The Problem with AI Writing

~ Sasha ~ Leave a comment

“Writing and reading is a way of underscoring that human connection is important. That you can know my mind and I can know your mind — which is a vastly consoling idea…So may times in my life, I felt a more articulate version of myself emerge after a period of writing. And when that happens, the world changes.”

– George Saunders, author of 13 books and a recipient of the National Book Foundation’s medal for Distinguished Contribution to American Letters

George Saunders, author of Lincon in the Bardo and many other works, is an acclaimed author and essayist who has also been called “the ultimate teacher of kindness and of craft.”

I’ve been casting about for an explanation of what’s worrying me when I read more and more AI-generated content. Saunders’ explanation—you can listen the whole conversation here—gets to the heart of the matter.

The question is: what is writing, really? And Saunders’ answer is anchored in the idea of two people knowing each others’ minds, and the beauty in that connection.

That’s the thing that’s tripping me up with all the AI-generated writing, a doubly confusing experience I’m also finding my own AI helper(s) to be radically useful: as brainstorming partners, as “I think this thing isn’t quite right, but I’m not sure how to make it better,” as a project planners… but very rarely as a writer, and never as a writer of this blog.

Like George Saunders, I’m writing for two reasons: to figure something out (a sharpening of my understanding that comes from sitting with and articulating an idea), and to personally connect with readers.

And something breaks when I’m not the person writing the words, and when I’m reading words not written by a person.

I’m sure you’re having this experience as often as I am: working your way through an article or an email or some other document, and you come across a sentence or a phrase that is so stylistically ChatGPT that you stop…and in that moment, feel a strong sense of disconnection.

For example, I was reading this interesting post about searching job listings and pay rates to understand what skills AI firms are paying for to feed their models (answer: “the bottleneck for AI is no longer information (facts); it is expert reasoning (process).) While the research and the conclusions in the article are interesting, the writing is so clearly authored by ChatGPT that I quickly disengaged.

The reason for that disengagement Saunders’ severing of human connection.

It’s as if there’s an implicit equation that I’m carrying around in my head, something about balancing:

The author’s effort in getting the words just right =  My effort as a reader to sit with and deeply understand what the author is saying.

Because when the author cares enough to toil over every word, that means that they are carrying around an idea that matters deeply to them.

If the author truly cared, if the author takes the work personally, then I do too.

(aside: if I’m reading something equivalent to a textbook. If I just am acquiring knowledge or skills, I’m fine with the computer writing most of that text).

Whereas, if my effort in deciphering a 1,000 word post is greater than what it took the author to create it…something feels fundamentally off. I feel like I’m being had, that that essay is part of the mountain of words generated by a computer model that doesn’t mean much, really, to the person who “wrote” it.

What’s curious is that the models will get better and this moment will pass. What happens when it’s impossible to tell the difference?

I don’t know how to answer that with confidence, but I’ll stand by my view that I’m reading because I want to see through a window into the mind of another person—whether it’s fiction or nonfiction, analysis or some fantastical world.

The intent and the human behind the words are the reason writing comes alive. It isn’t just words on a page, it is the effort, struggle and care of one person opening up their mind and heart. That’s why I’ve rewritten this post four times in 12 hours 🙂

We write what we believe, what we care about, what we’ve thought about, and then we share that with others. The connection is personal, the words are the medium.

The moment that connection is severed, I find it much harder to show up as a reader with my full attention.

Fast, Intentional, and Grounded

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I keep on thinking about the question Abby posed last week: how do we move quickly without rushing?

The dilemma, and the assumptions behind it, can be illustrated like this:

We all know the Fast and Rushing quadrant well.

It’s a version of “OMG I have SO much homework…” “No I have SO MUCH HOMEWORK!” that surfaced sometime in school. Busy becomes a way of life, and we get hooked on the buzzing tension. That rushing, frantic feeling can accompany getting a lot done. But often, we start to unconsciously equate fast with frenzy, and it’s no surprise that we often end up at a breaking point.

Ironically, it’s also possible to take that same energy into the “slow” quadrant: fear takes hold of us, and we cannot face reality. The tasks we are able to  accomplish pale in comparison to everything that needs to be done, so we do less. Yet we still find ourselves expending a tremendous amount of energy on worry and fear. We are paralyzed.

