I recently sat down to attempt something I’ve been dreaming of for a long time: using Artificial Intelligence (AI) to automatically create a high-quality book summary.

As I wrote in my Ultimate Guide to Summarizing Books, writing book summaries is one of the very best ways I’ve found to absorb an author’s ideas deeply into my own thinking, while also creating notes I can use as “knowledge building blocks” to reference and reuse far into the future.

That said, summarizing books “manually” is incredibly time-consuming, often taking 10-20 hours in addition to the 5-10 hours it took to read the book in the first place. If AI is going to take over any job from me, I would want it to be this one.

In this article, I’ll describe my attempts to use ChatGPT, OpenAI’s leading AI chat platform, to create book summaries that fulfill my learning needs in a small fraction of the time and effort otherwise required. 

Experiment #1: Asking for a complete summary

My first attempt was straightforward: I simply asked ChatGPT (the most advanced version, based on the latest GPT-4 model) to write a summary of the book Slack by Tom DeMarco (affiliate link).

I chose this book very purposefully to give ChatGPT the best possible chance of writing a good summary:

  • It has sold reasonably well, ensuring there is enough material written about it online
  • It long predates the September 2021 cutoff of ChatGPT’s training data, having been released in 2002
  • I read the ebook and saved excerpts in my Second Brain, which means I can compare the ChatGPT summary with my own notes
  • It’s been more than 5 years since I read it and I’ve forgotten virtually all the main ideas, which should allow me to evaluate ChatGPT’s summaries more objectively

Here’s what it came up with:

(Note: I’ve included a number of ChatGPT prompts and responses in this article, but it can be a bit tedious to read multiple summaries of the same book so feel free to skip the text boxes unless you want to see the detailed responses)

Prompt: 

Please write a summary of the book Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency, by Tom DeMarco

ChatGPT:

Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency, written by Tom DeMarco, is a thought-provoking book that challenges conventional management practices and the widely held belief that efficiency is the ultimate goal of an organization. DeMarco argues that a relentless pursuit of efficiency can lead to burnout, disengagement, and ultimately, decreased productivity.

The book introduces the concept of “slack,” which is the time and resources set aside for employees to reflect, learn, and innovate. DeMarco emphasizes the importance of slack in fostering creativity, growth, and adaptability. He presents several case studies and examples that demonstrate the benefits of incorporating slack into the workplace, including higher employee morale, improved decision-making, and increased problem-solving abilities.

DeMarco also critiques traditional management practices, such as overloading employees with work, cutting staff, and constantly pushing for efficiency, which he contends can lead to burnout and decreased performance. Instead, he advocates for a more balanced approach, where managers focus on nurturing their employees’ talents, providing opportunities for professional development, and maintaining open communication channels.

Throughout the book, DeMarco provides practical suggestions for creating a work environment that encourages slack, including flexible schedules, encouraging collaboration, and fostering a culture of trust and autonomy. He emphasizes that by embracing slack, organizations can become more adaptable, innovative, and ultimately, more successful in the long run.

In summary, Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency is a thought-provoking exploration of the importance of slack in modern organizations. By challenging traditional management practices and advocating for a more balanced approach, Tom DeMarco provides valuable insights for managers and leaders looking to create a more adaptable, innovative, and successful work environment.

Putting on my editor’s hat for a moment, this summary is solidly mediocre. It follows a standard format and style that you might expect to read in any book review. Here are 3 specific negative aspects:

  • Overuses clichés: It uses a number of clichés that don’t really communicate anything, such as “thought-provoking” and “balanced approach”
  • Boring, conventional language: I remember that much of the value of the book was in restating commonly known truths in new and surprising ways, yet ChatGPT used conventional, rather boring language throughout (such as “relentless pursuit of efficiency,” “improved decision-making,” and others)
  • Lack of specifics: There’s also an unfortunate lack of detail, with ChatGPT’s summary hinting at “several case studies and examples” without mentioning any

Now switching to my writer’s hat: interestingly, even this mediocre result set off a few lightbulbs for me.

First, it made me realize that what I mean when I say “book summary” is very different from what most people would expect.

