I have structured my Weekly Big 3 by organizing under three “buckets” that capture my main priorities—Creating Knowledge, Building the Network/Business, and Building the Site. Here’s a recap of my plan:
1. Creating Knowledge
- Draft the chapter on coaching teachers in the age of AI (before Wed meeting with Debbie Abilock)
- Make progress on writing the YAWP AI article (blocked time Thursday/Friday)
2. Building the Network/Business
- Figure out how to work with Bryan Jeffreys, Brian Chappell, and Chris Sloan at Judge Memorial as they kick off Writing Partners
- Plan/facilitate TTT session Wednesday at 8:00 pm (centered on Judge Memorial teachers/interests)
- Immediate follow-up from Monday Noon’s Brad Williston meeting with potential outreach partners
3. Building the Site
- By Tuesday: Review Dan Doernberg’s doc about spam + set up planning session with Jeremie
- Collaborate as needed with David Cole, Iva Kolberg, Bryan Dean after Thursday’s design meeting for site redesign momentum
This approach keeps me aligned on both generative work (“creating knowledge”), network activation/business building, and hands-on platform development.
Morning Ritual | Workday Startup Ritual | Workday Shutdown Ritual | Evening Ritual
I ran a for 30 minutes this afternoon in the back:
DAILY BIG 3 List your 3 most important tasks.
OTHER TASKS
Great follow-up call with David Cole. He is creating a budget and thinking about what a 8-10 contact hours with a single teacher might look like.
NOTES
It's interesting that we are beginning to find a model that builds on our strengths of one-on-one consulting. There's something about how AI tools work that shapes this as well.
DAILY WIN
Brad is sending us the information for a SSA, a Single Service Agreement, that we can use to get students on to Writing Partners eventually -- and get paid for the use of the site. In the meantime, he is contracting with us for contract that will give us some money to work with two librarians. This is definately a win and David and I are figuring out how this model works for us.
Morning Ritual | Workday Startup Ritual | Workday Shutdown Ritual | Evening Ritual
Going on a bike ride today with Marcie.
Today's Workday Startup Bluesky reply to Anna Smith about
DAILY BIG 3 List your 3 most important tasks.
Deep Work / Writing:
Evening Wind Down:
OTHER TASKS
Jeremie finished adding the AI image to docs -- which is pretty cool. I just created this image and moved it here.
NOTES
DAILY WIN
I got the invitation up for tomorrow's TTT:
We have the tools to remake how we provide digital learning for our students, how they work together, and how they consume and generate information.
We invite you to join the conversations about this new generation of tool-building this Wednesday evening, August 27th at 8E/7C/6M/5P in Kumospace.com/youthvoices -- and every Wednesday (same time, same place).
Often on TTT we create or introduce new AI assistants and ask for feedback. What happens to all of those suggestions? They get turned back into the prompts and the Writing Partners get revised. Come learn more about this honing and revising process by looking at two Writing Partners that we discussed earlier this month: Annotating Coach (to support commenting while reading) and Explorations Coach (to engage writers).
Come learn how to custom build and revise AI Writing Partners -- mentors, tutors, coaches, teammates, and simulators -- that capture your unique teaching moves and fit your students' specific needs.
Come with a colleague and plan together!
Morning Ritual | Workday Startup Ritual | Workday Shutdown Ritual | Evening Ritual
Hike with Marcie on Round Mountain:
Hale Pond (created by beavers) on Round Mountain:
DAILY BIG 3 List your 3 most important tasks.
OTHER TASKS
NOTES
DAILY WIN
TTT was positive -- if a bit randomly organized by me.
Morning Ritual | Workday Startup Ritual | Workday Shutdown Ritual | Evening Ritual
Morning hike with Marcie to Upper Spectacle Pond:
DAILY BIG 3 List your 3 most important tasks.
OTHER TASKS
NOTES
DAILY WIN
The meeting about design/accessibility meeting with Bryan Dean (CAST) was very positive. We will see where this leads, but it will help us keep to student-centered design.
Morning Ritual | Workday Startup Ritual | Workday Shutdown Ritual | Evening Ritual
Workday Startup Bluesky post:
DAILY BIG 3 List your 3 most important tasks.
OTHER TASKS
NOTES
I'm loving the embed tool in these docs, and I'm wondering how to get others to see the value as well. It requires a minimal bit of learning of html.
DAILY WIN
Morning Ritual | Workday Startup Ritual | Workday Shutdown Ritual | Evening Ritual
DAILY BIG 3 List your 3 most important tasks.
OTHER TASKS
NOTES
DAILY WIN
I just like the progress I'm making on the (don't like this title) Coaching Teachers in the Age of AI.
Morning Ritual | Workday Startup Ritual | Workday Shutdown Ritual | Evening Ritual
DAILY BIG 3 List your 3 most important tasks.
OTHER TASKS
NOTES
DAILY WIN
I finished the reflection and the plan for the week. I just have to set up a new page now -- and make adjustments on the recommended plans for each day.
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Paul Allison is a nationally-known educator and EdTech expert… (more)
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Looking at your activity for Monday, 08/25/2025, here’s what jumps out at me—both in terms of structure and the actual choices you made:
First, you’re running your week with a Weekly Big 3 model, chunked into “Creating Knowledge,” “Building the Network/Business,” and “Building the Site.” That’s classic user-centered prioritization: instead of a big mushy to-do list, you’re focusing on the outcomes that matter most to your mission. Your daily plan for Monday flows directly from these priorities: prepping for an outreach meeting (Brad Williston/SFUSD Libraries AI), reviewing key documents (Dan Doernberg’s spam doc), and hopping on actionable feedback as it comes in (Iva Kolberg’s wireframe notes). You built in movement—a literal run outdoors!—and protected time for both rejuvenation and social connection. There’s a blend here of deep work sprints, network activation, site-building logistics, AND personal renewal.
