In a previous post, I talked about letting Digital Tim post to Blue Sky.
At that point, he already had a decent amount to work with – blog posts, DJ sets, media reviews, Q&A entries – all solid, all me. But there was still something missing.
Those things are relatively set in stone. They capture who I am, sure… but they don’t capture the in-between stuff. The fleeting thoughts. The throwaway observations. The things you’d never turn into a blog post, but absolutely would post on Twitter or Blue Sky.
Because let’s be honest – when people post to social platforms, they’re not writing War and Peace. It’s fire-and-forget. Quick thoughts. Half-formed ideas. Mood snapshots.
That’s the bit Digital Tim was missing.
Enter: the Observation Layer
The solution was pretty simple conceptually – an observation layer.
These are short, lightweight thoughts I have throughout the day. Each one captures:
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The observation itself
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A category (which usually maps to an existing persona)
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Whether it’s public or private
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The mood (positive, neutral, negative)
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An importance score from 1–5
A 1… basically “meh, probably irrelevant”.
A 5… rare, meaningful, and something the LLM should really pay attention to.
Perfect. Problem solved… almost.
The UX Problem (aka: this would get annoying fast)
Here’s where reality kicked in. To add an observation, I had to:
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Grab a device (usually my phone)
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Open Safari
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Navigate to the Digital Tim control panel
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Log in
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Type the observation
That’s a lot of friction for something that’s meant to be quick and disposable and I knew full well that after a week or two, I’d stop doing it.
So… yeah. That wasn’t sustainable.
Cue Apple Shortcuts
I’ve used Apple Shortcuts before, and they’re pretty dope.
After about an hour of tinkering, I built a shortcut that lets me:
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Grab my phone
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Hit the action button
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Dictate my observation
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Pick options for category, mood, importance, and privacy
That’s it.
What used to be a multi-minute faff is now a 20-second flow. UX baby!
Because my phone’s basically always with me, I can now capture thoughts as they happen, instead of telling myself “I’ll add that later” (which is code for “I’ll probably forget!”).
Wiring It Back Into Digital Tim
From there, it’s just plumbing:
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The agent gets access to public observations only
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The prompt is updated so it understands what observations are
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The data is reprioritised so observations carry a bit more weight than static content
Right now, this is only hooked into the Blue Sky posting version of Digital Tim – but the plan is to feed it into the chatbot version too.
Why This Matters
This one change makes Digital Tim feel way more human. He’s no longer just referencing:
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“Here’s a blog I wrote”
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“Here’s a DJ set I uploaded”
He’s also posting things like:
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Day-to-day observations
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Passing thoughts
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Mood-based takes
…you know, like an actual person would.
And looking forward, this gets even more interesting.
If I log that I’m feeling under the weather, then later decide to go to the gym – Digital Tim can factor that in and say, “Maybe give it a couple of days.”
So now the data isn’t just what I’ve done – it’s how I felt.
Thoughts, not just actions.
Layer by layer, Digital Tim gets a little bit smarter… and a lot more realistic. Boom!
