Free Product Idea: One Fine Day


I travel quite a bit for work.  

I'm also mildly OCD, so I have a mini-ritual of sorts whenever traveling to a new city of buying a new Lonely Planet "Encounter" travel guide for that city before traveling there.

They're handy little books, pocketable at 6x4 inches.  They contain a condensed listing of major sights, restaurants and the like, with a decent detachable map at the back.  I appreciate the density of the information and also the slightly offbeat selection of places each editor includes which a more conservative guide might skip over.

The ritual part is that I enjoy adding a new book to my collection slightly more than I do using the things.  On my bookshelf, they are a visual representation of where I've been and gone, all in a nice orderly set, each city marked by a unique color on the spine.  When I arrive back home, I take the book out, place it next to its brethren and stand back to admire the set and reflect a bit on my trip.

I've gone so far as to buy a book for a city I've visited in the past and don't necessarily intend to visit again, just to pad the collection.  Some of the places I visit don't have a book in the series and so I am forced to buy one of their larger books as an ill fitting substitute, and this irks me more than I care to admit.  

Many people have this sort of relationship with travel.  One of the most cliche visual representations of a traveler is a weathered suitcase covered with stickers from various locales.  I know fellow travelers who collect kitschy souvenir spoons or refrigerator magnets in a similar way.

Ultimately, what we traveler/collectors are attempting to do is collect experiences, and yet, the actual experiences are often much more mundane and anti-climactic than our collections might belie.   

To the Product-mobile!

There are any number of travel products in the world, from television shows to books to websites.  All effectively seek to create a repository of information about places one could visit.  The good ones winnow down the vast world to a manageable list of places one should actually visit.  The best ones offer a glimpse into the experiences of people in those places, be they visitor or inhabitant.

That's all well and good, but in my experience, the place is really not the thing I'm after.  I often arrive at a location I've heavily circled in one of my trusty travel guides, only to be profoundly disappointed because it didn't match my imagined expectation of what it would be like to be there.  

It's the experience rather than the place that I'm after, and travel guides often lack clues as to how a traveler should engage with a place once they've arrived.  Also, some experiences worth having don't really have a locale at all.  Some exist in time.  Others can only be had by being with people.

So, how about a travel site that is focused on these experiences instead of just places?

What does an experience look like?  To me, the format for sharing an experience is a narrative and chronological description of a span of time.  Something like:

"I woke up in the early dawn, still acquainting myself with the time change, and bored, I grabbed my camera, hopped a train to Shinjuku station and walked around the neighborhood.  Tokyo is a very different place at 5am.  The bustling crowds are replaced by occasional pairs or threesomes of still drunk stragglers from the izayakis, squinting at the daylight as they stumble to their beds.  An army of somber men in little helmets and orange vests comes out to clean the streets and pick up bags of garbage set out the night before by the businesses and homes.  Most of the shops are closed and their garish displays of baubles shuttered behind steel doors."

This content should be richly linked to locations on a map, business listings, photos, and other related content.

The core use-cases for a minimum viable product would be something like:

  • Contributor posts new experience. 
  • Traveler searches for experiences related to a place, time or person. 
  • Traveler "pins" an experience.

I'd eschew a commenting system in favor of a more simplistic bookmark/like system.  I think that provides the right degree of moderation without distracting from the content.  It may later still be worthwhile to provide a feedback mechanism for readers to interact with contributors, though I envision this as being a private exchange.

This "pin" system could also serve as a way for travelers like myself to collect those experiences that I've already shared with the author.  This may require a second "done that" pin that segregates future vs. past experiences, though I'd want to observe how people use a single "pin" feature before deciding on that.

Advertising is an obvious source of revenue, high-traffic travel content is generally quite valuable, though incorporating it would need to be done with some care lest it cheapen the experience.

It might also be interesting to consider a "pay what you want" or even fixed subscription model with revenue sharing amongst the top contributors.  This would greatly encourage contributors to post high-quality content and would foster a sense of innate value in the community that would lead to a more engaging experience.

To go to market, I'd begin by launching a closed beta, inviting notable travel writers/bloggers to try out the platform.  This would serve to create an initial nucleus of high-quality content and would accelerate the iteration of the design and function of the site towards the easy creation and beautiful presentation of that content.

