Jodie and I had some work on holistic assessment published a few days ago—you can read it here.

This post isn’t a recap of the paper; it’s a set of ideas inspired by having ruminated on what we wrote. The points below are an attempt to capture some of the questions and propositions that have come out of this reflection.

1. What are theories good for?

I spend a lot of time defending theory.

A common complaint about this is that this isn’t practical; this is because theories are theories. Talking about theory as a homogenous category doesn’t help the issue. My coffee preference is a theory. My idea about what is ‘sky blue’ is a theory.

Why should a theory be practical?

To my mind, what is implied in this idea is that we want something of theory. But is this wanting really an expectation that theory will do something for us? Are we comfortable with the idea that we might need to do something with a theory? And that in the process we will probably come up with an intuitive, tacit, twist on the original stimuli?

It makes sense to think about theory as stimuli. We tend to encounter them in moments that are separate those in which they hope they will help us (e.g. reading something about productivity on the internet, ostensibly to help us be productive later).

Some theories provide recipes for us to test out, others are more like firm rules w’ve tested and established (my coffee preference), and some of them are about zooming out to think about the way things are—getting these differences mixed up seems likely to lead to dissatisfaction with theory.

Is theory the same thing as philosophy (or as philosophising)? I’m not uncomfortable with that idea.

2. ‘Explanations run out somewhere’

This is Wittgenstein’s idea, and I feel like I’m quoting it on a weekly basis.

The gist, to my mind, is this: what is meant is not equal to a given set of words.

We use words to signify things all the time. Some of these usages are more ‘official’ than others—words lend a firmity to things, especially when we title a bunch of words with something like ‘rules’ or ‘guidelines’ or ‘law’.

The tension I find interesting is in the point at which we realise that words can’t usually say all of what is meant.

At the same time, claiming that a set of words does do this opens up a claim; sometimes a claim to power. The individual aligned to the words has some sort of authority.

3. Human works are composed along a spectrum of divergence

When people do things (what I am calling ‘works’), they generally do them one of a larger set of possible ways they could be done.

In a factory, things happen in a very consistent way.

In the ways we talk about what people do (especially when we set 300 students the same task, like write an essay on topic ‘x’) we sometimes give the impression that this applies to other things.

The point is that there is not really such a defined recipe for success for many normal (and abnormal) tasks. To ‘cook dinner’ is flexible (that is, divergent) work; more so than the directive to ‘bake me an apple pie following this specific recipe’. How do we account for the fact that said recipe perhaps includes ingredients not available in the time and place w find ourselves?

When ‘official’ signage is applied to divergent works, there is a risk that remarkable outliers are lost. The cost might be what William James called ‘unselected geniuses’.

For more about James and his genius theory, see the introduction and first chapter of this book.

For more about the concept of divergence, read our paper, or read this one by Royce Sadler.

4. Statements and criteria offer different impressions of knowledge

This is an idea I came to via Stanley Cavell’s Claim to Reason (1979). Here’s the gist of the idea, in Cavell’s own words:

When epistemology raises the question of knowledge, what is asks for are the grounds of our certainty. But we are reminded that what we call knowledge is also related to what we call getting to know, or learning, e.g., to our ability to identify or classify or discriminate different objects with and from one another. Criteria are criteria of judgment; the underlying idea is one of discriminating cases, of identifying by means of differences…

In the modern history of epistemology, the idea of judgment is not generally distinguished from the idea of statement generally, or perhaps they are too completely distinguished. The problem is not that in focusing upon those forms of utterance which are characterized by their exclusive possession of truth or falsity a philosopher fails to attend to other “uses” of language… The problem is to see whether the study of human knowledge may as a whole be distorted, anyway dictated, by this focus.

The focus upon statements takes knowledge to be the sum (or product) of true statements, and hence construes the limits of human knowledge as coinciding with the extent to which it has amassed true statements of the world… The focus upon judgment takes human knowledge to be the human capacity for applying the concepts of a language to the things of a world, for characterizing (categorizing) the world when and as it is humanly done, and hence construes the limits of human knowledge as coinciding with the limits of its concepts (in some historical period).

