Shoulder Advisors 101 (Excerpts)

The term “shoulder advisor” comes from the cartoon trope of a character attempting to make a decision while a tiny angel whispers in one ear and a tiny devil whispers in the other.

Many people have multiple shoulder advisors.  Some, no doubt, carry a literal metaphorical angel and devil around with them.  Others may sometimes hear the whispers of some of their favorite beloved fictional characters.  It’s quite common in my experience for people to have shoulder copies of their parents, or their best friends, or their romantic partners, or particularly impactful teachers or bosses or mentors.

There is simply some kind of subroutine in the brain of most humans that is capable of taking in training data and learning what a given person (or character, or archetype) would say, in a given situation. It’s predictive software, likely evolved in response to the need to model other chimps in the ancestral environment, and strongly selected for due to the fact that being able to model those other chimps accurately generally paid off big.

Selection criteria: emulability and usefulness

In order to use shoulder advisors, you have to have shoulder advisors, and whether you’re building up a whole shoulder council for the first time or just trying to expand and curate an existing ensemble, some appointees are going to prove much more valuable than others.

Assume you had no preexisting council, and were brainstorming a list of possible advisors with the intent to winnow it down.  You might try writing down four or five names for each of the following categories:

  • Close family members (whether they’re still close or not)
  • Longtime friends (whether you’re still friends or not)
  • Impactful teachers and mentors
  • Current bosses, employers, coworkers, or clients
  • Characters from TV shows and movies
  • Characters from books or other media (including those you’ve invented yourself)
  • Politicians, comedians, authors, celebrities, and other notable public figures
  • People who’ve blown your mind or changed the way you look at the world
  • People you have had serious disagreements with

Once in possession of a list of ~40 names, I claim the next step is to filter it based on the presence of two qualities: emulability and usefulness.

Emulability is the degree to which your brain can, or could likely learn to, successfully boot up a copy of this person and “just push play” on it, such that the copy in a sense “runs itself.”  Authors sometimes talk about their characters “coming to life,” and producing their own dialogue or wresting the story in an unexpected direction or even verbally arguing with the author inside their head—this is high emulability.

In practice, emulability is often immediately obvious; you can just pluck a name off the list, imagine them sitting beside you (or reading over your shoulder, or lounging on the other side of the room) and just see how they react to what’s happening to you right this second, and the claims that they hear me making.

In the event that this kind of imagination is not yet easy for you, though, there are a couple of qualities you can use to assess the emulation potential of a given shoulder-person, before putting in a bunch of effort.

The first of these is total training data.  People you’ve interacted with 100x more than average will tend to be more emulable just because you’ve absorbed more instances of “X happened, and they responded with Y.”

The second major component is something like uniqueness or quirkiness or internal consistency.  If someone has a very specific vibe, it’s easy to vividly imagine their particular responses.  Ditto if someone has strong opinions, or narrow special interests.

Boring(-to-you), quiet, unopinionated, and “normal” people are thus quite hard to emulate, but that’s okay because even if you could emulate them, you wouldn’t get much out of them most of the time.  You’re looking for the kind of people who have the potential to change your course— to think of things you wouldn’t, make suggestions that aren’t obvious, say the things you need to hear.

Which brings us to our second major filter: usefulness.

By “usefulness,” then, what I am trying to gesture at is “I suspect my life would benefit from small, well-timed injections of this person’s way-of-being.”  If you are (according to yourself) too timid and hesitant, then you might look for people who are avatars of boldness, or who tend to be encouraging and supportive and make you feel confident, or who are eccentric and surprising.  If you are (according to yourself) too reckless and unreliable, then you might benefit from shoulder advisors who are avatars of caution, or who tend to pipe up with nervous hesitations, or who are good at noticing the little details before they turn into big problems.

And if you don’t know what your flaws are, or how best to go about improving yourself according-to-your-own-values, then maybe you’re looking for people who are generally insightful and clear, or who are good at turning uncertainty into concrete and actionable suggestions, or who are (perhaps) somewhat scathing and unafraid to utter harsh truths.

Improving the effectiveness of the council

Taking as given that you have some number of shoulder advisors who are either active or who you intend to start consulting, what next?

The key value of a good shoulder advisor is that they say the thing you need to hear, at the moment you need to hear it.  It doesn’t take much to tip a tough decision from one direction to the other, or to start (or break) an affective spiral or chain of if-then behaviors.  A shoulder advisor is a specific instantiation of the general wish “if only I’d thought of X before Y happened”—you’re trying to make it more likely that you will, in fact, remember X, especially where X is something not particularly native to your current way of doing things.

Taking the second part first, there are two ways to make sure that you hear from your shoulder advisors at the critical moment:

  • Build the habit of making an explicit, effortful check; pause and actively boot up your shoulder advisor in response to various triggers, e.g.:
    • You’re about to make a major decision
    • You’re noticing a strong feeling of temptation
    • You’re noticing a strong feeling of certainty
    • You just said a bunch of hateful things about yourself
    • You’ve just made some kind of absolute declaration
    • You’re considering changing the plan (or sticking to a plan you feel an impulse to change)
  • “Teach” your shoulder advisors to appear on their own

A couple of tips, as you explore this space:

  • Don’t ask your shoulder advisors questions.  Just like people tend to get better results from telling themselves “it went wrong” and then letting their brain tell the story of why (rather than asking themselves “what might go wrong?”), it’s better to just imagine the person in the room with you—imagine them hearing the previous minute of conversation, or visualize them sitting over in the corner, watching and forming opinions, and just sort of let them say their piece.  This can be a difficult skill to learn, if you don’t have experience with it, but be patient—if your shoulder advisor isn’t speaking up or making faces or anything, just keep on imagining them as you think thoughts at yourself or review your plan or whatever.
  • Also, don’t just summon your shoulder advisors to weigh in on Big Issues, especially if you’re practicing.  Vary the triggers, and reward your brain for causing the shoulder advisor to show up at all, for whatever reason, even if it’s while you’re making breakfast or while you’re in the shower or just to say something snarky about the person in front of you in line.  Like in (some forms of) meditation, where you don’t stop your thoughts from wandering, but rather practice always returning your focus to where you want it, you’ll get better results if you think in terms of “how much practice are my shoulder advisors getting at booting up from nothing?”

Once you’ve got a cast of characters who are willing to show up at all (or at least one solid imaginary friend), then you can worry about nudging their contributions in an actually useful direction.

If at all possible (especially in the early days), get your real advisors to not only correct your shoulder advisor’s core thoughts and ideas, but to flesh out why they think what they think, and where your shoulder copy went wrong/what it doesn’t seem to understand.

If your shoulder advisor is fictional, this is somewhat harder to do, but a good substitute is to write down a draft of their first contribution, then review it a day or two later with a critical eye.  Even moreso than copies of real people, your fictional shoulder advisors are free to mutate in whatever direction is useful for you.

Ultimately, the idea is to give regular feedback to whatever part of your brain is running the emulation.  Upvotes for what works and feels true, downvotes for what doesn’t, but most importantly, more training data.  It’s fine if your shoulder advisor gets frustrated and impatient as you ask it to say more and more words—let it be frustrated and impatient in whatever way is characteristic for that individual, and just keep recording.

Duncan Sabien, 2021, Shoulder Advisors 101