The Lost Art Of Serendipity

ser·en·dip·i·ty  /ˌsɛr ənˈdɪp ɪ ti/ –noun

1. an aptitude for making desirable discoveries by accident.

2. good fortune; luck: the serendipity of getting the first job she applied for.

Internet retailers have been struggling with a challenge since the first time a shopper clicked “Add to Cart,” and so far I don’t think anyone has really cracked it.

Recently we’ve had a number of discussions in our office (and more in the pub) about the difference between the online and offline shopping experiences, and the subject of online product discovery is one we can’t seem to get to the bottom of.  It appears that many retailers are in the same place, and despite their best efforts, online retailers just can’t duplicate what we’ve termed serendipity.

That feeling of walking into your favorite bookshop and picking something up in a section you don’t normally go into just because the cover leaps out at you.

The moment when you stumble across some unutterably stylish, drop dead gorgeous dress in the store you don’t normally go into, but your friend dragged you protesting into.

That magic moment where you discover something.

Amazon has had a good go at it, and I confess I’m a huge fan of its “people like you buy stuff like this” functionality, but it does suffer from a major flaw. Like many of my Forrester colleagues, I use Amazon to buy a lot of gifts that I don’t ask to have wrapped. So Amazon thinks I’m crazily into books on vintage fashion and Waybuloo toys. Well I’m not. But my wife and 2-year-old niece are. Go figure which one likes which. So I regularly receive invites to buy more books and toys I really don’t want.

Anyone spot the odd one out on here ?


You would imagine Amazon could get a little smarter on working out that maybe I buy these things around Christmas and a couple of other key dates?

Gift buying aside, while it is pretty good at suggesting things that I probably would like based on what I’ve browsed and bought, it really doesn’t have a hope of suggesting anything leftfield that I might love. If I’ve never looked for it on Amazon, then Amazon doesn't know I’m into it.

Apple has had its go with Genius, which seems to have morphed into Ping. While I find the recommendations iTunes makes for me don’t stray far from the mainstream, Ping seems like a valid attempt to harness the power of other people’s off-beat taste in music to give me a bit of inspiration. At least here is a way of iTunes being able to suggest things to me based on more than just my own repeat behavior patterns.


I thought Pandora did a great job because it tried to dig a little deeper and work out what was actually emotionally engaging in our musical tastes, but we are still banned from listening to that here in the UK.


So I stick to @zanelowe on Radio One for my musical advice.

So how do online retailers generate that genuine discovery, rather than relying on shoppers “Spearfishing” (as my colleague Sucharita puts it) product selections with a virtual harpoon? Absolutely, sometimes I’m on a shopping mission to buy that one thing I NEED and you can all get right out of my way until I find it. But at other times I don’t want to spearfish, I want to float in a balmy Mediterranean sea looking at all that it has to offer until I find something new and interesting.

I’m convinced social networks have a part to play here, letting me see what my friends are browsing and buying, and that does seem to be where Ping is heading. But do I really want to invest all that time in building yet another social network on another vertically unintegrated platform?

I believe that this is still a place where multichannel retailers can differentiate themselves. As more and more people turn to the Internet for regular purchases, or to research products that they have a defined need for, physical stores have an opportunity to turn themselves into showrooms that engage shoppers, take them on a journey, and show them something unexpected. Something they didn’t even know they needed.

Now don’t get me wrong. This isn’t easy. But I expect to see us really challenge the format of our physical stores over the next few years, and I also expect the really good online retailers to get much better at bringing back some of that feeling of Serendipity.



I think there is a HUGE problem in amazon's approach

The problem, in my eyes, of amazon - is that it never amazes.
It only gives things that are similar to the things that you are looking at RIGHT NOW.
Serendipity gives you things that you WEREN'T looking for right now and suddenly you think: "YES.... THAT'S IT!"
Your list shows it all to me: it's all more or less the samey....

I get serendipity through something else: Share My Playlist.
It's an add-on to Spotify.
People make lists... and some of these lists are REALLY GOOD.
I listen to the list because there are a number of things I would normally listen to... but there are a lot of things on this list that I a) had never heard of before or b) would not have listened to if they weren't on this list.
Because of this I start following their playlists.... I let other PEOPLE (not alogorithms) curate what I will listen to - and THAT is how I get serendipity.
In a bookstore it also is the PEOPLE who say: this should be on display because it really is good.
It is the MAVEN who decides!
Not an algorithm!

Someone at a music conference once explained the difficulty of suggesting songs depending on "People who listened to this": it's funnel shaped! It's more relevant when more people have listened to this (or liked something)... meaning more mainstream. In the end they started doing this with thousands of songs as startingpoints and all ended up with 1 of 7 very commercial songs.
The problem is that this train of thinking (basing this kind of things on past experience with 'similar' customers) is that it never goes for the quirk... where you find serendipity

P.s. try following Atzedevrieze in Spotify for a number of great music lists.... all very diverse!


Thanks for the comments - I do agree with you, and you sum up what I was getting at with ths line...

Serendipity gives you things that you WEREN'T looking for right now and suddenly you think: "YES.... THAT'S IT!"

I've not tried Spotify but people keep telling me to, so I will do.

Serendipity also applies to Digital Marketing

Very interesting thinking - yes, recommendations are good, but it's the ability to find the things I didn't consciously think about, that will fire up my neurons and give me the fantastic feeling that I've found something. For me personally this is the reason I never listen to the pop-music channel all the time - since the 25 songs that get airplay get boring after a short while. Instead it's (sometimes, not all the time) inspiring to listen to talk radio about topics I never imagined I could find interesting.

Lately I've been thinking that this way of thinking, the "serendipity-effect" could also be applied in Digital Marketing - meaning that, yes, predictive marketing will be huge, but it'll not take all the power out of a good old fashion "run-of-network" campaign. The interesting part is of course how strong the effect is...

Amazon and serendipity

@ Eric Woning
On Amazon people don't make lists, but they do write reviews. Browsing reviews is a very time consuming business, but worthwile. I guess there is no serendipity without browsing. When I notice someone has written a comprehensive review and shows he know his Jazz / Worldmusic / Rock etc., I always click on the name and go through the other reviews. This way I made many a new discovery and extended my taste in music.

Ideally, I'd lke to be able to keep a list of reviewers and be notified once a reviewer posts a new review. Unfortunately, I couldn't any contact details on the Amazon site to file a request to set this up. I did send a similar request to, a DVD/Blu-ray/games rental site. Picking films isn't easy when you've seen them all and serendipity might the cure.

Algorithms vs Networks

I do still think there is a place for some kind of algorithm generated suggestions, but one thing I've not seen implemented yet is the ability to say "No, I don't like that" and actively teach the algorithm that it's suggesting things you think suck.

Serendipity + Social Networking

Thoughtful article on the usage of serendipity. Amazon leaves a lot to be desired when it comes to making intelligent recommendations about the products you want and products you didn't even knew you wanted. Companies like Hunch are doing something interesting by making recommendations for just about anything based on your personality (defined by a series of seemingly random questions they ask you upon sign up). At StreetSpark, we saw a lack of serendipity in the social networking arena and wanted to introduce people based on the activities they were already doing on social networking sites like Facebook, Foursquare, and Twitter (as opposed to a static list of interests in a profile that is rarely updated). Since the app is also location-based, it introduces you to people around you with whom you share something in common. We like to think that we give serendipity a helping hand in meeting the people you want to meet or didn't even know you wanted to meet.