Tag: writing

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.

Is “Polished” Writing a Good Thing?

~ Sasha ~ Leave a comment

How we communicate evolves with time and with the medium.

I write my texts (mostly) like I write my emails, resulting in my kids repeatedly telling me that it sounds “aggressive” when I put a period at the end of a text message.

(They also want me to use exclamation points much much more! LOL)

While I’m comfortable with the idea of tone and style evolving over time and in different contexts, I’m uncomfortable with what happens when we no longer need to struggle with a blank page. I’m skeptical that it’s a good thing that Gmail is now offering to “polish” my posts and that LinkedIn suggests “rewrite with AI” every time I string a few words together.

Clear writing and clear thinking co-evolve: I don’t know anyone who writes well who doesn’t think well; and how we express our thoughts in written form is a great way to reveal whether our thinking is as clear as it needs to be. I also know that convenience will win out—why wouldn’t it?—and that the cost of all of this convenience will be mostly invisible.

It’s already established that AI is most useful when you have subject matter expertise, so you can tell the difference between good and bad, and use these tools as leverage for your strengths.

How do we avoid systematically undertraining ourselves as strong writers and strong thinkers, to use the tools without having them replace an activity that sharpens our mind?


 

Charles Darwin on Why We Write

~ Sasha ~ 1 Comment

I came across this via Austin Kleon, quoting Charles Darwin (emphasis added):

“Let the collector’s motto be, ‘Trust nothing to the memory;’ for the memory becomes a fickle guardian when one interesting object is succeeded by another still more interesting.”

And:

[A naturalist] ought to acquire the habit of writing very copious notes, not all for publication, but as a guide for himself. He ought to remember Bacon’s aphorism, that reading maketh a full man, conference a ready man, and writing an exact man; and no follower of science has greater need of taking precautions to attain accuracy; for the imagination is apt to run riot when dealing with masses of vast dimensions and with time during almost infinity.

We write for many reasons, but the most important is to capture and crystalize our half-formed thoughts while they happened, because those seeds of insights are fleeting; and because the act of writing, over time, sharpens both our writing and thinking.

I’m constantly amazed to find that a few jotted notes can transform into some of my most impactful business ideas or blog posts.

And, despite this, I can easily trick myself into thinking that all the important stuff is “in my head” at the times that I don’t bother to write things down.

I know not everyone is going to write a blog.

I’d still encourage you to find a way to regularly capture your half-formed ideas, and to take the extra step of developing them into something—you decide what.

Inevitably, you’ll become a better observer.

And there’s nothing better than stumbling across an old thought you had and turning into something crisp, clear, and helpful.

I Get a Cookie

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It turns out that Jerry Seinfeld has a 24 hour rule.

Whenever he writes any new material, his rule is not to show it to anyone for 24 hours.

The rationale is that writing is a brave, creative act. We humans need and deserve positive reinforcement every time we engage in that act of bravery.

Part of the way we preserve that is by shielding anything new we’ve created from others’ eyes. This allows us to experience the halo of “I did it” before experiencing the crush of “maybe it’s not any good.”

In fact, Jerry advises that when we do a brave act of creation, we should give ourselves a (metaphorical or actual) cookie.

Time and again, I find myself skipping this congratulatory step, the one in which I get to bask, for just a moment, in the knowledge that I was brave today, that I created something new.

Instead, I nearly always ship off that new thing to someone for their quick reaction and feedback (time’s a-wastin’). Or, just as bad, I finish my first draft, put down my pen, and notice how much time that took and all the other undone things on my to do list.

One solution that helps me is having time in my calendar for “brave work:” empty spaces that are only for creating new things. This way I know what that time is for, and I cannot beat myself up for other tasks that remain undone. This also helps me remember that brave acts of creation and efficient time management exist on different axes.

Finally, I remind myself of the advice of one of my favorite yoga teachers: we can leave our problems and our worries outside of the studio door, because we can be sure that they’ll be there waiting for us when our practice is done.

So, maybe it’s time to resolve that our best work should be free from prying, critical eyes for a day.

Without knowing there’s some psychic reward waiting for us on the other side, why will we ever dare to take the plunge?

The Paradox of Discipline, and Four Questions to Ask Ourselves

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The more I listen to interviews with great creators, the more they echo the same themes. It goes something like this:

The act of creation is exceptionally hard and painful.

Writing, in particular, is torture.

It’s great to have talent, but without a disciplined process for creation, talent means nothing.

