The useful thing about defining good design as a form-context fit is that it tells you where you will find the form. The form is in the context. To find a good relationship, you do not start by saying, “I want a relationship that looks like this”—that would be starting in the wrong end, by defining form. Instead you say, “I’m just going to pay attention to what happens when I hang out with various people and iterate toward something that feels alive”—you start from the context.

The context is smarter than you. It holds more nuance and information than you can fit in your head. Collaborate with it.

If you want to find a good design—be that the design of a house or an essay, a career or a marriage—what you want is some process that allows you to extract information from the context, and bake it into the form. That is what unfolding is.

The opposite of an unfolding is a vision. A vision springs, not from a careful understanding of a context, but from a fantasy

Anything that increases the rate and resolution of information you get from the context will help. And anything that makes it easier for you to act on the context.

A common reason we filter information and become blind to the context is that we bundle things when we think. Thinking about our career, we might think in abstractions like “a job.” But really a career is made up of a bunch of different things like a salary, an identity, relationships, status, a sense of meaning, and so on. It is often easier to find a fit if you unbundle these things, and think about the parts that matter to you individually. Do you actually need more status? Or can you find a better fit if you go low status?

Another common reason the feedback loop of unfolding often works poorly is that people have decided on a solution already. They have turned on their confirmation bias. They have decided that a certain solution is off-limits. Let’s say you are 34 and haven’t found a partner but want kids. If we unbundle this, it is clear that the problem of having a kid and the problem of love are not the same thing, so you could solve your problem by having a kid with your best friend instead. But this feels weird. It is not the vision you have for your life. And it seems dysfunctional. Observe that feeling—it is, perhaps, a part of the context. There is some information there. But to unfold, do not write off any solutions. Leave them all on the table; let them combine and recombine. Many good ideas look bad at first. To increase the rate at which you understand the context, you want to develop a certain detachment. When the context thrashes one of your ideas, you want to say, “Oh, that’s interesting.” It takes practice. But it is worth getting better at. Reality is shy—it only reveals itself to those who, like honest scientists, do not wish it to be something else.

The faster you can collide your ideas against reality, the faster you get feedback.

The school system is centered around visions, not unfolding. You are asked to make decisions about realities that are five, ten years down the line, and you get no feedback on your decisions.

you’re less torn by anxious attachments when you recognize how something must naturally and necessarily unfold.

Knowledge is freedom from getting mad at facts.

Detachment does not mean you don’t care what happens. It just means you don’t care whether a specific thing happens or not. You want to know the outcome of the coin-toss (you care), but you don’t care whether it is heads or tails even if you’ve bet on heads (you’re not attached to a specific outcome). The important thing is that something happens, which means you’ve successfully kept play going, but without keeping score.

Emotional Self-Management: I like to think of this as accepting the emotions you have instead of having emotions about having emotions in an endless stack.

Fear. Not fear, plus anxiety about fear, plus guilt about anxiety about fear, plus shame about displaying guilt about experiencing anxiety about having fear. This is emotional focus. Instead of retreating from an emotion through layers of additional emotions until you find one you can deal with, you experience the actual emotion for what it is.

Forget trying to decide what your life’s destiny is. That’s too grand. Instead, just figure out what you should do in the next 2 years.

Visuals can stir up feelings or paint a scene in an instant. However, they may not always nail down the details or explain things as clearly as words can. Words can be very precise and give you all the information you need. Yet, sometimes they miss that instant impact or emotional punch.

For each visual you add to your presentation, you should ask yourself “What does it really say?” And then check: Does it enhance the meaning of my message, or is it purely decorative? Does it belong at this point in my presentation? Would it be better for another slide? Is there a better image that says what I want to say?

Computers don’t feel, and that means: they don’t understand what they do, they grow images like cancer grows cells: They just replicate something into the blue. This becomes apparent in the often outright creepiness of AI images.

AI is really good at making scary images. Even if the prompt lacks all hints of horror kitsch, you need to get ready to see or feel something disturbing when you look at AI images. It’s like a spell. Part of the scariness comes from the cancer-like pattern that reproduces the same ornament without considering its meaning and consequence.

Placing pictures next to each other will invite comparisons. We also compare images that follow each other. Make sure that you do not inadvertently compare apples and oranges.

When placing multiple images in a grid or on one slide after the other, ensure they don’t clash in terms of colors, style, or resolution. Otherwise, people will focus more on the contrast between the images rather than their content.

