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In This Issue
The preorder is live, and the bonus is not what you’d expect. Twelve questions about you, the prompts and skills to go with them, and nothing in it asks you to be marketable.
How to hand off work you don’t know how to do. Four moves, one prompt you can steal, and how to tell whether it actually worked.
$60,000 in pitch prizes and a $130,000 A.I. job. Applications close August 9th, so time to lock in.
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Context Training is available for preorder! It publishes September 4.
The preorder bonus is the part I actually want to talk about, because it is not what people expect.
It’s called Your World, In Your Words. Twelve questions about you, the prompts and skills to go with them, and eight short videos. Spend as long as you want on any single question. Nothing in it asks you to be useful, employable, or marketable.
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You can’t teach a machine your world if you’ve never put your world into words for yourself.
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That’s the whole reason it exists. Almost every reflection exercise you get handed is really about your work. This one never asks about your work at all. If the honest answer to what you could talk about for hours is comics, the answer is comics.
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Now available for preorder
Context Training
The #1 Skill in A.I.
Teach A.I. Your World So It Stops Guessing
and Starts Working For You · September 4
Then claim your bonus, Your World, In Your Words, at seedandsociety.com/book/bonus
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Season 3 of the podcast is here too. Like how this newsletter expanded to include professionals, the show evolved to speak to them as well. A founder who has become the constraint in their own business, and a professional who wants to be the one on their team who actually knows how to use this, are solving the same problem from opposite ends. I sit in both chairs every week, and from either one it looks identical.
Something I’ve been sitting with. I’ve spent close to $300,000 across my life on professional development, and that includes my three degrees. Roughly $60,000 of it since last year, on coaching, classes, courses, and certifications. I’d spend it again. When someone teaches you, they teach you from their perspective, and they hand you something you didn’t know you needed to know.
And I applied nearly all of it. That is the only reason it was worth the money.
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Knowledge is everywhere. You cannot say you did not know.
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Which is why I don’t think information is the gap. Most of what I paid for, you could find free by this afternoon. What you can’t download is having done it.
Execution is the advantage. It’s the difference between hoping, and having.
Here’s what made that land for me. I don’t know much about SEO. I never learned it properly and I have no plans to. My blog A.I. employee does know it, and it knows my business, so it writes what my people are actually searching for. It has me ranking on Google and driving real traffic to my site. I didn’t become an SEO expert. I built something that is one, and taught it my world.
How to hand off work you don’t know how to do
Twenty years in HR makes you excellent at HR. It doesn’t make you good at selling, at scoping work so it stays inside the hours you agreed to, at marketing, or at getting an invoice out the door. Every one of those is its own domain. You either learn it well enough to run it, or you find someone who has, the same way people hire you for what you know.
Inside a company it’s the same shape with different names. You can be the best analyst in the building and still have no idea how to get your work seen.
Until recently there were two options and both were expensive. Learn the domain, which costs years. Hire someone who knows it, which costs money you might not have yet.
There’s a third now. It’s worth doing properly, because most people do it badly and then decide the tool doesn’t work.
Ask for the outcome, not the domain. “Help me with SEO” gets a generic answer, because it’s a generic question. Try this instead:
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“I want the people who need what I do to find me. Do deep research into their pain points, how they shop, and what they are already paying and searching for to solve their problem. Then make me a list of outreach strategies organized from the ones I can fully automate with A.I. to the ones that need more of my personal involvement, and the revenue potential of each.”
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Give it the part only you have. Who the work is for. What good looks like to you specifically, not in general. And what you already tried, plus what happened when you did. That last one saves the most time and gets left out the most.
Make it explain itself while it works. Ask why it made each call. You’re not trying to become an expert. You’re trying to build enough judgment to catch it when it’s wrong.
Then judge it by the outcome, which is why you started there. Is it getting you more views? Leads? Revenue? Or inversely, is nothing selling and no one engaging? Assess the data and either double down or pivot. The speed at which you can test and iterate is the fastest it has ever been, and that speed is the real advantage.
Action gives you the information you didn’t know you needed. Evidence, then confidence, then results. You can’t read your way into that sequence, because reading only ever gets you somebody else’s evidence.
| Grants & Other Opportunities |
$60,000 in pitch prizes and a $130,000 A.I. job
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AltCap Your Business 2026
What: A pitch competition, $35,000 first place, $20,000 second, $5,000 fan favorite · Cost: Free to apply · Deadline: August 9, 11:59 p.m. CST · For: Business and nonprofit owners under $500,000 in annual revenue
The application window opened July 17 and closes a week from today, so this is a this-week decision. Finalists pitch live on November 18. Past winners can’t reapply, which means the field resets every year.
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AI Training and Enablement, Neuberger Berman
What: Teaching an entire investment firm to use A.I. well · Pay: $110,000 to $130,000 · Where: New York, in office · For: Four years in training, enablement, learning and development, or internal communications
Read what they’re actually asking for: build the curriculum, run the workshops and the executive briefings, make the guides and the videos, track adoption across the firm. A global asset manager is hiring a full-time person to do Context Training™ in house. The posting asks you to make technical concepts clear to non-technical audiences. It does not ask you to write code.
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TEDxReisterstown 2026, UNBOUND
What: A speaking slot at TEDxReisterstown, Baltimore, theme UNBOUND · Cost: Free · Deadline: None posted, applications open now · For: Anyone with an idea worth eighteen minutes
The event is November 2026 and their site says apply now. Nine themes on one stage, and they describe the audience as willing to change its mind, which is the only kind worth standing in front of. No posted cutoff, so the real deadline is whenever they finish casting.
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| More Money, Time, & Options |
This Week on the Podcast
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S3 E1: Context Training: Are You Thinking Agentically?
Season 3 opens on the question underneath all of this: are you starting from the outcome and finding the shortest responsible path, or are you doing the task the way it has always been done, faster. Most people are doing the second one and calling it A.I.
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See all of Season 3 and follow the show →
Love the show? Rate it on Apple or Spotify, then grab your free Six-Figure Month Calculator (instructions included).
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🛠️ One Thing To Do Today: name the domain you keep avoiding
Write down the parts your work actually runs on. The craft you’re known for, then selling, delivering inside the hours you promised, marketing, and the back office.
Put a check next to the ones you genuinely know. Circle the one you keep avoiding.
Now hand that one to your A.I. Tell it what you’re trying to do, what good looks like to you, and who it’s for. Ask it to teach you the part you’re missing, and then to do the next step with you. You are not trying to become expert in it. You’re trying to stop being blocked by it.
If you preordered the book, Context Training, the twelve questions in the bonus are built for this kind of honesty, pointed at you rather than the business.
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