In partnership with
8 bits for a Byte: As the year closes, I want to start with something simple and true:
Thank you.
To you—the readers who reply, forward, challenge, and encourage. To friends and family who put up with the obsession and the late nights. To the builders and leaders who keep showing me what "real work" looks like.
AI Quick Bytes has been a place where I've been thinking out loud—sometimes clumsily at first, then with more clarity over time—about one question that won't leave me alone:
What does the AI–human Venn diagram of collaboration actually mean? And how can we use AI as a tool to make our best selves more possible?
Two years of writing. Two years of learning in public. And a professional direction shift that honestly surprised me.
Scroll down to Bit Eight and tell me what you think—your feedback shapes what I build next.
Book a Coaching 1:1 Call With Me
Walk into your next leadership meeting with a plan—not a pitch for more time. In one 30-minute session, I'll help you build a 10-page Strategic Implementation Framework tailored to your company'...
Let’s Get To It!
Welcome To AI Quick Bytes!
Bit 1: A PERSONAL NOTE, FROM THE HEART
Happy Holidays Byters! This year had real highs and real lows.
My brother passed. There's no clean sentence for that. Just grief, and the way it reshapes your sense of what matters.
We put two dogs down. That kind of loss is quiet but heavy—it changes the feel of a home. On the flip side, we adopted Schmidty from the SPCA, and my heart is healing.
My son graduated college and landed a job in his fall semester. He's thriving on the East Coast. I'm proud of him in the way that makes you pause and realize time is moving. (Yes—my ongoing goal is still to lure him back closer to San Francisco.)
And somewhere in the middle of all of it, I had a realization I'd been avoiding for years: I modeled my pace of life on Anthony Bourdain—restless, always moving, always chasing the next experience. That pace isn't sustainable.
Bit: Ambition doesn't require burnout; the next chapter requires a foundation.
So it's back to the basics. The good basics: Yoga. Hiking. Meditation. Pickleball. Boogie boarding. Skiing.
My son challenged me to run a half marathon by June. I've challenged myself to be ready to go all out skiing in Switzerland in 2027. And I've had to face my last remaining vice: I love to eat. If I want to build what I feel called to build, I'm going to train and eat like an athlete.
Because I still believe something that's also true: One day, I will be an overnight success. But it will have taken me 30 years to get there.
Build real AI and tech skills, faster
Udacity helps you build the AI and tech skills employers actually need—fast. Learn from industry experts through hands-on projects designed to mirror real-world work, not just theory.
Whether you’re advancing in your current role or preparing for what’s next, Udacity’s flexible, fully online courses let you learn on your schedule and apply new skills immediately. From AI and machine learning to data, programming, and cloud technologies, you’ll gain practical experience you can show, not just list on a résumé.
Build confidence, stay competitive, and move your career forward with AI and tech skills that are in demand.
Bit 2:
Quote of the Week:
Bit 3: THE LEARNING FLYWHEEL
Alvin Toffler said the illiterate of the 21st century won't be those who can't read and write—but those who can't learn, unlearn, and relearn. That idea has become my operating system.
Here's what I've experienced firsthand:
Writing leads to learning.
Learning leads to creating.
Creating leads to better writing.
A loop. A flywheel. A compounding engine.
AI doesn't make you smarter; learning to learn makes you smarter—AI just accelerates the flywheel.
This is one of the most important opportunities for knowledge workers this century: not just to "use AI," but to work in ways that compound.
ACTION BYTE: Identify one skill you want to develop in Q1. Write about it weekly—even 200 words. Watch the flywheel spin.
Bit 4: THE FORGETTING PROBLEM
Here's the thesis I'm walking into next year with:
We don't have an "AI problem." We have a forgetting problem.
Most organizations aren't stuck because the models aren't powerful enough. They're stuck because they can't hold onto what they already learned.
The "why" disappears.
The tradeoffs get lost.
The assumptions fade.
The same decisions get relitigated.
Work gets re-done—quietly, endlessly—until everyone is busy and nothing compounds.
We have more information than ever: docs, decks, Slack threads, tickets, recordings. But when you need the one thing that matters—how a decision was made—it's missing.
Bit: Information isn't understanding; decisions that don't carry forward cost you twice.
That creates a tax every knowledge worker pays: the context tax.
Three Key Takeaways:
Alignment meetings multiply when institutional memory fails
Strategy gets rewritten instead of refined—compounding stops
Confusion masquerades as "communication issues" when the real issue is lost context
AI won't fix this by generating more content. It fixes it when it helps us preserve understanding—so decisions actually carry forward.
ACTION BYTE: This week, pick one recurring decision in your org. Document the "why" behind the last call—tradeoffs, constraints, assumptions. Save it where your team can find it.
Bit 5: WHY THIS WON'T BE ADOPTED TOP-DOWN
One more thing I'm confident about: This isn't "enterprise AI" in the way most people mean it.
The next era of tools won't be deployed first. They'll be chosen.
Remember the early days of Slack? IT didn't roll it out. Teams adopted it because it made them faster, clearer, less exhausted. Then organizations did what they always do: they standardized what their best people were already using.
Bit: Adoption doesn't start with procurement; it starts with one person solving a real problem.
That's the adoption curve I'm building for:
Bottom-up.
Human-first.
Work-first.
Not procurement-first.
Bit 6: Monday Funnies
Stop planning. Start building. With beehiiv, this the end of the year is a great time to get ahead. Build a website with AI, launch a newsletter in minutes, and start earning through the Ad Network. Use code BIG30 for 30 percent off your first three months. Start building for 20 percent off today.
Bit 7: WHAT I’M BUILDING
I’m not sharing the mechanics yet. I’m sharing the problem, because it’s universal.
What’s missing isn’t another productivity tool.
What’s missing is a knowledge working environment that preserves context over time.
Bit 8: YOUR INPUT REQUESTED
If AI / Human context decay is a familiar pain—click below and share one example of where it fails today, and what you wish improved. I’m collecting patterns.
Until next time, take it one bit at a time!
Rob
P.S. Thanks for making it to the end—because this is where the future reveals itself.