(pp. 16–17, bolding my own)

What’s the thought here?

Cavell seems to be talking about the difference between claims and queries as bases for knowledge.

Criteria are flexible, comprising a non-exhaustive set of components making up the benchmarks (standards) against which we experience things (not just academically recognise them).

What are statements then?

Perhaps these are claims that are established as ostensible criteria.

5. How can the difference between ‘official’ and ‘formal’ criteria be usefully teased out?

I used to use the word ‘formal’ to talk about fixed aspects of the human world, in the sense of things set in place via policy (or other types of rules and regulations).

I thought about this idea differently after listening to Emily Akuno give a key note at a conference this year on assessment in music. Her point (as I understood it) was that form inheres in most aspects of social practice—for example, children’s play may be a formal activity in this sense (when order is present).

I like ‘official’ as an alternative term, because it points to some designation by an authoritative figure about the importance of something, usually in an explicitly signed way.

What follows is a personal philosophy of writing (or making anything, really). There is so much to say on this topic that it could easily be a book — if there is a part of this article you think is worth additional detail, feel free to leave a note in the comments.

In the last few years I have had very many conversations with students about the act of writing. The context leading to these conversations is usually one of the following:

1. The student/s are figuring out how to write research theses (usually while learning the research ropes at the same time).
2. The student/s have multiple pieces of written assessment due on the same date (case in point, my current education students have an average of 6000 words due across three courses, all at 3pm on August 4th).

My own observation is that attempts to help students deal with such tasks usually hinge on technical knowledge — the idea is that providing genre-specific information (e.g. a formula for essay structure) will help students to produce the corresponding kind of work.

What seems to-be less discussed (outside of creative writing circles) is the significance of the subjective dimension to writing.

A brief philosophical aside: In this case, I’m using the word subjective to refer to the personal realm of experience — I am understanding subjectivity (emphasis on the ‘ity’) as a personal process unfolding through time that mediates what happens (i.e. what the students actually does, when they sit down to write).

Small perfectionism rant

The subjective dimension matters because this is the engine room of the creative process that actually results in the pieces of writing that these students will eventually submit.

Subjectivity is also the bastion of perfectionism. A key issue with perfectionism is that it prevents students (and the rest of us!) from actually finishing things. Worth noting is that one doesn’t need to self-identify as a perfectionist to feel perfectionistic inclinations (e.g. “wow, that’s a crap sentence, I’ll just delete that and come up with something better before I move on”).

Here are some things that I think can be used to resolve this tension.

Setting expectations

Setting expectations about the practice of writing can help in regulating how one feels about it when in the thick of things.

Concretely, it is worth noting that there is no single recipe to success in most genres of writing. This can be an uncomfortable thought if you’re used to having scaffolds provided (e.g. “use headings x, y, and z to structure the essay”). While we can observe general features of genre based on observation of historical events (e.g. what we have decided to call an essay in the recent past), the fact is usually that is no single, precise set of steps that will yield a successful (or poor) outcome.

One solution to this is immersion in exemplars that the local community largely agrees upon in terms of their quality.

The diversity of ways in which a good example of work can exist helps to illustrate how perfectionism constitutes a deficit discourse. The practice of writing can be understood as about crafting something that rises to the occasion, rather than finding the solution. If the solution is presented as a single, ostensibly perfect exemplar, then perfection is paradoxically unattainable, since it would require direct plagiarism of that once exemplar (anything else would be less perfect, after all).

Similarly, presenting an abstract framework (e.g. a description of genre features) as a model of perfection sets an unattainable bar.

The main reason for this is that a framework is not equivalent to the corresponding piece of work (e.g. a concept map of essay structure is not the same as an essay; even an essay about essay structure is not the same essay we usually ask of students). The risk here is in claiming that a perfect qualitative standard exists, when the game (in education) is usually a quantitative one (i.e. achievement on a fixed scale). That written tasks are by definition flexible should be clearly established.