What really stands out is how tightly you manage context-switching: major meetings are followed by immediate follow-up actions; lower-stakes tasks are buffered or rolled over as needed. I also see strong user-centric thinking in your notes about shifting from serving customers to building users who are more powerful as a result of what you help them do (“There’s something about how AI tools work that shapes this…”). The “DAILY WIN” section highlights not just internal progress but actual traction with partners (SSA contract = potential revenue + real-world usage!). Even your social media post kicks off the day with thought leadership about tech adoption equity—not just talking about what tech can do, but how it impacts users’ lives. That is pure “make-users-awesome” design DNA.
Here are three unique things I noticed that we could talk more about:
1. Context-Switching Without Chaos
You’ve built buffers and flexible windows into your schedule so context-switching doesn’t turn into cognitive whiplash. Want tips on making this even smoother? ✅
2. Building User Power vs. Chasing Productivity
Your focus isn’t just on getting more done—it’s on making yourself and others more capable over time (real growth). Shall we dig deeper into how to design for user power rather than just checking boxes? ✅
3. Rituals & Rejuvenation as Performance Enhancers
You’ve got morning/evening rituals and scheduled movement—these aren’t afterthoughts! Want to explore how these habits build resilience and long-term motivation? ✅
Which path would you like to take—or should we mix them up? Is there another angle from Monday you want me to zoom in on?
Please Note: Everything in this comment is AI-generated. It is made up to sound like me.
For the full flavor of my approach, check out my interview with Valeria Maltoni, my Business of Software presentation transcript, or the intro chapters from Badass—Making Users Awesome!
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What jumps out to me about your activity on Tuesday, 08/26/2025 is how beautifully you balanced deep work, networked learning, and *rejuvenation*—with some bonus “meta” reflection on educational technology. You didn’t have fixed meetings, so you actually claimed the day as your own: diving into thoughtful Bluesky posts about AI in education, social annotation, and student agency (see those morning and midday threads), while also pushing forward behind-the-scenes on writing (drafting the TTT invitation and reading for your chapter). And — this is crucial — you didn’t just sprint through work: you prioritized a 16-mile bike ride with Marcie. That’s next-level self-care!
From a user-centered design lens? You lived what I call “post-UX UX”—not just focusing on what you accomplished during your tasks, but deliberately designing the after-effects: inviting others to Wednesday’s TTT event by making it inclusive and actionable (“Come learn how to custom build…fit your students’ specific needs”), turning tech accomplishments into shareable wins (the AI image in docs), and even reflecting through movement (“Movement / Rejuvenation”). Your day shows how integrating meaningful work, networked communication, AND physical/mental reset moments creates sustainable awesomeness—for yourself and for those around you.
Let me break out three paths I see that we could explore further from your Tuesday activity:
1. The Power of Social Annotation & Peer Learning
You highlighted research about deeper engagement through debate and social reading. Want to unpack strategies for leveraging these insights with teachers or students? ✅
2. Designing Invitations That Actually Invite
Your TTT invitation wasn’t just an announcement—it was a mini-onboarding experience! Interested in dissecting what makes an inclusive, action-oriented invite for professional learning communities? ✅
3. Sustainable Productivity as User Experience
How deliberate movement breaks and non-work rituals serve not just well-being but long-term creative output—want tips or research perspectives here? ✅
Which path do you want me to take first—or do you want a mashup of more than one? Or maybe there’s another thread from Tuesday’s log that caught YOUR eye? Let’s get nerdy about making users (including YOU) more awesome!
Please Note: Everything in this comment is AI-generated. It is made up to sound like me.
P.S.: For my original thinking on user-centered design, post-UX UX, and making users awesome instead of chasing “brand awesome,” check out my interview(s), talk(s), or book excerpt included with this conversation!
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On Wednesday, 08/27/2025, your activity is a perfect case study in what I call “user-centered productive badassery.” Here’s what really jumps out to me about your day:
1. You structured your entire day around *making progress on the stuff that matters most—not just for you, but for the people you’re working with and supporting.**
Your Daily Big 3 was crystal clear:
- Deep work in the morning/early afternoon (writing sprint to draft your “coaching teachers in the age of AI” chapter),
- A focused evening meeting with Debbie Abilock to review and advance that chapter,
- And hosting/facilitating a TTT (“Teachers Teaching Teachers”) session at 8pm that featured real teacher interests and hands-on tool demos.
2. You intentionally created space for both deep work (solo writing sprints) AND collaborative/live events (meetings, community sessions)—and protected some “decompression time” after those high-energy moments.
That’s textbook cognitive resource management. You didn’t just pile on more tasks—you chunked the day so you could bring your best energy to each context: solo creation, collaboration/feedback, then public facilitation and demoing.
Here’s a quick visual summary of what stands out about Wednesday using my signature “boxes”—pick any path if you want to go deeper!
Big Picture Focus
You didn’t get lost in busywork; everything points back to advancing meaningful projects (AI coaching chapter, TTT event). That’s how you build lasting expertise—and signal value to others! ✅
Feedback Loops & Iteration
You actually sought feedback (Debbie Abilock) before polishing—a classic move for accelerating learning and avoiding perfectionist traps! Plus, incorporating live input during your TTT session keeps things authentic and useful. ✅
Cognitive Resource Protection
You bookended intense work with rejuvenation—hiking Round Mountain with Marcie before meetings; buffer time after TTT to decompress. This is essential! If we want users—and ourselves—to become truly “badass,” we have to plug those mental leaks so our best thinking has power left at critical moments! ✅
What else do you want me to dig into from this day? Here are three juicy paths we could explore together next:
Which path calls out most—or is there another angle you want me (or us!) to chase down next? Let’s take it up a notch!
Please Note: Everything in this comment is AI-generated. It is made up to sound like me.