Repeating what everyone can see is bad practice. To make pictures and text work, they need to have something to say about each other.

Don’t write next to the image what people already see. A caption is not an ALT text.

The most powerful combination of text and image happens when the text says about the image what you can’t see at first sight, and when the image renders what is hard to imagine.

Do not be boring or overly explanatory. The visual should attract their attention to your words and vice-versa.

If a visual lacks meaning, it becomes a decorative placeholder. It can dilute your message, distract from what you want to say, and even express disrespect to your audience.

Many case studies read to me like school homework: they knew what the answer and the process were “supposed to be” according to the textbook, so made up the story to fit. In reality, as you point out, it’s never smooth and linear. It’s messy and loopish. If you’re doing a good job, you rarely end up with anything remotely like you anticipated when you started out.

abandon your dogmatic and idealistic view of the design process, and keep learning about how flexible, messy, and beautiful it is.

I don’t speak about the “ideal” design process for a simple reason: it doesn’t exist. Design is never linear, and all projects are unique. The point is to show and explain your path from the kick-off to the final result in the portfolio.

If you tell a story, include the details and the things that didn’t work and how you adapted to overcome the problem, the design manager will empathise with you. For the five minutes it takes to read your case study, they’ll be in your shoes. It’ll remind them of all the times when they had similar problems and it’ll make them appreciate you and your struggles as a designer.

When I first started meeting founders, I wanted to help with anything and everything. Unfortunately, that's neither realistic or possible. For example, I have many responsibilities at my day job that must come first. Over time, I have honed in my pitch to be explicit about how I can and can't help. See the notes above about ways to be helpful, and find your own unique combination of value to bring to the table.

My contract typically looks like this: We agree to meet ~X hours per quarter/half/year Multiply by Y contracting rate Y ⨉ X = some dollar amount Z Divide Z by the startup's latest price per share to arrive at a number of advisor shares to grant

Be founder-friendly! It's a big deal and a lot of paperwork to get a smaller check or advisor on the cap table (unless they already have a lot of operational infrastructure in place) – this usually means being relaxed about the commitment paperwork or helping out pro-bono for the first few hours while they work through the logistics.

Finding founders you work well with can be a numbers game; you won't be sure what you like doing until you've met a handful of founders, done several advisory meetings, and poked at different types of problems. It's okay to dip your toe and warm up to the process before committing a lot of time and energy to this. I started slow, and have been steadily sharpening my own intuition about what kinds of products and founders get me excited, and where I can add unique value

If you're pursuing the career path someone else has taken, you're going to be frustrated when you don't get the same opportunities they did.

Let’s say you present 3 directions to a client: directions A, B, and C. These are our initial 3 branches. You have a client review, direction C is the winner, and so you iterate again. 3 more branches: C1, C2, and C3. Another review, another winner, another round of iterations: C2.1, C2.2, C2.3. Branch out, choose one, zoom in, branch out, repeat.

Sometimes, the design process requires us to zoom out. Let’s say you present those 3 creative directions, A, B, and C, but nothing lands. Back to the drawing board. You might keep pushing forward with branches D, E, F. Nothing lands. You’re forced to zoom out and realize that you’re not even on the right parent branch.

Poor design meets one need while creating a dozen others. Good design resolves problems without negatively affecting anything else in its ecosystem. We call this lens of thinking "systems thinking." It tends to separate the genuinely great designers from the pretty-great ones. The designers who do tremendous work know that what they're creating does not exist within a bubble. They understand that the context of what they're making plays a vital role in how the team should build it. They know how what they create affects everything it touches, particularly the people. The design is intentional. Trade-offs are known, weighted, and decided on. Not only in the immediate problem space but in the surrounding spaces too.

Generalists can pursue broader themes, questions, and lenses which, across their interests give them a deep perspective from breadth.For example, a specialist is someone who is obsessed with chess and spends their waking hours practicing, playing, and studying.A generalist is someone who is obsessed with the idea of game-play, and has researched and gone deep on sports, childhood psychology, board games, and philosophy.

Embracing being a coordinate on the map for a point in time is about allowing yourself to be seen as something specific. Generalists can feel trapped by that but the truth is being specific, and being on the map for others is a way of being in service. If you never pin yourself down (just for a time) you miss the benefits of being connected or in service.