Picking Apart Decisions
Talking about asymmetries in daily life, being stuck in decisions, and working through decision agony.
The Teardown
Wednesday :: January 10th, 2024
Common Moments Lacking Balance
Many moments in life are asymmetric. You, on one side, have more or less information about something than the person on the other side. My phrasing doesn’t need to tie to strict sides per se. But in essence, you might encounter a circumstance that has asymmetric qualities. Here are some examples that stand out to me:
Buying a car
Buying a house
Buying a stock in a company
The first two examples differ from the third because someone typically sells those assets to you. You speak with a real estate agent that clips their share of your money to service you. Whether they truly sell or not is debatable, but it might be true that they possess knowledge that isn’t easy to find otherwise. A car sales associate has a binder full of information about a car that you want, but will only offer you bits of information. They’ll disappear into dark smoky rooms to grab an initial quote that helps convince you that you are getting an unbeatable price.
So far, the advantage seems to tip toward the person offering the thing. They appear to know more about the thing than you. You are at a disadvantage.
But the scale often tips the other way. In particular, in car buying, the salesperson knows everything about the car they’re selling but they know nothing about you. There are lots of questions they can’t answer without some level of inquiry, for example:
What motivated you to walk in the dealership at all?
What matters to you as a buyer? Do you know what you’re looking for? Do you have a clear sense for what you don’t want?
What’s your budget? Is there room? Are you ready to walk away?
What’s your income? Is this a stretch, somewhere in the middle, or toy money?
Do you have to do any work to get to a decision - plug something into a sheet, research on consumer reports, speak to other dealers?
Do you need to consult anyone else?
These questions coalesce to one idea: making decisions. The seller must decide whether to sell you something and compromise for one or more reasons. The buyer must decide whether buy something and compromise for one or more reasons. You’re dancing together, pushing and pulling each other to understand a potential point of compromise.
Starting With Asking Why
I brought up common transactional examples because they help illustrate common asymmetries. In a recent conversation, my wife explained that I help her do more of something that I do all the time: question assumptions.
In my post about looking ahead this year, I described my personality this way:
I sometimes describe myself as always dissatisfied. But perhaps another framing fit for this post is: always curious.
The tendency to question something often pops up at work. I am that annoying person that asks why when someone asks me to do something. I want the context. But I’m not avoiding the work. Instead, I like to have all the available information because it helps me do better work. There is obvious asymmetry because I am asked to do something without much context and have to decide whether to inquire or not.
In some moments, the quick calculation is clear. I’ll power forward on the ask without the context and revert as fast as possible. That allows me to pass the resulting shiny work gold back to the person and ask for feedback. Sometimes I get it, sometimes I don’t. But there are moments when repeating that exchange more than once helps with extracting more information. What matters to you in this ask? Oh, it’s A, B, C? Oh, ok. I’m glad we know and can revise what we’ve done. It is, one one hand, exhausting, but, fun. You get more conversation with that person and more information from them.
And Now, The Inquiries
What I didn’t describe in that probably-annoying work exchange is how I ask questions. And, in broad terms, the same process applies to decisions.
I had two recent conversations that sparked a geek-out on this topic. In one conversation, a founder friend and I spoke about how to form valid ideas for businesses. You want to start a business, have an idea, and want to test it. One question I ask, both out loud to people and also as inner-monologue, is this: do people give a shit to solve this problem? Sometimes, the answer seems to be yes. Otherwise, I’m skeptical. If I have enough conviction about the idea, I have to gather up facts and opinions about why people might give a shit.
The second conversation focused on direct inquiries. And, in this moment, let me refresh you on the Socratic Method. Colorado State University has a “Teaching Tips” page that describes how it applies to student-teacher interactions. First, in high-level philosopher speak:
Developed by the Greek philosopher, Socrates, the Socratic Method is a dialogue between teacher and students, instigated by the continual probing questions of the teacher, in a concerted effort to explore the underlying beliefs that shape the students views and opinions. Though often misunderstood, most Western pedagogical tradition, from Plato on, is based on this dialectical method of questioning.
Then, there is a more practical description.
The Socratic Method says Reich, “is better used to demonstrate complexity, difficulty, and uncertainty than to elicit facts about the world.” The aim of the questioning is to probe the underlying beliefs upon which each participant’s statements, arguments and assumptions are built.
What I like in this passage is the probing of beliefs. Decisions are also based on beliefs. You might have pre-determined views that prime your decisions one way or another.
