Tag Archives: digital strategy

Dec 09 2025
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Christmas Shopping Observations, Part Two

What happens when the system finally learns to listen.

Last week in Part One, I described why Christmas shopping feels hostile, why even the most basic purchase turns into a strange performance of archaeology, jargon and filters masquerading as understanding. The real problem wasn’t the products but the machinery. The fiction that a PLP grid is somehow an acceptable translation layer between human intent and retail stock.

This week is the other half of the story: the thing that replaces it.

Because the truth is, we’ve spent twenty years designing for systems that never deserved that level of obedience. We pretended the homepage was the grand entrance, the digital lobby with its scented candles and seasonal banners. We treated it like the flagship store: polished, high-stakes, endlessly debated at internal stakeholder meetings. Meanwhile, almost no one arrived through it, or if they did, they were there for a split second. Most people dropped in sideways, via Google, a WhatsApp link, an email, or a moment of panic at 11 p.m. The homepage was the UX and UI theatre we performed for ourselves and our clients.

Agentic systems make that fiction impossible to sustain. They don’t care about your reception desk and your neatly prioritised way finding. They don’t even see it. They take what you mean, “something thoughtful, about forty quid, she hates clutter, nothing scented” and drop you straight into the one, tiny corner of the site where the decision will live or die. A place that, inconveniently, most retailers still treat as a functional afterthought: the product-detail page.

A minimalist Scandinavian study at dusk, softly lit by a small desk lamp. Snow falls outside the window. On the wooden desk sits an open laptop showing a clean product page with only a few curated gift suggestions. A small, neatly wrapped present rests beside it, suggesting a calm, intentional shopping experience rather than the usual frantic grid of options.
A glimpse of the future: no endless grids, no filters, no festive panic, just a system that actually starts where you are.

The PDP becomes the real front door because in an agentic journey the start isn’t a place, it’s a sentence.

This is where that old inventory-obsessed model buckles. Catalogue commerce was built on the premise that customers begin at the top and drill down. Agentic commerce begins at intent and works sideways. The sitemap is your fiction, not theirs. The system no longer needs your categories. It needs your clarity.

Be under no illusion though, this ain’t easy. This only works if the agent can explain itself. When a system gives you two options instead of two hundred, you need to know why. Not academically, emotionally. Why this jacket and not the other one? Why this feels like her. Why this fits your mental model of who she is. The explanation is the reassurance loop. Without it, the whole thing becomes another opaque machine; efficient, yes, but untrustworthy in all the ways that matter.

And then there’s the serendipity problem. Efficiency is addictive, but clinical. If we strip out every detour, we drain the pleasure along with the friction. The answer isn’t a return to the grid; it’s controlled looseness. A suggestion or two just off-axis. Something adjacent. Not twelve rows of “you may also like” tat, just enough to keep the experience human. Discovery without the search-and-filter trauma.

None of this is a theoretical exercise for me. I genuinely spent years trying to push natural-language intent into car retail at JLR, long before the technology was mature enough to meet the ambition. I saw how people really shopped: not by wheelbase or trim code, but by anxiety, context, and use-case. “Capable in the mud.” “Seven-seater that doesn’t look ridiculous.” “Can get all the family crap in it for Cornwall, without a roof box.” All perfectly rational human requests – treated as nonsense by the old machinery. The ideas weren’t wrong. They were simply early.

Now the technology has finally caught up. And with it, the entire structure of how we design retail subtly shifts. From catalogue to conversation. From homepage theatre to product truth. From filters to language. From the warehouse to the person.

None of this saves Christmas, of course. But it does save us from the annual pantomime of pretending that people enjoy buying gifts and products more generally through a system that refuses to understand how they think or consume any of the deeper context that matters. The future isn’t more choice. It isn’t more filters. It isn’t even more intelligence.

It’s fit.

Fit between intent and suggestion.
Fit between the context you’re in and the thing you’re shown.
Fit between the human messiness of December and the machinery that finally stops treating you like a clumsy clinical user story.

Christmas shopping isn’t a test of skill. It’s a test of whether the system knows how to listen. And for the first time in a long time, it might.

AI: This piece was assisted with Ai. I used it for the tags, the post excerpt, image generation and some sub-editing. Ideas, references, and anecdotes are all mine.

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Dec 04 2025
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Christmas Shopping Observations, Part One.

Why Christmas shopping feels hostile, and why ‘catalogue commerce’ makes it worse.

