Tim Difford

Full write-up on Substack — includes the token cost breakdown, the email address rule you’ll want to steal, and how I built most of this with Claude’s help (yes, really). [backroadz.substack.com/p/how-i-turned…] cc @EP_OnTheLine @liamottley_ @mreflow #Claude #AIWorkflow #ContextEngineering

One word typed at the start of any session kicks off the full boot sequence: read the index, read the brief, sweep email, deliver a structured briefing. No prompting. No re-explaining. Just context, ready.

Every AI tool has the same problem: it forgets you between sessions. I spent weeks fixing this. Here’s the system I built — a Claude setup that self-briefs, self-heals, and boots up ready to work every morning. 🧵

So I built a self-healing layer. Three components: 1.Stale detection at boot — warns if HANDOVER is >24hrs old 2.Nightly scheduled task — sweeps email, patches the brief automatically 3.Transcript catch-up — reads the tail of any session that ended mid-flow

Each matter gets a HANDOVER.md — full current state: open actions, key contacts, what happened last session, what’s next. The problem: it goes stale. Sessions hit context limits and end without updates.

Keep it on the Low down 🤫 #htafc

Player Ratings from Town’s convincing victory against Manchester United u21s in the EFL Trophy this evening. #htafc open.substack.com/pub/weareterri…

@htafchelp hi - have tried for a couple of days on various browsers and devices and cannot get rid of errors preventing purchase of Doncaster tickets. Any advice?

@fjordenco are there any stores in Sydney where I can buy a Fjorden bundle? e.g. Leica store?

@StevenChicken wow Fiery Furnaces - great shout!

@officialhtsa Great stuff - cheers

@timdifford Hi Tim. Likewise! Working on the minutes over the weekend, so hopefully sometime next week.

@officialhtsa Good to connect at the AGM. Where can we find out what happened at the ATT meeting? Thx

normal service is resumed #htafc

@Fordy206 Working but no comms

Anyone else’s ifollow not working? #htafc

Anyone got comms on iFollow? #htafc

@StevenChicken I’d agree as a rule but your tone is off here.

Also if you're watching your team win 4-0 and all you can think to do is rub salt in the wounds of a manager who has already been sacked, you are an appallingly classless individual and ought to be ashamed

Football was poor but the best thing I saw today was #pafc travelling support. Great commitment. #htafc