When I summarize a book, I’m not trying to distill its contents into the shortest possible form. In fact, my book summary blog posts tend to be thousands of words long in their own right! My summarization process is about zeroing in on only the ideas and arguments that are most unusual, surprising, counterintuitive, or directly applicable to my own life and work, and then elaborating on those points.

In a sense, my book summaries are original essays with my own interpretation of ideas, which just happen to draw on a single book as raw material. I’m not trying to write a “fair and balanced” summary that gives equal coverage to all chapters. In fact I’m trying to do the opposite: to see how far I can extrapolate from the author’s writing and bias their ideas in favor of my own needs and goals. 

This means that often, I’ll spend a lot of time on a few ideas that the author mentioned only in passing, while leaving out other ideas completely even if the author gave them major emphasis. In other words, what I consider important is not necessarily what the author thinks is important. They’ve done some valuable research, but I choose which conclusions to draw from that research and how to apply them.

Second, seeing ChatGPT’s first attempt made me realize that the primary way I wanted to apply the ideas in DeMarco’s book was to individuals, not organizations. I hadn’t even remembered that his book was mostly about teams and organizations. All I care about is how the same concepts could apply equally well to individual professionals.

That realization reminded me of why I wanted to summarize this book in the first place: I find myself in a season of life when I can’t optimize my time anymore. With two kids in tow and a household to maintain, I necessarily have lots of “slack time.” I remembered reading this book and wanted to revisit it to see how I could make peace with that fact, and maybe even use it to my advantage.

These initial insights and realizations give me a lot of fuel for the next iteration of my prompt, in which I’ll give ChatGPT a lot more direction to see if it can produce the kind of summary I’m looking for.

Experiment #2: Providing guidelines and instructions

Prompt:

You are a highly opinionated, controversial writer of how-to content. Please rewrite the summary above through the lens of personal productivity and individual psychology, minimizing mentions of teams and organizations and instead applying the book’s concepts and principles to individual knowledge workers.

In particular, describe how a new parent with two kids at home and many responsibilities might be able to use the lessons from this book to make peace with their new lifestyle, and even turn that seeming disadvantage into new opportunities for creativity, fulfillment, and pleasure. Be as specific and concrete as possible.

Don’t use any common clichés from business writing; come up with inventive, colorful, surprising ways of describing things. Include as much detail as possible, citing key sources, research findings, examples, and case studies to support key arguments. Don’t try to include equal coverage of all the main ideas in the book; emphasize what is most unusual, surprising, or contrary to common expectations of how people and companies think.

ChatGPT:

Slack: The Untold Key to Unlocking Your Inner Genius While Juggling Diapers

Throw out those self-help books preaching productivity and hyper-efficiency! Tom DeMarco’s magnum opus, Slack, tears down the façade of total efficiency and unearths the secret sauce to personal productivity: a smorgasbord of reflection, learning, and innovation. So, strap yourself in and prepare to savor the juicy morsels of wisdom that will revolutionize your life, even as a new parent buried under a mountain of responsibilities.

Picture this: your house is a war zone, riddled with the debris of countless diaper changes and the symphony of wailing children. Amidst the chaos, you discover that inefficiency is not the enemy. In fact, it’s the key to unlocking a treasure trove of creativity and fulfillment. Embracing the art of slacking isn’t just for the corporate world; it’s a philosophy that transcends cubicles and spills into the realm of personal growth. 

In one groundbreaking study, researchers found that those who embraced periods of slack in their daily routines were more likely to experience a surge of creative insights and develop innovative solutions to complex problems. The takeaway? Let your mind wander as you cradle your offspring, for it is in these seemingly idle moments that the seeds of genius are sown. 

To transform your life as a new parent, you must first declare a truce with inefficiency. The ceaseless pursuit of productivity will only smother your creativity and leave you gasping for inspiration. Instead, as DeMarco suggests, indulge in the “slacker’s siesta,” a deliberate interlude for rest and reflection. During these breaks, you might find yourself daydreaming about a bold new business idea or devising a foolproof strategy to conquer Mount Laundry. 

Next, take a page from DeMarco’s book and embrace the power of “serendipitous collisions.” These unplanned encounters, whether with neighbors, friends, or fellow parents, can spark a wildfire of creativity and ingenuity. So, attend that playdate or join that local parent support group; you never know what brilliant ideas might emerge from the crucible of shared experiences.

