Welcome to the second half of 2025 
(Said with utterly disbelief).

This week’s Jimmy Brief is brought to you by a specific incident with a senior business analyst. It was just a small interaction – over a backlog feature of all things – but it got really stuck in my brain. The incident played on repeat in my brain like this terrible song from circa 2000.

The whole thing sort of derailed my entire day. That evening I almost missed a scheduled online chat with a friend, turned up late, and brought all sorts of intense frazzled energy to the situation.

Though I can confirm that I eventually did calm down.

And once I had, I spent a ton of time thinking about it. Unpacking it. Examining just why it irked me so much. Really thought it through. If you’ve followed me for a while it might seem like I get wound up every day over everything, but I promise that it is rarer than you’d think.

This article is the the conclusion of my mulling. It is also sort of a rant. But also sort of not a rant? The incident wasn’t a blow up – I doubt the other party can even recall it – and yet, felt important? No matter how many times I tried to write about another (more interesting) topic, I couldn’t. This article just wanted to be written. So here it is.

I’ve been told it is a tad more meta than my usual fare … so YMMV.

Who’s Reality Are You Serving?

We love to talk about serving our users and customers. But we so often forget this applies to our own work too. Every document, feature description, and slide deck you create has a customer. And each one has users.

And in case you’re in any way confused about this  – it’s not you. It is never you.

This is about remembering who you’re actually serving when you’re translating between worlds. And why the key thing I look for when I’m involved in interviewing for in-between type roles like yours and mine is the ability to understand the difference between the map, the territory, and yourself.

Read it on my website now 👇

As always, I would love to hear your thoughts on this (or anything else), so do reply to this email, DM me on LinkedIn, or send me a letter via carrier pigeon. 

I cannot tell you how much I like hearing from y'all!

And until next time, stay excellent! 💖
Hannah

PS: Bonus question! Does anyone else do personal quarterly planning? If so – I’d love to know how you tackle it and if it’s working for you? Call it professional curiosity about other people’s approaches!