Stoic Designer

Sometimes the stars align just so and your to-do list explodes with actionable insights that, pursued, improves your design, makes your product easier to use, adds credibility to your cause, or grows your userbase. You find that except for substituting excitement for shame your anxiety around the to-do list isn’t too different than if it were a list of bugs.

A to-do list is a to-do list. You prioritize a positive one no differently.

* Will not pursuing this insight kill you, your colleagues, or leave either of you destitute and in shambles? Probably not. Don’t lose your s**t.

* Will popping this insight from the to-do list entirely deprive the world of good? Making a form easier to use to join a mailing list is morally different from making a form easier to use to apply for government benefits. Both make a user’s life a modicum easier, but one is a niceness - the other a kindness.

* Does anyone really care if a thing gets done? You’d be surprised how many don’t - even your users.

* Is the pursuit of an insight out of your immediate control?

Pursue only things-to-do that are in your control, keep your business afloat, do good, and has a good Kano model score (meaning that users actually care), and you’ll find your list of actionable insights dramatically paired.

Craft virtuously.

Clicking that ❤ in this issue of Stoic Designer is an easy, no-sign-in-required way to signal to the great algorithms in the sky that this writeup is worth a minute of your time.

If it’s easier, you can listen to Stoic Designer in your podcatcher of choice.

Remember that design is not art, but a practice.

Michael Schofield

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit stoic.substack.com

Note: I don’t love “recovery experience” as a term, but I’m sorely decaffeinated. Halp.

We advocate this meditation-of-evils practice the Roman Stoics called praemeditatio malorum where, in planning, we imagine the worst-case scenarios and make contingencies for them.

The capital-d Design process common among many of us actually has mechanisms that embody this ethic like the beta test, like QA, and so on. We do our best to shore-up our thing against failure.

Inevitably, though, things break. A server goes down, an API key gets revoked, form validation fails on a legit phone number - there is such a sparkling variety to the things that can go wrong that they are hard to imagine in full.

So, when things will, we set-in to triage the situation where the pressure of time-constraint, reputation, and the like will strain even the most stoic constitution. Thus there is an opportunity here to design the recovery state so that rebooting the server, repairing the database, swapping-in a new key, fixing and redeploying the form UI, are as easy — as usable — as possible.

Consider this in your design work going forward. Murphy’s law comes for us all.

Craft virtuously.

Liking (❤) this issue of Stoic Designer is a super way to brighten my day. It helps signal to the great algorithms in the sky that this writeup is worth a few minutes of your day.

Stoic Designer is also now a podcast. You should be able to find it on your podcatcher of choice in the next day or two.

Remember that design is not art, but a practice.

Michael Schofield

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit stoic.substack.com

There’s this satellite image of the hurricane Dorian that shook me. There are neither grids nor map-markers, no projections, no data. It is this still of a dangerously awesome-in-the-true-sense destroyer an “inch” — fifty or so miles — from the south-Florida coast. Somewhere there in the wisps of cloud that demarcate Dorian’s outer rain bands is Ft. Lauderdale - where I live.

My family and I spent the labor day weekend here moving s**t inside, waiting in half-hour long lines to fill-up on gas, freezing ziplocks filled with water just in case Dorian wobbled from its projection and merc’d us.

It was too wet to really go outside. Traffic sucked because folks were in a tizzy. Collective anxiety put a damper on the holiday, like a mental fog luring the house to nap randomly, play games, and doze again. Such was the weekend.

Circumstances have me suddenly thinking a lot about DevOps - which for someone who styles himself a service designer is like pulling teeth, or rather should you imagine the technology stack as a pond where the end-user interface is the shore, then I am wading chest deep. I hate this s**t.

But, on Monday, I sat here at my kitchen table fussing over an event queue while Freeport was blended by an eyewall churning property and people in roaring 200mph gusts for a dozen hours straight, stationary - roaring.

How lucky we are to be merely inconvenienced.

Memento mori.

Liking (❤) this issue of Stoic Designer is a super way to brighten my day. It helps signal to the great algorithms in the sky that this writeup is worth a few minutes of your day.