Finally, in a world that often demands the impossible, shed the weight of unrealistic expectations. Instead of lamenting your perceived shortcomings as a parent, celebrate your newfound mastery of the “effortless multitask.” Relish the pleasure of nurturing your children while simultaneously honing your skills as an innovative thinker.

Slack isn’t just another management book; it’s a clarion call for a seismic shift in our approach to life. By casting aside the oppressive chains of productivity and embracing the sweet nectar of inefficiency, you too can navigate the tumultuous seas of parenthood and emerge as a creative powerhouse, brimming with inspiration and purpose. So go ahead, slack away, and unlock your inner genius—one diaper change at a time.

Putting on my editor’s hat again…this is really bad. I’d say it’s actually worse than the first one in a few ways:

  • Pandering, patronizing language: Often found in parenting books, this kind of language tries to make parenting sound “cool” but comes across as annoying (“symphony of wailing children”)
  • More clichés: It replaced the clichés of business writing with the clichés of self-help, which are even worse (“emerge as a creative powerhouse, brimming with inspiration and purpose”)
  • Generic examples: The examples it cites are incredibly generic and unhelpful (“the power of ‘serendipitous collisions’”)

Oh boy. I’m going to make two changes and try again:

  • I’m going to replace the style of “writer of how-to content” (which is where the self-help clichés are coming from) with “software engineer” (since that is where a lot of the interesting language in the book comes from)
  • I’ll remove the reference to kids and parenting, since I’m mostly interested in applying these ideas to my work life, not my household (notice the further refinement in my own understanding of what I’m trying to achieve)
 

Experiment #3: Removing references to self-help and parenting

Here we go (changed parts are underlined):

Prompt:

You are a highly opinionated, controversial software engineer who uses precise terminology from engineering and scientific disciplines. Please rewrite the original summary at the start of this conversation through the lens of personal productivity, individual psychology, and technology-focused knowledge work. Minimize mentions of teams and organizations and instead apply the book’s concepts and principles to how individual knowledge workers manage their time and energy.

Don’t use any common clichés from business writing; come up with inventive, colorful, surprising ways of describing things. Include as much detail as possible, citing key sources, research findings, examples, and case studies to support key arguments. Don’t try to include equal coverage of all the main ideas in the book; emphasize what is most unusual, surprising, or contrary to common expectations of how people and companies think. Be as specific and concrete as possible.

ChatGPT:

Slack: Hacking the Matrix of Knowledge Work with the Chaos Theory of Personal Productivity

In Slack, Tom DeMarco demolishes the flawed algorithm of the “efficiency cult” and ushers in a new paradigm of personal productivity for knowledge workers, inspired by the principles of chaos theory. The book challenges the status quo, offering a disruptive blueprint for harnessing the power of inefficiency, akin to the butterfly effect, to unleash a storm of creativity and innovation.

DeMarco’s concept of “slack” is the antithesis of the traditional notion of productivity, which revolves around rigid time management, prioritization, and linear workflows. Instead, slack represents the whitespace in our workdays, the unallocated buffer zones in our mental RAM, where serendipitous sparks can ignite and give birth to breakthrough ideas.

To apply DeMarco’s principles to knowledge work, one must first defragment their cognitive hard drive. Engaging in mind-wandering activities, such as going for a walk or indulging in a power nap, can catalyze the process of synaptic reorganization and increase the probability of generating novel insights. In a seminal study, scientists discovered that participants who embraced mental slack exhibited heightened creative problem-solving abilities and cognitive flexibility, akin to overclocking the brain’s processing power.

Next, embrace the stochastic nature of inspiration. DeMarco highlights the importance of unplanned interactions and unexpected connections, akin to a random walk algorithm, in fostering innovative ideas. For knowledge workers, this could involve participating in online forums, attending webinars, or engaging with peers on social media platforms. These seemingly aimless encounters can serve as the initial conditions for triggering a cascade of creative thoughts and out-of-the-box solutions.

Furthermore, DeMarco posits that the pursuit of hyper-efficiency can lead to cognitive burnout and diminished performance. To counteract this, knowledge workers should experiment with polyphasic sleep patterns, designed to optimize mental alertness and increase REM sleep, thereby enhancing memory consolidation and creative synthesis. By adopting a more flexible approach to time management, individuals can optimize their mental bandwidth and reduce the likelihood of cognitive overload.

