💀 Principled Decision Making, Back Roads, and May Retrospective


Happy May 31st, fam. This week in design stoicism:

  1. Principled Decision Making

  2. Back Roads of Your Self

  3. May Retrospective

Principled Decision Making

A friend expressed interest on twitter about applying stoicism to agile, which can be a ripe environment for exposing all sorts of organizational drama. I replied that stoicism's been -- for me -- a good fit, because its decision-making tree is simple.

I look at Stoicism as a framework designed to bootstrap systems. Its emphasis on perspective and prioritization is baked-in through daily journaling (like this newsletter) and daily practice, so that in in times of need that habit of thinking -- that system -- takes over. I emphasize this process of system creation because I trust systems more than I trust intentions. Good user experience research is always first to cut when budgets are tight, deadlines are looming, and stress is high - unless it's baked into the system of how the company works.

In our creative work we can - and should - systematize our decision making process, too. Decision trees make life easier, and when they're well constructed they are more likely to lead to sound and successful decision making at a high rate, making for scalable decision-making.

Marcus Aurelius had two steps prior to taking action (remember, the decisions he made were regularly, literally, life and death):

"The first thing to do - don't get worked up. ... The next thing to do - consider carefully the task at hand for what it is, while remembering that your purpose is to be a good human being."

I adapt this kind of thinking into even more obvious steps thaaaat I'm going to dub right here and now the memento mori / malorum loop. In Latin, class: memento mori, praemeditato malorum, memento mori. Make a calm decision structured around strong principles.

1. Memento mori (1): is this decision really that big of a deal? Unless you're about to die, or - through inaction - you're about to kill your users, friends, and colleagues, you have space to breathe. Relax.

2. Praemeditato malorum: what's the worst that can it happen if your team botches this decision?

3. Memento mori (2): does that really matter? Probably not. You have time to do this right.

I take this further in design specific work and apply my design-validated discovery system:

4. Is [feature/bug/problem] valid? Is the demonstrable need for this thing and its solution/approach represented in our research / feedback catalog?

The answer to this question determine whether a discovery phase is kicked off or we can start work on the deliverable. Then, let's say that deliverable is code, it runs through other decision making systems:

5. Does this code pass code review?

6. Does this feature pass build and regression tests?

7. Is this feature accessible?

8. Does this feature pass QA?

Et cetera.

These kinds of decision making systems probably already exist in one form or another in our work, existing to make decision making less fatiguing and scalable (even automatable). Systematized stoic principles designed to evoke clear-headedness adapt comfortably to any of these.

Back Roads of Your Self

This morning I want to to share this concept I like: "the back roads of your self." For context, here's the quote from Marcus Aurelius.

"People try to get away from it all - to the country, to the beach, to the mountains. You always wish that you could too. ... you can get away from it anytime you like by going within. ... Are you complaining about the things the world assigns you? ... Or is it your reputation that's bothering you? But look at how soon we're all forgotten. The abyss of endless time that swallows it all. ... So keep this refuge in mind: the back roads of your self. Above all, no strain and no stress. Be straightforward. Look at things like ... a human being, like a citizen, like a mortal."

He uses the "back roads of your self" in the same way some guru would tell us that we have mountains within, that retreating inward - briefly, he points out - is a way to charge the battery.

I however like the imagery because of what it implies about travel, about the connective tissue of a city or small town as a metaphor for not just inner depth and peace, but also shortcuts. The busy thoroughfare is the obvious path, but the familiar local will know not just one but other routes to get from Point A to Point B.

What are the implications of learning these back roads? And, in this interpretation, what are they? Back roads are the result of pattern recognition, of just paying attention. Do you know how to calm yourself when you're feeling irate, or envious? What are the buttons you have to push to illicit an action you want? When you're getting in your on way, do you know what you need to do to go around?

Consider these back roads not just as a meditative mumbo jumbo and inner peace, but as a metaphor for the practical value of self awareness.

May Retrospective

Another month's in the rear-view mirror, designers. Like the end of any sprint or project, let's just take the end-of-the-month excuse to weigh the work and the person.

What went well this month? What didn't go so hot? What can we do to make June better?

I want to tease-out a few more specific questions from the standard sprint retro prompt based on Stoic qualities we want to keep in mind. Ask yourself:

  1. Did I procrastinate and, if so, why? Procrastination is a signal that we aren't being true to ourselves: whether that's to our desires to actually do the thing, the trepidation that makes us postpone taking action, our frankly just our limits about how much work we can take on.

  2. What will I do so that I don't procrastinate in June? Procrastination is a character flaw that prevents us from living-up to the kind of designer or developer we want to be. We need to make it our priority to identify the reasons we procrastinate - and nip them. Sometimes, it's just about saying out loud that - you know what - you're not going to do that podcast anymore.

  3. Did I lose my cool, did I lose my cool often, and why? Being cool-headed isn't about suppressing emotion, but by convincing yourself that there's very little of real importance that deserves all that mental energy involved in losing your shit. Your design decisions are worst for panic and pressure. Your dignity suffers. The quality of your day suffers.

  4. What can I do in June to armor myself against losing my cool? Memento mori.

  5. Are the things that matter - my friends, my family, my users - better off in June because I existed in May? For as much or as little as you choose to live in society, is it better for you being there?

  6. Am I better off in June because of the choices I made about how I spend my time and with whom I spend my time? Be real.

Stoicism isn't about dicta and maxims but practice in making your day-to-day what you want it to be by identifying everything that's dragging it down and cutting the straps.

See you in June. Craft virtuously,


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