Stoic Designer is also now a podcast. You should be able to find it on your podcatcher of choice in the next day or two.

Remember that design is not art, but a practice.

Michael Schofield

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit stoic.substack.com

Getting sprint estimation right is the kind of headscratcher product management twitter fusses over on the daily, but while we can’t agree on the nitty gritty we imagine the same u/dystopia. Behind one door, deadlines* evaporate in favor of inspired predictions based on sane systems of work established organically by solid [design] principles and a light hand. Behind the other, a developer mill.

Both are modular agile blooms optimized for their hosts. A symbiotic relationship of system and culture. One welcomes the operational data like an omen, looking for signs of a flood so that it can move to higher ground; the other utters b******t like “the sprint estimate is a contract.”

As a community we focus so intently on systematizing the craft both to adapt to the growing pains of scale and — I think — to legitimize our next rung on the career ladder — design systems, design ops, research ops, service blueprints, etc. — that we must strain to remember that systems, like algorithms, embody the biases of their creators.

The system is a tool. You wouldn’t fawn so over a hammer.

Craft virtuously.

*| When I ported Stoic Designer from MailChimp, the migration missed a few of the early-birds, like “The Deadline is Arbitrary.” I 👏 have 👏 feelings 👏 about 👏 deadlines. Anyway, I’ll copy it over soon with a touch-up and audio version.

Liking (❤) this issue of Stoic Designer is a super way to brighten my day. It helps signal to the great algorithms in the sky that this writeup is worth a few minutes of your day.

Stoic Designer is also now a podcast. You should be able to find it on your podcatcher of choice in the next day or two.

Remember that design is not art, but a practice.

Michael Schofield

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit stoic.substack.com

Grief is on my mind. A thunder of mass shootings again sobered the nation to dovetail the death of a relative this weekend, so that just about everybody I know — for one reason or another — was feeling glum. If you’re interested you can read on twitter my guesswork about how Stoics might respond to a mass shooting, but for Stoic Designer I thought I’d adapt griefthink to designs, projects, or experiments that go wrong, have had their time, and slip the cable.

In agile, at the end of a sprint we perform a retrospective. When s**t goes wrong, we call it a post-mortem. This term — Latin for after death — is lifted from detective-work that refers to the examination of a dead body to determine the cause of death. In design and development work, teams who headscratch together after an incident (like, deleting then having to restore entire mailing lists) are there then performing a post-mortem to understand more acutely what happened and — more importantly — why.

It is one of the many death rituals designers use to assuage the pain of negative feedback, poor metrics, poor management, and the like, although too few are Wednesday-Addams enough to go full goth with it.

But Stoicism uses memento mori not like Hot Topic mallrats but as a purely practical reminder that - yo, time is short, get on with whatever’s important.

In fact, grief to the likes of Seneca was an opportunity to practice gratitude.

Has it then all been for nothing that you have had such a friend? During so many years, amid such close associations, after such intimate communion of personal interests, has nothing been accomplished? Do you bury friendship along with a friend? And why lament having lost him, if it be of no avail to have possessed him? Believe me, a great part of those we have loved, though chance has removed their persons, still abides with us. The past is ours, and there is nothing more secure for us than that which has been.

Find that deep sense of gratitude for the opportunity. Practicing the lessons learned from that person is the way in which that person lives on.

This is how we should see failed designs, dead products, bogus experiments, wireframes red-penned and thrown in the trash. How is it that we are better for them?

Craft virtuously.

Liking (❤) this issue of Stoic Designer is a super way to brighten my day. It helps signal to the great algorithms in the sky that this writeup is worth a few minutes of your day.

Stoic Designer is also now a podcast. You should be able to find it on your podcatcher of choice in the next day or two.

Remember that design is not art, but a practice,

Michael Schofield

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit stoic.substack.com

We all have rough days. Joyless projects - even if they’re not particularly difficult - you slog through tap your morale like it’s a tree sap. This s**t makes you less productive, reduces the quality of your craft, inspires you the next morning to sleep-in or call-in sick. Day after day, tedious design work or engineering, inane obstacles, baffling people, will turn the footing under you into quicksand.