In summary, Slack rewrites the source code of personal productivity by leveraging the principles of chaos theory and emphasizing the value of inefficiency for knowledge workers. By embracing mental slack, engaging in random interactions, and adopting flexible time management strategies, individuals can tap into their inner wellspring of creativity and innovation. So, unplug from the matrix of efficiency and embark on a thrilling journey through the chaotic landscape of personal productivity.

That’s actually a bit better! It’s mostly just replacing the clichés of business and self-help writing with the clichés of technology writing, and I suppose tech language just happens to appeal to me more personally.

A few other things I noticed:

  • Hallucinations: This summary makes several references to chaos theory, but the book doesn’t mention chaos anywhere! This is a complete hallucination, likely as a result of ChatGPT conflating “inefficiency” with “engineering.” Then it mentions the “butterfly effect,” which the book doesn’t mention either. So it’s building on its first hallucination with further ones!
  • Bad advice: ChatGPT’s summary recommends experimenting with “polyphasic sleep patterns” as a way to apply the book’s ideas, but DeMarco makes no mention of this. Another hallucination, and I’d guess one that runs exactly counter to the book’s main arguments.
  • Good synonyms: It did come up with a few good synonyms for “slack”: whitespace, unallocated buffer zones in our mental RAM, and synaptic reorganization

At this point, I’m wondering which kinds of sources ChatGPT has access to in writing its summaries. To improve my instructions, I need to know what material it has to work with.

Experiment #4: Exploring ChatGPT’s training data

One of the advantages of a conversation-based tool is you can simply ask it!

Prompt:

Can you please tell me what sources you are drawing on for the responses above?

ChatGPT: 

As an AI language model, I have been trained on a diverse range of text sources, including books, articles, websites, and research papers, up to September 2021. For the responses above, I drew upon my knowledge of Tom DeMarco’s book “Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency” as well as my general understanding of management, productivity, and psychology. 

However, some elements in the responses, such as specific studies, examples, and analogies, were used creatively to enhance the narrative and make it more engaging. While these elements may not be directly attributable to specific sources, they are inspired by my knowledge of productivity, creativity, and neuroscience research. 

Please note that as an AI language model, I am unable to access real-time or up-to-date information. My knowledge is limited to the training data available up until September 2021.

Aha! So the hallucinations were a result of “specific studies, examples, and analogies” being “used creatively to enhance the narrative and make it more engaging.” It does mention that it drew upon “my knowledge of the book” but I wanted to know if it actually has access to the full contents of the book.

Prompt:

Do you have access to the full text of the book Slack, by Tom DeMarco? If not, which sources are you drawing on related to that book?

ChatGPT:

As an AI language model, I do not have direct access to the full text of Tom DeMarco’s book “Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency.” However, I have been trained on a wide variety of texts, which may include summaries, reviews, and discussions of the book.

My knowledge of “Slack” is based on this indirect information, and I synthesize the key points and ideas from the book in my responses. This means that my understanding of the book may not be as comprehensive as if I had direct access to the full text, but I can still provide an overview and discussion of its main concepts and principles.

Ok, so it does not have access to the book’s contents, which explains why it has trouble citing specifics. Instead, it is relying on “summaries, reviews, and discussions” of the book to create an “indirect” summary. This explains a lot about the limitations of its output – it’s essentially writing a “summary of summaries,” trying to guess at the contents of the original book through the medium of other people’s writing about it.

This leads me to the next experiment: feeding ChatGPT my own notes with excerpts from the book as part of the prompt.

Experiment #5: Providing my excerpts from the book

At this point, I’ve spent an hour reading very generic summaries of DeMarco’s ideas, and am honestly second guessing whether his book contains anything interesting at all. Maybe it’s not possible to generate the kind of summary I’m looking for because the book isn’t relevant to my needs in the first place.

I purposefully avoided reviewing my notes on the book up until this point to make my evaluations of ChatGPT’s output as neutral as possible, but now it’s time to dive in and see what it’s been missing.