That, to me, is the main difference between the top and bottom half of this graph: not the amount we get done, but the amount of mental energy we spend cycling through worry.

We know how it feels to end up in this place: no matter how much we accomplished, it’s feels impossible to truly stop at the end of the day.

We can’t stop our minds from churning even when we’ve closed the laptop.

We’ve gotten on such a stimulation high—maybe, even, from crushing it all day—that we spend the rest of the night stimulating ourselves more, scrolling or finding other ways to get a dopamine hit.

As our brains gets used to this pattern, the pattern itself strengthens. We get to a point where, thanks to long stretches (months, years) of both moving fast and being frenzied, we assume that “fast” and “frenzied” are inseparable.

Think, for a moment, what fast and intentional looks like: maybe a professional athlete, or an animal in the wild that knows exactly where it’s heading.

There’s an efficiency of movement, a calm focus, no wasted energy, and a power that comes from a lethal combination of relaxation, clarity, and aggression.

“How much we do” and “how we do what we do” move on independent axes.

To be clear, I’m as likely as the next person to get caught up in worry, in unproductive cycling through “what if’s,” of a sense that if I slow down for even 20 minutes to sit and really think about something that I’ll have fallen behind.

But that mode makes me neither more effective nor happier, so I’m trying to observe it to see if I can let it go.

When I come up short, bouts of intense exercise and moments of unbridled laughter and joy with loved ones are a great way to reset.

How to Move Quickly in 2026

~ Sasha ~ 1 Comment

My 2026 started with a blanket of snow: six inches of unexpected, fresh powder in the Vermont mountains.

I was there on a surprise 3-day snowboarding trip with my 14-year-old daughter. We braved single-digit (F) temperatures, ignoring the impacts of an ice storm that had blanketed (read: ruined) the mountain just a few days prior.

The half a foot of snow was dumb luck—a ‘dusting’ was expected—and it was amazing.

We were on the first lift at 8:01am, in 5 degree weather, and had the most perfect four hours to start off 2026.

2025 was not an easy year for so many of us. So many things that we took for granted shifted or disappeared, and I, at least, spent a tremendous amount of energy fighting to stand still.

The good news is: we are here today, stronger for what we have endured, and more confident in our resilience for having made it through 2025.

The snow that started this year is a fresh, clean, undisturbed canvas.

It’s not a canvas that lasts forever. And, yes, that sheet of hard, unforgiving ice might be just below the surface.

But we can allow ourselves the space to start again, and we can believe in the possibility of renewal and new possibility.

My friend Abby Falik writes a newsletter called Taking Flight. In her most recent post, she poses the question:

Sometimes, when I’m running late, I play an inner game: Can I move quickly without rushing?  The grip loosens. Breath returns. A possibility cracks open and I’m more likely to arrive present.

I have no illusion of approaching 2026 in low gear, no pretense that it won’t be challenging and intense.

Rather than hiding from that, my goal is to pull strength from the knowledge of what I achieved in 2025—despite all the challenges—coupled with a commitment, thanks to Abby’s nudge, to move quickly without rushing.

I remind myself: the speed and quantity of what I do can be high without the frenzy that comes from rushing. I can be fast and thoughtful, speedy and intentional, and grounded throughout.

So can you.

Happy 2026.

Quality is Non-Linear

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Imagine a scale for “quality” that goes from 0 to 100, where quality is “anything that makes something good or special.”

As a novice, I look at that scale and trick myself into thinking it is linear: the difference between what it takes to be able to produce a quality of 40 vs a 30 might be the same as the difference between what it takes to go from 90 to 100.

As in: when I started played guitar, I couldn’t reliably pluck the string I wanted to, let alone do it rhythmically.  (0 to 10)

Then, I could find the string most of the time, but I only plucked down, not up and down. (10 to 20).

Now that I can do that well, and now that I’ve mastered ten other plucking skills, I’ve been told that my picking technique has too much wrist, I’m holding my pick perpendicular to the string when it should be at a slight angle, I should be executing a relaxed figure 8 pattern over each string….all this just my first year of lessons. Imagine what next year will hold!

The expert knows that, as we make progress, we learn about nuance and details that were previously invisible.