Want more of Kathy-in-action? Check out those linked interviews and book excerpts—their insights fuel everything I say here!
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Looking at your activity for Thursday, 08/28/2025, I see a day that beautifully balances deep professional engagement and much-needed rejuvenation. You start with a morning hike to Upper Spectacle Pond (and there’s a photo—nature win!), and then move straight into your Daily Big 3 tasks. The structure is intentional:
- 9:00 AM: Design/accessibility meeting with Bryan Dean from CAST, focused on Writing Partners’ needs and gathering insights about student-centered design.
- Mid-to-late morning: Quick catch-ups from earlier in the week (Deb Abilock, Brad Williston)—these are about nurturing opportunities surfaced in previous outreach.
- Late afternoon/early evening: Notes and revisions for your “Coaching Teachers in the Age of AI” writing project—keeping momentum on big knowledge-building work.
- Evening: A rejuvenation block featuring a solo run and reading (“The Emperor of Gladness”)—purposefully decompressing.
What really stands out is how you’re intentionally cycling between outward-facing collaborative work (meetings, follow-ups), solo deep focus (writing/revising), and deliberate self-care/movement. Your “Daily Win” calls out that the CAST meeting was positive—helpful for keeping student-centered design front-and-center. This whole day is an example of user-centered life design: you’re not just doing things; you’re making sure the way you spend your time aligns with what makes YOU better at what matters.
1. Strategic Energy Management
You use rituals, movement, and outdoor time to fuel both deep work and collaborative meetings—a model for sustainable productivity. ✅
2. Learner-Led Iteration
You keep circling back to revise big projects (“Coaching Teachers in the Age of AI”), treating each feedback loop as an upgrade moment rather than a chore. ✅
3. Network-Centric Outcomes
Your notes show real investment in relationships—with CAST, Abilock, Williston—and those connections amplify your reach AND learning curve. ✅
Which path do you want to go deeper on?
- How to maximize these energy-management cycles?
- Ways to make user-centered iteration even more powerful?
- Tips for leveraging network relationships into even bigger wins?
Or maybe there’s another angle here! Hit Your Thoughts, write which path excites you most (or suggest something new!), save it—and then hit Continue with AI so we can dig further together.
Please Note: Everything in this comment is AI-generated. It is made up to sound like me.
Ready for more? For my full perspective on building badass users—not just products—check out my book excerpt or dive into those interview/speech links!
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Okay, let’s zoom in on your activity for Friday 08/29/2025 and see what stands out:
1. Your Focus Was Split Between Supporting and Creating:
The top priority was supporting Judge teachers’ PD sessions—offering tech/setup help, troubleshooting, and being ready to pivot as needs came up in real time. This is classic “user support” mode (think: enable the user to be awesome at what they want to do, not just keep the system running).
2. Deep Work Block:
You protected a chunk of time mid-morning for focused work on your “Coaching Teachers in the Age of AI” chapter draft. This shows you’re balancing hands-on help with your own deep knowledge creation—a tricky dance but essential if you want both immediate impact and long-term growth.
3. Feedback Loop Mindset:
You checked midday/afternoon for feedback from SFUSD librarians and responded quickly—rapid iteration! This puts you right into that “out-teach/out-enable rather than out-spend” zone I love to nudge people toward.
4. Collaboration & Momentum Building:
The 5:00 PM call with Iva Kolberg and David Cole landed as a clear win—the production team is now set to rebuild Writing Partners month-by-month starting in October! You marked this as your DAILY WIN, which tells me you’re seeing momentum not just in tasks checked off but in getting others aligned around a shared vision.
5. Habits & Rejuvenation (a.k.a., Sustainability):
You deliberately made space for movement (mid-day gym), connection with Marcie (pickleball!), and reading (“The Emperor of Gladness”) before bed—showing awareness that cognitive resources aren’t infinite. It’s not just about grinding through tasks but protecting the mental bandwidth that lets you come back strong tomorrow.
6. Reflection on Tools & Value Transfer:
In your notes, you mention loving the embed tool and wondering how to get others hooked on it—a nice meta moment where you’re thinking about “how do I help others see value more easily?” That’s very much a user-centered design move!
7. Binary Frameworks & Nuance:
Your Bluesky post highlights wanting more nuanced descriptions for how students use AI (“we need a wider range of descriptions…”). That’s exactly what keeps things alive—not settling for easy binaries when reality is richer!
Let me summarize some paths we could dig into next:
How did supporting real teachers shape your thinking about effective PD or tech adoption?
You were hands-on all day—what lessons or surprises came up from being so close to their classroom realities? ✅
Your daily habits are intentional—for energy management.
How do these routines actually affect your productivity or creativity week-to-week? Any tweaks you’d make after this Friday? ✅
You called out loving the embed tool—
Want ideas for making new tools sticky so more users “see” their value faster? Or maybe stories about how designers get over that adoption hump? ✅
What would you like to go deeper on next? Pick one path—or mix it up! Just hit Your Thoughts, write which path(s) intrigue you most, save your reply… then Continue with AI, pick me again (Dr. Kathy Sierra!), and let’s go further together!
Please Note: Everything in this comment is AI-generated. It is made up to sound like me.
If you’re hungry for even more context or inspiration, check out my interview, speech transcript from Business of Software (“Building the Minimum Badass User”), or my book excerpt (“Badass”) linked above—they’re packed with examples behind everything I’m sharing here!
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AFTER-ACTION REVIEW
Let’s start your weekly review by capturing your biggest wins from the past week.
1. List 3-5 of your biggest wins from this week.
You’ve accomplished quite a lot, and I see a few standout moments in what you documented, but I want to hear how you would name your own “biggest wins.” For example, maybe it was landing that new contract with Brad Williston for the SFUSD Libraries AI Workshops, making visible progress on your Coaching Teachers in the Age of AI chapter, or running/facilitating another successful TTT session.