I started by asking ChatGPT how many words I could fit in its “context window” – the word limit of how much text I can provide in my prompts. It estimated about 1,000 to 1,200 words. I wanted to keep this in mind as I summarized my own notes using my typical process, known as Progressive Summarization (basically an advanced form of highlighting). 

Slack contains about 46,000 words, and my saved excerpts totaled 6,867 words, which meant I had saved about 15% of the original text as excerpts in my notes. I would need to select no more than 17% of that 15% (or about 2.5% of the entire book) to be able to feed into ChatGPT’s context window.

After progressively summarizing my excerpts, I moved each of the highlighted passages into a separate document, which you can see below:

Note with all excerpts from the book Slack

This new document totaled 1,618 words – slightly too big for ChatGPT to absorb in its entirety, but close enough! I copied and pasted the entire text of this document, with no structure or additional context added, into a new ChatGPT conversation (to avoid the bias of our previous discussion) and here was the result:

Prompt:

Please write an in-depth summary of the book Slack by Tom DeMarco, drawing on the excerpts from the book below:

[Pasted my excerpts from book]

ChatGPT:

In his book, “Slack,” Tom DeMarco addresses the efficiency-flexibility quandary faced by modern organizations. He argues that as organizations become more efficient, they lose their ability to change. This is problematic because adaptability is essential for survival in today’s rapidly changing business environment.

DeMarco proposes that the concept of “slack” can help organizations become more adaptable. Slack refers to the time when reinvention occurs, when workers are not 100% occupied with operational tasks. The author notes that organizations he admires do not show a strong sense of hurry, which allows them the flexibility to change and grow.

In modern organizations, work is often divided among knowledge workers who are constantly shifting between tasks. This task-switching leads to inefficiencies, with a significant amount of productive effort being lost. DeMarco believes that maintaining some slack can lead to more focused and efficient work.

Slack can also be seen as a form of investment that brings several benefits, including increased flexibility, better employee retention, and the capacity to invest in new initiatives. By viewing slack as an investment rather than a waste, organizations can foster an environment that allows continuous change and adaptation.

However, DeMarco also discusses the negative effects of stress on organizations, which can lead to demotivation, burnout, and loss of key personnel. He argues that when stress is the problem, slack is the solution, as it allows employees to maintain focus and reduce the risk of burnout.

The book also touches on the importance of vision in guiding organizational change. Without a clear vision, flexibility becomes an abstraction, and the organization may resist all change. A strong vision helps employees understand the necessity of abandoning their mastery of the familiar and embracing new skills and approaches.

Additionally, DeMarco emphasizes the importance of fostering a safe environment for employees to learn and adapt to new changes. This includes avoiding behaviors such as mockery, sarcasm, and public humiliation, which can be detrimental to the process of change.

Risk management is another crucial aspect of adaptability. DeMarco argues that organizations must be willing to take on risks in order to succeed in the current business climate. By identifying and canceling risk-free projects, organizations can allocate resources and time to transformational initiatives.

In conclusion, Tom DeMarco’s “Slack” highlights the importance of maintaining flexibility and adaptability in modern organizations. By valuing and investing in slack, organizations can foster an environment that supports continuous change and growth, ultimately leading to long-term success.

This is far better than anything we’ve seen so far, since it actually includes key points and opinionated stances from the book. A big leap forward!

Experiment #6: Combining my excerpts with guidelines

Now I’ll combine these excerpts with the instructions and guidelines I had come up with previously (asking it to apply the content primarily to individual productivity, to avoid clichés, and to use colorful and specific language).

Here is what it came up with:

Prompt:

Please rewrite the summary above through the lens of personal productivity, individual psychology, and technology-focused knowledge work. Minimize mentions of teams and organizations and instead apply the book’s concepts and principles to how individual knowledge workers manage their time and energy.

Don’t use any common clichés from business writing. Include as much detail as possible, citing key sources, research findings, examples, and case studies to support key arguments. Don’t try to include equal coverage of all the main ideas in the book; emphasize what is most unusual, surprising, or contrary to common expectations of how most people and companies think. Be as specific and concrete as possible.

ChatGPT:

In “Slack,” Tom DeMarco presents a compelling argument for the importance of cultivating slack in one’s personal life, particularly for individual knowledge workers managing their time and energy. By applying the book’s concepts and principles to the domain of personal productivity, we can challenge conventional wisdom and explore the surprising benefits of incorporating slack into our daily routines.