Your practice of stoicism has toughened you against wily external forces, but - honestly - it’s hard to ignore the uneven footing when the mud is literally sucking off your boot.

I’ve found it useful to - like practicing stoicism - practice gratitude each day (well, most). I mean “practice” in the sense of deliberate practice: straining your muscle to improve performance. That is, can you train your mind to be reasonably grateful by default? In the sense of stoicism being an operating system for life, “default gratitude” seems like a desirable setting.

My programming isn’t particularly optimistic, so I practice gratitude using the system from the 5 Minute Journal, which adapted to Stoic Designer looks like this:

* First-thing before work, in your journal, finish this sentence: “In my current project I am grateful for __________.”

* Then, write 3 things you’re going to do today — so, small, achievable things — to ensure that by the end of the day you feel good about your work.

* At the end of the day, come back to your journal and write 3 good things that happened.

At first, honestly, this feels hokey. But by the end of the morning you have deliberately opted to see the bright-side, which over time becomes a trained perspective.

Craft virtuously.

Liking (❤) this issue of Stoic Designer is a super way to brighten my day. It helps signal to the great algorithms in the sky that this writeup is worth a few minutes of your day.

Remember that design is not art, but a practice,

Michael Schofield

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit stoic.substack.com

Not too long ago we were designing this kickstarter-like feature we could use to help fund specific local journalism, and circumstances being what they were our team didn’t have the bandwidth to prototype a new thing without dropping something else. So, someone outside of that small silo did it. It was just a draft, screenshots puzzled-together in a word document, not intended to be pixel perfect but to start the conversation.

Still, part of me bristled. The layout wasn’t “right,” or whatever. I nitpicked.

We were, however, engaged in a democratization of design I’d been advocating, with this a conversation starter we could proof against user-testers before refining a solution that met a demonstrable need. I nitpicked, knowing this, I think because it wasn’t mine.

I’m a creature of pride and envy and I often find I have to actively combat wounds against my ego or the longing for greener pastures. It’s times like these, bristling because a prototype is too prototype-y, that I have to remind myself: this s**t’s just shapes and fingerprints on a screen. Circles sweaty thumbs smush and a stock photo that screams its inauthenticity.

Pride is a master of deception: when you think you’re occupied in the weightiest business, that’s when he has you in his spell.

Marcus Aurelius would practice this sort of “gross reduction” to humble himself, an emperor, when he would catch himself lured by his own grandeur.

Like seeing roasted meet and other dishes in front of you and suddenly realizing: This is a dead fish. A dead bird. A dead pig. Or that this noble vintage is grape juice, and the purple robes are sheep wool dyed with shellfish blood. …

Perceptions like that—latching onto things and piercing through them, so we see what they really are. That’s what we need to do all the time—all through our lives when things lay claim to our trust—to lay them bare and see how pointless they are, to strip away the legend that encrusts them.

Craft virtuously.

Liking (❤) this issue of Stoic Designer is a super way to brighten my day. It helps signal to the great algorithms in the sky that this writeup is worth a few minutes of your day.

Remember that design is not art, but a practice,

Michael Schofield

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit stoic.substack.com

Seneca, on the brevity of life, condemns this idea of dying doing what you love - particularly when what you love is your work:

How disgraceful is the lawyer whose dying breath passes while at court, at an advanced age, pleading for unknown litigants and still seeking the approval of ignorant spectators.

All the dicta and principles of stoicism try to concentrate all that you spend your time on from day to day and everything that you really value into a single, dense venn diagram, so much so that should you die — which you will, memento mori — doing what you value, and what you happen to value is your work, that this seems like as good a way as any to give up the ghost.

But the work itself is a means to an end, not the end unto itself. It is a vehicle for practicing what you preach, engaging your mind only in time you won’t regret to have wasted on your death bed. Your work is a medium through which you express your best self. Let the work become more than that and you’re back at the starting line.

Your work doesn’t matter.

Craft virtuously.

Liking (❤) this issue of Stoic Designer is a super way to brighten my day. It helps signal to the great algorithms in the sky that this writeup is worth a few minutes of your day.

Remember that design is not art, but a practice,

Michael Schofield

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit stoic.substack.com