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The Red Thread This Week:
“All advice is autobiographical." — Austin Kleon
We closed out our 20 episode, season 1 run of Slackers with a builder named Keegan Knapp.
Keegan is deep in AI tooling as an active practitioner. He's spinning up synthesized executive teams in markdown files. He's running agents that scrape competitor sites every night while he sleeps. He built a web app called GrindWell.ai for his 10yr old daughter that spits out a new AI-generated golf practice session every day. It costs him three or four dollars to run.
He said something late in our conversation that now lives in my head rent free:
"All the jobs I've had now, it's because I was curious about doing the things the job entailed. A lot of what we're doing with AI is probably positioning ourselves for a job, or job description that hasn’t been written yet."
Then this week, I read a piece by Tom Webster titled "Don't Take Career Advice From Me." Tom is someone whose perspective I respect a lot. And his piece argues, more or less, the opposite of what you'd take from the Keegan conversation.
He says the optimistic AI-for-builders narrative is being delivered almost exclusively by people whose careers are insulated from being wrong about it. And the people taking that advice often can't afford to be.
I think both takes are right.
Every piece of advice you've ever received, about your career or otherwise, was a map. And every map was drawn by someone walking through their own terrain, not yours.
Some maps are useful in your territory. Some are useful in parts. Some are beautifully drawn descriptions of a country you don't live in.
The question for builders and leaders right now isn't whether AI changes your work for better or for worse, (“yes” to both btw) it's whether the AI “advice map” you're following is drawn for the territory you're actually standing in.
So the Red Thread this week is about calibrating where you are, and really considering the maps before you follow them.
~ Jaime
🔑 The Unlock
Two Jobs Pretending to Be One
I love this point that Tom made in his piece:
"Content marketing," he wrote, "is two jobs pretending to be one."
Swap "content marketing" for almost any modern creative or knowledge-work role and his point still holds up.
Coaching. Consultant. Educator. Senior marketer. Independent strategist. Specialist with a podcast. Founder running a small team.
The 1st job is strategic POV work.
Brand building. Original research. Distinctive judgment. The diagnostic conversation that changes how a client sees their business.
The thing only you can do because you were in the room.
The 2nd job is commodity production.
Landing pages. SEO writing. Slide decks. Social content. The lead magnet you update twice a year.
The tasks that fill your daily calendar, turn out deliverables, then you’re on to the next one.
Most working professionals spend more of their week on the second job than the first, regardless of what their title says or what they think of themselves as.
This pattern isn't new. It happened to journalism. It happened to marketing agencies. It's happening right now to associates at law firms whose senior partners keep insisting the work is too nuanced to automate.
The senior partners will be fine either way. The associates will not.
When a profession contains 2 jobs and a technology shift arrives, the top tier tends to survive longer than the broader labor market that supports them does.
And the people at the top, in good faith, keep handing out “advice maps” drawn from where they're standing…which is not where most of the people reading those maps are usually standing.
So the question isn't is the advice good? The question is whose situation is this advice calibrated to?
Here are the 3 positions to consider:
1️⃣ Mostly the 1st Job
If most of your week is strategic POV work — diagnosing, deciding, judging, shaping, deciding what matters — AI is the greatest professional gift you've ever been given.
This is the world Keegan is operating in. He brings strategy and product judgment to the table, and the tools fill in around him.
He can spin up the engineering team he doesn't have. He can synthesize the user research panel he can't afford. He can build the thing he's been carrying in his head for years and ship it on a weekend for the cost of a coffee.
If you're a builder whose value is putting the right decisions in the right order, or a leader or founder whose value is strategic decision making, AI can dramatically enhance your ability to deliver.
2️⃣ Mostly the 2nd Job
If most of what you produce every week is commodity output, the threat is a bit more uncomfortable than “AI might do your job better than you.”
This is because the consumption surface that justified the work, (i.e. the places where people can receive and engage with what you make,) is being eaten in real time.
