H2H: Writing from human conversations is my AI chatbot rebellion
E225 Rest & Recap 32 - Writing from Conversations + Word of 2026
Consider this my private rebellion. Writing from conversation is how I aim to prevent AI from crowding out the Human:Human interactions in my life. These genuine conversations create tangential ideas, planting seeds that I hope will grow into oak trees. And my subsequent discussions with my AI chatbot? It provides the manure.
Your mission, should you choose to accept it:
Find a cozy corner. Pick up your phone, open your screen, hit that old fashioned šicon, or pick up your home phone āļø in real life - and start a conversation. Look into their eyes if its a video call. Listen to the cadence in their voice. And experience the joy of a conversation with another human being.
Who is your person today? When will you call?
Rest element 32: Conversations
Undistracted. Conversations.
Slowing down to listen to the other personās thoughts.
Casual, low-stakes conversations release feel-good hormones. They subtly underline the fact that we are part of a community, increasing our sense of tribal security and reducing stress.
Caveat: This may not yet work for you if your children are under the age of six. But trust me, a day will come when you return home from a christmas gathering and realize that you WERE able to finish a thought and complete a sentence! And it will be bittersweet, like the day they no longer sneak into your bed to snuggle at 4:38am.
Rest series: Every 7th edition of this newsletter is dedicated to Rest and Recovery.
Rest is a crucial 21st-century (survival) skill. Done right, proactively programming in rest and recovery breaks prevents burnout.
Here is a full directory of all the rest topics we have covered to date. We explore different techniques and discuss rest in each of these issues. They span discussions on the value of sleep to the value of community time as a rest element. It has also been added to the navigation bar for easy access.
Recap: Digest of issues 218 - 224
āYou should write about that and share it!ā Each edition shared a snippet from a live conversation with a real person (usually over Zoom or Google Meets).
Each edition in this cycle also included 5 rest edition lessons, building to a compendium. [Hit a glitch. This will soon be live on the website]
Here is a recap of what we have read over the past six seven(!) weeks.
TL;DR
21st-CENTURY AND HEIRLOOM SKILLS: Proactive rest is not a luxury item. It is self-care.
RAISING FUTURE-READY LEADERS: 10X thinking.
FUTURE OF WORK: A few AI related discussions. āItās like giving a 13-year-old the keys to a F1-racer ⦠and no instructions on how to hit the brakes.ā
HIGHLIGHTING WHAT OTHERS HAVE SAID ABOUT ā¦
(Click each edition to read the full story) Each edition started off with a conversation ā¦
Dream BIG!!- Moonshot goals and 10X thinking
People can set their minds to magical, seemingly impossible ideas and then through science and technology bring them to reality. That then sets other people on fire. The(n) other things that look impossible might be accomplishable.
As a parent, my biggest takeaway from this 10X experience was not to impose the boundaries of my thinking on the possibilities for my children. The quote above has stuck with me.
Read Justin ās reflection. His Substack is titled based on true stories: procrastination stretches to fill the time we have. And yet our capabilities stretch to fill the vision set.
Time is your most valuable resource. Spend it on you and yours first.
āI wish Iād met you 15 years agoā
A beachside conversation surfaced a very important lesson from a risk manager who was so busy protecting otherās assets that she forgot to protect herself, her time and energy.
āProactive rest is not a luxury item. It is an act of self-care.ā
Neural Foundry made this observation: Wonderful take on incremental skill building. The way you frame teh snorkeling progression as a metaphor for learning anything later in life is really smart. I tried something similar with paddleboarding last summer and the 'one step better each time' approach took so much pressure off. Sometimes we forget that mastery isnt about perfection, it's about showing up with patience and curiosity.
If you were gifted a perfect window of time, what would you do with it?
āSo - got any more trips planned?ā Emma Dorge (Emma Dorge) asked as we hopped onto our call.
āWindows of time and opportunityā and the 1000-day radar seemed to capture the most attention in this cycle. Beyond the 17 comments on the post, this issue triggered many cocktail party conversations and email chatter.
I use my window of opportunity to schedule in travel.
But Rick Lewis - who travels extensively to give his keynotes - made a great observation on what he would do if he had window of time: I have a harder and harder time with planning ahead as the years progress with the world changing so rapidly. Every day feels like a new discovery or adjustment that I could not have foreseen. But this has got my wheels turning. What do I see in the next 1000 days? After 40 years of copious amounts of business travel, traveling isn't one of them. Sticking close to home for a while sounds like the kind of vacation I'd love.
Should we have Driver's Ed for AI?
Would you hand your fifteen-year-old the keys to your $40,000, 4,000 lb block of metal known as your Tesla ⦠without any safety instructions on how to protect themselves and those around them as they drive? Would you allow them to discover that freedom (creativity) and independence (productivity) without some basic Driverās Ed or Learnerās Permit?
