Webstock 2016 – Celebrating the web’s values

Webstock turned ten last week. It is a conference that celebrates the web and its makers – the creativity, the magic, the craft and everything in between. Although Webstock is hosted in Wellington, they have an excellent reputation and attract great speakers from all over the world. It has been on my radar for a couple of years and this year I finally managed to go to Wellington. It was an amazing experience, an emotionally exhausting ride on the rollercoaster – in a good way. Hands down, the best conference I’ve ever been to. 

Speakers typically have a tech background (web development, software engineering, UX design, long-time bloggers), but the presentations were mostly non-technical. While the Above All Human conference three weeks ago in Melbourne focused on startups and entrepreneurship, this conference focused on the web and its values and culture. You get a good idea of what Webstock is about from last year’s closing note by Natasha Lampard, where she talks about onsens, entrepreneurs and the long-game (also written up here).

A key asset of Webstock is the diversity of its speakers regarding gender, background, race and topics. None of the talks could or should be compared with each other. Therefore, by the end of the first day I stopped trying to figure out what my favourite talk was – they all were really good. Because of this diversity in topics, it took me some time to recognise the common thread: They all talked about a shared set of values, promoting and preserving values like openness, contributing, inclusiveness, simplicity and caring deeply about your work, not your ego. It is a conference that is undeniably, beautifully, human.

The team around Natasha Lampard, Mike Brown, Deb Sidelinger, and Ben Lampard organised a great event. Not only great speakers, but also a great venue, great food, great swag and great entertainment. If you organise events and want to get better, Webstock is an excellent reference point. Scott Berkun wrote about what makes Webstock so good some time ago.

Before I go into the depths of my notes, my main takeaway of the two days was:

Care about what you create and care about it deeply. Do not care about ego. In the end you want your work to be known, not yourself.

Dare to put yourself out there and contribute to the larger community. Stand for something. That makes you vulnerable, but the benefits of connection far outweigh the downsides of discomfort. To quote the wonderful Anna Pickard: “Show the world your biscuit face, because the world probably likes your biscuit face.”

Below is a write-up of my notes and some links. If you have any questions, please approach me – it was an amazing experience and I will talk about it with delight. By the way, Hollie Arnett has another good write-up of her Webstock notes, as well as Amy Potter, who posted her sketchnotes on Twitter.


Heather B. Armstrong opened the conference with “The Fraud of Authenticity”, suggesting that we are increasingly faced with posed and polished pictures and videos. Instagram, Pinterest and Facebook celebrate the perfect, the posed and stylised life. For a lot of pictures on those platforms you can hardly tell whether it is stock photography or “real”. Kids especially will have a hard time to distinguish. At some point you are no longer an audience, but solely a consumer. She encouraged the audience not to forget “the dirty side of the room”. Let’s make sure that our children don’t grow up thinking that life needs to be perfect. Talk about imperfection, struggles, experiences that are not fabricated or engineered. If we don’t do that, at some point nobody wants to see the dirty side of the room anymore. Until the videos are ready, have a look at the XOXO videos, where Heather gave a similar talk last year.

Steve Hillenius spoke about “Designing Interfaces for Astronaut Autonomy in Space”. Design and user experience are critical to enable long distance space missions in the future. Design can bridge the gap. Right now six astronauts (generalists) on the international space station are covered by ~100 controllers in mission control (specialists). As space exploration moves further away from earth, communication and coordination becomes increasingly difficult. For example a round trip communication to Mars take between eight and 45 minutes. This creates the need to create software that helps astronauts become more autonomous to be able to make decisions with limited or no input from mission control. NASA is now designing system that hide complexity and help astronauts take over specialist roles by coding them in software. For example, for mission planning, astronauts can move time slots by getting visual indicators what is allowed and what not (go- vs. no-go-zones).

Luke Wroblewski spoke about “Screen Time”, discussing the current challenges of designing screen interfaces. How to adjust interfaces for input (keyboard, mouse, finger, stylus, …), output (TV, phone, tablet, …) and posture (screen in 1ft distance (phone) vs. 10ft distance (TV)). On input, support as many means as possible and communicate what is possible, screen resolution and size are poor proxies to determine best input methods. On output, as screens become larger, you need to support both landscape and portrait mode vs. only supporting portrait mode for a phone app; use scalable pictures and web types. On posture, a good proxy for interaction is the distance to your screen (1ft vs. 10ft). He ended with an open question, what kind of interfaces come after glass (voice, wearables, VR, AR, …)? Vimeo has an earlier version of his talk.

Ethan Marcotte spoke about “The Map and The Territory”, that we need to work on re-inventing the web in a way that will allow us to onboard the next billion users who will be a very different audience. This “new normal” will exclusively access the web via mobile devices that are less powerful. They have restricted access to electricity and bandwidth. This will be the new normal going forward. We therefore need to start a conversation about sustainable web design that is defined by reach and accessibility. Starting points include “reducing” (set weight budgets for websites, how big, how fast load times) and “revisiting” (start with a basic responsive design and expand only based on ROI). Vimeo has an earlier version of his talk and Luke Wroblewski’s notes of Ethan’s talk.