DeMarco contends that the efficiency-flexibility quandary, often observed in organizations, can also manifest in individuals’ lives. As we strive for maximum efficiency, we risk becoming inflexible and less adaptable to change. By embracing slack, or periods of downtime, we allow ourselves the mental space for reinvention, learning, and personal growth.

Modern knowledge workers often find themselves multitasking and switching between tasks, leading to significant inefficiencies. DeMarco’s research suggests that task-switching can result in a direct loss of productive effort of more than an hour per day. By introducing slack into our schedules, we can minimize task-switching and enhance our focus on individual tasks.

Embracing slack as an investment in personal productivity can yield multiple benefits. These include increased flexibility to adapt to changing circumstances, improved work-life balance, and the capacity to explore new ideas and opportunities. By viewing slack as an investment rather than a waste, individuals can foster a mindset that supports continuous personal growth.

One surprising aspect of DeMarco’s work is the emphasis on the importance of vision in guiding personal change. Without a clear vision for our lives, flexibility becomes an abstraction, and we may resist change, even when it could be beneficial. A strong personal vision helps us understand the necessity of abandoning our mastery of the familiar and embracing new skills, approaches, and ways of thinking.

Another counterintuitive insight from DeMarco’s work relates to the management of stress and pressure. Many individuals believe that working under pressure can enhance productivity. However, DeMarco argues that stress can lead to demotivation, burnout, and decreased effectiveness. By incorporating slack into our routines, we can manage stress levels and maintain focus, ultimately leading to greater personal productivity.

Finally, DeMarco’s discussion on risk management is equally relevant to individuals. As knowledge workers, we must be willing to take on risks and explore new opportunities. By identifying and eliminating activities that do not contribute to our personal growth or align with our vision, we can allocate time and resources to transformational initiatives.

In conclusion, Tom DeMarco’s “Slack” offers valuable insights for individual knowledge workers seeking to improve their personal productivity and adaptability. By embracing the concept of slack and challenging conventional wisdom, we can cultivate an environment that supports continuous personal growth and long-term success.

A few observations on what it’s still lacking:

  • Incorrect attribution: ChatGPT successfully applied Slack’s ideas to individual productivity, but incorrectly attributed those interpretations to the author himself; since it doesn’t know what’s in the book, it can’t distinguish between the source text and its own interpretation.
  • Lack of connecting reasoning between points: Since my excerpts were taken from completely different parts of the book, with thousands of words of “connective tissue” between them missing, ChatGPT can’t really provide that context on its own. For example, it merely says that “By introducing slack into our schedules, we can minimize task-switching…” without explaining why that is.
  • Lack of original explanation and understanding: Pretty much all the original, interesting observations (“viewing slack as an investment rather than a waste”) were taken verbatim from my excerpts, which of course were taken verbatim from the book. ChatGPT isn’t adding explanation, only rearranging and modifying how they’re presented in prose form.
  • Missing subtle distinctions: Such as DeMarco’s use of the word “risk” not in the sense of “danger,” but as “risk of missing the schedule.” However, without the full context of the book, it’s likely a human would have missed this as well.

By far my strongest critique of this summary, however, is that it’s still terribly bland and boring. It sounds like the author is arguing in favor of “taking a break and relaxing sometimes,” which is about the most cliché piece of advice imaginable. Do we really need to be convinced that “too much stress may lead to burnout”?

But since I have access to the “raw material” of my excerpts, I know that DeMarco is actually making a number of highly original and bold claims. Or at least framing common wisdom in new and surprising ways. Somehow most of the energy and inventiveness of the original writing has been lost, even when many of the best excerpts were supplied in the prompt.

Experiment #7: Providing my own outline of the book

I wanted to try one final experiment combining everything I’d learned: to give ChatGPT a helping hand by telling it what I thought were the book’s most important claims. 

I reorganized my excerpts into an outline, with 7 of the most important points as headlines and supporting excerpts indented under each of them (you can view it here). I also removed any excerpts that weren’t related to these 7 key takeaways, which conveniently reduced the word count from 1,618 words to only 641 words.