December always brings the same rituals. Sitting in front of a website with a sense of mild dread. The kind one reserves for using a train station toilet, or getting into the coffee queue after parkrun. The intended tasks isn’t difficult or unpleasant in theory, just buy something thoughtful for someone you care about, but Christmas shopping always manages to feel like cognitive trench warfare. Retailers would have it as “the season of gifting”, the rest of us call it, problem solving with a shot glass of Baileys.

So, for some context, let’s go back to a couple of of weeks ago when I was trying to get myself a replacement down jacket. A bit like when I was trying to get Jo some new Asics, this wasn’t an extravagant task. It wasn’t even particularly interesting. Just a bit of a like-for-like replacement for a much-abused Rab. All I needed was a sub expedition-grade jacket. Black, simple. I know my sizes, I know I needed about 850+ fill power and I was ambivalent about much else. I had a shortlist of brands I like. But dozens of models, filters that are inconsistent across brands, categories that mean nothing to people outside of the industry and a product hierarchy that is the baffling output of a Content Management System (CMS) that’s been operated by a chimp1.

I wasn’t searching as much as performing archaeology. Sifting through layers and brushing off the irrelevant collateral.

A narrow, snow-dusted street in Stockholm’s Gamla Stan on a muted December afternoon. Warm ochre buildings rise on either side as bundled-up shoppers walk away from the camera. Soft shop-window lights and minimalist Christmas displays glow against the cold, creating a calm, human-scale contrast to typical frantic holiday retail.
The Christmas shopping we think we’re doing, before the dropdown menus, filters, and “Gifts for Her” pages slap us back into reality.


In design terms this is what we might call the Gulf of Execution, or as my colleagues and I at Dare liked to call the Experience Gap: the distance between what a human means and what the system is willing to accept. My intent was simple – “warm, minimalist natural down for standing around on platforms, by sports pitches and walking to the pub” – but the interface insisted I drop that down into a dialect of drop-down, checkboxes and jargonist euphemisms. A human request translated into machine-and-catalogue syntax. Little wonder the whole thing feels like a joyless chore.

And Christmas retail only amplifies this.

Every major high street site trots out its annual performance of “Gifts for Her”, a festival of generic filler: candles, scarves, bath sets, socks. The occasional novelty gift set embossed with typography that looks like it was designed at 4pm on a Friday whilst sucking on a fetid vape. It’s all indexed by price bands: “Under £10”, “Under £50”, “Over £250” – as if women are primarily sorted by budget code rather than, say, personality or taste.

No mother wants another hand cream selection.
No thirty-something woman wants coordinated gloves.
No partner wants to receive something that clearly began life as a procurement exercise.

The whole structure is built around the warehouse, not the person. It’s inventory logic masquerading as emotional intelligence. And the moment you notice it, you can’t unsee it: most “gift guides” reveal almost nothing about the recipient and everything about that the retailer wants to shift.

This is the failure baked-into catalogue commerce. It doesn’t matter which brand you pick; the underlying assumption is the same: that human desire can be expressed through filters, and that personality cab be captured in a category label. It’s tidy, rational and optimised. It’s also completely blind as to what makes shopping human in the first place.

Because real gift-buying begins long before the visit to the website. It begins in the cluttered contradictory emotional territory that sits just outside the browser window: What does she already have? What does she love? What has she told me about? What will she pretend to love? What feels thoughtless? What feels too much? What feels like you didn’t think at all (Hint: anything at Boots that comes in a gift box)? Retail ignores all of this and forces you straight into the grid (what we call the Product Listings Page (PLP) ), as if the process were orderly. Spoiler alert, it never is.

This is why Christmas shopping feels hostile. It’s not that the options are universal bad, just that the interface tries to convince you it understands and reflects your mental model when it plainly does not. Handing you a hundred variants of the same filler and expecting conversion gratitude. Somewhere between the filters, the categories and the bath sets you sense the truth: this isn’t built for you. It’s built to organise the warehouse.

Don’t worry though, there’s a better story coming, and the technology to enable it is finally here. But this isn’t the piece for solutions, it’s about naming the problem plainly as it is and without the retail gloss.

Next time I’ll get on to the other half of the picture: the system-level shift that’s going to quietly rewrite the entire experience from how we search to where the journey really begins.

For now its enough to acknowledge the obvious: Christmas shopping isn’t about solving and indecisiveness problem for dumb consumers. It’s a broken model designed around systems that are not built to reflect how people think, feel or choose, especially in December.

Part Two: How agentic solves this, and more.