In my ever-existential brain, there tends to be some base set of work that must occur to make decisions. So, if I’m buying a car, I’m thinking about why I’m trying to buy it. What do I need? Or is it instead something want? What colors are a must vs. not bad to have but not ideal? Do I want a manual or automatic transmission? Do I want seat heaters?
These are all answerable questions. But there are two nebulous components to the work. One is time. The other is more like qualitative research.
Maybe I’ll read reviews of the various cars. Perhaps I’ll look at historical resale values. There are endless internet forums with anecdotes from owners and other folks. I want all of the information. But, what is my plan to wrap it all together to decide? And what level of information is all the information?
At that dealership, the person selling me the car must pry open my brain to learn about the process. The salesperson can also go one step further and presume they knows the answers. In that mode, they’ll ask me questions or make prompting statements and then present a series of options.
To play out the scenario, it might look like this:
Them: Ok, good to talk about the car. To be honest, I’m not sure that you’re going to buy today. And I’m thinking of some possible reasons out loud. Is it because:
[A] you want to buy instead in 6 months
[B] you need to do some research or talk to someone first, or
[C] you don’t actually want this car.
Me: It’s B
Them: Ok, great, then what’s your plan for getting to a point with that research that gets you ready?
You might have a little puke in your mouth after reading that interaction. Is that salesperson an asshole? Are they too pushy? That’s for you to decide. But the interaction is instructive for the decision process. Part of what comes out in this systematic method is the agony of the decision - what will hold the person back from buying. In general terms, it illuminates what stops the person from making a decision.
An Actual Example
I used an example that tortured me not long ago: buying a car. I’ve recently waded into and back out of buying after discovering or crafting some opaque reason to avoid a decision. That verb is key to my point: I’m avoiding a decision. The why changes depending on the underlying circumstance, but the symptom is almost always there.
The mark of my avoidance was similar each time I almost bought something. Many months ago, I bid on a car on Bring A Trailer - an auction website that specializes in collector cars of all types. I was uninformed, bid low, and entered the action at the beginning of the seven-day auction period. The car ultimately sold days later for over 3x what I bid. I didn’t bid again despite wanting that particular car.
Months later, I placed a bid on another car on the same site. This car was much more interesting. It was one of eighty-one examples of cars delivered to the United States painted that color from that make, model, and year combination. It was also fitted with a manual transmission, something rare these days. People (in the United States) just don’t order them that way anymore. The problem (IMO) is so acute that both BMW and Volkswagen are ditching manual transmissions entirely in their 2025 model-year cars.
Anyways, my bid was much higher in absolute terms. And, this time I prepared to buy the car at my bid price. I won the auction.
I lost the car.
What I won was the intention of buying the car. So, I needed to translate intention to action and dollars. As the highest bidder, the seller received my contact info. We talked, he pushed, and I folded. I thought the price was high, but it wasn’t out of my budget. But, despite agreeing to move forward, I balked and then passed. I felt I needed more conviction to move forward. Of course, the more I spoke about it out loud, the more I convinced myself I didn’t want or need it. I sabotaged my own process.
Breaking Down My Decisions
This background boils down to an ongoing effort to make faster and less anxious decisions about, well, everything. This post so far also pulsed through my veins, hitting this virtual paper fast. In a post titled Find Your Calling and Avoid Productive Distractions, writer Jen Hitze describes something inspirational she read about writing:
One of the most thought-provoking pieces of literature I've come across recently is this poem by Charles Bukowski. In it, Bukowski claims that if you truly want to be a writer, your story must burst out of you. He advises against writing if the creative process is imitative and arduous rather than being an outpouring of individual style and freedom. He further warns against writing for the sake of money, fame, or superficial appeal.
I liked this concept: a way to draft something on paper is to embrace whatever story bursts out of you. She adds her own spin on the idea.
Rather than telling you what work you should avoid (mirroring Bukowski's approach), I'll urge you to embrace the work that genuinely captivates you—something that springs forth effortlessly, independent of external incentives, and uniquely expresses your true self.
Like the concept in that quote, the idea that sprung in record time from my mind was to detail how I am working to reorient my decision process today. I’m in geek-out mode.
Of course, I am and this process are, collectively, a work in progress. I’m trying to look at everything in a consultative manner. Most of my decisions or inquiries require a basic level of information, some probing and structured exploration, and finally a break point. Most of my historic agony was not around knowing about these components. It was, instead, due to lack of systematizing my approach to addressing, resolving, and moving on.
I’m going to report back on a periodic basis to let you know how it’s going.
You don’t have to disclose here, but I want to know what both of these cars were!