We human beings do everything we can to avoid the hard work of creating our art. To counteract this, we must create rituals and structures that make it impossible for us to hide: time every day in which the only thing we can do is produce. (For example, per Neil Gaiman, “I would go down to my lovely little gazebo at the bottom of the garden, sit down, and I’m absolutely allowed not to do anything. I’m allowed to sit at my desk, I’m allowed to stare out at the world, I’m allowed to do anything I like, as long as it isn’t anything. Not allowed to do a crossword, not allowed to read a book, not allowed to phone a friend, not allowed to make a clay model of something. All I’m allowed to do is absolutely nothing, or write.”)

We must be forgiving with ourselves when we are creating, and brutally tough on ourselves when we are editing and refining.

This isn’t going to be fun. But if we are to do our best work, if we are to give our gifts to the world, we have to be willing to grind out the effort each and every day, no matter how hard it feels and how little we feel like doing it on that particular day.

Now, I believe that these insights apply to everyone, not just to “creative” types. No one said that doing excellent, meaningful work was going to be easy, and I expect that writers and artists are just living the fully-distilled version of creating work that matters.

If these insights are to apply to all of us—and I believe they do—then we have four questions we need to answer honestly:

  1. Am I willing to care, at a personal level, about my work?
  2. Am I willing to take personal, emotional risk to put my best into my work?
  3. Will engaging in this kind of sustained, daily effort help me grow?
  4. Am I going to decide to learn how to put in sustained effort over time?

This framing feels fundamentally different from conversations about “work-life balance” and the perennial elevator small talk of “just three days until the weekend.”

In one view, work is something to be endured and minimized so we can refresh in our free time, and work being hard is an indication of something being wrong.

In another view, work being hard is the necessary precondition for it being meaningful, because there is nothing worth producing that doesn’t require risk and struggle.

While this doesn’t mean that all work we find hard is rewarding, it means that we cannot use “hard” as a barometer for something being wrong at work.

Somewhere, somehow, each of us has to find our own version of discipline.

For example, I don’t have access to Neil Gaiman’s gazebo, nor do I write fantastical fiction or comics. But both Neil and I need time alone, time to think, time with the proverbial blank page; time when we’re looking straight at a problem we don’t know the answer to; time when our job is to sit there until we produce one thing that is one small step in the right direction.

Discipline is often not fun. It is, at a minimum, the act of sitting with discomfort and delaying gratification because we know that this is what it feels like when we do real work.

Of course, most of us have not figured out what our art is, we don’t know what we are uniquely suited to do in the world.

That’s OK. We don’t need the full answer today. We need, instead, to decide to start doing meaningful, personal work as soon as possible.

And how do we start? Not with musing, reflection or pretending that if we wait long enough inspiration will touch us. That’s a great way of hiding.

Instead, we start with building a practice of creative discipline into our days, weeks and lives: we put ourselves in situations every day where we ask ourselves to make one small thing that we are proud of, one small thing that is over and above the exact thing we were asked to do.

With this mindset, our work becomes something we can take personally, and each thing we ship can be different and better for what we’ve put into it.

From the moment we decide to take our work personally, we start to show up like professionals, and, bit by bit, we watch the yield that comes from refusing to be swayed too quickly by the thoughts that all of us have: this is too hard; this might not be good enough; if I care a little less, then I won’t be hurt if I come up short.

Caring less and risking less are great ways to stay safe in the short term, and even better ways to ensure that we stay where we are in the long term.

Whereas if we shift our attitude towards our work and learn how to build discipline into our days, we set ourselves down the harder but much more rewarding path of sharing what only we have to offer through our work.

The Confidence to Cut

~ Sasha ~ 1 Comment

Jerry Seinfeld described the two personas we need to inhabit to be good writers.

The key to writing, to being a good writer, is to treat yourself like a baby, [to be] nurturing and loving, and then switch over to Lou Gossett in Officer and a Gentleman. and just be a harsh [expletive], a ball-busting son of a…When you’re writing, you want to treat your brain like a toddler. It’s just all nurturing and loving and supportiveness. And then when you look at it the next day, you want to be just a hard-ass. And you switch back and forth.

I love it: a gentle nurturer, treating my brain like a toddler, and then a hard-assed drill sergeant who is relentlessly reviewing, looking critically and, most important, cutting.