(Note that this is not a critique of abstract frameworks, only of a certain way in which they might be used).

Defining drafting clearly

To my mind, drafting is under-discussed in higher education courses — it is usually falls in the mysterious bag of ‘assumed knowledge’.

The key point is this: a draft is not meant to be the finished product. To put an even finer point on it; a draft is not meant to be the same as the draft that came before or which will come after. It is a moment in a progression.

In my definition, drafting is a three-phase process.

1. The first draft is in the first moment in which the subjective engine of the individual produces something durable (usually a mark on a page or screen, but it is worth noting that thoughts have durability too).
2. The second (and third, fourth, fifth, etc.) drafts occur when the first draft is actively stored as a previous draft. The definition is in the decision of the individual here. When working digitally, this might be in the action of replicating the work (e.g. by saving a fresh copy of a file). If working in an analogue way, it might mean tucking a stack of papers to the side with a sticky note on them that says ‘draft #1’. If working mentally, it might mean actively saying to oneself, “that bit of thinking is my first draft”.
3. The last draft is the last draft. We tend to recognise it only after it has happened.

Deciding that the first draft will be the last draft is usually a hard way to go (unless the artefact in question is a very brief email or text message, perhaps), since it promotes relentless self-censorship.

The reason for this is that the act of writing usually produces instant feedback — we tend to see what we have written right away. Unless we are prepared, we might react without thinking (e.g., by mashing the backspace key). The cost here is that we switch prematurely from a process of drafting to one of editing.

Countering the tendency to edit prematurely

One way to put the editing tendency on hold is to practise seeing oneself on the page.

The best way to do this that I’m aware of (based purely on my own experience) is free-writing. Free-writing is basically the process of writing whatever comes out in a stream of consciousness sort of way. The good thing about rambling on the page is that we have an opportunity to practise observing what we have made without applying any strict expectations about quality to it — try this before you judge its effectiveness.

Some things that help with free-writing

1. Set a timer (to prove a sense of closure to the exercise; start with one minute if you’ve never free-written before).
2. Write very quickly; faster than you feel you can think, even.
3. Do not use the backspace key.

The point is to stay in motion

Alongside the opportunity to practise looking in the metaphorical mirror, free-writing is also a good opportunity to develop a tacit knowledge of what it means to write fast.

Being able to write fast is helpful because it can help to produce draft material quickly. This, in turn, is useful because having a draft (even a mental one) is the only way to extend one’s thinking on a topic. Drafting is basically self-reflective learning in action.

For this reason, if we don’t know what comes next, we may as well write something and see where that leads — try writing “bacon and eggs” next time you get stuck.

Some ways to stay in motion

When putting pen to paper, hand to keyboard, or mind to thought, there are some useful ways to keep things moving when drafting feels like wading through sludge.

• As above, do not use the backspace key until the first draft has been archived (the point, especially at the beginning, is to get to the next draft as quickly as possible).
• Try writing in dot points — this helps to relieve the self-expectation that one needs to produce complete sentences and/or paragraphs.
• To find order, try comparing one dot point to another and asking, “which should come first?”
• Try limiting the writing either to questions or statements that imply some sort of position — later on , this is not a bad policy for working headings. The idea here is that these types of statements provoke a more specific response than do free-floating key words (what can be said in response to a free-floating word of relevance — say, ‘validity’; almost anything!).
• Moving frequently from one draft to the next can help to provide personal permission to delete content with abandon (i.e. avoiding a sunk-cost scenario).
• Set a timer, to know that there is an end to the whole thing.

A point about waiting as a resource for staying in motion

I’ve mentioned a few times above that drafting can be a mental process too.

It should be clear by now that this article general argues for drafting as a process of discovery. Once we’re comfortable doing this on the page, we can try allowing some of this to go by in the mind. Rather than capturing everything that comes along (as in pure free-writing) we are now sifting for relevant things.