The rest is left, as they say, to the reader.

The Tyranny of Choice

There is an interesting tension in product design between features/functionality and usability.

On the one hand, users of an application, as they gain expertise, demand sophisticated and nuanced features that allow them to do more varied tasks and create more efficient workflows.

On the other hand, new users to an application are intimidated by large menus and palettes of buttons that deter them from getting basic value from the application.  

More often than not, designers err on the side of features/functionality because they are necessarily experts of their own product and thus subjectively over-value those features that broaden and deepen the experience.

This, as some established product teams eventually learn, can be a recipe for failure as they race ahead of the mass of potential users waiting behind their early adopters.

One interesting way to look at this problem is to consider how, for people, choice can be a bad thing.  

At first blush, this seems very counter-intuitive   

In almost any domain, it always seems better to have more and varied choices.  More styles of clothing, more flavors of ice cream, more ways to get to work in the morning, more colors of paint.  And companies work very hard to give consumers these choices.

And there's no denying there are a lot of good things about choice.  

Novelty is one of the strongest human emotions.  So too is self-identity, and a plethora of choices allows us to construct for ourselves an experience to suit and, sometimes, identify it to others.  The t-shirt is one of the the most elegant vehicles of self-expression ever invented.  Imagine explaining to a Victorian how people would someday display, emblazoned on their chests, their current thoughts about philosophy, culture, and ideas.

And yet, people complain bitterly about the complexity and pace of change that these same choices induce.  We're punished each day by thousands of decisions, some important, some trivial, but many made poorly because of lack of time or energy.

The Rise of the Curator

I signed up recently for Bombfell.  Their service is to deliver you an article of clothing on a set schedule (i.e., monthly) and for a set amount ($69).  You choose some parameters for what you'll receive, like your sizes and preference for long vs. short sleeves, and a personal shopper picks something within those parameters and sends it to you.

I signed up out of interest for their model after reading an article, but after 4 deliveries, I'm quite enamored of them.  

The clothing they choose for me often falls somewhat outside of my standard repertoire, but not embarrassingly so.  As it turns out, this is exactly what I want, though I didn't know it when I signed up.

Another service I started using is Quarterly.  They provide care packages of curated swag, again as a subscription, selected by notable writers, entrepreneurs, organizations or other personalities.  I've yet to receive my first package (from Mark Frauenfelder), but I find myself anticipating it as I would a gift from a friend.

The thread that ties these two services together (and they with this blog post) is that they are fundamentally about taking away choices, rather than creating them.  And they do this while still retaining the novelty and self-expression that come with making good choices for yourself.  

Curation is a bit of a buzzword, even though it's a concept as old as media.  The lasting engagement of broadcast television despite the near-infinite choice available online, is an example of successful curation.  Any story, whether told to friends or written down in a book, is really just a curated set of experiences, arranged to clearly express a larger idea or emotion. 

Both remain compelling, in part, because they liberate their audiences from the tyranny of making endless choices.

When designing a product, it's worthwhile to consider the "cost" of choice in your design.  Walk through your most important use-cases and:

  • Score -1 point for each choice the user is presented with.  And, yes, every widget on that toolbar is another choice.
  • Score -2 points for each time a user is forced to choose between multiple options in order to continue.  
  • Score -5 points for each instance the same choice is presented multiple times without regard to what a user has previously chosen.  
  • Score -10 points for every choice that has serious repercussions if made badly ("Do you want to save that?  Yes/No/Cancel", I'm looking at you..)

On the positive side. consider how your application can make good decisions on your users' behalf.  Use your expertise of the domain and your product to provide a guided workflow that shows the user how to work or play without wasted steps.  Share your deep and nuanced perspective of your content by providing curated spaces where users can passively discover and absorb it.

Done well, good decision making on the behalf of the user, like Bombfell and Quarterly, can be a wonderful product in and of itself.

Deadly Engagement

The Seven Deadly Sins has been a meme since long before there were memes.  


Since they were canonized by Dante, seemingly every philosopher/writer/poet has at some point featured them in a essay, story or poem.  This is because they so succinctly encapsulate the motives of every terrible thing ever done by a human being to another.  