This is why quality is not linear, it is logarithmic: the closer we get to “great” the more skill, will, and effort it takes to improve a little bit more.

This means that the move from 40 to 41 could take as much time and effort as getting from 0 to 10: because improvement at the beginning was relatively easy, it was the work of going from terrible to OK, and maybe all the way to decent.

But good to really good? Really good to great? Great to exceptional? Exceptional to best in class?

Each of those is a full journey: being open to the idea that better exists; taking the time to understand what it entails; building that new skill on top of your already-strong foundation; having the attention and patience to master the next micro-skill and the one after that.

This is why greatness is both expensive and rare. It’s why, at the 3-star Michelin restaurant Sukiyabashi Jiro, apprentices, who train for 10 years, aren’t allowed to touch the fish for the first few years. The same goes for expert watchmakers, knifemakers, and makers of F1 racecars.

If we’ve had the patience and discipline to develop mastery of any skill in any domain, we understand this intuitively, because we’ve walked that path. We just need to retain the humility to see that each new journey, each new skill, will have as much depth and nuance as the skill we’ve already mastered.

And if we work with people who haven’t yet developed mastery—of other skills or these skills—it can be difficult to communicate clearly about “the distance from here (where you are) to there (where you’d like to be).”

As in: we’ve all met the bright-eyed newbie who “wants to do strategy” as if that’s something that is 6 months away and just requires “good analytical skills”—when the reality is that good strategic decision-making is the accumulation of years analyzing, thinking, putting yourself on the hook, making the tough call, being right or wrong, living with the consequences, and doing it all over again.

The job of the expert, then, is to cultivate curiosity in the novice, to point out all the progress he’s made, and, also, to show, with patience and a commitment to detail, the difference between “90% there” and “100% there.”

And the job of the novice is to have the humility to say “I got to this point quickly, it’s possible that I don’t fully understand what it takes to be great, but I’m willing to keep being curious and keep on putting in the work.”

 

What Are We More Afraid to Miss?

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Which scares us more:

  • Missing something, or
  • Not devoting enough time to the important things.

To explore this question, here’s a short parable of modern work life: how I manage my Inbox.

Starting 15 years ago, I established my current approach to my Inbox. It is based on the philosophy that there are two kinds of emails:

  1. Ones I need to act on
  2. Ones I don’t need to act on

The approach is brutally simple:

  1. The first group is unread
  2. The second is read.

No filing of any kind. Search works great. Zero inbox is meaningless; zero unreads is not. Voila!

This approach, plus ruthless use of the “mark as spam / block sender” functionality in my Gmail interface, has served me well for years.

Last week, for the first time in ages, I decided I needed to adjust my system.

I think it’s because of an explosion of workflow-related emails: Calendar updates, Calendly updates, Zoom meeting updates, Docusign updates, Box updates, AI recording updates, etc.

Combine this with the general flotsam of subscriptions of varying degrees of usefulness, and the ratio of must read:optional to read emails in my Inbox had gotten out of whack.

My solution to this is that I caved in to using filters in Gmail (I’m sure there are many better solutions (Superhuman, etc.).

What’s interesting is the experience of setting up those filters: it’s the task of taking every nonessential but interesting email and putting it somewhere other than my Inbox—the only part of my email world that I’ve looked at consistently for more than a decade.

The feeling is the same one I have when there’s an “internal meeting I could join but maybe don’t have to join.” You know the one: the content is important, you will probably learn something and maybe will make the meeting a little better. But do you absolutely need to be there?

The same goes for the Slack channel that’s been there forever that I rarely read; the client call that might be helpful to join even though someone else is running the meeting; the conference that I always attend, even though I can’t show concrete business results.

Most of us feel short on time—including time to be unproductive. We ache for open space, time to be generative, time to do the things that matter most… “once all this stuff is out of the way.” We tell ourselves that there’s no real way to create this kind of space.

One way to explore if this is true is to experience the fear of missing something: that essential email, that meeting where a wrong decision gets made, that photo op at the conference….

Perhaps that fear is justified, and the consequences would be significant.. Maybe success is defined by you getting to everything right on time; you being present to optimize each and every decision; you seeing all the edge cases and fixing them immediately. That might be what we need most from you.