If we’ve calibrated our expectations appropriately, one useful approach is to practise actively waiting for relevant ideas to come down the mental stream.

Try sitting with a pen and a blank sheet of paper (and nothing else; especially not a smart phone) for five minutes with a particular topic in mind (perhaps an essay question). You might experience an initial moment of tension — what should you put on the page? Once a little time elapses, it turns out to be very difficult to think of nothing worth writing (and if only irrelevant things come up, write them down).

My hunch is that this approach can work because there is not an equal probability of any possible thought occurring to us.

Put another way, we are more likely to think some things than other things. Part of the reason for this is that we have been exposed to some things more than other things. If we are writing an essay, for example, the books or papers (or conversations) we have had in the past influence this reservoir of possible thinkings.

For similar reasons, it is worth noting that we can feed this reservoir; with reading or listening material certainly, but also with other things (e.g. the specific experience of sitting to write at a sunny park bench, or in a corner of a library).

The end

The point of writing this article was to get down some long-standing thoughts about the subjective side of writing (especially as applicable to the student context).

I have largely avoided touching on technical specifics. This is not because I do not think technical specifics are not important (emphatically, they are), but because I feel the subjective side of the process to be largely under-discussed. The point, to my way of thinking, is that the subjective aspect of writing regulates our ability to access a posture of curiosity within the drafting process.

If this is useful, or there is something you feel is worthy of further attention, please leave a comment — this will help me to direct future writing in a useful way.

Questions to ask when stuck (or trying to explain a good day)

The other day I came up with 100 reasons to write an essay.

It got me thinking about other impractically long lists that I could use for thought-provoking reflection. This one is for when you’re in the thick of a project and trying to understand what’s going on. Specifically, they all ask about some aspect of the question, ‘how am I relating to this thing I am trying to do?’

Here’s the list; most could have the word ‘why’ added to the end:

1. Am I tired? Am I wired? Or somewhere in between?

2. Do I know when I’m alert and when I’m not?

3. Do I know what a good one looks like?

4. Do I know what a bad one looks like?

5. Do I know someone who’s done it before?

6. Where am I on the hunger spectrum?

7. How well can I deal with ‘bad’?

8. What will stop me from concentrating?

9. What will help me concentrate?

10. What’s good about the task?

11. What am I dreading (or otherwise unenthused) about it?

12. Do I know why?

13. Am I iterating, or trying to make a single perfect copy?

14. Am I treating this task as the most important thing in the world?

15. Am I treating this as the least important?

16. Does exercise help?

17. Can this be done on the footpath, or outside?

18. Am I resisting finishing it?

19. Am I being perfectionistic?

20. Am I procrastinating?

21. Who is it for?

22. How does it help?

23. How does it help me?

24. Am I playing it safe?

25. Am I taking an unnecessary risk?

26. Is this an investment, or an enjoyment project?

27. Is there a return on energy here?

28. Is there a backup plan?

29. Is there a backup copy?

30. Would I do this if I had to do it every day for the rest of my life?

31. If no, do I have a good reason for persisting?

32. What will I learn from the work?

33. What opportunity to teach is there within the work?

34. What’s my exit strategy?

35. How will I persist when you get tired?

36. How will I stay on task?

37. How will I deal with an epiphany when one comes along?

38. What will I do if I have an idea away from the desk/computer/workshop (etc. etc.)?

39. How will I know when I’m burning out?

40. Do I know what help I need?

41. How will I get the help?

42. How will I get feedback?

43. How will I give feedback?

44. How will I know when to quit?

45. What’s my theory of inspiration (how will I understand its role, and deal with its absence)?

46. How will I find space away from the project?

47. What don’t I know?

48. What do I know?

49. What’s the story, I’m telling myself, and why is it true?

50. What’s the story I’m telling myself and why is it false?

51. What are the costs of doing this work?

52. What are the benefits?

53. Where else could I be doing this work?

54. What attitude am I bringing?

55. How will I prepare to work?

56. How will I finish a working session?

57. How will I deal with getting stuck?

58. How will I explain it to someone else?

59. When is the deadline?

60. How will I renegotiate the deadline if I have to?

61. How will I fund it?

62. Who am I responsible to?

63. What have I promised?

64. How would I finish it today if I had to?

65. What would I do if I had a year?

66. Would I do this if I could avoid it?

67. Why does it need to be done now?

68. Why might it not be the most important thing right now?

69. What will happen if it fails?

70. What will happen if it succeeds?

71. Why is it worth doing regardless of success?

72. What is my guiding myth?

73. How will I know I am on the right path?

74. Do I need to know I am on the right path?

75. How could I be more specific?

76. When would it be useful to be less specific?

77. Do I believe that there is a secret here that I don’t know? Why/why not?

78. Whose agenda am I serving? Why?

79. Am I doing this to avoid doing something else?

80. Is this healthy, and does it matter?

81. Do I believe that things will be better if just get through this?

82. Can I recognise the difference between being in motion and being stuck?

83. Do I know what to do with advice/criticism?

84. Do I know how to solicit advice/criticism?

85. Do I know what I’ll do when it’s finished?

86. Where am I on the optimism-pessimism spectrum?

87. Do I think my close friends and family are likely to be helpful if I talk to them about it?

88. What are my fears?

89. What are my hopes?

90. How can I be more concise?

91. How can I be more elaborate?

92. How can I be more accessible?

93. Am I being honest? Does it matter?

94. Who do I have to thank for the opportunity to do this?

95. Who (or what) is this thing dedicated to?

96. Why am I grateful for this?

97. Am I on the hook?

98. Am I scared?

99. Am I confident?

100. Can I see the next step?

Lists are very satisfying creative tools; especially when they are impractically long.

Taking some inspiration from Kathleen, I wanted to see what would happen if I tried to come up with 100 reasons to write an essay. Perhaps I am trying to think of ways to convince my university students that essays are not, in fact, the devil incarnate in literary form.

Here’s what I came up with.

1. To practice staying in motion

2. To find things

3. To know what isn’t yet known

4. To practice waiting

5. To practice seeing yourself on the page

6. To learn to make a point without saying it explicitly

7. To learn to make a point by saying it explicitly

8. For entertainment (to practice, being entertained by the process, rather than expecting it)

9. To have done something hard

10. To grow an idea

11. To participate in a tradition

12. To call oneself an essayist

13. To find something between formal writing and poetry/narrative (read Chesterton for this)

14. To write a lecture/speech

15. To adapt a lecture/speech

16. To attempt to emulate great writers

17. To contrast against great writers

18. To become a better writer

19. To become a faster writer

20. To write nonsense

21. To write something other people can read

22. To write something nobody els need read (but which might still be illuminating)

23. To set the stage for the next piece of work (before the sun goes down no less!)

24. To find a way into (and appreciate) mundane parts of the world

25. To escape mundane aspects of the world

26. To explore (or create) a world that doesn’t exist at all (and yet still write about it in an essay rather than a narrative)