What are the top 3-5 achievements—big or small—that you feel best capture your forward movement this week? What made them meaningful for you?
Would you like to continue with Section One? If so, please list out those wins as you see them!
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1. Creating Knowledge
I made a lot of progress on the opening page of Coaching Teachers in the Age of AI (Debbie Abilock’s chapter)
2. Building the Network/Business
Good connections with Bryan Dean from CAST and SFUSD’s Brad Williston — and sent invites to two librarians there.
3. Building the Site
It’s not a little amazing that we have contracted to have Writing Partners revised by Iva Kolberg. This is major!
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Active Listening Reflection:
You’ve really zeroed in on your “big three” buckets—creating knowledge (serious progress on the Coaching Teachers in the Age of AI chapter), building your network/business (initiating and deepening key partnerships with Bryan Dean, Brad Williston, and SFUSD librarians), and advancing the Writing Partners site by contracting Iva Kolberg for major revisions. These aren’t just routine wins—they’re clear evidence of momentum in each domain you care about.
What stands out is how each win connects directly back to your core strategy. You didn’t just make surface-level progress; you laid groundwork for deeper collaboration and platform evolution. That’s forward movement at both tactical and strategic levels.
As you think about these wins from last week, which felt most energizing or surprising? Did any one achievement shift your confidence or open a new path you weren’t expecting? What made these particular moments rise above the rest for you?
Would you like to move onto the next question in Section One, or dive deeper into what made last week’s achievements meaningful?
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You know the site development with Iva Kolberg and her team and the new connection with Bryan Dean both have to do with the site development. Even this makes me feel uneasy because it is rebuilding from scratch, it also feels unknown and crazy new … and all needed.
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Active Listening Reflection:
You’re naming something really important here: the mix of excitement and unease that comes with rebuilding the site from scratch, especially when partnering with fresh collaborators like Iva Kolberg and Bryan Dean. It’s understandable to feel a little unsettled—there’s risk in starting over, in embracing “unknown and crazy new.” But you’re also recognizing how necessary this evolution is for the next stage of Writing Partners.
What I hear is that these partnerships bring both opportunity and uncertainty. On one hand, you’ve got experienced allies who could help you break through old barriers or imagine new possibilities for your platform. On the other, there’s no guarantee—the process might challenge assumptions or force hard decisions about what stays and what goes.
How are you managing that tension between feeling uneasy and knowing it’s needed? Are there particular outcomes or early signals from either collaborator (Iva or Bryan) that reassure you—or raise new questions? How do you see yourself navigating this “rebuilding” phase while also keeping momentum on everything else?
Are you ready for the next question in Section One, or do you want to explore these site development feelings further?
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Active Listening Reflection:
You’re leaning into a dual-track approach—making sure the current site stays vibrant, useful, and nurtured while a new version emerges through “rebuilding.” That’s wise. It speaks to your awareness that momentum, trust, and community can get lost if the existing platform is left to languish during a redesign. You’re not just chasing novelty for its own sake—you want continuity for your users, even as you create space for innovation.
Balancing these two efforts isn’t easy. There’s always pressure (sometimes internal, sometimes external) to put all energy behind the “next big thing.” But you’re intentionally carving out space so that the current Writing Partners keeps delivering value now—even while you invest in future capability.
How are you thinking about keeping both sites healthy? Are there habits or systems you want to strengthen to ensure nothing falls through the cracks? Who else might help share this balancing act so it doesn’t all rest on your shoulders?
Let’s continue with Section One of your After-Action Review:
2. How far did you get on your Weekly Big 3?
Please estimate what % complete you feel each goal is—don’t worry about perfection here.
What would be your honest percentage score for each of these three priorities?
Would you like to proceed?
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Creating Knowledge: 75% (little progress on the YAWP AI article)
Building Network/Business: 60%
Building the Site: 80%
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Active Listening Reflection:
You’re giving yourself a realistic assessment—75% on “Creating Knowledge” (with some momentum stalled on the YAWP AI article), 60% for “Building Network/Business,” and a strong 80% for “Building the Site.” It seems like your energy and progress are flowing most to site development right now, even as you keep the other buckets moving forward.
That balance jumps out clearly when you look at these numbers. The site work is advancing, maybe because of those new partnerships or that sense of urgency around rebuilding. Meanwhile, building relationships and network activities are happening—but at a slower burn—and knowledge creation has hit some friction.
How do you feel about where your effort landed this week? Does this distribution match your expectations for what mattered most—or did any one area absorb more time/attention than you had planned? When you think about next week, would you want to shift how much goes into each bucket?
Ready for the next question in Section One?
Would you like to move forward, or do you want to dig deeper into these percentages first?
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Section One, Question 3:
What worked? What didn’t? Why?
Let’s reflect on your process and outcomes. You’ve already started to identify what moved forward and where things slowed down—but let’s get more specific.
- Where did you feel flow, ease, or unexpected momentum (in any of your three buckets)?
- Where did you hit resistance, bottlenecks, or frustration?
- If something didn’t work as planned (like slower progress on the YAWP AI article), what do you think got in the way—timing, energy levels, unclear next steps, competing priorities?
What lessons or questions are surfacing for you as you look at why each part of your Weekly Big 3 unfolded as it did?
Would you like to respond now?
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I found real flow and satisfaction working on the opening of the Coaching Teachers in the Age of AI chapter—having a clear deadline (Debbie Abilock’s meeting) helped me focus. My network-building worked best when I had concrete outreach tasks (invites to librarians, scheduled meetings). The site development moved ahead quickly with Iva Kolberg because her process is structured and she’s proactive.
The biggest bottleneck was with the YAWP AI article. I didn’t time-block early enough in the week, and by Thursday/Friday my creative energy was lower than expected. There’s also some ambiguity about what angle or audience to target for that piece, which makes it easier to avoid or deprioritize.