AI Overviews, Claude, ChatGPT. The discovery layer that made commodity content economically viable for 20+ years is being restructured, whether your output is great or mediocre.
Tom called this out directly in his piece, and I think he's right.
Real, sustainable value has now migrated up the stack to the “1st job,” zone, and the work that lives below this new line is going to get compressed first, and fast.
3️⃣ Somewhere In Between
From what I can tell, this is where most readers of this newsletter actually live.
Some POV work, some content calendar-filling. Some weeks more of one than the other.
You have a body of work that's genuinely yours; the talk you give, or the framework clients pay you for.
The point of view that earned you the seat.
But your week is also full of stuff that doesn't really need ALL of you (like revising docs and decks you've rebuilt multiple times this year, for multiple clients, from the same material.)
You're not at the top of the ladder. You're not at the bottom either. You're in the part of your career where you still have time to choose what you build next.
But only for a short window. And the choice is much harder to make from a position of necessity than it is from a position of strength.
The honest question for most of us isn't am I safe? It's which job is actually eating most of my week?
💡 Mindset Shift
All advice is autobiographical.
The first question to ask when you take advice shouldn’t be is this person smart, because let’s assume they are and that’s why you’re listening.
A better question is whose terrain was this advice – this map – drawn for?
Because the desire to do work you're proud of is available at any rung of the ladder.
A few questions to consider:
What does your calendar say about the job you're actually doing?
If your current work disappeared tomorrow, would your body of work travel with you? Or would only your resume travel with you?
What does your GitHub (not your LinkedIn) look like? Where can we see your commits? The newsletter archive, the podcast feed, the portfolio, the client list — the proof of what you've actually built, not where you've been.
The advice you've been taking about AI — whose terrain was that map drawn for? Yours, or the map maker?
Most of the AI career advice in circulation right now is being given in good faith by people whose runway makes them mostly insulated from being wrong.
That doesn't make the advice bad, (or inherently wrong,) but it does make it incomplete.
🎲 Prompt Playground
The Calibration Audit
Copy + paste this prompt into your AI tool of choice:
You are a career strategist helping me honestly assess where I sit in a profession being reshaped by AI.
My context:
My role, title, or how I describe what I do: [describe]
What I actually spend my week doing, not what my title suggests, what my calendar shows: [list]
The rough split between strategic POV work (judgment, diagnosis, deciding what matters) and commodity production work (filling a calendar, hitting a deliverable) in my actual day-to-day: [estimate the percentage]
People whose career advice I've been following on AI: [list 2 or 3]
What I know about their situation: years of experience, financial position, whether they own their audience, whether they're employed or independent, etc.: [briefly describe]
Help me evaluate:
Based on my actual week, which tier am I operating in right now? Be direct. Don't flatter me.
Is the advice I've been following calibrated to my situation, or to the situation of the people giving it? Where's the gap?
If my current role or business model compresses in the next 18 to 36 months, what's the most defensible move I can make from a position of strength right now, rather than waiting until I have to move from a position of necessity?
What's one thing I should start building this quarter that travels with me regardless of where I work or who my clients are?
Ask me clarifying questions before answering. Be honest, not comfortable.
⚡ Before You Go
This issue was sparked by 2 pieces that might resonate with you:
Slackers Ep. 20 with Keegan Knapp — the optimistic, tactical, "here's what's actually possible right now" frame. Worth the listen if you want to see what real AI workflow looks like in practice.
Tom Webster, "Don't Take Career Advice From Me" — the labor-economics counterweight. Direct, throws a few punches, and worth a read IMO.
Here are other ways I can help:
🗓️ 1:1 call: Grab 15min on my calendar.
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🚀 Speaking & workshops: Hit reply, let’s talk.
🤖 AI Prompt Library: 12 prompts to use AI as a strategic thinking partner (free, no sign up required)
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Thanks for spending time with Red Threads this week, I’m glad you’re here.
~ Jaime