Outline of the book Slack

I created a new chat window to eliminate any previous context and gave ChatGPT the previous prompt along with my outline. Its initial response was also in outline form, and after asking it to turn its outline into prose, here was the result:

ChatGPT:

Slack, as described by Tom DeMarco, is the degree of freedom required to effect change. It is the time when reinvention and learning happen, away from the operational business. It is an investment in personal growth and adaptability, rather than being seen as waste. In a world where constant change is the norm, incorporating slack into daily routines and schedules is essential for personal growth, adaptability, and success.

The efficiency-flexibility quandary states that increased efficiency often leads to a decrease in flexibility. This phenomenon, first noted by geneticist R.A. Fisher, can be applied to knowledge workers who focus on being as efficient as possible, potentially sacrificing their ability to change and adapt to new situations. Slack comes to the rescue by providing space for flexibility and adaptability.

However, the absence of slack creates a dangerous delusion that being constantly busy is equivalent to being effective. In reality, this lack of slack leads to a fragmented state where knowledge workers are unable to focus on a single task and end up constantly switching between activities. Research shows that each task-switch imposes a direct penalty of over twenty minutes of lost concentration, resulting in a loss of productive effort of more than an hour per day.

By incorporating slack into one’s life, individuals can enjoy several benefits. These include flexibility for ongoing growth and change, better retention of personal motivation and well-being, and a capacity to invest in personal development. On the other hand, a lack of slack can lead to stress, demotivation, and an increased risk of burnout.

To create slack, it is important to reduce the focus on quantity and embrace uncertainty. Risk-taking is essential for growth and transformation, so it is crucial to pursue projects with inherent risks rather than those deemed risk-free. By stopping nontransformational work and dedicating resources and time to transformational activities, individuals can adapt, learn, and grow in a constantly changing world.

Now we’re starting to get somewhere. ChatGPT is turning the excerpts I supplied it with into a rapid drumbeat of bold claims, each one related to and building on the one before. There are fewer clichés and qualifications, making the line of reasoning stronger. 

It still misses some things, such as including the key detail that “This phenomenon…[was] first noted by geneticist R.A. Fisher” without including the giraffe example that makes that detail relevant. Even though the conclusion includes tantalizingly interesting and counterintuitive points (such as the importance of rejecting projects that are free of risk, because they won’t be transformational enough) it still veers off into cliché again in its attempt to reach a nice, neat conclusion.

And of course, by this point I’ve already done most of the work of summarization that I was trying to avoid in the first place! Getting to the outline is the hardest part, because it involves making a long series of difficult decisions about what to include and in what order, which is an incredibly taxing mental activity for us humans. I’ve arrived at a decent summary that is perhaps 50% as good as one I could have created myself, while saving perhaps only 20-30% of the total effort needed to get there.

Four conclusions from this experiment

First, I concluded that supplying ChatGPT with the best excerpts from one’s reading greatly improves the summary it can provide, especially when those excerpts are organized into an outline that provides a particular point of view.

The main challenge is distilling the excerpts enough to fit within the context window (though upcoming improvements to ChatGPT include a vastly larger window that will fit more than 15 times as much text).

Second, you can’t instruct ChatGPT to come up with “surprising” or “counterintuitive” ways of explaining things, because those qualities depend on sensitivity to a cultural zeitgeist made up of millions of people’s joint expectations, plus access to a wealth of details to put a fine point on its assertions. Instead of being surprising, it will merely use words like “surprising” and “counterintuitive” in its otherwise boring description.

Third, ChatGPT is always tending toward cliché, which by definition is the “aggregate average” of the greatest number of writers on which it was trained. You have to constantly come up with inventive ways of getting it off that well-worn path. 

Fourth, I conclude that reading books is still worthwhile, even in an age of Artificial Intelligence. Besides the personal enrichment from the experience of reading, there are key details, subtle distinctions, and gestalts of meaning that come from reading and notetaking that can’t (yet) be reproduced by even the latest language models. 

In fact, it seems that having a personal collection of excerpts from one’s reading, whether written down by hand or synchronized with a notetaking app using a service like Readwise, is an even greater asset than before. The decisions you make about which excerpts are worth saving constitute a unique interpretation of a book’s ideas that isn’t shared by anyone else on the planet.

In a world of infinite, instantaneous summarization, the one with the most unique data to summarize wins.

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