AI: This piece was assisted with Ai. I used it for the tags, excerpt, the image generation and some very light sub-editing. The ideas, references, and anecdotes were all mine.

  1. Plot twist. I ended up with the Shackleton Ronne. I browsed online for weeks. I did huge amounts of research and comparison and then I went to the wonderful store on Piccadilly and spoke to a great sales assistant there who worked with me to ensure it was absolutely the right fit and will see me out for prob 5-10 years of use. ↩︎

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Aug 13 2025
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You’ve Booked the Flight. Now Feed the Cat.

Or, What a Ryanair journey map taught me about real UX.

There’s a type of interface that shows up on Dribbble every few months: flight check-ins, boarding passes, baggage-tracking dashboards. Always slick. Always serene. The UI equivalent of cucumber water.

Most of them start at Choose your seat and end at Enjoy your flight. Which is tidy. But also nonsense.

A few years ago, I worked on a project for Ryanair. I drew out a journey map (with pens, natch), not the polished, stakeholder-pleasing kind, but something closer to the real emotional terrain of travel. One that began well before the confirmation screen. One that started, in fact, with the cat.

Because booking a flight isn’t a clean beginning. By the time anyone taps “Book now,” they’ve already trawled five sites, tried to align half-term dates with the one cousin who replies to group chats, checked weather reports, and googled “Do I need a visa for Croatia?” even though they’re flying to Naples.

Life admin, not travel ambition, is what usually kicks things off. That’s where the journey begins.

The diagram traced everything from that fraught pre-booking stretch through to the post-trip hangover, highlighting the emotional and logistical clutter that most airline UX avoids. Not because it isn’t there, but because it’s messy. And mess doesn’t fit neatly into a product roadmap.

There’s the bit after you book, when nothing much happens, except everything might. The vague unease when no one’s confirmed your seats. The passive-aggressive alert that “something has changed” in your itinerary, but you’re left to figure out what. The nervous rechecking of emails. The slow panic over cabin bag dimensions.

Then comes the day itself. A spike in interaction. The printer runs out of ink. You’re stood at Departures at 6:30am trying to download Peppa Pig episodes with 4% battery and no signal. Your toddler’s hungry. Your partner’s tense. And you’re still wondering if you packed the Calpol.

And yet… this is the brand moment. Not the glossy UI, not the neat API integration. Just this: the knot in your stomach, the uncharged phone, the boarding pass you can’t pull up without a connection.

The map tried to capture that. Not to romanticise it, but to acknowledge it.

Even on the return leg, the friction isn’t over. Passport queues. Lost luggage. The existential despair of a train replacement service. You get home, open a week’s worth of mail, find a parking fine, trip over a stray shoe from the hasty departure packing, and realise you didn’t leave anything for the cat-sitter.

Most journey maps stop at wheels-up. Ours didn’t. Because experience doesn’t follow a clean arc. It loops, it stutters, it sags in the middle. Thoughtful UX understands that.

A tired parent, dressed in a dark winter coat with a fur-lined hood, stands in a dimly lit Swedish airport baggage claim area late at night. They are looking down at their phone, which shows a 4% battery icon. To their left, a child sleeps soundly in a dark grey stroller. A large, dark suitcase tilts precariously next to the parent, appearing as though it might fall. In the background, an empty luggage carousel stretches out, with a few other suitcases scattered on it. Further back, blurred figures of other travelers are visible, and the warm glow of a vending machine can be seen on the far left. The overall atmosphere is one of exhaustion and quiet resignation.

Of course, Ryanair won’t build an app that books your pet-sitter or packs plug adapters. But this kind of messy map reveals where the brand can quietly show up—not with a feature, but with timing, tone, and the rare dignity of being understood.

Maybe that’s a 6-sheet in the departure lounge that says “Still cheaper than therapy.” Maybe it’s an email that clears, not clouds. Maybe it’s an in-seat comm that drops the marketing voice for once and just says: “Made it. Welcome back.”

Even for Ryanair, in fact especially for Ryanair, those moments can build memory, trust, and repeat business. Because no one remembers the boarding pass. They remember how they felt when the wheels touched down, the keys were missing, and the cat looked at them with contempt.

You’re not designing for delight. You’re designing for 4% battery, no signal, and a queue that won’t move. That’s where memory lives. And maybe loyalty too.

AI disclosure: This piece was written with the assistance of AI, used strictly as an editorial and thinking partner. All ideas, edits, and final phrasing are mine. ALT text and tagging were also generated with AI support.

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