Most of the time, our writing has too many words. These extra words are a place to hide, an excuse for 80%-there thinking that’s directionally correct but still fuzzy.

The false safety of extra words and high-falutin language is how we avoid laying our ideas bare.

When we cut, our ideas stand naked and exposed to the world. They can be seen clearly, unadorned. The unadorned is bare, but it is also beautiful.

It’s an act of courage to cut away all the unnecessary bits, to stop burying our best thinking in extra blather.

We cut, we cut, we add a bit, and then we cut some more.

On and on until one of two things happens: either we learn that this idea isn’t good enough, or we discover the distilled essence of what we want to say.

Cutting is an act of confidence and bravery. When in doubt, cut.

Orwell on Un-slovenly Thoughts

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In Politics and the English Language, written in 1946, George Orwell mused, “Most people who bother with the matter at all would admit that the English language is in a bad way.”  Imagine if Orwell had been able to see what unfolded over the next 70 years.

You may not consider yourself a ‘writer,’ and it’s possible that writing doesn’t feel integral to your work. Even so, consider this a nudge to invest in your writing—the yields are broader than you might imagine. Writing is not a narrow skill, like juggling or doing a cartwheel. It is a mirror into the mind: we cannot write clearly and persuasively if we are unable to think clearly and persuasively; and as we move the needle on our writing, we sharpen our powers of observation, analysis and storytelling.

Writing with the intention to change minds hones our abilities—to see what’s around us and develop insights about what we see, to understand the worldview of the people whose minds we aim to change, and to communicate in ways that shift thinking and actions.

Begin by choosing to write more. This is much more helpful than choosing to write well. Trying to write well is the best way to end up not writing a lot, and you cannot write well if you’re unwilling to write poorly. This means finding places to write: that could be investing in making your emails 50% better by making them shorter and more human; or you could sign up for a site like 750words.com, a private site where you commit to writing every day, just for you.

Imagine having this kind of transparency and accountability about your writing!

Then, stop writing the way we think we are “supposed to” write. It’s hard to pin down when, exactly, business-speak was created (though the Atlantic has a few theories), but the main function of so much passive tense and invented verbs (“downsize” “rationalize” “incentivize”) and catchphrases (“run up the flagpole”) is to obscure rather than to clarify, making your writing worse.

© Scott Adams

Your job isn’t to “increase the frequency of your articulation of stated arguments and objectives through engagement in writing- and writing-related activities,” your job is to “write more often and be more persuasive.” Please, please, write like you speak. We, your readers, want to read something written by another human being, and we experience human-ness when your voice comes across in the words you put down on paper.

To practice, before you hit the “publish” or “send” button, read what you’ve written, to yourself, out loud. Ask yourself: does this come out naturally? Is this how I speak? If not, cut, edit, and replace: remove words, replace words, say things in 5 words instead of 12. In the end, your writing will sound like your spoken voice: clear, simple, natural. Your goal is to express formed thoughts and emotions in as few and as precise words as possible.

Read more. Pick the kind of reading that speaks to you. The more you read the more good writing becomes part of your world. You may even inadvertently start mimicking authors you like, which is fine as a start: over time, your own voice will come out.

In the end, all of this is an investment not just in your writing but in your clarity of thought. It’s a chance to avoid the pessimistic concerns that Orwell describes as the self-reinforcing loop of poor language:

A man may take to drink because he feels himself to be a failure, and then fail all the more completely because he drinks. It is rather the same thing that is happening to the English language. It becomes ugly and inaccurate because our thoughts are foolish, but the slovenliness of our language makes it easier for us to have foolish thoughts.

As we give attention to our writing, we rescue ourselves from our own “foolish” thoughts. Over time, we clarify our own thinking, increase our capacity to persuade, and develop the skill of taking unstructured observations and turning them into clear, structured, persuasive words on the page.

Where do Blog Posts Come From?

~ Sasha ~ 1 Comment

I’m always curious how others come up with blog post, so I figured I’d share my approach after 11 years of blogging.

Being a writer of any sort means paying attention, and blogging has kept me on a constant, quiet lookout for moments of insight: a topic I find myself or my team struggling through, a conversation or article that touches on a bigger theme.

These sorts of moments happen unpredictably in all sorts of places. When they do, I jot them down. If I’m in front of my laptop, I’ll write a headline or a few sentences in Word. More likely, I use my phone to send myself a short email with the blog title in the subject line and a few notes. These emails are sketchy at best, and they’re occasionally frustratingly indecipherable. But they often are enough to go on as long as I get back to them quickly.