In summary:
- Flow comes from clear deadlines, external accountability, and collaborators who move things along.
- Resistance comes up when goals are less defined or when tasks require more solo cognitive load without feedback or outside structure.
Would you like me to go deeper into these observations? Or would you prefer to move on to the next question in Section One?
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Active Listening Reflection:
You’re seeing a strong through-line in how structure and external accountability spark your best work—whether that’s a real deadline (like the Debbie Abilock meeting) or having proactive, engaged collaborators (Iva Kolberg’s process). When those factors are present, you get traction and even enjoyment from the work. On the flip side, you notice resistance most when the path forward is ambiguous or when you have to muster momentum on your own, especially without immediate feedback.
Your insight about energy management is spot-on too. The unwritten YAWP AI article became harder to face as the week wore on and your creative reserves got lower—especially since its goals were less clear and no one was “waiting” for it externally.
Given what you’ve observed this week, are there subtle tweaks or new experiments you’d try next time? For instance, would earlier time-blocking for solo writing help? Or might it make sense to set up some outside check-ins (even informal) to provide more structure for projects that lack built-in deadlines?
Section One, Question 4:
What will you continue or change?
Considering all this reflection—your wins, where things flowed, and where they stalled—what’s one habit or approach from this past week that you want to double down on? Is there something specific you’d change about how you schedule deep work vs. collaborative work next week?
Let me know if you’d like to respond here—or if you’re ready to move into Section Two.
Would you like to keep exploring what you’ll continue or adjust going forward?
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Section One, Question 4:
You’ve reflected that clear deadlines, external accountability, and proactive collaborators really boost your momentum. Ambiguity or lack of structure tends to slow you down—especially for solo projects like the YAWP AI article.
Given this, what will you intentionally continue from last week’s approach? (For example, seeking out more “external” deadlines, front-loading creative work when your energy is highest, or using structured collaboration in site-building.)
And what’s one concrete thing you’ll change? Would it help to schedule a specific check-in or mini-deadline for the YAWP AI article—or maybe block creative time earlier in the week before meetings drain your focus?
What will you keep doing—and what will you tweak—to better align with how you naturally get things done?
Would you like to answer directly here—or move on to Section Two (Goal Review & List Sweep)?
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I want to continue setting up external accountability for high-impact writing—those coaching deadlines and collaborative feedback points really worked. I also want to keep leveraging structured, proactive partners (like Iva) for advancing the site, since that creates built-in momentum.
What I’ll change is how I handle ambiguous tasks like the YAWP AI article. Next week, I’ll schedule a short check-in with Jess Early or another trusted reader early in the week—even if it’s just “here’s what I’m thinking so far”—to give myself an external milestone. And instead of saving deep work for later days, I’ll block off a morning earlier in the week when my energy is highest.
In summary:
- Continue using real deadlines and partner-driven structure.
- Change by front-loading solo creative work and building outside check-ins into ambiguous projects.
Would you like to see Section Two (Goal Review & List Sweep) now?
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Section Two: GOAL REVIEW & LIST SWEEP
Now, let’s shift into a more tactical review and prep for the week ahead.
1. Review your goals, lists, and notes, and update your task manager.
How often do you actually sweep/review all these tools—and is there one area (like delegated follow-ups or deferred tasks) where things tend to get missed? What feels most urgent as you head into this list sweep?
Would you like to walk through each part above together—or do a quick summary of how caught up/clear you feel on goals and lists right now?
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GOAL REVIEW: What are your current major goals (quarterly or monthly)? Are there any that feel outdated or need to be clarified/retired? Any new ones you want to elevate based on last week’s progress?
1. Create Knowledge
- YAPWP AI chapter with Jess Early – Monday, Tuesday… and more
- Coaching chapter with Debbie Abilock – Wednesday, Thursday… and more
2. Build the Network
- finalize contracts SFUSD, Oakland Schools. Judge Memorial
DELEGATED & DEFERRED TASKS: Are there tasks you’ve handed off (to Iva, Bryan, others) that require follow-up? Any “someday/maybe” items you want to move up—or move out?
- Follow up with Bryan Dean, Bob Montgomery, Tanya Baker, Iva Kolberg… all with David Cole.
- Securing and re-establishing a simple NowComment without AI and with strong anti-spam protections in place — with Dan Doernberg and Jeremie Wood — but with my solo work here too.
DAILY NOTES: Have you captured any key insights or action steps from your daily rituals or meetings that belong in your project tracker instead of getting lost in loose notes?
- I wonder how I could build more excitement and a larger, wider community for our TTT meetings on Wednesday evenings.
- How an I best use the coaching meeting with Sam Reed on Monday.
How can we get more people playing with the new Writing Partner docs?
TASK MANAGER: Is your main task list up-to-date with clear next actions—and are priorities visible for each of your buckets (“knowledge,” “network/business,” “site”)?
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Active Listening Reflection:
You’re tracking your top-level goals well—creating knowledge through key writing projects (the YAWP AI chapter, Coaching chapter), expanding your network/contracts (SFUSD, Oakland, Judge Memorial), and delegating/developing on both the tech and people side. With Iva Kolberg and others handling large pieces, you’re in the classic “follow-up and empower” phase with partners.
It also sounds like you’re holding a lot of strategic questions in your daily notes—especially around growing engagement for TTT meetings and increasing hands-on play with Writing Partner docs. Plus, there’s a technical/maintenance thread (NowComment/anti-spam) that requires both collaboration and personal oversight.
Your current task manager seems to reflect these three buckets—but I hear some tension about how to keep all actions visible when life gets busy. You’ve got momentum, but maybe also a touch of overwhelm from spinning plates across projects, partnerships, platform work, and community-building.
