“Ok Boomer” and the Generational Divide

A 3D animation style scene featuring the phrase 'OK boomer' in bold, colorful, floating letters above a vibrant green field under a bright blue sky with a few fluffy white clouds. and a rainbow
(Image: DALL-E 3)

One thing I dislike about the phrase “OK, boomer”, besides its incredible condescension, is that it pretends all individuals of a certain generation are alike.

Trust me when I tell you we are not.

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The Flag and the Flag

US flag on a flagpole with a progress pride flag beneath it.
(photo: leonotenboom.com)

It was time to replace our well worn U.S. flag, but I was hesitant.

I’d planned on raising the new flag the day after the election, with the assumption that Harris would win. Needless to say that didn’t happen.

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Like? Subscribe! Support!!

A cartoon-style image of a character resembling Elmer Fudd, but with distinct differences to avoid copyright issues. The character is bald, wearing a hunting hat, and a plaid shirt, seated at a desk, leaning toward a computer screen. On the screen, a blog homepage is displayed, titled 'Ducks And Wabbits Weekly,' with a prominent 'Subscribe' button at the bottom.
(Image: DALL-E 3)

“Traditional media” is broken. It’s an echo chamber for singular perspectives that are driven by business and other interests. Examples abound, but the perhaps the most clear was Washington Post’s recent failure to endorse any presidential candidate. It’s a billionaire owner making a decision not because it’s good for the public or the press, but to protect his interests from a certain outcome. It appears to have paid off, perhaps at the cost of the country.

“Social media” is broken. Algorithms control what we see, and what we see is an attention bubble full of engagement bait. Most social media platforms exist only to show us more of what we’ll engage with, rather than what we actually ask for. Platforms that don’t are struggling because people end up finding their feeds, while exactly what they asked for, boring in comparison.

So, what’s the solution?

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Clapbacks Are Just One Hand Clapping

They’re not as clever, or as impactful, as you think

A PC computer screen showing two people on opposite sides of the screen, pointing fingers at each other and laughing mockingly. Both individuals appear to be engaged in a heated yet sarcastic exchange, with exaggerated facial expressions.
(Image: DALL-E 3)

I rarely go a day without seeing a social media comment that “politician A just put politician B in their place!” or that “A scored massive points with their clapback to B!”.

“A clapback is a quick, sharp, and often witty response to criticism or disrespect. The term is often used to describe a comeback that is particularly effective or memorable.”
– via perplexity.ai

No. Just … no.

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Things I Learned From My Father

A timely word I remember to this day

A woman in a lush forest. The woman is facing away from the viewer, towards the dense foliage. She is wearing casual hiking attire and her hair is tied up in a ponytail. The forest is vibrant, filled with tall trees, a variety of green shades, and dappled sunlight filtering through the leaves.
(Image: DALL-E 3)

I’ve learned many things from my father, and I’m grateful for all of it.

Some I learned by example, some by counterexample, and some simply by listening to what I was being told.

It’s the latter that comes to mind today. All because of bears.

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Fascism, the Past, and Our Future

Please don’t let history repeat itself.

The Stone Man
“The stone man” (1953), National monument: Prisoner before the firing squad in Camp Amersfoort/The Netherlands. Click for larger image. (Image: leonotenboom.com)

My parents lived in The Netherlands during World War II. The country was occupied by the Germans for several years prior to the war’s end. My parents lived through that occupation, including the famine.

This was not just some “inconvenience”. My father told me stories of diving into ditches to avoid being captured and conscripted by a passing Nazi patrol. He and his brother did get captured once, but in a fit of “either way we’re probably dead” decision making, when they saw an opportunity to run, they did. They got lucky.

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Unhappy People Want A Cause

A politician at a podium speaking to a large crowd, viewed from behind the speaker. The crowd is filled with a variety of unhappy facial expressions and raised fists, signaling discontent and protest. he background is adorned with red, white, and blue bunting, adding a patriotic element to the scene.

I recently finished reading Magic Slays, book 5 in a light fantasy series by Ilona Andrews, set in an interesting alternate world that includes periods of time where magic is real.

There are factions, and zealots, and conflict, and more. The thing you’d expect from an engaging story.

But a series of paragraphs late in the book, as the characters were preparing for its major battle, caught my attention for reasons I think will become clear.

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Did Tolstoy Understand Social Media?

When words from the early 20th century feel spot-on in the 21st

Leo Tolstoy postage stamp
Leo Tolstoy (Image: canva.com)

As the new year starts, I elected to change my daily reading source. For the past couple of years, I’ve been reading passages from The Daily Stoic. This year I’m starting A Calendar of Wisdom by Leo Tolstoy.

Same idea, an essay a day for the entire year.

Tolstoy grabs my attention right out of the gate on January 1.

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You Are Entitled to Your Opinion

But not absolution from the consequences

Shouting into a bullhorn
(Image: canva.com)

We often hear people complaining they’re being discriminated against, losing friends and acquaintances, and even being “cancelled” because of the opinions and beliefs they hold and express, or the practices they engage in. Somehow they seem to feel that they should be able to hold, express and practice without consequence.

Because, of course, they believe their position is correct. As the One True Answer, it should obviously be honored and respected. Not to do so is, itself, disrespectful.

That’s not how it works.

