The Perfect Work Routine

It's in here I promise

Michigan State’s campus was built without walking paths. 

Instead of trying to lay out the ideal network of sidewalks, the designers erected the main buildings, planted some grass, and let the students take it from there.

As classes got underway, natural “desire paths” started to form. Students carved dirt lines across the green through repetition, wearing away at the grass where their habits determined the walkways should be.

Once these natural paths became clear, the school reinforced them with concrete. And by not trying to enforce a layout before seeing what students needed, they avoided the ugly sight of beaten paths cutting between the lanes of a presumptuous grid.

MSU understood, explicitly or not, that trying to force people into predetermined constraints on their movement wouldn’t work. No matter how lush and well-statued the paths were, the walkers of shame would find their own way.

II: Deep Rituals

One of the most popular productivity books of the last decade is “Deep Work” by Cal Newport. In it, Cal recommends prioritizing “deep work”: distraction-free, challenging, creative work that pushes you to the limits of your abilities. 

He contrasts it with shallow work: logistical style tasks often performed while distracted.  Checking email while tabbing back and forth to Twitter, data entry, reorganizing your to-do list, management consulting, things that don’t add much value to the world. 

On its own, that’s great advice. If you spend 10 years writing three hours a day, you’ll be in a more interesting place professionally than if you spend that time responding to emails. 

My gripe with Deep Work is the prescription for how you’re supposed to do it. Or at least, how I thought Cal was prescribing Deep Work when I originally read it.¹ Multi-hour long chunks of completely uninterrupted time, deeply focused on the thing that will most move the needle in your work. 

I have always felt guilty about my complete incompetence at this task. I might occasionally eke out a three-hour chunk of focus, but it’s rare. Attempts to block off seven to nine am as focused time eventually fall apart. Attempts to block off any time period as focused always seem to break down. 

And I feel conflicted about this consistent deterioration in my attempts at a Deep Work ritual. When I get invited to play Pickleball or to an early lunch during my Very Important Focused Time, I don’t want to say no. Part of the point of work, after all, is to fund a life where you can goof off in the afternoons.²

What I eventually realized is that it’s okay if I don’t follow this overly rigid prescription. People work better in different ways, and trying to force someone else’s method to your natural rhythm will just drive you crazy. I have the apparently rare ability to sit down, bang out 1,000 words of decent article prose in 30-60 minutes, then get up and go goof off for a while to recharge. I can squeeze those chunks in at various times throughout my day, and as long as I hit my target daily word count and publishing schedule, it’s fine. I don’t have to try to force myself into someone else’s system. 

I experienced a similar demotivating frustration reading “Daily Rituals,” which lays out the routines followed by great creatives throughout history. On the one hand, you could read it as an ode to the highly regimented life. The paragons of structured deep work who diligently created for decades following a methodology that would leave any process engineer salivating. 

source

But fitting with my apparently chronic tendency toward self-judgment, reading it filled me with guilt over the fact that I have no daily ritual. And without a daily ritual, perhaps I’ll never create anything great. Obviously, every great creator had a neat Daily Ritual, why don’t I? I felt like I needed to pick one to adopt and follow religiously so that I too might amount to something. 

But now when I look at it, I see the opposite. None of these creatives read a blog post on productivity and said “I must adopt a regimented schedule!” They more likely slid into routines that may or may not have been close to the ones portrayed based on their natural rhythms and desires.³

Their Daily Ritual, to whatever extent it was truly daily or truly a ritual, was likely an emergent phenomenon. They did not read tons of productivity books and then pick the routine that seemed best to them, as many of us feel compelled to do. They worked, and over time, their ideal routine for sustained output emerged. They started walking and reinforced the paths with concrete as they went. 

III: Dubai Barbies

When I visited Dubai with my family a number of years ago, I remember getting two distinct, contradictory feelings about the city.

First, it’s an incredible testament to the power of human will and ingenuity. They built one of the most lavish and impressive cities in the world in the middle of the desert. They built the tallest building in the world. Their airport clubs you across the head with awe at what can be accomplished by harnessing oil money, autocracy, and disregard for labor rights. 

But it also feels hollow. It’s the architectural personification of a vapid LA barbie or ken doll with too much lip filler. Nice to look at and fun when you’re drunk but ultimately soulless. You sense that if the wind picked up, the buildings along the periphery would topple and reveal themselves to have been cardboard all along.

Not pictured: labor camps

I can’t help but feel the same about these overly architected attempts at perfect work styles. Dozens of apps networked together into some ideal routine. The Rude Goldberg machines of these creators are impressive, albeit with a suspiciously high inclusion of tools with affiliate programs, but are they ideal? Or are they attempts at concocting systems extreme enough to engender curiosity and attract email signups? Perhaps it resonates with them, but copying and pasting one onto your own life is unlikely to provide you that same sense of alignment. You will end up walking off their 10-lane highway eventually, seeking the garden path where you’re most at home.

In pursuit of the ideal work style, I think the best we can do is start with as green a quad as possible, then let the paths carve themselves over time. As we see what routines and styles are most resonant, we can reinforce them through technology, routine, or simply remembering what works well for us.

When the path we’re on isn’t working, the solution isn’t necessarily to find some new slab of concrete to jump to. But rather look at where we want to go and start walking. Someone else’s system or routine might work for getting them where they want to go, but it’s unlikely you’re headed in the exact same direction. 

To the extent stories of others’ routines are useful, it’s only to sample them for bits and pieces of what we may want to try applying to our own path. We should not expect to find the perfect answer to work and life in someone else’s structure. Rather, we should find a bit of stone, a bridge, or perhaps a nice planter, that we can borrow to see if it serves us or not.

My routine is weird. I’ll write for one, maybe one and a half hours, then go for a walk or to the gym or read.⁴ I’ll capture little notes on my phone⁵ and when the writing energy has pent up enough to be frustrating I’ll sit back down for another thirty or sixty minutes and let it all flow out. If I try to focus for longer than two hours I end up down some Reddit rabbit hole or digging into crypto prices and inevitably end up asking myself “how did I end up here?” I don’t set fixed times for work, I just try to get that first chunk in as early in the day as makes sense while prioritizing family and social time above it. Then hope I can squeeze in one or two more later.

That’s just what’s worked for me, though. Please don’t wipe your mind of the preceding 1500 words and think this is a recommendation. It’s where I landed, and I’m able to churn out what I feel is a respectable amount of writing between my book, this newsletter, and my occasional crypto posts, but it may not be what makes sense for you.

Don’t worry about finding the perfect system. It doesn’t exist. Start walking, experiment occasionally, and reinforce the paths that work for you.

1. I skimmed through Deep Work while editing this post and realized he does have a brief section on “Journalistic Deep Work” where you squeeze in bits of Deep Work whenever you can. I somehow completely missed this the first time and took away that you needed to be more regimented than this would suggest.

2. “…put your desk in the corner, and every time you sit down there to write, remind yourself why it isn’t in the middle of the room. Life isn’t a support-system for art. It’s the other way around.” - Stephen King, On Writing

3. The book, obviously, could only be based on what people said they did for some period of their lives. As someone who has written many times about productivity, I can guarantee you that most people do not religiously adhere to 90% of the prescriptions they shout into the void.

4. Sometimes I’ll edit during these adventures, I’m actually editing this article on the vibration plate at the gym right now. Hello friend!

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