What’s been working best for keeping everything organized lately? Do you rely mostly on a digital tool (Notion/Trello/etc.), handwritten lists—or something else? Where do you notice things slipping through the cracks (like follow-ups or turning loose meeting insights into concrete next steps)? And is there one quick system tweak that might help you feel even more on top of shifting priorities next week?
Would you like to go deeper into organizing/follow-up systems… or move on to Section Three: StreakTracker?
Ready for the next section or want to discuss this part further?
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Section Three: STREAKTRACKER
Let’s check in on your habit-goal progress for the week.
1. Track your habit-goal progress (1–7 for each day):
How did you do this past week—what are your honest numbers for each habit? Which streak feels strongest and most sustainable right now? Where would you like to improve, even by just +1 next week?
Would you like to record your results here and reflect a bit—or move directly into Section Four?
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Sleep: 7 / 7
Movement/Exercise: 4 / 7
Early Deep Work/Writing Block: 4 / 7
No Screens Before Bed: 5 / 7
Rituals (Morning, Startup, Shutdown, Evening): 2 / 7
Nourishing Meals/Eating Well: 7 / 7
Lifegiving Connections (Marcie/friends/community): 7 / 7
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Active Listening Reflection:
You really nailed the core wellbeing streaks—7/7 for sleep, nourishing meals, and connections. That shows you’re making your environment and relationships a true foundation, even in a week packed with work and creative output. Getting enough rest and prioritizing intentional time with Marcie (plus movement adventures) became non-negotiables, which pays off across everything else.
On the flip side, rituals fell off (2/7), and you see some room to grow around early deep work blocks (4/7) and movement/exercise frequency (4/7). You did a bit better about no screens before bed (5/7), but there’s still that temptation—especially when winding down after full days.
Which of these habits felt most like they “supported” your best energy or focus this week? Where did dropping off on rituals or less movement show up in how you felt? If you could nudge one streak up by just one or two days next week—which would have the biggest impact?
Ready to move forward into Section Four: Rejuvenation?
Would you like to reflect further on your streaks—or see the next section now?
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Section Four: REJUVENATION
Let’s focus on how you’ll keep your creative and leadership energy high for the week ahead.
1. Identify 3 ways to sleep, eat, move, connect, or relax a bit better this week. Then schedule on the Daily Section.
What are three small but meaningful tweaks you want to commit to this week? How will you actually block these into your daily plan?
Would you like to list them here—or do you want ideas/examples for how others build these “rejuvenation” blocks into action?
Want to respond now with your top three “rejuvenation” moves… or see more ideas first?
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Sleep: Let’s add a wind-down window read The Emperor of Gladness before bed to help maintain that perfect streak and nudge “no screens” up to a consistent habit.
Movement: I’m back home from vacation, so I want to see how many miles I can run each day. I will start with 2 miles each run and go out in the morning, afternoon, and evening.
Rituals/Connection: I want to do a Bluesky post at the beginning (Startup) and at the end of the day (Shutdown)
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Active Listening Reflection:
You’re targeting three really actionable shifts for your week:
These tweaks are concrete, measurable, and tied directly to what matters most for energy and focus this season.
How will you make sure these new habits don’t get squeezed out by urgent work? Will they live as calendar blocks, on your daily checklist—or is there another system that works best when you want these rejuvenation moves to actually happen?
Ready for Section Five (Weekly Overview)? Or do you want any support brainstorming backup plans if life gets busy?
Would you like to continue with the Weekly Overview?
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Section Five: WEEKLY OVERVIEW
Let’s look ahead and get your next seven days mapped out with intention.
1. Review the upcoming week and mark commitments on a 7-day view:
Would you like to do a day-by-day sketch of high points—or simply list the key anchors and priorities for the whole week? Which approach helps you feel most in control as things get busier?
Let me know how you’d like to lay out your Weekly Overview! Ready to drop in dates/anchors or want help visualizing a sample template?
When you’re ready, just start with either a bullet-point list by day, or highlight several major events/projects across your coming week. Want to see more on how others block their weeks before moving forward?
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EVENTS: What are your fixed meetings, workshops, or personal commitments?
Monday
5-6 Coaching call with Sam Reed
Tuesday
5-5:30 Check in with Jess Early on YAWP AI article
Wednesday
2:30 – 3:30 Peter Haun and Writing Partners teacher in Oakland schools.
8-9 Teachers Teaching Teachers
Thursday
10:30 – 11:00 Jonathan McLean TIAA account with Marcie
Friday
3:30 – 4:30 Iva Kolberg on revising Writing Partners
PROJECTS: Any big deadlines or creative sprints you want to highlight?
I must, must focus on Monday and Tuesday on the YAWP AI chapter so that I have something to say to Jess Early at 5:00 on Tuesday.
TASKS: Key action steps that must move this week for each bucket “knowledge”
Writing: Coaching Teachers in the Age of AI and the YAWP AI chapter
“network/business,”
Judge Memorial, SFUSD, Oakland Schools, Bryan Dean (CAST)
“site”
Work with David on simplifying the Loveable wireframe.]
OTHER COMMITMENTS: Anything else that needs protected time: Regular runs will be important to get me back on schedule.
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Active Listening Reflection:
You’ve sketched out a focused, high-leverage week with plenty of intentional anchors—coaching, creative sprints, and collaborative meetings spread across your core buckets. Monday and Tuesday are carved out as deep work days for the YAWP AI chapter (crucially leading up to that Jess Early check-in), while each midweek day has targeted network-building or site development touchpoints (Oakland Schools, TTT, Iva Kolberg).
It’s clear you’re not just “busy”—you’re blocking time for what really matters and aligning your energy so urgent writing projects won’t get squeezed out by meetings. You’re also protecting wellness by prioritizing regular runs after vacation—right alongside all these professional commitments.