Or it might be that there’s more resilience in the system than you expect.

That the cost of tracking and sifting through everything is real.

That setting a different bar for “what requires me” would create such a seismic, structural shift in your days and your weeks that it would be a little bit, or even a lot, disorienting.

This is what the sixth stage of Kevin Kelly is all about: “finding those things to which you are uniquely suited, and doing only those things.”

Not the places you can add value, not the things you are best at. The things that only you can do.

It’s a really high bar, and it cuts against the culture in most organizations.

It’s also worth exploring.

Podcast Alert: Patrick Thean

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Patrick is an author, CEO coach and mentor, and I was happy to get the chance to join his podcast recently. Our discussion covered topics that will be familiar to readers of this blog and, as always, I discovered that talking about a topic helps me understand the topic better.

If I had to summarize my reflections from the conversation, they are:

  1. How we do anything is how we do everything
  2. One way to learn how we do anything is by digging into new domains we are exploring

What follows is a conversation that starts with 60 Decibels,  my motivation for doing work in the social sector and my Generosity Experiment; but quickly turns to learning to play the guitar, my favorite AI use cases, and the attitude Patrick and I would suggest towards getting over your lingering AI resistance.

You can listen to the full podcast here (20 mins):

• Apple: https://bit.ly/3GB5W0P
• iHeart Radio: https://bit.ly/40eTeLU
• Spotify: https://bit.ly/4lqkhfM

The Road Runner

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My son, who has been lifting weights regularly, has a 12 week cycle. 12 weeks of doing the same exercises in the same order before you switch.

He told me that there’s some science that says that the first 8 weeks of improvements are just your body getting used to doing these movements— muscles firing more in conjunction, tendons adjusting —and meaningful change in strength at the level of muscle fibers only happens in the last 4 weeks.

It’s a useful metaphor for all changes: the first steps in the process are just getting used to doing the new thing. I don’t need to be stronger or faster to improve, I just need to spend regular time in the activity, and all my existing abilities will come together more effectively to produce a better output.

So if I’m trying to run more, I just need to run more, even if that’s a tiny bit every day. The every day is what matters the most, much more than effort or time or the perfect coaching.

Consistency –> New habits –> Reordering of our internal systems –> Improvement

The amount of “improving” we need to do is less than we think and easier to achieve than it appears.

We just have to remember to form new habits, and it all starts with the mantra:

That thing that’s terribly hard for me today will be easier for me tomorrow if I just do it today. 

Thin slice your skills, and your story

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Last weekend, we visited my daughter at college. She’s a first-year student, and is running on her school’s cross-country team. On Sunday, parents and siblings were invited to join the team for their long run (typically 10-15+ miles).

Clearly this is an invitation one should decline!  Which might explain why exactly three parents (myself included), plus two younger sisters (including my youngest daughter) showed up in the pitch black at a woodsy parking lot at 7:25am on a Sunday morning.

None of our group of five had illusions of keeping up with the XC team. But it appeared that I was the only one in our small group who had not been running regularly.

One of the parents, a regular marathoner, popped out of her car and announced, “We agreed we’re running 8 miles at an 8:30 pace.” I knew I was way out of my depth. The four of them (including the 13 and 14 year old) did, in fact, run 8 miles at an 8:20 pace. I, working very hard, managed half that distance at a slower pace.

As I finished the run, it was tough not to compare myself with everyone who ran further and faster than I did, and tougher still not to tell myself a story about my fitness.

“I’m just not in the kind of shape I used to be in.”

A few days later, I came across a video of a running coach giving a scientific explanation of the value of Zone 2 (comfortable pace) running.

The gist of it is: your heart, your circulatory system, and the energy transfer system that gets oxygen to the mitochondria in your cells all improve dramatically when you run at 60% pace. Specifically, the mitochondria, which convert oxygen to energy, get more efficient at that process; they even move closer to the surface of the cell (!!) if you’re running consistently.

Something about that explanation clicked for me. I’ve not been running, so I’ve not being doing the exact activity he said helps with oxygen transfer, so I don’t do that efficiently. That led to a much more specific, useful story:

“Having not run regularly over the last 10 months, my body is less used to converting oxygen to energy, and my mitochondria aren’t hovering around the surface of my cells to create maximum efficiency.”