I go back to these sketches of ideas on the train to or from work. I dedicate 10-15 minutes to the first draft of each post. If things are going well, that’s enough time for a decent rough draft. Or, I discover that the idea isn’t a post after all, and I let it go.

I save these as drafts on my laptop, and at any given moment I have 10-20 drafts at various stages of doneness. I label them as drafts so they’re easy to find, and I’ll return to them from time to time. All of this happens in Microsoft Word.

The morning before my publish deadline, I read through near-finished drafts and find a post that feels right at that moment. This is a time of polishing. I cut as many unnecessary words as possible, especially qualifiers. I push for specificity in my language and try to breathe life into the points I’m making (not “trying to make,” which I just edited out) with specific examples. Ideally, I proofread, though I should do a better job of that by reading the whole post out loud.

Letting posts sit, as drafts, for a few days or weeks is the biggest change I’ve made to my approach since I started blogging. I made the shift when I shifted to fewer posts (1-2 / week) than I used to publish (3-4 /week). I’ve no doubt that posts are stronger thanks to this change, but ideally I wouldn’t have traded quantity for quality.

Nearly everything I’m describing happens on the train I take to and from work. I do my best writing first thing in the morning, usually at the beginning of the week when my head is clear. I mostly edit at night.

Having a place—the train—where I do the writing helps: whether it’s sitting in the same chair or the same train, putting yourself in the same location to write seems required for almost all writers. As Stephen King famously said, “This isn’t the Ouija board or the spirit-world we’re talking about here, but just another job like laying pipe or driving long-haul trucks. Your job is to make sure the muse knows where you’re going to be every day from nine ’til noon. Or seven ’til three. If he does know, I assure you that sooner or later he’ll start showing up.” Exactly.

My last step is to put the posts into WordPress, do a final reread and make last tweaks, and I hit the ‘Schedule’ button.

The best part is, eleven years and more than 1,100 posts in, when I hit that ‘Schedule’ button I still have absolutely no ideas which posts will have a big impact and which ones won’t. That’s all part of the process, one that’s equal parts faith and commitment.

(As a bonus, if you’re specifically interested in becoming a blogger, this post has helped a lot of people: What I Talk About When I Talk About Blogging.)

I have nothing to say

~ Sasha ~ 2 Comments

Most of the time, most ideas worth writing about don’t show up fully formed at the precise moment we stare at a blank sheet of paper.

Indeed, if we expect all of our useful, original ideas to show up only after we settle into the chair, we are setting ourselves up for a lot of frustration.

The ideas come at other moments.  Our job is to remain curious and attentive, so that we stop for long enough to notice our glimpses of passionate insight, of outraged exasperation or of simple, concise observation.

When these moments occur, we must hold on to them for long enough to write down the feelings we have, the core of the insight, and a few scratches about how the argument will flow.

Once that’s done, the writing boils down to the relatively simpler act of putting words around the thoughts so others can see them too.

Fundraisers in the Digital Age

~ Sasha ~ 1 Comment

One of the characteristics I don’t see people talk about as much when looking for successful, modern-day fundraisers are writing skills and digital proficiency.

It’s easy to think that the traditional job interview is a great way to find good fundraisers, and it is a good place to start. Fundraising meetings have a lot in common with job interviews: the potential funder is trying to figure out your story, your motivation for being there, and whether she connects enough with you and with what you’re saying to make a commitment to investing in a relationship with you and, over time, with your organization. A lot like hiring.

But it’s a mistake to stop there.

We know that today everyone lives on their devices. This means that a big part of the modern fundraiser’s job is to maintain and feed a web of relationships: a good fundraiser invests heavily in a core group of 20 relationships but is keeping a lower-touch pulse on as many as 100 relationships at various stages. This has gotten much easier thanks to technology – if you do it right.

The modern fundraiser’s secrets weapons are things like the ability to quickly craft a great email before or after a meeting; to sift through a lot of information online and find that one story that’s going to further the conversation you just had with a potential funder; to know when to call or to text or to write a handwritten note, and what tone and style to use in each medium.  If you can do this all fast and without breaking a sweat you can feed the network and be present and top of mind in many people’s lives.

This means that great fundraisers do more than just create connection in the room. Great fundraisers are a sense-makers, companions on the philanthropists’ journey to understand context and where their own philanthropic efforts fit in and can make a difference.