Sure, I’m super proud of the 20 years of design experience and 10 years of being a successful freelancer I have under my belt—sounds pretty legit, right?—but the truth is those years of experience came with tons of mistakes and setbacks.
The books below are handy collections of tips, hard-won wisdom, and general guidelines for what I’ve found works (and doesn’t work) in design and in freelancing. I hope they’ll be a guide for those taking their first steps into these areas and help budding designers and freelancers take a shortcut to success, with fewer tears and ramen meals.
June 19, 2019
Tim Cook’s Stanford Commencement Address
“First things first, here’s a plain fact.
Silicon Valley is responsible for some of the most revolutionary inventions in modern history.
From the first oscillator built in the Hewlett-Packard garage to the iPhones that I know you’re holding in your hands.
Social media, shareable video, snaps and stories that connect half the people on Earth. They all trace their roots to Stanford’s backyard.
But lately, it seems, this industry is becoming better known for a less noble innovation: the belief that you can claim credit without accepting responsibility.
We see it every day now, with every data breach, every privacy violation, every blind eye turned to hate speech. Fake news poisoning our national conversation. The false promise of miracles in exchange for a single drop of your blood. Too many seem to think that good intentions excuse away harmful outcomes.
But whether you like it or not, what you build and what you create define who you are.
It feels a bit crazy that anyone should have to say this. But if you’ve built a chaos factory, you can’t dodge responsibility for the chaos. Taking responsibility means having the courage to think things through.
And there are few areas where this is more important than privacy.
If we accept as normal and unavoidable that everything in our lives can be aggregated, sold, or even leaked in the event of a hack, then we lose so much more than data.
We lose the freedom to be human.
Think about what’s at stake. Everything you write, everything you say, every topic of curiosity, every stray thought, every impulsive purchase, every moment of frustration or weakness, every gripe or complaint, every secret shared in confidence.
In a world without digital privacy, even if you have done nothing wrong other than think differently, you begin to censor yourself. Not entirely at first. Just a little, bit by bit. To risk less, to hope less, to imagine less, to dare less, to create less, to try less, to talk less, to think less. The chilling effect of digital surveillance is profound, and it touches everything.
What a small, unimaginative world we would end up with. Not entirely at first. Just a little, bit by bit. Ironically, it’s the kind of environment that would have stopped Silicon Valley before it had even gotten started.
We deserve better. You deserve better.
If we believe that freedom means an environment where great ideas can take root, where they can grow and be nurtured without fear of irrational restrictions or burdens, then it’s our duty to change course, because your generation ought to have the same freedom to shape the future as the generation that came before.
Graduates, at the very least, learn from these mistakes. If you want to take credit, first learn to take responsibility.”Tim Cook’s Stanford Commencement Address
I think one of Steve Jobs’ most powerful speeches was his 2005 Stanford Commencement Address (the one about connecting the dots), but it’s very possible this is even stronger. Steve was talking from a personal perspective - Tim is talking from a societal perspective but still manages to make it just as personal and private.
June 18, 2019
The Cost of Lies
What is the cost of lies? It’s not that we will mistake them for the truth. The real danger is that, if we hear enough lies, then we no longer recognize the truth at all. What can we do then? What else is left but to abandon even the hope of truth and content ourselves instead with stories? In these stories, it doesn’t matter who the heroes are. All we want to know is who is to blame.The Cost of Lies
June 18, 2019
You care more about your privacy than you think
Friction is largely underrated in user experience design. Some of the people who understand friction’s effect best, alas, are those purposely designing privacy controls to make them even just a bit harder to use, understand, or discover.
The lack of friction in the Sign In With Apple experience — especially using a device with Face ID or Touch ID — is a key part of why I expect it to be successful. It’s not just more private than signing in with Google or Facebook, it’s as good or better in terms of how few steps it takes.
Designers need to design for what people will do, not what people should, in theory, do.You care more about your privacy than you think
June 18, 2019
Let’s assemble like the Avengers and... do work
It’s been two years since I launched my second book, Mastering Freelance, which, in turn, was launched two years after my first book, User Experiences that Matter. It doesn’t take a genius to do the math and understand why I’ve lately been considering my next venture outside of my normal work. Truth be told, I even have an outline of what my next book could be. However, I have a sneaky feeling that a third book is not what I am aiming to do at this point. I’m sure a third book will come one day, not just now.
I’ve been trying to get back into more reading lately and while I was reading Paul Jarvis’ book, Company of One, an idea started to form… but first, let me give you some context.
I’ve been a consultant for more than 10 years. I’ve been successful at it and love the freedom it gives me. I can’t ever see myself taking a full-time role again as I love running my own business too much. But does that mean there’s no other way? Something in Paul’s book sparked an idea in me, that maybe it’s not either/or. Perhaps it’s about choosing your own path.