That feels a lot less damning, and a lot less existential, than “I’m just not in the kind of shape I used to be in.”

The difference is important, because the “what kind of shape am I in?” story is personal, it’s big, and it might have some staying power in terms of how I see myself, the choices I make about health and fitness, etc.

Whereas the more specific analysis leads to very different conclusions about what is or isn’t going on with my mitochondria and the specific actions I could take to change that. This narrow story doesn’t ladder up to a mess of inaccurate meaning. It doesn’t entice me with a woeful tale of the long, declining path I’m on.

I just haven’t been running, and if I were to run more, I’d get better at running.

What I’m doing here is thin-slicing my story. Visualize it like this, with the highlighted part describing the story I’m telling myself.

I could just say “I’m just not in the kind of shape I used to be in.” That kind of story looks like this.

And this is a story at the level of identity, one that’s much bigger and much more personal than what actually happened.

Whereas a story that starts with “Having not run regularly over the last 10 months, my body is less used to converting oxygen to energy…” looks a lot more like this.

This story, focused on specific skills and aptitudes, stays at that level. I can decide that developing those skills is (or is not) something I want to invest in. But that whole conversation is very contained, and it runs little / no risk of taking on a life of its own.

You can apply this thinking in a million situations, as in:

I just got rejected on this sales call, again.

  • I’m a terrible salesperson OR
  • I’m not calling the right people / not identifying a need correctly / not asking the right questions

A teammate didn’t help me when I asked for help.

  • They don’t like me or care about my success OR
  • What’s going on in their day? / Did I make it super clear what needed to happen by when? / Did I express both the what and the why behind my request?

My boss is mad that there was a mistake in the materials we presented to the client.

  • I’m a total screw up, I’ll never succeed in this job OR
  • I need to create a system where I give myself a 24-hour break before doing a last review of client-ready materials

Thick-sliced stories about our identity keep us stuck. They are the antithesis of a growth mindset, because “I” (our ego) is always at the center of these stories.

Thin-sliced stories, fed by thin-sliced skills, are both more accurate and more useful. They highlight what’s really going on and where we can focus our energy. With a thin-sliced story, a shortfall, a misstep, or a slow run is just what it is, nothing more, nothing less…and certainly not a verdict about you as a person.

I Bought This Tesla Before I Knew…

~ Sasha ~ 2 Comments

At this point, you’ll have seen or heard about this bumper sticker.

This flavor of virtue-signaling is particularly ham-fisted, but it’s also an example of something that happens all the time.

What interests me about this is the ways in which our likelihood to act is impacted by our internal narrative.

“I bought this before Elon went crazy” communicates, presumably, some sort of solidarity along the lines of, “Just so you know, I’m not in favor of the authoritarian tendencies, the dehumanizing of people, the willingness to pull billions of dollars of life-saving spending on a whim. I’m a good person just like you.”

That last sentence is likely true, but the much more accurate sentence is, “While I’m sickened by what’s going on, that unease is less important to me than the inconvenience of selling my $80,000 car to buy another $80,000 car.”

And that’s really the rub: we plaster the sticker on the car, and it serves as a release valve, in the form of saving us from an uglier story about ourselves than the one we’d like to believe.

We repeat this pattern in hundreds of smaller ways. It shows up every time we talk about something being broken without putting ourselves on the hook to fix the broken thing.

“Coming into the office more doesn’t make sense because we just take our calls from the office instead of from home. No one takes advantage of the in-person time.”

“I would love to advance in this company, but I can’t because I never get any feedback.”

“People on my team don’t take responsibility for their actions. There’s no follow-through.”

“My kids are addicted to their phones; it’s impossible to get their attention.”

“The culture around here doesn’t make people feel valued for their unique contributions.”

“I just can’t get this build right because the user requirements aren’t clear.”

“Morale just isn’t what it used to be. People aren’t feeling a sense of connection.”

“We’re just not taking advantage of all that AI has to offer. Everyone is being so timid.”

