Wander Well

Not all who wander are lost. I am. But not all.

For most of my life, I have seen learning as a journey upwards. Always up, never down, never sideways, and certainly not backward.

Take, for example, learning basic networking principles, a topic I fail to learn at every attempt. Each time I set out, it feels like a momentous mountaineering expedition. My memory is full of journal entries like this:

Day 3: Freezing cold again today and headwinds brutal. A CIDR address avalanche blocks the way forward. Will take hours tomorrow to dig through. Rations enough for another two days, but Linux Academy shows three more security group labs in the tomorrow’s lessons and oh god the VPC is coming back I have to <illegible>

Educators agree. Classes roll into units that string into curricula that constitute grades that ladder into schools. Education is a stairway that goes up and up and up, whether to Shangri La or the realm of the Forms, I’ll never find out because the ones who come back from there start writing in LaTeX and using equations.

But then I became a parent. And as if a switch flipped, I started learning continuously, effortlessly, and have continued to for years now. Just by being present and making choices. Without intending to learn, without climbing towards a destination, without that sense of embarcation that marked all my previous explorations.

These days my journal entries are quieter. A typical lesson goes like this:

1/27/22: Walked with Will this morning. Cloudy today, a breeze and jackets. He held my hand. Outside our house, he pointed out a squirrel. Good find, buddy, I said, and, oh, look there’s another one. Where do they live? he asked. In the trees, I responded. Like right there? He pointed to a fuzzy ball in the tree in our front yard that was made out of stuffing from our new patio chair. Yes, just like that, I said, and sighed.

A father and son take a leisurely stroll on a cloudy day in a flyover state. The Apple Watch doesn’t even register it as a workout. You impressive data professionals reading right now can learn nothing from my son and this squirrel.

I do, though. I learn from moments like this. They remind me that the world is full of joy (holding hands with my son) and laden with questions (have you seen a squirrel’s nest before?) and that I am an active participant in all of it (as is my patio chair).

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You can learn by climbing, and you can learn by wandering.

I won’t discount the climb. Great climbers receive recognition, opportunity, and a deluge of messages from LinkedIn recruiters. The climber elevates themselves above the clutter of specifics so that she can stand under — understand — The Thing as closely as possible. At the summit, she looks down and sees the world in a new light, as an abstraction that takes her breath away.

But keeping your breath — this is the essence of the wander. A wanderer does not look outwards so that she can transcend the details; she looks inwards so that she can immerse herself in the details. A wander relishes in the specifics of both time and space. It’s not the singular Thing beyond space and time that the wanderer seeks, but the confluence of Things within a singular moment. Above all, a wander is an experience.

I hit on the idea of wandering as a pedagogical tool when I began to learn guitar. I initially approached it as I do programming problems: like a climb.

Me: I want to be 80% proficient at guitar playing. I should learn all the technical skills, working myself up to playing simple songs, then harder songs, then writing my own songs.

What the internet gave me was lesson after lesson of unstructured enthusiasm.

Instructor: What’s up!!! Let’s skip all the basic concepts and get you playing those songs you want to play, or you’re going to hate guitar and quit! Just mimic these 5 painful hand contortions, strum to the beat, and enjoy yourself! If you don’t enjoy this one, go to another one and enjoy that one!

The best instructors, including the ones I met in real life, treated the art as a horizontal learning experience. When I attended with my become-at-least-fifty-percent-proficient attitude, these gurus set me down. “Feel it, hear it, enjoy it,” they would say, again and again.

What these instructors understand is that guitar-playing is foremost an experience to be wandered through, not a set of techniques to be conquered.

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To put a finer point on all this: a wander is a form of learning that has no correct route and no pre-determined destination. If a climb is all about “working backward”, then the wander is about “unfurling forwards”.

It must start somewhere — say, doing an analytics project with Twitter data. But there is no judge of whether it was the “right” project and no clarity around whether it’s complete. You could spend 5 hours, 10 hours, 100 hours on the project and never quite be done. This is not at all true with climbs, which we typically want to finish as fast as we can with maximum “learning retention”.

I know it’s time for a wander — not a climb — when I find myself in a new situation with many variables, especially ones that are unfamiliar. If you looked at where my time was spent in these periods, you would see random coffee chats, random time spent downloading Github repos, random Snowflake queries. I am not trying to get things done, I am trying to feel out the world I am in.

There is much for data professionals to learn from wandering.

Take one skill: exploratory data analysis. An analyst approaches a new dataset not with authority but suspense. What unknown terrors await? He comes well-equipped — flashlights, sample jars, rations, and bug spray. But at first, he is not searching for a signal so much as listening to the ambient noises. He may find that he is in a swamp, knee-deep in a sludgy goop. Or he may be pleasantly surprised by a tidy field, carefully manicured and tended. (Ha!)

The point is, a great analyst doesn’t treat a new dataset like a criminal to be interrogated — “What’s a guy like you doing without 5% of your primary key values on Friday night?”

Instead, he treats it like a new acquaintance to be known. “I see you’re not a fan of non-null primary keys… Can you tell me why?” Listening carefully, the analyst learns not just about the data, but about its producers, his own organization, and the viability of that big project he just took on.

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One of the best ways to wander at work is to dogfood your product.

If you are being paid, you are doing something for someone. That someone is a person, with their own objectives, existing within a particular context, experiencing your product or service. You can try to intellectually understand that experience… or you can just experience it.

For example, I don’t know the first thing about what drives people to pay hundreds of dollars for a toy, card, or comic book. Yet the product I work on at Whatnot facilitates exactly this kind of transaction. Sellers have built huge followings by creating very entertaining live auctions selling collectibles, such as Pokemon cards or Funko Pops.

The fastest way for me to understand the Whatnot seller experience is to gain experience as a Whatnot seller. So that’s what I did last week — I set up an auction, purchased inventory, prepped trivia questions, and started streaming.

My Whatnot auction was a retail disaster but a successful wander.

The auction was a retail disaster. I lost 5 dollars every single minute for an hour. I bought more than $400 worth of science fiction novels and sold them for a total of $96. My most active buyer was my wife. My most active chat participant was my father-in-law, who encountered payment issues.

As a wander, however, the experience was a resounding success. I begin this work week brimming with new questions:

• It didn’t feel like I got enough organic traffic. Is the recommendation system I support working as well as it could?

• The books I sold were effectively going for a 90% discount. Is that incredible buyer opportunity captured anywhere for analysis or viewing?

• The trivia portion of the auction was a lot of fun. Can I lean into that for future livestreams to increase engagement?

Dogfooding projects your mind into the real world. You forget about the product arguments you won when building the thing and instead experience the thing.

If you are lucky, you’ll feel delighted. You might also experience horror, a sense of “I cannot believe we are putting customers through this, it must be changed”. But this, too, is good fortune — now you have something to fix.

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If you are just starting out as a data professional, don’t skip the climbs. You need to build stamina and breadth of knowledge to stay with the rest of your team. You need to build experience under pressure in different terrains and under surprising conditions.

But make time to wander. Dig through the internals of that package you rely on. Build a random application that you think might be useful and publish it. Don’t wait for your supervisor to authorize it, or try to tack on “learning objectives”, or tie it into your five-year plan. Just step outside and start walking.

I have learned that climbs give you tools, but wanders change your worldview. And as I expand into new career territories, I find myself doing more of this horizontal learning. Like Binx Bolling in The Moviegoer, I can say, “Before, I wandered as a diversion. Now I wander seriously and sit and read as a diversion.”