Harry Roberts was next. His specialty is CSS and was a bit surprised when he realised two weeks ago that he had to give a non-technical talk. As a result, he crowd-sourced his topics via Twitter and came up with work-life balance (it’s hard, do your best – you don’t need to separate them dogmatically, if you have fun), hobbies (super important to remove yourself from work – give a shit about something that doesn’t pay you, find something that is the opposite of your work, ideally something that you can do anywhere), openness (what sets the web industry apart, don’t take it for granted), the web (it’s more than just zeroes and ones, it’s about the people), cocktails (shake only drinks with dairy or juice, stir everything else) and advice (even the best advice goes out of date, know when to use new information – the web is too young for traditionalists). He also published his slides online.

Nick Gray declared that “Museums Are F***ing Awesome”. He discovered museums a couple of years ago and started doing tours for his friends under the title “Ten things I love in this museum and three that I want to steal for my home”. This quickly grew, up to the point where he now operates a company around this concept. It’s best to just watch him in action. Main takeaways for me were that good museum tours are all about the guides (be engaging and create a connection with their audience), the games (make it fun, do cheers, take pictures – everybody looks awesome in a museum) and gossip (don’t just deliver the facts, find the raunchy bits and tell them).


Last, but not least on day one came Debbie Millman who was a true highlight of the day. She talked about “On Rejection, or how the worst moments of your life can turn out to be the best”. She gave a very honest talk about all the rejections in her life, how painful they were, but also how helpful they became to get her where she is now. If you have these moments when it possibly couldn’t get worst, rejoice, because it probably can’t. She appealed to be wary especially of those successes that never become a purpose, i.e. where you are never fully engaged. She closed her talk with two quotes. (1) “If You Aren’t Getting Rejected On A Daily Basis, Your Goals Aren’t Ambitious Enough” – Chris Dixon and (2) “You can be the ripest, juiciest peach in the world, and there’s still going to be somebody who hates peaches.” – Dita Von Teese.

Day two started with Karen McGrane talking about “Adaptive Content, Context, and Controversy” laying out the differences between responsive design (same content, displayed differently based on device) vs. adaptive design (serving different content or design based on predefined criteria like device, context or person) vs. m-dot (separate website for mobile). The main difference between responsive and adaptive is that responsive design has the intelligence on the client side, while adaptive has it on the server side. Try to cover as much as possible through responsive design and resort to adaptive only for the cases where it makes sense. She also appealed to not use heuristics too much, when deciding what kind of content or functionality to offer to users, e.g. when you’re in the car driving you will receive a different view of maps than when you are walking. In 95% of the cases users are better served by getting shown the same information and choosing how to adapt to it themselves.

Alexandra Deschamps-Sonsino talked about “The End of Ignorance”, suggesting that through the ubiquity of sensors, we are in a position to make more informed decisions, such as how to adjust asthma doses based on air pollution or making smarter use of water. As a result our kids will approach life’s challenges very differently and we should encourage them to do so by. through teaching them about sensors through Arduinos or learning how to code rules. She appealed to put APIs in front of all public services so that people can connect sensors to publicly available information sources and build and share their own solutions. I especially liked her closing statement: “We already know what this change will look like. Now we should embrace it and make it happen.” Her slides are available online on slideshare.


Next was Slack’s Head of Editorial Anna Pickard, who talked about “Bug Fixes & Minor Improvements, Write Large (aka Humorous Self-Flagellation and the Multiple Benefits of Being Old On The Internet)”, or how Slack approaches writing and coincidentally established release notes in the app store as a literary genre. She talked about the value of using the written word to connect to users as humans. They aim to be understandable, friendly, empathetic, honest, with courtesy and inclusive in everything they publish – be it their Twitter feed, their blogs, the copy in their app or even release notes (a good approximation of their voice and tone is in the Mailchimp content style guide). They try to create elements of surprise and delight. An example is error messages that are understandable but also relatable, playful but not whimsy, real but not marketing real. She appealed to achieve a healthy balance with this kind of writing (“the difference between a little bit of salt and a platter of salt”; “A guitar solo is fine, but a concert shouldn’t be all guitar solos.”). To quote one of her slides: “Colour all the way to the edges. Colour the parts no one can see, too. Say nice things in places no one is expecting, and some won’t even notice. Do not be afraid of putting yourself into everything you do, but don’t make it all you do. Fill all crevices with wadded-up joy. Make people happy.” In that context, a good presentation to watch is from last year’s Webstock: Kate Kiefer Lee – Writing in the Real World.