When we articulate a concern about the current state of affairs, we might be doing one of a few overlapping things:

  1. Group creation: by signaling that I see the world the way you do, I create solidarity with you
  2. Narrative to self: by naming something I dislike, I maintain my self-image as someone who doesn’t support that negative thing
  3. Venting: getting something off our chest so we can get ourselves unstuck
  4. Persuasion: attempting to convince others that something is not the way it should be (ideally to enlist them to make change)
  5. Exploration: engaging in dialogue to figure out more clearly what’s going on that needs to be fixed
  6. Enlisting authority: we inform someone with greater ability than ours about a problem that we’d like them to address

And while it’s true that all of these actions can be done with more or less intention to act, typically the first three decrease pressure to act (because they are focused on internal / shared narrative) and the second three increase pressure to act.

For example, our favorite bumper sticker:

  • Group creation: identifies us (to ourselves, others) as anti-Musk
  • Narrative to self: “I’m a Tesla person with an anti-Musk bumper sticker. That’s a little less uncomfortable.”
  • Pressure to act: goes down, because I feel like less of a jerk

Because what’s at play is:

  • The amount of discomfort the “bad” thing creates for us (Musk = bad; Tesla = Musk; therefore Tesla = bad)
  • The amount of discomfort we think action would create for us

Anything that decreases our discomfort, by definition, decreases the likelihood that we’ll take action.

The subtlety we discussed last week is that good diagnosis can decrease discomfort (“I figured something out!”), so it runs the risk of decreasing pressure to act.

And, remember, powerlessness is not a viable excuse because we all have some agency. Our problem is that agency involves inconvenience, discomfort, or personal / professional risk, and none of those is particularly pleasant.

Here’s an easy way to see what’s going on: for every observation we make, let’s add an action in the form of an “I” statement. As in:

“Coming into the office more doesn’t make sense because all we do is take our calls from the office instead of from home…and I’m planning to take forward a proposal to create a scheduled lunch hour for everyone twice a week.”

“I would love to advance in this company, but I can’t because I never get any feedback. I’m terrified, but I’m going to ask my boss for detailed feedback in our next 1:1.”

“People on my team just don’t take responsibility for their actions.  There’s no follow-through. I’m going to start a shared accountability chart and put my name and weekly To Do’s at the top of the list, and ask others to also fill it out each week.”

“My kids are addicted to their phones; it’s impossible to get their attention. We’re banning phones at mealtime and starting a ‘all phones in the kitchen drawer starting at 9pm’ house rule. These rules also apply to grown-ups.”

“The culture around here doesn’t make people feel valued for their unique contributions. I’m initiating a 10 minute ‘amazingness hack-a-thon’ each Friday where our team shares at least 1 amazing thing each team member did this week in or outside of work.”

“I just can’t get this build right because the user requirements aren’t clear. I’m locking the Product Manager, the subject matter expert, and my engineering lead in a room for 2 hours and we’re going to leave with 100% clarity on the spec.”

“Morale just isn’t what it used to be. People aren’t feeling a sense of connection. I’m going to schedule one 15 minute virtual coffee a week with a colleague, and I’ll come in with three questions that ensure I have a chance to learn more about them and their work.”

“We’re just not taking advantage of all that AI has to offer. Everyone is being so timid. I’m going to invite 10 people to a 2 hour after-work AI hackathon where we come up with 10 ideas that could move the needle, and we will start working on them.”

We can chuckle at the guy with the bumper sticker, but we’re all wearing bumper stickers of one kind or another.

The most dangerous one is the one that says, “I’m so good at figuring out what needs to be fixed that I’m able to stay completely in my comfort zone.”

All meaningful change involves some degree of discomfort and risk. How much is up to you.

What to Wear in the Rain

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If it’s pouring rain out, and you’re heading for a walk, you have two good options.

A completely waterproof boot, one that will keep your foot totally dry.

OR

A flip flop, one that will allow your foot to get soaking wet, but you don’t care, because it’s your foot and it’s a flip flop.

Meaning, when your external environment changes radically, there are only two smart ways to react: you either decide you use the tools you have to fight it head on and win, or you choose to fully embrace the new reality.

Unfortunately, all too often we opt instead for a soggy shoe, soggy sock strategy, one that leaves us squishy and uncomfortable because we planned poorly and didn’t fully acknowledge that our world has shifted.

(and, no, this post isn’t only about AI).