Mohammad Khan and I got on the call to talk about writing. As we segued to talking about the impact of AI on writing, and a previous conversation with my niece who was sitting her driving test, the thought appeared āWhy are we not doing Drivers Ed for AI?ā As if the Internet heard my call, the next day there was an excellent actions-packed thinkpiece by Nate titled āThink of it like Driverās Ed but for AI.ā
What lessons of the rollout of the Internet and smartphones do we want to avoid repeating, inspired by the Jon Haidt book Anxious Generation. This will not be my last conversation on staggering access to AI for everyone - particularly teenagers - requiring them to show AI navigation basics.
Lee Arnold responded with exactly the next level questions I was hoping this article would trigger: On the question of AI: Since the drivers of it are making money hand over fist with this stuff, the last thing they are concerned with are the consequences of it. To a man, they tell us to adjust - yet we have no framework to know what weāre supposed to adjust to, or how to do so.
Theyāve let the tigers out of their cages, then tell us to deal with it. So I think what youāre doing here is great. Yet shouldnāt it be incumbent on them to educate the public about what to do with it? How about them shoveling a few of their billions to universities for mass AI ed programs?
They donāt do this because hereās my take - they donāt know any more what the consequences of any of this is than anyone else.
Iām not opposed to this. Itās that the spearheads of this have to really lead, and lead from the front - not from behind.
Ved Shankar noted: I really like the driver metaphor with AI. I don't think Nate's tips on anchoring to reality are limited to just kids to be fair. (Ved, I agree with you. A very noteworthy article to read.)
Meeting real people in real life! Internet Serendipity Tour - Toronto edition
Real conversations. With REAL people. Longer than 40 minutes on a Zoom call!
When you have an in-person conversation with someone you discover:
They are not 2x2 inches tall.
They are multi-faceted. Our online interactions are usually centered round a very narrow part of the total person.
It was a treat to get comments from new friends Michelle Hsu and Marvyn Paul (who liked my library stack metaphors!) I really enjoyed your piece! Looking forward to more
But I am particularly proud of getting a comment back from the master organizer himself David Nebinski : I love this write-up! Thanks for coming, Karena!
Did you attend a Serendipity Tour City stop? Send us a link to your writeup.
āWrite about that!ā inspired A conversation with Emma Dorge on how I was planning this cycleās theme inspired this editionās topic which
My frustrating experimentation with AI art drew some comment!
But it was the Rest conversations that drew more interaction
Ved Shankar was sharing the ideas and philosophy forward: I was suggesting something similar to a friend who is burning out (via a sabbatical) but it met a lot of resistance because there was too much in his life to take a pause from atm (freshly married, new responsibilities in a job)
and James Bailey was particularly struck by the simple visual on replenishing our personal battery. He wrote: āChoose when you recharge. Or you will be forced to.ā
All of us at work are spent and are either burned out, or on the edge. We recently did our business planning for 2026 and set goals that were 1/2 of what our goals were for 2025 and what we achieved. The reason, we need to have an energetic and sustainable foundation which to operate our business.
I realized when I read the quote above, that it may not be enough. Iām going to revisit our plans with our leadership team and make sure we still arenāt biting off more than what is presently called for.
Thank you Ved and James!!!
We closed with the bonus Christmas blessing edition - with a plea and a prayer for Peace on Earth:
My Word of the Year 2026:
I have selected a word in recent years that guides my decisions and shapes my thinking. 2025=COMMUNITY 2024=10XABUNDANCE 2023=HellYEAH 2022=NO ā¦
This year, I chose a vector setting. It aligns with the āarrowā in my logo:
My vector setting for 2026: You CAN dream big. And you CAN inspire others, too.
I am always curious to discover the resolutions, goals or words that others have picked. Share them here:
Sarah Seeking Ikigai ⦠I just saw your lovely article on this topic!
Do you like the concept that every 7th edition is a Rest edition? These digests make a great issue to share with others as you invite them to join our Tribe of difference-makers.
Our small and supportive community in Tribe Tilt believes in the best of humanity - connecting people, sharing ideas, and exploring thoughts respectfully. We believe we can make a difference to the people and places that are precious to us. The best idea can come from anyone, anywhere, at any time.
Until then, stay healthy. From there, all else becomes possible.
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See you next week!
Karena













Karena!! I love this:
"You CAN dream big. And you CAN inspire others, too."
You personify this by just being yourself!
I'm thinking that my vector is: "Slow down, to speed up." I'm feeling that 2026 is about deeper, not faster.
I'm grateful we are in each other's lives ā¤.
I so appreciate you empowering human connections with this conversational format Karena. It was like going on a walkabout with you through the Substack neighborhood and stopping in at the residences of friends for a chat.