Annie Machon followed Anna. She is a former MI5 intelligence officer who left the Service to blow the whistle about alleged criminality within the intelligence agencies in the mid 90ies. Her talk “The Panopticon: Resistance is Not Futile” was an appeal to appreciate the value of privacy as a fundamental human right that is the basis for most other human right as well as democracy. She argued that once you feel watched at all times, you start self-censoring yourself. You can no longer be a fully engaged citizen, which creates a situation where democracy starts to wither and die. It was an amazing talk, reminding me of Jason Bourne. You can find a version of the talk on YouTube.

Last in the succession of British speakers was Tom Coates with “The Shape of Things”, a talk about consumer IoT and how whilst the hardware is getting there, the software layer is still underwhelming. “The network should amplify a tool’s core purpose, not just put another web browser or Twitter client on a device.” Consumer IoT has the potential to achieve a vision, where we interact with objects directly (“enchanted objects”) instead of relying on abstractions in the form of screens and icons. The value of consumer IoT will depend on how easily users can interact with the service layer, but make no mistake: 95% of the value will be in the connected service layer, not the user interface. He promoted general-purpose user interfaces and interaction patterns that can be applied onto multiple use cases rather than having to re-learn for every new use case. A good services layer (1) gives control, (2) supports you from the initial set up to the day you recycle it, (3) understands that it will be used by multiple people, (4) is able to work easily together with other things you have, (5) does not expect you be a programmer and (6) communicates clearly and politely in ways that are timely and familiar. To make IoT work we need to find better patterns how the world works. Luke Wroblewski has again a good write-up of the talk.

The most emotional talk of the conference was Keavy McMinn’s “How to mend a broken identity”. She works as an engineer at GitHub and I was totally unprepared for this talk as I expected something about online identities. However, she started talking about how her strong sense of identity as a wife was ripped away from her. Her divorce came unexpected and she was not prepared for it. She built herself up from that loss and became involved in tri-sports, redefining herself as an athlete finishing several ironman distance races. This again came to an abrupt halt when she was hit by a car and had to undergo several surgeries and a long recovery that she’s still working on. I had two main takeaways: (1) don’t be too dogmatic about your identity, but have something what she called “an elastic identity”. As an example she said that despite her injuries, she still regards herself as an athlete, as someone who pushes her body to be the best it can be. (2) You don’t need to be tough to get through a tough situation. Instead be honest and don’t default to the “I’m fine response”, accept help when somebody offers it and proactively ask for help. In the end it takes a community to get through those tough situations. This was probably my favourite talk of the two days. There is an old version of her talk “What is your Why” on YouTube

The last block of speakers started with Michael Lopp, Pinterest’s Head of Engineering, with “Fear is a Liar” about writing more and better, rather than just consuming and creating little moments through photos and 140 character messages. Instead engage with a topic and write about it, because (1) it teaches you how to structure your thoughts, (2) teaches you how to build an informed and defensible opinion (an opportunity to deeply care about something) and (3) calms and slows you down. The nemesis of writing is fear, which creeps in in various forms like doubt and procrastination. Accept that there is no right way to write, start writing and put yourself out there. We all have something to say, therefore explain in clear terms what you know, build an opinion and rant. This talk gave me quite a bit to think about. In the end I came to the conclusion, that fear is not a liar, but rather a sad potato that uses very unfortunate means to provide constructive criticism. I wrote it up a few days ago under On writing – Where Creativity, Fear and Action go on a road trip.


Next up was Cindy Gallop who spoke about “Why The Next Big Thing In Tech Is Disrupting Sex”. She pitched her website MakeLoveNotPorn and the idea behind it (educate the world that porn is not the norm). I saw her last year in Melbourne and she is impressive to watch. She combines the skills of a seasoned marketing executive with the passion of somebody who deeply cares about a greater cause. If you’re not afraid of strong language, go watch her TED Talk about Make Love, Not Porn. I loved two quotes from her in particular: “You will never own the future if you care what other people think” and “Women challenge the status quo because we are never it”.

The last session of the day was Casey Gerald’sThe Gospel of Doubt”, telling his story from growing up poor in Texas, getting into Yale and Harvard and founding MBA’s Across America. He encouraged the audience to not necessarily seek the shelter of certainty, but have more doubt instead, challenging common beliefs and building your own opinion. I will leave it at that and wait patiently for the Webstock video footage to re-watch his talk.

Natasha Lampard delivered the closing note. She is one of the co-founders and organisers of Webstock, and pointed out that it is never too late to start something new. She told the story of an Italian astronaut who had a late calling at the end of his twenties as well as a quote from a lady who was well into her nineties: “If I knew that I would get that old, I would have started playing the violin at the age of 60. By now I would have nearly 40 years of experience.” While we celebrate young entrepreneurs and their drive, we should not mistake that for discouraging an older generation from starting something new. If you have something to contribute, a calling or a purpose that you want to pursue, don’t let age be a factor that holds you back.