27. To practice drafting

28. To practice finishing

29. To practice ideating (something to write about)

30. To practice tone (is this advice? a defence? a moral tale?)

31. To see how far one can go before it isn’t an essay anymore

32. To find the boundaries between essay as form and essay as function

33. To build some track record

34. To escape a genre that may be dominating one’s time

35. To say (or figure out) what you mean

36. To say (or figure out) something you definitely don’t mean

37. To try on someone else’ clothes

38. As a meditative exercise (e.g. a freewritten essay)

39. Because you have to (perhaps you are at uni)

40. To let off some steam

41. To get it right

42. To see where you went wrong

43. To see what is in the space between one’s own way of thinking, and that of another

44. To practice reacting (read in the presence of a writing implement)

45. To put something technical in accessible language

46. To find the technicality in something simple

47. To practice grammar

48. To write ungrammatically (yet correctly)

49. To try out different perspectives

50. To finish something in one sitting

51. To converse with the page

52. To practice brevity

53. To practice verbosity

54. To practice making an argument

55. To learn about imperfection

56. To develop an early idea

57. To extend an old idea

58. To make something out of nothing

59. To reduce something

60. To write a story on the sneaky

61. To defend something

62. To attack something

63. To sidestep something

64. To try writing with different media (pen and paper, computer, etc.)

65. To have made something today

66. To experience different places (writing in a cafe is not the same as writing in the dark watching a movie, or listening to a radio playing quietly in the background)

71. To see where words run out

72. To attempt a version that doesn’t involve words

73. To practice a language

74. To ask ‘what if?’

75. To document something

76. To remember something (or perhaps, someone)

77. Perhaps you have nothing better to be doing

78. Procrastination

79. To use up that spare paper

80. To write with that nice pen you were gifted

81. To find an excuse to visit somewhere (perhaps you wish to write in the quiet corner of a gallery)

82. To get some peace

83. Because one feels obliged

84. To pay the bills

85. To practice dealing with frustration and disappointment

86. To practice dealing with fulfilment

87. To escape another genre

88. To practice calligraphy (or perhaps, touch typing)

89. To enter a competition

90. To practice drafting

91. To be generous

92. To be selfish

93. To open up

94. To shut down

95. To make a good thing

96. To make a bad thing

97. To polarise

98. To unify

99. For the right reasons

100. For the wrong reasons

---

Later, I asked ChatGPT the same question. Enthusiastically (and with a preference for full-stops I do not share) it said:

Certainly! Writing an essay can be a beneficial and rewarding experience for various reasons. Here are 100 reasons to write an essay:

