly, but they may never lead to some ultimate achievement or conclusion. I could benefit from any productivity system, but not without a purpose. Or, more specifically, I needed to find some way to connect what I was doing in the world with who I wanted to be in the world. I had, in short, to grow up.
Thinking this out loud, not to mention writing it down, reminded me of philosopher John Kaag writing on Thoreau's self-loathing in Walden — Thoreau’s own book about escaping to live essentially (sound familiar?)
Thoreau’s problems were born of privilege. Kaag writes, “the neurotic difficulties one faces when absolutely nothing is really wrong,” but where the “freedom of choice caused … no end in anxiety.” Choice is a luxury, yes, but it means being “absolutely responsible for your choices,” writes Kaag, and sometimes “[t]otally, utterly, inconsolably alone in deciding what to choose.”
What I’ve learned most recently, having spent more time, not with Allen or Newport, but with the philosopher William James, is that the labor of living — or making your living feel alive — is stubbornly ongoing and then over all too soon. I’ve tried, in other words, to appreciate that “freedom means being conscious and aware enough to choose what you pay attention to and to choose how you construct meaning from experience,” the writer David Foster Wallace famously urged in his 2005 Kenyon College commencement address: “… if you cannot exercise this kind of choice in adult life, you will be totally hosed.”
And no one wants to be totally hosed.
But I’ve also come to realize that in place of traditions now abandoned and the small communities that may have given our parents (and their parents) somewhere to call home, this generation (my generation?) has been sold the idea of “finding your purpose” without recognizing the deep roots and stability any such purpose might require. Perhaps even more in our pandemic moment, it’s this sense of stability we miss the most.
When the superstructure of our too-much-too-fast-and-for-too-little modern world started to corrode last spring, it revealed that the true cost of our always-on culture. For some, this last year has been celebrated for revealing resilience — and assuredly, for all of us, in ways we’ll be surprised to learn, it has.
But it’s also illustrated the lie of our sense of work-life balance. At best, we have work-life balancing: we’re each responsible for an overstocked wait tray while navigating a busy room as people randomly jump up from their seats. It makes sense that we want systems to control the chaos. We want the authority to shout across that crowded room: “Stay seated.” But the calm is unlikely to come from simply doing what you usually do more efficiently.
It should come as little surprise, then, that so many of the lessons I’ve tried to teach myself are little more than attempts to scratch compass markings onto the map of my life: coordinates to guide me through tomorrow. Productivity was one of the stories I thought I could attach myself to. A story that I hoped would have a kind of meaning.
Alas, despite all my best intentions and commitments to self-improvement, I don't have any “life hacks” that can make you better at whatever it is you do. I’ve just learned to be wary of productivity and its capacity to banish the most important of life’s questions — how should I live? — to the Someday/Maybe file. I suppose that’s its own kind of victory.
NOTABLE LINES
Really good fiction could have as dark a worldview as it wished, but it’d find a way both to depict this world and to illuminate the possibilities for being alive and human in it.
David Foster Wallace told Larry McCaffery, an English professor at San Diego State, in a 1991 interview.
A well-built fictional world doesn’t have to be seamless, or rational, or even coherent. It just needs to be robust enough to convince the audience to believe in it.
Charles Yu, author of Interior Chinatown: A Novel, in Harper’s Magazine, “Reality After Trump.”
If there’s going to be a digital public sphere, we simply cannot let Facebook dominate it with all the power of a nation-state and none of the political accountability.
Jacob Silverman, author of Terms of Service: Social Media and the Cost of Constant Connection, from this week’s “What I’m Reading” below.
What I’m Reading
Why liberal democracies do not depend on truth by Dylan Riley (New Statesman)
Riley, a sociology professor at the University of California, urges us to reconsider how we frame the so-called challenges to modern democracy. More specifically, he argues we’ve conflated democracy with liberalism. The emphasis placed on “common” or shared “truths” is to mistake the content of a particular political society with the architecture of its legitimate power. Truth is not missing, Riley argues, but the conditions for rational debate certainly are.
Facebook is a Global Mafia by Jacob Silverman (The New Republic)
Can you picture Zuckerberg surviving the Australian outback? Neither can I. From Palo Alto, the Facebook CEO is playing his own game of political chicken with the Australian state re: syndicated material rights and payment for access. The debates on this are legion and, for even the engaged, fraught with so many particularities and insider-language, it can be difficult to understand the consequences. This piece is inflammatory, clearly, but offers a broad overview of the tech giant's supra-national power. For detailed (and more balanced) handling of the case, though, Casey Newton can be your wise guide. His Substack newsletter/community is here.
Author’s note: Part of this experiment was to open space for discussion and, so doing, share some of the more personal aspects of life — particularly at a time where so many of us are trapped inside, under lockdown, or simply without the kinds of social connections we long for. While I’m not sure how frequent these more personal essays will be, I offer them as both entertainment and invitation. A signal that there are others out there right now, many of us struggling in different ways to figure out how we can best feel alive in a world on pause.
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