Ever since starting MailChimp 18 years ago, I’ve always been told that my way was wrong. My way has never been to “be big.” My way was always to “be useful.” My company has become a global brand with millions of customers, over $525 million in annual revenue, and almost 1000 employees united by a single mission to help companies of one and entrepreneurs. Go figure. There’s not one, right way. Only your way. Paul’s book, Company of One, can help you find your way.BEN CHESTNUT, CEO AND FOUNDER OF MAILCHIMP
Just like Ben’s way was never to “be big”, neither is mine. But lately, I’ve been starting to miss being PART of something bigger. I miss having my own team. I miss working with people that are so good in their industry that I have to give 150% at all times just to keep up. I want to take on bigger projects together with other small-business owners like myself. Most of all, I want to challenge clients in their belief that “bigger is a safer bet”. My guess is that Hertz have learnt this lesson by now.
More people does not equal success
I’m always amazed at how long the idea that more people equals a better business continues to live on. But it’s always one of the first metrics that people tend to focus on - how many people work at a company? The original Super Mario Bros. was created of team of 5 people and it seems that even launching a website now requires a team of 25+. Why? Because we live with the idea that the more people we assign to something, the less likely we will fail. I’m not sure if I’ve ever worked on a project that benefitted from just having more people… a project benefits from making sure it’s the right people.
“Who you hang out with determines what you dream about and what you collide with. And the collisions and the dreams lead to your changes. And the changes are what you become. Change the outcome by changing your circle.”Seth Godin
I think a lot of freelancers share these same feelings - wanting to be part of a collective, while remaining independent. Wanting to have access to vetted talent to support them in projects while not being locked in to a structure. Wanting to have colleagues and water-cooler chitchats while still having the option of their own office. So my humble idea is looking something like this: Let’s form the Avengers.
Spiderman, Iron Man, Black Panther, Captain Marvel all have their own characters and their own movies. But when they need to fight Thanos, it’s pretty sweet to be able to team up. And, like the Avengers, it’s sometimes necessary to have that extra support to have a successful outcome. It takes the whole team to get the job done. Honestly, there’s no “one way” of running businesses and I strongly believe that clients will find a solution like this “useful” if not necessarily “big” (I don’t think it should be more than 15 people ever).
“When filmmakers make films, they pick the people who best embody the role. David Fincher doesn’t always use Brad Pitt, even though he was fantastic in Fight Club and Se7en. Christopher Nolan doesn’t always use the same lead actor either. Leonardo DiCaprio was awesome in Inception, as was Guy Pearce in Memento, as was Christian Bale in the Batman movies, but you couldn’t interchange them because of how well they were cast. Leo as the Dark Knight? “I’m the king of the world, Alfred!” Too weird.”Superfriend.ly
Making a commitment
I don’t have a timeline for this venture and I certainly don’t have a deadline. But I shared some of this on social media last week and it spurred some interest and sharing it even more publicly will force me to act on it. It also gives YOU the option to reach out and talk to me - be it as a potential collaborator or as a client. As a potential client, I’m particularly interested in knowing more about what pain points (second Mario Bros reference of this post!) you’re currently experiencing working with agencies.
June 13, 2019
Big Mood Machine
“At Spotify we have a personal relationship with over 191 million people who show us their true colors with zero filter,” reads a current advertising deck. “That’s a lot of authentic engagement with our audience: billions of data points every day across devices! This data fuels Spotify’s streaming intelligence—our secret weapon that gives brands the edge to be relevant in real-time moments.” Another brand-facing pitch proclaims: “The most exciting part? This new research is starting to reveal the streaming generation’s offline behaviors through their streaming habits.”Big Mood Machine
I prefer Spotify over Apple Music and generally think their playlists are better curated but something about this is deeply disturbing. The notion was always that “If you’re not paying for the product, you are the product” - but with Spotify we are paying so one would assume that it would be enough. Apparently not.
Apple’s bet on privacy is beginning to make more and more sense.
It would seem that the legacy culture of these organisations stifles new and leaner working practices. Ultimately, these companies are built on delivering large, waterfall driven change programs, rather than embrace the rapid iteration and evolution of digital best practice.Hiring a Management Consultancy for Digital Is a Mistake
June 07, 2019
Simplicity is a war
This post was originally titled “simplicity is a battle”, but it dawned on us that that’s not strictly true – battles can be lost, while a war can still be won. Similarly, you can win battles while still losing a war. Simplicity is a war because it’s eroded in small battles that occur daily, often faster than the blink of an eye. You can win many battles for simplicity, but still end up with a complex product or company.
Simplicity is a war. And it’s being lost with thousands of tiny battles.Simplicity is a war
June 07, 2019
Dos and dont’s on designing for accessibility
Karwai Pun is an interaction designer currently working on Service Optimisation to make existing and new services better for our users. Karwai is part of an accessibility group at Home Office Digital, leading on autism. Together with the team, she’s created these dos and don’ts posters as a way of approaching accessibility from a design perspective.Dos and dont’s on designing for accessibility