TWA-006 · Hurrah! Membership is open!

Hey hey,

The last few weeks have been rough :(. But productive :).

I’ve been juggling health issues at home while landing big projects at work, and practically that looked like shutting out the world and not sleeping much. I was extremely focused and heads down: working, building, running (not enough), or tending to the family. I kept up an intense pace for a handful of weeks, and now I’m taking some time to sleep more, eat better, and recuperate.

Thankfully, all the stressors are resolved now, and I have more headspace for pushing forward on my personal projects. Starting with this one:

🎉 Thriving with AI Membership is live! And y’all get first dibs on the founding member bennies.

Why a membership

I want to build a community around, and offerings for, folks using AI to Thrive. I have lots of ideas for what would be valuable, and offering a membership allows folks to support me while I support them on their path.

I want a place to work on Thriving with AI together, with real purpose and projects instead of hypotheticals or hype slop. So my first offering is a dedicated place and time to do just that.

First up: office hours

Membership starts with live office hours with me. Thirty minutes, 8 to 8:30 AM Pacific, alternating each week between two tracks - @Work and @Home.

@Work for making progress on your own work: writing, research, a useful tool, a better way through a recurring task. No technical title required.
@Home for making more room in everyday life: planning, organizing, understanding your finances, exploring an interest.

One membership covers both tracks. Come to either or both.

Every session opens with a few minutes on recent AI developments - what happened, what matters, and what you can safely ignore. Then we get into questions and try things together, including 5-10 minute hot seats on one specific challenge. I’ll bring what I’m working on and learning, including the parts that didn’t go so well. Bring what you’re tinkering with, try an example I’ve prepared, or just listen in.

I imagine this to be valuable in 4 distinct ways:

Keep up with what’s changing in AI, what matters for you, and what you can safely ignore.
Ask your real questions in a safe space, and learn what’s relevant to you rather than what’s trending.
Get inspired by what I and other members are actually building, including what didn’t work.
Make progress with a standing time and place, and people expecting you, to push your own projects forward.

The first @Work session is Tuesday, November 3. The first @Home session is Thursday, November 12. The full schedule is on the page, holiday shuffles included. Members get the calendar invitations automatically when they join.

More member offerings are coming in 2027. Office hours are just the start.

Founding members

Inspired by 1000 True Fans (opens in a new tab), no 100 True Fans (opens in a new tab), and taking into consideration its critiques (opens in a new tab), I want to honor those who jump in from the get go.

The first 100 people to sign up are founding members, and they get two perks for as long as they stay subscribed:

$10/month instead of $18.
50% off future member offerings through ThrivingHenry that aren’t already included in your membership (consulting and coaching excluded). (And because I hate coupons and always forget codes, your discount auto-applies at checkout. Big NO to marketing bullshit that actively disrespects loyal supporters.)

After those 100 spots, membership jumps 80% to $18/month. After there are enough offerings, it’ll be even more.

Check it out and let me know what you think.

In motion

Everyone I know, in one place

I’m consolidating people across all my different networks into a single database. It has been a shockingly complex task: compiling everyone from every walk of life into one secure database, with interaction timelines from every channel I use (email, texts, WhatsApp, LinkedIn, Circle). I’m about 75% done. The next big lift is merging duplicate records and pulling out vendors, so what’s left is a clean list of real people I’ve had at least one meaningful interaction with. I’ll do a proper writeup when it’s all said and done.

The xkcd comic "Chat Systems"

xkcd: Chat Systems (opens in a new tab)

One stream for all my comms

Staying current on all my comms channels is the single biggest, and most chronic, stressor in my life. I constantly feel like I’m letting people down … because I truly am. I hate losing the thread, and I know it’s a miserable experience on the other side. My inner circle isn’t immune either - I’m an equal opportunity terrible replier. It’s shitty for others, and it weighs incredibly heavily on me.

And yet nothing I’ve tried in the 10+ years I’ve been aware of this has produced meaningful, sustained change. The reasons compound the crap:

My comms are sprayed across multiple channels.
A message often needs an action I can’t take the moment I read it, so “only handle it once” doesn’t work and I fall behind.
The actions vary wildly, so I can’t batch them.
There’s no clear sense of priority, and no good way to flag something for later.
Open threads are hard to track and organize into coherent streams.
There’s a ton of noise, more every month with one-time codes and spam.

So I’m building the systems and infrastructure to cut through that noise and help me do better. It isn’t live yet. I’ve been working incredibly hard on it, and even the prospect of a sustainable solution is lifting my spirits tremendously. I couldn’t be happier with how it’s turning out, and I’m pumped to share more when it’s done.

Smaller strokes from the keyboard

I’ve been honing new ways of double tapping OpenAI and Anthropic models so each builds on the other’s work.
I’ve been decently impressed with Anthropic’s harness improvements in the last week or so. Some very compelling new flows are helping me organize and land complex projects more effectively.
The knowledge base I wrote about last time keeps paying off. I’ve already gotten a lot of value from it on both personal and professional projects.

Reading

Bobby Morrison, 10 Practical Lessons From Building an AI-Native Company (opens in a new tab). I met Bobby at a networking event recently and was impressed by his depth and candor. He writes about winning converts by taking away the most boring tasks first, and building a culture where the first impulse is to self-solve. Bonus: he actually did it as CRO at Shopify.
Ilya Finkelstein, Brandolini’s World (opens in a new tab). AI is changing the game in science funding and publishing, and it’s not clear how to stop the slop.
The Economist’s run on effective altruism: the cover story, How effective altruism conquered the world (opens in a new tab); the leader, Effective altruism is this century’s biggest idea (opens in a new tab); Will MacAskill’s response (opens in a new tab); and Can effective altruists grow up? (opens in a new tab). Given all the recent hyperbolic coverage of EA, I found this a compelling and balanced discourse.
Every, Getting Started With Open Models (opens in a new tab). This is a very practical guide to running models outside the big labs’ apps. I’m not quite there yet. I will be in the next 3-6 months, and I really appreciate the nuts and bolts of this piece.

OK, that’s an outlier letter in length. A lot going on!

Until next week,