My Productivity Obsession and Its Discontents

On Optimizing for Optimal Optimization

The Mandate Letter, by Jason Rogers, focuses on the evolving state of men and masculinities. Thanks for being here. If you were forwarded this email, get your own:

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Is there any better feeling than reaching the end of a to-do list? Specifically, that dopamine whoosh that arrives when you strike through a final item and deliver yourself into the endless possibility that comes with being free of all of your tasks? 

I’m not sure there is, which is why I started this essay all jazzed up to tell you about my new approach to productivity. The method is a bit of a Frankenstein — as if the “Pomodoro Technique” and Getting Things Done had a baby after getting it on. 

However, the more I thought about this essay, the more I came face to face with the fact that self-improvement and efficiency occupy a fraught place in my life. So, instead, I’d rather explore my tendency to overly-optimize my day. 

Before I dive in, it’s important to note that this preoccupation with perpetual refinement isn't exclusively a guy thing. The New Yorker staff writer Jia Tolentino wrote an excellent essay about the tyranny of athleisure, barre, and kale titled "Always Be Optimizing” in her recent book

Nevertheless, it’s hard to ignore the fact that best-selling productivity books are written mainly by men. And judging by the explosion of male-led podcasts on the topics, dudes are also the primary audience for bio-hacking, meta-learning, and the quantified self. 

As I’ve already indicated, I count myself among the interested (read obsessed), especially when it comes to workflow. When a new email client comes out, I usually try it. And it has taken superhuman strength from me to resist plunking down $30/month for Superhuman, the latest email fad.  

I’ve used so many different note-taking apps (Evernote, Notability, now Roam, to name a few) that I honestly don’t know where to find anything. Further, my desk overflows with all kinds of productivity junk.

I recently bought a (useless) digital highlighter. And, when I was still working in an office, I toted around a pen that recorded both audio and digital notes.

Once, an old boss glanced across a conference table at the flashing red light on my device and said with a grimace, “Is that thing recording? Don’t you need my consent?”

The fact that I am so susceptible to articles with titles like “The Productivity Guide: Time Management Strategies That Work” leaves me conflicted. I pretty much always click and think, “Yes! I won’t open my email until noon!” At least until another productivity article pops into the queue. 

Of course, there’s nothing wrong with wanting to find more effective ways to use my time. However, at this point, I don’t fully trust myself to determine whether I’m researching a valuable time-saver or have been sucked down another rabbit hole of productivity porn. 

Sometimes, I wonder if it’s genetic.

My mom meticulously organizes everything that she does in color-coded binders. My dad has a compulsive appetite for briefcases and pocketbooks. Every time my wallet wears out, he brings out a ponderous bag of his leather castaways, and I go shopping.  

Of course, I’m joking. In actuality, much of my angst stems from my fencing career. After rising to the Olympic level, I felt the need to plan and measure my efforts. This led to voluminous training spreadsheets, fastidious food journals, and endless lists of SMART goals.

And I went through such pains to unify my efforts into one integrated training plan that it felt like I was trying to develop the fencing equivalent of the theory of everything

My methods certainly helped inch me toward excellence. But they were also fiddly and exasperating. I grew irritable when practice deviated from my plan or if I left specific exercises undone.

In retrospect, I can see that I was so stressed out about whether or not I was going to succeed that, in my tedious tracking, I micromanaged the one thing that I felt I could control. 

By putting my entire waking life under a microscope, I forgot how to take pleasure in anything. Worse, when I made myself a scrutinizing observer of my behavior, these methods quickly became obstacles.

When I bought one of those sleep tracking wristbands, I began thinking so much about the quality of my slumber that I found it incredibly difficult to get to sleep.

Today, I struggle most with “free time.” Even when I go surfing, an activity I love, I often find myself slipping into the self-coaching mindset: “If I just put more little weight on my front foot on the takeoff….”

That’s followed by another voice: “For fucks sake, Jason, the whole point of this is to have fun!”

It’s complicated, of course. I don’t want to scrap my ability to focus on marginal improvements. It undoubtedly helped me succeed at fencing (and I hope it will help me excel at this humble craft).

But the obsessive in me is the one who won’t stop to smell the proverbial flowers because he’s too busy contemplating some inscrutable detail, driven on by the mania to live his life through the principle of kaizen

Needless to say, I’m not the only one with this issue. There are dozens of think pieces about our work-obsessed culture. Not to mention the fact that reclaiming the art of leisure is practically a sub-genre of books.

I should read them all. I should take more walks. Maybe, I’ll take up pottery. Yes, pottery seems a lovely pastime. But, in the meantime, I need to go check something else off the list. 

Department of Links

  • 🥻 Harris Reed’s Gender Fluid Fashion — This profile on the up-and-coming designer Harris Reed is pretty fantastic. Reed’s developed a reputation for playing with gender norms in his design, most notably the tulle ball-gown number that Harry Styles wore on the cover of Vogue.The New Yorker

  • 🎓 A Generation of American Men Give Up on College — College enrollment rates for young are down, way down. It’s gotten to a point where some institutions are effectively implementing “affirmative action for men.” The article doesn’t mention it explicitly, but I think the so-called creator economy is a significant variable here. If you believe you can make your money “influencing,” buying crypto or streaming, why would you sign up? —  Wall Street Journal

  • 🇨🇳 China’s Masculinity “Problem” — Apparently, Xi Jinping thinks it’s time for his citizens to “man up.” China recently banned “effeminate men” from appearing on TV. This is on the heels of instituting widespread physical education classes to “boost masculinity.” Hm. Time Magazine

  • 🧜‍♂️ Male Artistic Swimming — This is pretty rad. Artistic swimming (formerly known as synchronized swimming) is a new breakout sport for men.CNN


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