More than that, they describe the motives of everything ever done, good or bad, because what underlays them are the raw fundamental forces of our psyche.  You could describe personal fulfillment as somehow finding a homeostasis between them, lest one runs rampant and turns deadly.

So what can a mere product learn from all of that?  Here's a playbook for channeling each into lasting engagement.


I just like  Sloth ...

I just like Sloth...

Okay, this one is a layup.  Everyone is lazy.  The busier you are, the lazier you must be, because every moment wasted on a clumsy tool is magnified 10 or 100-fold.  

Let your users be lazy.

Go through every important flow through your application.  Sculpt and shape every action to minimize time and reduce the number of decisions.  Strip away anything and everything until you can no longer remove any of the parts.  Help your users to magnify and amplify the results of every action they take.


Users always want more more more.  Whether, features or content, they complain endlessly about not having the button that does that thing, or why the doodad they were looking for wasn't conveniently on the nav bar.  Usually you fend them off, with a stick, because they can't see how it would harm the core value you provide, but once in a while, they are right.

There are elegant ways of giving it to them.  

Any content driven application without great search should be ashamed of itself.  It's one of the harder things to pull off because some content requires a lot of curation to make it searchable (video, audio, images) and even text content, especially structured data, has to be finely tuned for the search index to surface relevant results.  Spend the energy and time.  Use analytics to study how people use it.  Find out what they query for and tune your indexes to give better more accurate answers.

Feature laden applications, particularly those with necessarily dense drop down menus and preference pages, should focus on plugability and extensibility.  Is there a good reason why you need to build a calendar into your application?  Why not integrate with a Google calendar instead, even better, support the iCal standard so each user can bring their own.  There are a multitude of other products out there that offer richer functionality than you can provide and cost you very little to implement.


Money, truly, is a double edged sword.  You want it from them, they most definitely don't want to give it to you.  You can give it away for free, but then you debase the currency of value you've worked so hard to create.

Advertising is a way of selling a bit of your soul (and your users souls) to get some of it, and for some products, with large user-bases and fickle engagement, it's the only game in town.

Times are a changing though.  It's never been easier to take a payment online and people are getting used to opening their wallets online.  

The worst thing you can do is confront the user with a "Buy" button on the first page view.  Freemium and trial-periods are useful for widening the engagement funnel, though can be technically difficult to pull off.  Largish up-front fees can be split across a monthly subscription to lower the perceived cost and also give you incentive to create more lasting engagement.  Pay-per service applications can use first-time free incentives and punchcard-like loyalty programs to gain users and keep them coming.

Most importantly, build value and price appropriately.  Value stems from saving people time, facilitating transactions, providing goods/services, or just plain amusing them.  Figure out what value you're providing and find a parallel product to anchor your pricing against, online or sometimes physical.  Be careful not to mistake having poured your guts out to create a thing for a dispassionate user's willingness to pay.  If all else fails, don't be afraid to start a tad high though and use promotional discounts to test lower price schemes.


The sexual imperative is so deeply ingrained in all of us that it subjectively shapes everything.  I believe, if Google's search index ever becomes self-aware, it's first conscious act will be to laugh raucously at the human male's obsession with breasts.  Why should they be spend so much energy admiring two bodily protrusions that nearly every woman possesses, that are only really useful to newborn babies and otherwise cause women a great lot of trouble supporting, covering, revealing, augmenting, reducing, and sometimes risking their lives for.  

And yet, if you're a man, then nothing in creation could make more sense then that elegant equation that describes the gentle curve from shoulder to stomach.

This does not mean you should put tits on your homepage.  

Rather the opposite.  Sex is too powerful a force for you to wield responsibly.  Respect it.  Respect that a hormone addled teenager will inevitably post pictures of their penis on your site, respect that some people will want to have open discourse about subjects that others (or even you) will find offensive, respect that some people will want to pick the username "BallsDeep", respect that no viewpoint is invalid and foster a community of mutual respect.  Most especially, respect their privacy.


There must be a thermodynamic equation for hatred.  I imagine that a college student "hates" having to wait 30 minutes for a pizza about exactly as much as a cavemen hated having to walk 5 miles to hunt an antelope.  This isn't to say we're spoiled, (though we are), more that we all have a certain amount of cussedness that has to be let out one way or another.