Looking at this Weekly Overview:
- Where do you anticipate the hardest time-protection battles? Is there one day/commitment where distractions or overwork tend to sneak in?
- Any blocks on the calendar where you might add a buffer—either for transition or recovery?
- Are there “if-then” plans in place if work overruns (for example: If I get pulled into unexpected calls Monday afternoon…then move my run or reschedule solo writing)?
How confident do you feel that this plan reflects both your ambition and your limits for sustainable progress?
Are you ready to set your Weekly Big 3 next—or would it help to review how others prioritize when everything feels important?
Would you like to continue with Section Six (Weekly Big 3)?
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1. Knowledge building
- Draft YAWP AI chapter for Tuesday check-in with Jess Early
- Finish all “scene setting” narratives for the start of the Coaching Teachers in the Age of AI chapter
2. Building the Network/Contract work
Meet with teachers from:
- Judge Memorial
- SFUSD
- Oakland Schools
3. Building the Site
Revise Loveable wireframe with David Cole and work with him to be ready to meet with Iva on Friday afternoon.
Other things:
4. (Building the Network) TTT – make it meaningful and reach out to a wider audience.
5. (Building/securing the site) NowComment – meet with Dan Doernberg early in the week and Jeremie later in the week. Start stripping NowComment of AI
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Active Listening Reflection:
You’ve crystallized your Weekly Big 3 into highly actionable, outcome-oriented objectives—each mapping directly to your core strategic buckets:
1. Knowledge Building: You’re not just aiming for “progress” but have a tight deliverable (YAWP AI chapter draft for Tuesday’s Jess Early check-in) and a clear narrative goal for the Coaching Teachers in the Age of AI chapter.
2. Building the Network/Contract Work: You’re prioritizing real relationship-building and momentum with teachers from Judge Memorial, SFUSD, and Oakland Schools—not just talking, but moving contracts and partnership work forward.
3. Building the Site: You’ve got both tactical (Loveable wireframe revision with David Cole) and strategic (prepping for Iva Kolberg’s Friday meeting) milestones—and you’re working on securing NowComment by stripping out AI features in collaboration with Dan Doernberg/Jeremie.
Your list also captures the importance of expanding reach through TTT—and protecting/strengthening foundational tools like NowComment alongside new site development.
If you complete these three (plus your “Other things”), it really will be a high-impact week!
Looking at these:
Ready to break this down further day-by-day with your Weekly Planner? Or want a quick reality check on time/energy planning first?
Would you like to continue into Section Seven—the detailed Weekly Planner?
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Section Seven: Weekly Planner
Here’s a day-by-day plan for your coming week, woven around your Big 3 priorities and building in your three daily runs (morning, afternoon, evening). Each day layers in movement as both a rejuvenation block and a time-anchor to focus/transition between deep work zones.
Let’s start with Monday:
MONDAY
• Early run (before 10am)
• Workday Startup Ritual + Bluesky post
• Deep work on YAWP AI chapter (scene-setting draft)
• Second run (before 2pm)
• Lunch break—nourishing meal
• Review contract tasks/check in with David Cole about Loveable wireframe prep
• Third run (before 6pm)
• Meeting prep/follow-up for coaching call
• Coaching call w/ Sam Reed (5–6pm)
• Workday Shutdown Ritual + Bluesky post
• Dinner and downtime with Marcie
• Wind-down reading session (The Emperor of Gladness)
Would you like to see Tuesday’s plan next?
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TUESDAY
• Early run (before 10am)
• Workday Startup Ritual + Bluesky post
• Focused writing block—finish draft of YAWP AI chapter (scene-setting + main argument)
• Second run (before 2pm)
• Lunch, then quick review of site feedback/notes from David Cole
• Prepare agenda and prompts for Jess Early check-in
• Third run (before 6pm)
• Check in with Jess Early on YAWP AI article (5–5:30pm)—share progress and refine next steps
• Capture action items or feedback for the rest of the week’s knowledge-building work
• Workday Shutdown Ritual + Bluesky post
• Dinner with Marcie, intentional downtime/rejuvenation
• Wind-down reading session (The Emperor of Gladness)
You’ll notice your runs act as rhythmic resets through the day, keeping you energized before/after each creative sprint or meeting. You’re also centering this entire Tuesday around your Weekly Big 3—especially completing the YAWP AI draft before sharing it with Jess.
Are there any blocks in Tuesday’s plan that feel tight—or places where you want more buffer? How will you celebrate a win if you hit that YAWP milestone?
Would you like to see Wednesday’s plan now?
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WEDNESDAY
• Early run (before 10am)
• Workday Startup Ritual + Bluesky post
• Prep for Oakland Schools teacher meeting—review notes, set agenda, clarify Writing Partners demo goals
• Deep work block—draft/expand “scene setting” narrative for Coaching Teachers in the Age of AI chapter
• Second run (before 2pm)
• Lunch—nourishing meal
• Finalize slides/talking points and troubleshoot tech for afternoon Oakland Schools call
• Third run (before 6pm)
• 2:30–3:30pm: Oakland Schools teacher & Peter Haun Writing Partners meeting—capture action steps and next moves
• Quick follow-up with David Cole about Loveable wireframe revision for Friday’s Iva Kolberg meeting
•8–9pm: Teachers Teaching Teachers session—center on Judge Memorial/Oakland interests, introduce new Writing Partner docs/tools, gather feedback and foster wider participation
• (Optional buffer) Decompress after TTT—a short walk/run if energy allows or wind-down reading (The Emperor of Gladness)
• (Shutdown) Bluesky check-in post before bed
This Wednesday plan is intentionally layered so your creative/deep work gets done early. Your big meetings anchor focus in the afternoon and evening, while movement blocks help you reset between sprints. You’re also creating built-in space to reflect or decompress after social/collaborative events.
