1. To start a successful freelance writing career, you either need to be independently wealthy or have a very understanding spouse.

  2. When you’re designing something, imagine you’re sitting in a room, helping a real person with the task at hand.

  3. “People come to us and say, ‘We’ve got this problem,’ and we’re immediately assuming that they’re asking us to come up with a solution. Whereas, the right answer is to say, ‘That’s an amazing problem. I don’t know the answer. Let’s figure that out together. Let’s work on that together. Let’s figure out what the best solution might be.”

    “We just don’t have the confidence to do that, because we were told right from the get go when we start school, that there’s only one answer for something. You get given a math test, and the math test says there’s a right answer and a wrong answer. You get given an English test and there’s a right answer and a wrong answer.”

    “We grow up with this belief that there are only answers. Instead of saying, ‘I don’t know, but here’s something else that we could consider.’ Or, ‘Let’s talk about that and come up with the best answer.’ We’re predisposed to think that for every problem out there, there has to be an answer and we’re supposed to carry that in our back pocket.”

    “Whereas in truth, we don’t know what the answers are, especially in this ambiguous future. How could I have possibly known that there were going to be this many devices available in 2016? How was I supposed to know that entire industries’ markets were going to be disrupted by simple ideas?”

  4. It is all well and good to talk about how you are using agile methods or implementing devops, but if your development budget doesn’t have a line item for iteratively improving the apps you just launched, you really are stuck in the past.

  5. Design Walkthrough—How does the design match up with the business problems we’re working to solve?

    Design Review—Is this design ready for moving forward or are their still issues to resolve?

    Design Demo—What is the user’s experience when using this design?

    Design Critique—What can we learn from this design we’ve created?

  6. When you’re a designer who’s been working on a project for a year or two, it’s very easy to think things are intuitive or obvious that are actually totally incomprehensible.

  7. Resist the urge to use text if there are ways to show rather than tell. Use text to prompt the “cause,” and let the user observe the “effect” by doing. [re: app onboarding]

  8. Most artifacts are thrown away, having the ideas in them deemed ‘not worthy of further contemplation.’ But, the process of creating them, critiquing them, and discussing their implications lives on. They become the basis to the teams common understanding of the problem.

  9. “Listen bub,” I say, “it is very impressive that you can teach a bear to ride a bicycle, and it is fascinating and novel. But perhaps it’s cruel? Because that’s not what bears are supposed to do. And look, pal, that bear will never actually be good at riding a bicycle.”

    This is how I feel about so many of the fancy websites I see. “It is fascinating that you can do that, but it’s really not what a website is supposed to do.”

  10. You can’t just have a great experience. You need to have a great marketing story, a great business plan, great engineering, and ultimately a great culture and process so that you can build on a great idea and evolve it quickly. I’ve come to appreciate staying power and slow success. The biggest challenge for designers today is considering how you design for something that needs to evolve and grow with a community of people over the course of years.

  11. There’s a fundamental misunderstanding that all coding is ultra-geeky programming, which simply isn’t the case. HTML is not a programming language. CSS is not a programming language. But because HTML and CSS are still technically code, frontend development is often put in the same bucket as Python, Java, PHP, Ruby, C++, and other programming languages. This misunderstanding tends to give many frontend developers, myself included, a severe identity crisis.

  12. Giving the presenter a chance to show their work without being interrupted by a string of questions turns out to be pretty important. After seeing the Chosen Ones [the observed magician group] in action, I immediately noticed how, in my design reviews, disruptive interruptions can be. It throws the presenter off and doesn’t give them a chance to tell their story about the design and what they’re trying to accomplish.

    Unfortunately, we often let the presenter also play the roles of facilitator and recorder. The wise kids at SYM let one of their own be the facilitator. (It was officially the VP’s job, but when that kid needed to perform, one of the other chapter officers would facilitate that meeting.)

    Recording all the ideas coming in is important and it’s really hard to do, even for seasoned adult presenters, when simultaneously trying to listen and take in the ideas. Having another person record the group’s thoughts gives the presenter the confidence that everything’s being recorded without needing to juggle listening with note taking.

  13. A good idea starts with one person, but only a team can bring it to life. We believe that being together, communicating directly, and providing constant feedback is the best way to build strong teams and do good work. Involving other people in your work also creates team-wide ownership.

  14. Being able to invest in design in an industry where it’s considered an afterthought has propelled our products further ahead, and that has come from designers in their work. Say we’re bouncing around ideas of what to build next, or what the next version of something should be. Having that product design perspective is key, because otherwise — if you think of setting the direction as an isolated process and then it gets sent out to all the teams designing it and implementing it, you lose the magic that is iterating and having the freedom to test things. That’s where all the really good things come out — not from the initial meetings. The actual implementation is where it matters, and I think that us having designers very early in there has made all the products we’ve built so much better.

  15. Invest in your process. A rock-solid process — a series of repeatable actions — is the golden goose to building creative confidence. These actions include: a) thoroughly exploring every idea you or your trusted peers can come up with. This might feel time-consuming and unexciting, but it’s also a pretty simple math equation: if you have explored literally every single option, you will also have come up with the best solution. As you become stronger in your craft, you’ll develop a keener sense for how to discard unpromising paths earlier so you can more quickly get to the best solution, but if you are stuck, never doubt the power of brute force; b) getting lots of early feedback from as many smart people as you can. Even if you hear different or conflicting things, understanding the range of viewpoints ensures you will consider the tradeoffs carefully. And if you start hearing that everyone agrees your solution is obvious, then great. Your work here is done; c) connecting with the real people you’re building for. It’s hard to overestimate the power of user research. Done well, it gives you an unparalleled understanding of the why behind how people think and what they do. Nothing builds confidence like research that validates the problem you’re solving is real, and that the solution you’ve come up with is really working for people.

  16. In Silicon Valley fashion, Cox prefers to recast past mistakes as healthy experiments and valuable learning experiences. “I think any good company is trying things, is forcing itself to try things, and you need to be able to put things out there and try and learn,” he says. “People only get in trouble if they’re not honest about failure.”