Portrait of a Learning Curve

Anything was possible, with grit and belief.

One put oneself in impossible situations, which forced one to shatter perceived internal barriers and rise to the challenge.

After all, the seed must split open in order for the plant to grow.

Yes, these are the kind of spontaneous thoughts churned out by brains doused in 90 minutes of daily yoga.

Loosely Vedic aphorisms aside, my operating principle at the time was that you got hired by saying yes, then worried about mechanics later.

In fact, I would go further: it was my job to say yes.

Producers produce things.

Developers develop things.

This meant making things happen, not shooting things down.

Plus, I didn’t see what was so insane about this idea — it just seemed… big.



But not impossible.

Not ill-advised.

My operating principle at the time was that you got hired by saying yes, then worried about mechanics later.

In fact, it was my job to say yes.

If my mind had such a thing as a feasibility analysis engine, it was trained on art and athletics.

Mulling over this idea of ramping up to tackling something huge and new, I thought about my recent first half-marathon.

The race was three times as long as earlier 5K runs I had done, but despite concerns over my super-rickety knees, I had completed it.

During training, the slope of difficulty was sort of a gentle log(n) — the more miles I added, the less each new one seemed to matter.

The race itself had been sublime and exhilarating.

From that vantage point, it seemed to me everything could be achieved with proper amounts of pacing and passion.

The notions of runaway complexity, of combinatorial explosions of test cases, of the fact that jogging in a straight line from point A to B was the exact opposite of what I was about to attempt, were all summarily ignored.

Suffice to say, this would be the last time in my life I neglected such things.

Rubber Hits the RoadOver the next four months, my teammates and I gradually, doggedly worked up a version of this thing.

Also, as best as we were able, we committed absolutely and fully to doing everything right.

And, we felt like we were doing everything right.

We chose modern, sensible technologies: python and pandas for the data science, PostgreSQL to hold it all, Django to orchestrate and deploy it on the web.

We were in communication constantly.

We traded volleys of technical emails about the smartest architectures, the savviest paths forward on all the particulars.

We dug into the latest in natural language processing.

I personally unraveled, sussed out, and carefully reassembled a dozen different California public data sources into clearer, more complete versions of themselves.

We worked perpetually, and really, really hard.

We wanted this thing to happen.

We wanted to manifest our client’s vision in the world.

We were genuinely driven toward it, beyond all distraction.

Yet despite all of that, despite all the grit, passion, and above-and-beyond-ness I could personally squeeze out of myself, it kept falling short.

Demos were supposed to be rituals of victory.

These demos were not like that.

Every two weeks or so, we would meet with the client to illustrate our progress and run a demo.

These were supposed to be happy meetings.

Demos were supposed to be rituals of victory.

In previous projects, I’d be stressed and panicked beforehand, but then I’d manage to push a little harder and suddenly I’d burst through.

The demo then came and things worked as promised and everyone was happy.

I’d breathe a sigh of relief.

I’d feel relaxed, satisfied, filled with that movie-ending, just-by-the-skin-of-our-teeth feeling.

I looooved that feeling.

These demos were not like that.

The successful instances of these demos involved the app limping its way slowly up to the lowest settable performance bar, and displaying some underwhelming and occasionally confusing result.

Success meant that nothing overtly exploded in front of already tense stakeholders.

It meant whatever elephants might be evident to everyone in the room, we could maintain a veneer of client-agency normalcy.

The failed instances, on the other hand, involved the app freezing or crashing while asking it to do pretty much anything.

Failure meant our poor project manager — pretty much as deft and sharp and diplomatic as they come — had to scramble on the fly for narratives that framed these events as completely normal on the Path to Assured Victory.


It bears mentioning that the success version here was the decided outlier.

The Finest TeacherIn the end, the publishing platform bit launched on time, and actually launched beautifully.

And, upon delivery date, the app did technically operate in the manner we had all agreed upon.

However, it was clear the client had lost faith — gradually but profoundly — along the way, and had internally pivoted in a more traditional direction.

As it played out, this direction worked, and they flourished, but with the Everything Machine pretty much abandoned.

Despite the arguably happy ending, it was my first visceral encounter with a true technical failure.

What the hell happened?.We worked so hard.

We proceeded so meticulously.

How did we do everything right but end up here?Well, the answer was that we didn’t do everything right.

We left no decision within the project unexamined, while ignoring whether the project itself was the correct one.

We doted on every micro while ignoring the macro.

Failure hurts, but is the finest of teachers.

The experience taught me three crucial things:Part of “making things happen” is sometimes asserting that things can’t happen.

This means tread carefully, even at the highest levels.

Don’t necessarily take the foundational tenets of the project for granted.

We only have so many professional hours on this earth — the most crucial decisions aren’t how to make things happen in the thick of things, but rather which thick-of-things are we most likely to make meaningful things happen in.

Adaptability is just as crucial to success as smarts, tenacity, and effort.

It was pretty much a complete news flash for me that you can’t just wad up a fat ball of IQ and perseverance, hurl it in an arbitrary direction, and expect reliable results.

Especially with any ambitious project, important new essentials about the nature and limits of what you are trying to do will spring up as you go.

Sometimes, these new essentials will be complete non-starters.

It is up to you to heed these for what they actually are, and adjust accordingly despite the upset it may create.

Adhering to an image of perfection for clients will often limit your ability to be adaptable.

This is a tough one.

A big chunk of what we hire professionals for is to put all that unpleasant stuff like uncertainties and missteps in a black box so we don’t have to deal with it.

Yet when things clearly aren’t working behind the scenes, the ability for client and agency to dialogue and re-configure things candidly in crisis moments seems to me the best option for averting future disaster.

Also,#4: Don’t try to build Everything Machines.

Remember when you learned that you legitimately can’t please all the people all the time?.It’s the same thing, and breaks down in the same way.

These principles inform my professional life to this day.

That said, there was a meta insight that I willfully ignored.

It would be another couple years of getting the technological snot beat out of me before I finally broke down and accepted the larger truth to which they all pointed.

Autodidacticism: the Sketchy PartsFree solo climber Matt BushRecently, I recognized the ghostly outline of these lessons in The Mythical Man-month, possibly the most beautiful book written about software development, and required reading for many a CS curriculum.

At the time of the Everything Machine, I had not read it.

Truth was, I hadn’t yet read a single book about my craft and how to do it properly.

Why?.Because like many others choosing the freelance programmer route, I was self-taught, a relentless autodidact, a free-roving iconoclast.

Learning to code was a means to live on one’s own island, a castaway life free from society, where one didn’t have to answer to anybody.

So, back to introversion.

The fact is that for many of us, writing code first presents itself as a beautiful, dense, endlessly engrossing mechanism to create a professional life free from the need to interact with other people.

This is its underlying allure: we cross that enticing bridge of technical knowledge, and then get to live quietly and safely inside our esotericism, without the gut-constricting uncertainties of human relationships.

For me, therein lay the Big Gotcha: learning to code is actually about learning to accept your need for the minds of others.

It is stepping off your protected island and admitting: doing this right is extremely hard, I know practically nothing, and the wisdom of other coders is the most powerful, precious commodity available.

It took me several years of coding to recognize this.

Yet once embraced, it has made me better at building software than the entirety of my time trudging away in defiant seclusion.

Don’t get me wrong.

I love being an introvert.

And I love my island.

I love my desert.

I guard and cherish my solitude like a treasure.

But sometimes, I must remind myself that the bustle from all those raucous, roving crowds of extraverts harbors deep wisdom, and — no matter how insular I consider my craft — it is crucial to listen.

Originally published at davemiddleton.

co on November 4, 2018.


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