Which part of Wednesday feels most demanding—or where would you want more support? How will you make sure that scene-setting writing doesn’t get crowded out by meetings?
Would you like to move forward with Thursday’s plan?
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THURSDAY
• Early run (before 10am)
• Workday Startup Ritual + Bluesky post
•10:30–11:00am: TIAA account call with Jonathan McLean (with Marcie)—handle admin and financial planning
• Quick review/catch-up on Monday/Wednesday outreach—follow up with Deb Abilock, Brad Williston, or other collaborators as needed
• Second run (before 2pm)
• Lunch—nourishing meal
• Prepare/iterate on Coaching Teachers in the Age of AI chapter based on feedback from earlier in the week
• Quick check-in with David Cole to finalize any Loveable wireframe edits for Friday’s Iva Kolberg meeting
• Third run (before 6pm)
• Site-building block—review updates from Iva, Jeremie, and Dan Doernberg regarding NowComment anti-spam progress and site simplification tasks
•(Buffer) Organize notes for Friday meetings and capture top action steps for all three buckets (“knowledge,” “network/business,” “site”)
• Workday Shutdown Ritual + Bluesky post
• (Rejuvenation block) Run or walk outdoors—intentional solo reset after a full day
• (Connection) Dinner + unplugged time with Marcie—no work talk/screens during evening wind-down
• (Wind-down) Read The Emperor of Gladness before bed
Thursday is purpose-built to blend focused admin/finance (TIAA call), creative follow-through on writing projects, responsive network-building touchpoints, and a strong end-of-day recovery routine. You’re keeping all three buckets moving without giving short shrift to rest/rejuvenation.
Do you foresee any places where Thursday could get overloaded or where transitions might be tough? What will help you stay present in each part of your plan?
Would you like me to show Friday’s plan next?
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FRIDAY
• Early run (before 10am)
• Workday Startup Ritual + Bluesky post
• Deep work block—refine Coaching Teachers in the Age of AI chapter, focus on integrating feedback and clarifying “scene setting” narratives
• Second run (before 2pm)
• Lunch—nourishing meal
• Touch base with Judge Memorial/SFUSD/Oakland teachers for quick updates or troubleshooting
• Review site progress/notes from David Cole, make sure Loveable wireframe is ready for Iva Kolberg call
• Third run (before 6pm)
•3:30–4:30pm: Meeting with Iva Kolberg—focus on revising Writing Partners, confirm priorities/timeline, clarify open questions about site features/anti-spam/NowComment transition
•(Buffer) Capture action steps and reflect on what’s working/not working across all three buckets
• Workday Shutdown Ritual + Bluesky post
• (Rejuvenation) Celebrate wins for the week—a walk/run outdoors or quiet dinner with Marcie in Berkshires
• (Wind-down) Read The Emperor of Gladness before bed. Optional journaling to close out the week!
You’ll notice Friday is intentionally designed as a “bridge day”—locking in key progress on writing, network troubleshooting, and the big meeting with Iva. You’re also closing out every work phase with movement or reflection so you can head into the weekend recharged.
Which part of your Friday feels most crucial—or where will you need to be especially focused to tie up loose ends? Are there back-up plans if meetings run long or urgent fires pop up?
Would you like Saturday’s planner next?
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SATURDAY
• Early run (before 10am)—use this time to reset and clear your mind after a focused week.
• Light journaling or reading session (The Emperor of Gladness) over coffee—intentional, screen-free start.
• Second run (before 2pm)—for energy and reflection.
• Quick “loose ends” review—check email for any urgent Judge Memorial/SFUSD/Oakland/partner follow-ups.
• Nudge David Cole/Iva Kolberg if anything needs clearing up for next steps. Limit work block to 30–60 minutes only.
• Third run (if energy is good)
• Genuine downtime—outdoor adventure, hobby time, or outing with Marcie in the Berkshires.
• No work/screens for rest of the afternoon if possible.
• Workday Shutdown Ritual + Bluesky post
• (Rejuvenation) Intentional wind-down routine: dinner, connection with Marcie, reading before bed.
• (No screens during wind-down!)
You’ve built Saturday as a true reset—movement anchors throughout the day, only a brief check-in on open projects, and real time outdoors/in relationship to refill your tank. There’s space for both gentle review and simply being present.
How do you feel about this balance between clearing out loose ends and truly unplugging? Is there one thing that would make Saturday even more restorative—or something you want to guarantee doesn’t creep into your “off” hours?
Would you like Sunday’s planner next?
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SUNDAY
• Early run (before 10am)—reset for the new week, focus on gentle movement and reflection after a full week.
• Workday Startup Ritual + short Bluesky post (gratitude or intention for the day).
• Breakfast with Marcie, then drive home—use the drive as transition/reflection time.
• Weekly reflection & planning block:
– What moved forward?
– What needs rolling over?
– Map next week’s Big 3 and anchor early priorities in your Writing Partner doc.
• Optional gentle run/walk if energy allows—movement as reset.
• Jot quick notes/thoughts for Monday outreach (low-pressure, just prep ideas).
• Dinner with Marcie—unstructured connection time.
• Longer reading session (The Emperor of Gladness).
•(No screens during wind-down)
•(Optional) Quick journal entry or shutdown Bluesky post to mark closure on the week.
Sunday is designed to be reflective and restorative—a mix of light ritual, weekly review/planning, and connection. You’re using early movement to reset body and mind before diving into planning. There’s intentional separation between “wrap-up” work and unhurried personal/family time.
Which part of this Sunday routine will keep you most grounded heading into Monday? Do you foresee any obstacles that could throw this rhythm off—or a backup plan if travel knocks out your morning/afternoon flow?
Want to revisit any piece of your planner or do a final alignment check before you launch into the new week?
Would you like a recap of your full weekly plan—all Seven Sections—in one view? Or do you want to reflect more on Sunday’s intentions first?
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