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Musings on AI, Learning, and Copyright

A photorealistic image representing the complexity and nuances of AI's relationship with copyright and content creation. The scene includes a human figure surrounded by a swirl of books, magazines, love letters, emails, essays, and scribbled notes, symbolizing the diverse content humans consume and internalize. Nearby, a large, abstract representation of an AI language model, depicted as a complex, digital brain-like structure, is absorbing a vast array of similar content, showing the immense scale of data it processes. The background is split into two halves: one side illustrates a traditional library, representing human learning and creativity, and the other side is a futuristic digital landscape, symbolizing the digital realm of AI. The central theme is the comparison of human and AI content consumption and creation, with an underlying question of copyright and originality, subtly represented in the image.
(Image: DALL-E 3)

One of the more contentious parts of the rise of AI is its relationship to the rightsholders for the content on which it is trained. Many consider it blatant copyright infringement.

I’m not so sure.

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Appreciating Progress

Work in Progress
(Image: canva.com)

I’ve previously expressed disappointment in people who seem to go out of their way to find fault in good news. They work to snatch negativity from the jaws of the positive.

There’s a related mindset I see that isn’t really negative … but it’s not really positive, either.

It’s something I see arising from black and white thinking and an instant gratification mindset.

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Looking for Negativity

Searching for ... something.
(Image: depositphotos.com)

I publish a daily newsletter called Not All News Is Bad. Several years ago I found myself in need of a reminder that there’s more going on in the world than the shitshow most news sources seem to focus on.

I forced myself to find at least one good news story every day. I started sharing that publicly, and eventually it became the daily newsletter. At this writing, it goes out to about 1,500 subscribers every morning.

It doesn’t happen often, but one thing that makes me shake my head is when a recipient of a good news story goes digging for negativity.

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What If You Missed The Meeting?

A framework for keeping your mouth shut

Zip It!
(Image: depositphotos.com)

We love our opinions. We really do. We’re so proud of them, and we’re so eager to share them with anyone who’ll listen, and many who won’t.

And yet, there’s the adage: “Opinions are like assholes: everyone has one, and no one wants to see yours.”

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OrganTok

Royal Albert Hall - Central View Square
The Organ of the Royal Albert Hall, London. (© User:Colin / Wikimedia Commons)

Social media gets a lot of negative press. It’s blamed for the increasing political divide, for increased rates of depression, particularly among teenaged girls, for being some kind of spying tool used by corporations and foreign governments, and more.

And, to be completely honest, much of that is probably accurate.

But it also overshadows the fact that there are some very positive things happening on social media as well.

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The Value of Curation

7 Takeaways is weird

So. Much. Information.
So. Much. Information. (Image: depositphotos.com)

I started 7 Takeaways it for myself, to “force” me to consume higher quality content more consistently. Apparently I start newsletters to make myself do things.

Curating for others was never on the agenda, not really. Besides, there are so many other curated newsletters, and many of them are so much better. Hell, I get some of my ideas from them!

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Retirement is Obsolete

Midjourney AI: "an empty rocking chair on a porch with an elderly man running through a field in the distance"
Midjourney AI: “an empty rocking chair on a porch with an elderly man running through a field in the distance”

I “retired” in 2001 at 44, after an 18-year career at Microsoft.

There was a spreadsheet (in Excel, of course) that calculated I was done. The meteoric rise of the Microsoft stock price and the serendipitous timing of my joining came together to give me options (including literally stock options), for which I am forever grateful.

However.

I was recently reading some articles discussing the traditional transition from the work-a-day world — aka a “job” — to a world of leisure and choice — aka “retirement”.

I was getting increasingly uncomfortable with the assumptions and preconceptions of what it means to retire.

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Please Answer the Question!

Please

Soapbox
(Image: canva.com)

I need to rant a little.

As you might expect, my “day job“, and a lot of my not-so-day-job, involves answering questions. It varies, of course. Some questions are simple yes/no, some are translating consumer terminology into more accurate terms and returning a “search result” from one of my websites to help, and so on.

Mostly it’s pretty simple Q&A.

Sometimes it’s less simple.

Sometimes it’s iterative. And sometimes that’s very, very frustrating.

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Getting it Done

Blacksmith, working hard.
(Image: canva.com)

(Long one, today. I didn’t plan on it, but here we are. Smile)

I’ve been asked a couple of time how I manage to do so much. If I look at what I produce each week, it adds up:

  • Ask Leo! Articles, Videos, direct answers, and Newsletter
  • Not All news is Bad
  • 7 Takeaways
  • HeroicStories
  • My personal blog and 65 Thoughts
  • My volunteer work
  • An assortment of other things

Even considering all that I don’t accomplish every week even if I’m supposed to (my wife has that list), it’s still quite a lot.

The answer to the question turned out to be longer than I expected. I have a combination of frameworks, routines, habits, tools, and mindset that are probably pretty unique to me. While I pay attention to a lot of “productivity porn”, as it’s sometimes called, I think I’ve ended up with a blend of approaches that work fairly well for me.

I don’t expect they’ll work for everyone. But let’s look at how I do what I do hoping you might find a nugget or two that resonates and can help you get s**t done.

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Requiem for a Once Great Nation

A Once Bright Light
(Image: canva.com)

To my foreign family and friends.

No, I can’t explain it.

The US was once the land of opportunity and freedom. Now it seems the home for hypocrisy and hate.

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How We Learn is Changing

Right? Wrong? It Depends!
(Image: canva.com)

I didn’t realize it at the time, but one of the most important skills I got from my education was the ability to find answers.

I wish education in general was more focused on that skill. Rather than accumulating (and, gak, testing for) knowledge, teach the skill set required to acquire knowledge as needed; a kind of “just in time” skill. When you need to know something, you know how to find it.

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