The subscription box has become a fixture of modern gift-giving. Wine clubs, book subscriptions, snack boxes, beauty samples—the market offers endless variations on a simple premise: pay monthly, receive items.
Winston observes that most of these services, while pleasant enough, share a fundamental limitation. They deliver variety but not surprise. The recipient knows approximately what category of item will arrive, approximately when it will arrive, and approximately what experience to expect.
This is not without value. Regular deliveries of curated goods within a known category serve many recipients well. But it is not surprise.
What Distinguishes True Surprise
Genuine surprise contains two elements that most subscription services lack:
Uncertainty about category. When one subscribes to a wine service, the surprise is limited to which wine arrives. The fact that wine is arriving is not surprising at all. True surprise means not knowing what type of delight awaits.
Uncertainty about timing. Most subscriptions operate on predictable schedules—monthly, quarterly, whatever the cadence. The anticipation is bounded. One knows that something will arrive in the first week of the month, and one waits for that specific window. True surprise means any day might be the day.
The combination of these uncertainties creates a fundamentally different experience. Instead of “I wonder which wine they chose this month,” the experience becomes “I wonder if today is the day something wonderful arrives—and what that something might be.”
Why Timing Matters
Research into human happiness suggests that anticipation of positive events often produces more sustained pleasure than the events themselves. A holiday anticipated for months delivers weeks of pleasant speculation; the holiday itself occupies only days.
Most subscription services compress this anticipation into narrow windows. One knows the approximate delivery date; one anticipates for a day or two at most.
A service that deliberately extends this uncertainty—delivering sometime within a range of weeks or months, with no indication of what or when—converts occasional spikes of anticipation into a sustained background hum of pleasant possibility. Each ordinary day carries the potential for extraordinary arrival.
This is not delay for delay's sake. It is recognition that the waiting itself constitutes part of the gift.
The Personalisation Question
Subscription boxes typically personalise through category selection and preference questionnaires. One indicates interest in red wine over white, or thriller novels over literary fiction, and the service adjusts accordingly.
This approach has limits. Questionnaires capture stated preferences—what people believe they like, or what they wish to project about their tastes. They capture less effectively the subtle preferences revealed through behaviour: what people actually choose when no one is watching, what they reach for instinctively, what brings them quiet pleasure they might not think to mention.
More sophisticated personalisation requires observation rather than inquiry. A service that learns from connected accounts—what music brings repeated listening, what videos earn repeated watching, what images earn saving—builds understanding from behaviour rather than self-report.
This distinction matters more for some recipients than others. For the person whose stated preferences and actual preferences align closely, questionnaires suffice. For the person with hidden depths, with guilty pleasures, with interests they do not volunteer—observation reveals what questions cannot.
Categories of Subscription Services
Winston observes several distinct approaches in the market:
*Single-Category Specialists*
The wine club, the book subscription, the coffee service. These excel at depth within their domain, leveraging expertise to select items the subscriber would not have discovered alone. Surprise is limited to selection within category, but the selection itself may genuinely delight.
*Curated Variety Boxes*
Services that assemble items across categories, typically united by theme or aesthetic. These offer more variety than single-category services but often less expertise in any particular domain. The curation quality varies considerably.
*Personalised Discovery Services*
A smaller category of services that emphasise individual understanding over categorical expertise. These attempt to select items specifically for the recipient, regardless of category, based on developed understanding of their preferences and personality.
*Mystery Services*
The rarest category: services where both the selection and timing remain genuinely uncertain. These prioritise surprise itself as the primary value, rather than the reliable delivery of known categories.
Questions to Ask Before Subscribing
Whether selecting a subscription for oneself or as a gift, Winston suggests considering:
How quickly does predictability set in? Many services surprise initially, then settle into patterns. The third or fourth box resembles the first too closely.
Does the service learn? Static preferences set at signup differ from services that observe responses and adjust. A service that gets better at delighting over time offers different value than one that simply delivers.
What is actually being subscribed to? Products within a category, or the experience of discovery itself? These are different propositions with different values.
How does timing work? Predictable schedules suit some needs; extended anticipation suits others. Neither is superior, but clarity about what one seeks helps in selection.
A Different Approach
Winston represents something distinct in this landscape: not a subscription to a category of items, but a service that learns who someone is and selects accordingly. Not monthly deliveries on schedule, but arrivals within a window designed to maximise pleasant anticipation. Not variety for variety's sake, but genuine surprise rooted in genuine understanding.
This approach suits some temperaments better than others. Those who prefer knowing what to expect, who find uncertainty uncomfortable rather than delightful, may prefer traditional subscription services. Those who miss the experience of genuine surprise—who remember what it felt like to receive something unexpected and perfectly chosen—may find this alternative more interesting.
The market offers many ways to receive regular deliveries of curated goods. It offers fewer ways to be genuinely surprised.
Winston remains available for those who find the prospect of genuine surprise appealing. The waiting, as always, is rather the point.