1. To explore a topic of personal interest.

2. To share knowledge and expertise.

3. To improve critical thinking skills.

4. To enhance research abilities.

5. To practice effective communication.

6. To develop a persuasive argument.

7. To inspire others with your ideas.

8. To express creativity and originality.

9. To challenge yourself intellectually.

10. To strengthen your writing skills.

11. To gain insights into complex issues.

12. To foster empathy and understanding.

13. To engage in self-reflection.

14. To contribute to academic discourse.

15. To clarify your thoughts and ideas.

16. To document historical events.

17. To analyse and interpret data.

18. To advocate for a cause you believe in.

19. To present a unique perspective.

20. To improve your vocabulary.

21. To organise your thoughts more effectively.

22. To impress and educate others.

23. To inspire positive change in society.

24. To promote critical analysis of a subject.

25. To participate in academic competitions.

26. To fulfil an educational requirement.

27. To demonstrate your expertise on a topic.

28. To create a record of your personal growth.

29. To share personal experiences and insights.

30. To contribute to a broader academic community.

31. To engage in intellectual discourse with others.

32. To showcase your writing prowess.

33. To present a well-structured argument.

34. To learn about different cultures and perspectives.

35. To impress potential employers or admissions officers.

36. To explore the nuances of a controversial topic.

37. To inspire others to take action.

38. To highlight the importance of a specific issue.

39. To engage in peer review and feedback.

40. To improve your problem-solving abilities.

41. To contribute to scientific research.

42. To share your passion with others.

43. To promote creativity and innovative thinking.

44. To inspire future generations of writers.

45. To participate in a writing challenge or competition.

46. To develop a deeper understanding of a subject.

47. To become a more effective communicator.

48. To contribute to public policy discussions.

49. To gain a sense of accomplishment.

50. To stimulate your intellect and curiosity.

51. To learn from the perspectives of others.

52. To leave a legacy of your thoughts and ideas.

53. To develop your analytical skills.

54. To inspire others to pursue their passions.

55. To contribute to the body of knowledge on a subject.

56. To engage in interdisciplinary learning.

57. To become a better reader by analysing texts.

58. To participate in academic research.

59. To promote open dialogue and discussion.

60. To prepare for future academic pursuits.

61. To influence public opinion on an issue.

62. To communicate complex ideas concisely.

63. To foster a deeper appreciation for a topic.

64. To develop a sense of discipline and commitment.

65. To challenge conventional wisdom.

66. To inspire critical thinking in others.

67. To encourage debate and discourse.

68. To showcase your ability to synthesise information.

69. To develop a better understanding of human behaviour.

70. To contribute to the advancement of knowledge.

71. To learn about the interconnectedness of different fields.

72. To build your professional reputation.

73. To improve your problem-solving skills.

74. To demonstrate your intellectual prowess.

75. To encourage introspection and self-awareness.

76. To enhance your persuasive writing abilities.

77. To promote empathy and compassion.

78. To express gratitude or admiration for someone.

79. To practice effective time management.

80. To inspire others to pursue lifelong learning.

81. To challenge yourself to achieve a goal.

82. To improve your ability to think critically and analytically.

83. To create a meaningful impact on others.

84. To engage in intellectual debates with peers.

85. To gain a sense of purpose and fulfilment.

86. To contribute to the cultural heritage of society.

87. To document and analyse historical events.

88. To inspire positive change in the world.

89. To showcase your academic achievements.

90. To connect with like-minded individuals.

91. To gain recognition for your ideas and insights.

92. To improve your academic and professional prospects.

93. To participate in intellectual discussions.

94. To educate others on a specific subject.

95. To leave a mark on future generations.

96. To build confidence in your writing abilities.

97. To explore the impact of technology on society.

98. To advocate for social justice and equality.

99. To inspire curiosity and a thirst for knowledge.

100. To become a more informed and engaged citizen.

Remember, writing an essay can be an incredibly valuable and fulfilling experience, and it allows you to contribute your voice to the world. Whether for personal growth, academic pursuits, or societal impact, the act of writing has numerous benefits that can positively influence both the writer and the reader.

Several weeks ago I started building a semi-virtual persona for my ideal assistant—I’ve given them an email address, some space in my calendar, and even named them Matt.

For the last couple of years I’ve wondered what it would be like to hire a PA—would it actually be a novel addition to my ‘team’ (of one), or an inefficient time-sink?

To try and understand how Matt might help, I’ve started allocating them tasks via email. Whenever something comes up that it would be convenient for me to have someone else do, I write a note to Matt as if I were addressing someone who doesn’t have the knowledge of the situation that I do.

Later, I set a timer on my phone and spend some time acting as Matt.

How it works

Concretely, I work through the pile of things that have landed in the inbox, completing what I can. It’s proven quite satisfying to have a ready-made list of easy wins (e.g., ‘order earplugs’), especially during brain-foggy parts of the day.

Things get a bit more interesting when Matt comes up against something that less well-defined, especially where the action needed requires something more complex from me. A good example that I tried out early on would be a directive like ‘please sort my inbox’. Matt can go a certain distance with this (e.g., clearing out spammy things, generic newsletters, etc.), but there’s a certain amount of mail I need to deal with myself.

This becomes a useful situation (rather than a dead end) when Matt has the wherewithal to write a constructive reply to the request (which lands in my usual inbox). Usually they are seeking further information, or indicating an aspect of the task that relies on my knowledge of a situation.

I think this simulated dialogue might actually be the most useful part of the whole experiment—a lot can get clarified in an actual back and forth between two participants (especially if empathy is part of the simulation!).

It’s a bit weird for sure, but expressing things for another reader is a good strategy for breaking down those seemingly simple tasks (e.g. answer that email… you know the one) that are incurring a lot of resistance.

Key takeaway

An important understanding is that I don’t need to provide Matt with a perfectly clear prompt. Of course, I try to do that (like any good employer of an assistant would), but some requests are, invariably, a bit too fuzzy.

I suspect that trying to get things right on the first go would probably be a waste of time; better to chase the flow that comes with iterating.

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