As a product owner, there are ways of channeling and harnessing that energy to create healthy engagement.  Providing a soap-box for your users to vent, whether about the driver who cut them off on their way to work or your product, is a way of delivering value in the form of emotional release.   

When their ire is directed at your product, it's an opportunity to learn from their pain.  Beware becoming a sycophant that react to every barb, but there is a sort of judo where you can turn your biggest detractors into your biggest proponents by simply promising a solution, then delivering.  


Envy gets a bad rap for being the most tasteless of all the sins.  Jealousy over what you don't have when you've probably got quite a lot, is after all, pretty base.  But the desire to compete is the fundamental force of all positive evolution, whether biological, social or technical.

Products must themselves compete for the over-saturated and multi-fractured attentions of users.  These days, a consumer-facing web application must compete, not just against similar products, but against every search result, every advertisement and every bookmark.

To do it, products should let their users wear the value they get from a product on their sleeve.  Nothing so contrite as a +1/Like button, or god forbid, a forced twitter post.  But with public forums and rich public user profiles that showcase their rich experience with your product.  When new or potential users see established users engaged with your product and enjoying themselves, they'll want in on the action.


Of all the sins, this is the one I'm most guilty of.  The need to feel just a little bit better than the other guy is hard to censor and easiest to luxuriate in.  I'm able to suppress it, for a time, in order to learn from and collaborate with peers, but there's still an insatiable hunger in me to do better/faster/cheaper than the rest.

Thus, it is one of the strongest ways of creating lasting engagement.  Users who take pride in using your product will form the nucleus for all your success.  They will be the standard bearers that spark viral growth on Twitter and Facebook, they will become the stable source of revenue that frees you to continue to take risks, they will brag about how they were there when and wear t-shirts with your logo on them.

People become proud of a product by feeling they've earned it.  This could be as simple as a badge for participating in a closed beta, as concise as a counter of posts, or as genuine as having their good idea get implemented and their name credited in the company blog.  It's about rewarding your users for their time and energy in making your product successful.

Customers Know Nothing and Yet Know Everything

While at Target, I had the opportunity to sit in on a user study on a kiosk application we were building to allow customers to load coupons onto "smart" credit cards to be used when they check out.

A similar usability lab.  Photo by  Kai Chan Vong .

A similar usability lab.  Photo by Kai Chan Vong.

Subjects were grabbed at random from the flagship store and offered a modest gift card to participate in the study.  Each subject was brought into a small room with a kiosk in the center and a large two-way mirror on one wall.  

A facilitator would begin by warmly thanking them for participating and guiding them verbally through a pre-scripted set of actions.

"You can load electronic coupons onto this card, try to use the kiosk to load a couple onto it...", while handing them a prototype card.

The person would take the card, peer at it oddly, and gamely try sticking it into...the printer slot, look embarrassed, then find the correct opening.  The facilitator would be careful to look placidly unhelpful no matter what the subject did.  On-screen, they'd touch the "Load Coupons" text label next to the big button...wait a moment...touch it again...wait a moment...then finally touch the button.  

On the other side of the mirror, half a dozen people sat in rapture.  A row of three usability high-priests sat hunched over microphones immediately in front of the mirror.  They'd whisper intently, "the subject has tried to insert the card into the wrong slot" and "the subject is having trouble finding the coupon button", while a dozen video screens showed the action from various angles.

It was fascinating, and slightly gut wrenching, to watch a real person flail at the thing we'd worked very hard on for months.  Your first instinct is to blame the subject for "not being computer savvy", but eventually it sinks in that you have to do better.

The study resulted in a dryly written report that lived in a massive binder that weighed 15 pounds.  An imposing and technical-jargon filled document that, ironically, was itself far less usable then the application it was studying.  

I'd guess that I only ever read about 10% of it, and yet, the experience dramatically altered my perspective about products and the importance of user experience.  Products are only as good as their interfaces, and letting a real customer play with it can tell you a great deal about how to make that interface better.  Not by asking them for feedback, but by simply observing them and watching your application fail them, sometimes in the most basic of ways.