Vacation strategy; books Claude away; Grok rewrites history: Newsletter 25 June 2025

Newsletter 100: A smarter way to go on holiday. Plus, Anthropic’s training on books rules “transformative,” defamation by blurbs, three people to follow and three books to read.

How to go away

Everyone needs time off. And people tend to disagree on how to do it.

There’s the “disconnect entirely” camp. They don’t check email, voicemail, Slack, or any other work-related channel when they’re on vacation. They’re blissfully out of touch, able to lie on the beach reading escapist fiction or climb to the top of Mount Baldy without a distraction.

Of course the downside of that is what happens when you return. Which of your projects were stalled — or totally derailed — while you were away? What are you going to do about the 3,000 emails waiting for you?

Then there are the “working vacation” folks. For them, time off is just a lighter version of a working day. They dive in and get stuff done, opting out of the shopping trip to the charming little town or the walk to the ice cream shop that the kids have been asking for. Ah, the kids. If you’re one of these folks, the kids will resent your lack of attention during your shared time off.

The working vacation crowd hits the ground running on the Monday after their holiday. Of course, the problem is, they hardly feel like they had a holiday at all.

I’m not a fan of either of these approaches. I’m a fan of maximum enjoyment and minimum pain. That means planning ahead, setting expectations, and treating myself — and my family — to a vacation that’s real.

I make sure that people I work with know that I’m not working on vacation and that I expect them to adjust their own projects around that. I send an email a week before I leave that sets out those expectations. This isn’t much different now that I’m a freelancer than it was when I worked for companies; only the recipients of the email have changed.

Once or twice day when I’m on vacation, I check emails. It takes no more than half an hour. It’s usually before everyone else is awake or when they’re relaxing in the afternoon. This is a low-stress activity.

I handle the emails in one of four ways:

• Ignore. Applies to most of the emails.
• Bookmark. This looks interesting, I’ll check it when I return.
• Delegate or quickly handle. As in, “Julie, could you check into what Jack is asking for?” Or “Here’s the link to the folder with that file in it.”
• Defer. “I’m currently on vacation; I’ll handle that when I return on Monday.” (Because I’m a freelancer, an occasional lead comes in when I’m away. I respond quickly and say, “Let’s do a call when I’m back from vacation. Are you free next Tuesday?)

I happen to be on team “Never delete an email.” If you feel an obsessive need to categorize and respond to every email, for you this will feel like work. That’s one reason I’m not on that team.

I have one more unique challenge: I blog every weekday. Before I go away, I prepare a bunch of posts that will go live while I’m away. And I write the occasional post about fun things I see on vacation, like this bookstore in an old church I visited in Scotland.

For this to work, I have to make sure:

• Everybody who needs me is aware I’m not going to be available or working.
• People I work with don’t need my help for every little decision.
• I’ve adjusted deadlines to address the time I’m not working.
• I am capable of relaxing after a little light work on email.

That’s preparation and mental discipline, but not to an onerous degree.

My vacations are low-stress and enjoyable, and so is my re-entry. How about you?

News for writers and others who think

A federal judge ruled that AI company Anthropic was within its rights to use books it had legitimately procured (bought or licensed) to train its AI. The reason: The resulting output is “transformative,” not “derivative.” If this holds up, the cost of an LLM training on your book will be the price of one copy. There are a couple of problems with this: To get access to the book, they have to either scan it (expensive) or break copy protection (illegal). Yet to be addressed — what’s the right approach for free content like open web sites, and can those sites opt out of being used for training?

Blurbs (brief quotes of praise) from Lisa Ko now appear on many books that she never blurbed. Harper Collins says, “This was due to a data error in one of our marketing systems and it is being corrected. It was not AI related.” (subscriber link, Publisher’s Lunch). Hijacking an author’s name and opinion repeatedly are professional identity theft. If this were me, I’d call it defamation, and I’d sue.

Elon Musk tweeted this about Grok, the AI from X.com: “We will use Grok 3.5 (maybe we should call it 4), which has advanced reasoning, to rewrite the entire corpus of human knowledge, adding missing information and deleting errors. Then retrain on that. Far too much garbage in any foundation model trained on uncorrected data.” This is an attempt at literal Orwellian thought control. Reality is messy. “Cleaning it up” means making it compliant with a single view of history; everything else goes down the memory hole.

Deep thinker on the teaching of writing John Warner writes in Inside Higher Ed about the push for universities to license AI for their students: “[OpenAI executive Leah] Belsky has as her charge to create ‘AI native universities.’ How you feel about these initiatives may depend on how you reflexively respond to that phrase. My response is some mix of ‘ugh’ and ‘yikes.'” I disagree, John. These students are going to be immersed in AI. Give them access and include faculty guidelines on how to incorporate into courses. That will be messy. But hiding from AI is not the solution.

Three people to follow

Chris Duffey, author and Adobe exec posting on creativity and AI

Derek Thompson , Atlantic writer (now Substack), coauthor of Abundance

Tom Albrighton , awesome copywriter and thinker

Three books to read

On Tyranny: Twenty Lessons from the Twentieth Century by Timothy Snyder (Crown, 2017). A call to arms and guide to resistance, with renewed relevance in 2025.

AI Human Fusion: A non-techy human-first approach to AI for busy leaders by Leanne Shelton ✨ (Major Street, 2025). Add AI to your organization without losing your humanity.

Empire of AI: Dreams and Nightmares in Sam Altman’s OpenAI by Karen Hao (Penguin, 2025). Pulling back the veil on the biggest AI company’s methods and motives.