To write about anything well, you have to do a lot of research. Even just trying to work out the chronology of a few years of one person’s life can take hours of interviews. If you’re writing about a scientific debate, you may have to trace it back 100 years through papers and books. To understand how someone sequenced 400,000 year old DNA, you may need to become excruciatingly well acquainted with the latest DNA sequencing technology. Once you’ve done all that, you will feel a sense of victory. You get it. You see how all the pieces fit together. And you can’t wait to make your readers also see that entire network of knowledge as clearly as you do right now. That’s a recipe for disaster.

When I was starting out, I’d try to convey everything I knew about a subject in a story, and I ended up spending days or weeks in painful contortions. There isn’t enough room in an article to present a full story. Even a book is not space enough. It’s like trying to build a ship in a bottle. You end up spending all your time squeezing down all the things you’ve learned into miniaturized story bits. And the result will be unreadable.

It took me a long time to learn that all that research is indeed necessary, but only to enable you to figure out the story you want to tell. That story will be a shadow of reality—a low-dimensional representation of it. But it will make sense in the format of a story. It’s hard to take this step, largely because you look at the heap of information you’ve gathered and absorbed, and you can’t bear to abandon any of it. But that’s not being a good writer. That’s being selfish. I wish someone had told me to just let go.

Find time to write at least a couple hours a day, every day. And I mean real writing, not dithering on the Internet telling yourself you’re doing “research.” Get a blank notebook and a pen if you have to. It’s in those long stretches of time with your own words, sentences, and paragraphs that you come face to face with all the great challenges of writing, and you find the solutions.

Make readers want to keep reading to find out how you got to that point. Practically speaking, a full-width banner image with bold colors and appropriate branding, as well as a mockup or two (mirroring your homepage thumbnail) is the most effective. Follow this with a short paragraph of what the project is about and its background. You should also include a list of details such as the project duration, how big the team was, tools used, and most importantly, what your specific role in the project was.

Following this, make your problem statement bold and clear. It doesn’t have to be too formal. Juxtapose this with your solution. This could be a parallel statement, or a combination of words and graphics once again showing your final product, but more specifically highlighting sections or screens that demonstrate how it solves the problem you just stated.

Everything you’ve written up to this point should be enough to give the casual reader a good idea of the project background and what the final product looks like. They’d probably be fine moving on to another page on your portfolio. But for people who want to read more on this case study, make sure to clearly but concisely tell everything that relates to the work that you did. Structure the rest of your case study after the introduction like this: Research — E.g. competitive analysis, interview and survey results, and personas (if any). User flow(s) — Important to give an idea of how the app is meant to be used. Ideation — E.g. information architecture/site map, sketches, low-progressing-to-high fidelity wireframes, usability testing feedback, annotated iterations, and before/after examples. Final design — Complete prototype containing your highest fidelity wireframes. You could walk through a specific user flow, or just showcase different screens. Here is where gifs, an embedded prototype (more on this later), and demonstration videos should be placed. Conclusion — All good pieces of writing need a conclusion to stick the landing. Talk about next steps first, because readers’ minds are still on the prototype. Then, if applicable, mention direct impacts of the work you did, such as specific growth or revenue metrics. Then, give it a personal touch by talking about what you thought of the project, and the lessons learned.

Abandon the idea that you are ever going to finish. Lose track of the 400 pages and write just one page for each day, it helps. Then when it gets finished, you are always surprised.

Forget your generalized audience. In the first place, the nameless, faceless audience will scare you to death and in the second place, unlike the theater, it doesn’t exist. In writing, your audience is one single reader. I have found that sometimes it helps to pick out one person—a real person you know, or an imagined person and write to that one.

If a scene or a section gets the better of you and you still think you want it—bypass it and go on. When you have finished the whole you can come back to it and then you may find that the reason it gave trouble is because it didn’t belong there.

If there is a magic in story writing, and I am convinced there is, no one has ever been able to reduce it to a recipe that can be passed from one person to another. The formula seems to lie solely in the aching urge of the writer to convey something he feels important to the reader.

a bad story is only an ineffective story.

So I do have kind of an extensive questionnaire, so we just touch on a few things, but one thing I think first and foremost is, what are your values? And I think it's really essential to do some sort of values clarification exercise. You can find a ton of them online. You can find a list of values and just pull out your core values and just compare them with each other because when you are aligned, it's great. Or when you're adjacent, it's also great. I might care a lot about excellence, Lenny, you might care a lot about learning. Fantastic. Those are great values that we can kind of, go together. I might care about excellence and you might care about work-life balance. Wow, let's talk about that because I think it's going to be really important as we go through our startup journey that we understand both of us, what does work-life balance mean and what does excellence mean?

One of the founders I worked with, he would text or Slack his co-founder on weekends and the co-founder wouldn't respond. And that was extremely frustrating to the person, to the co-founder I was talking to. And it turned out, after they finally addressed it, it really was about wanting to have some downtime and some, quote unquote, "Balance."

I'm so great at bringing things up." But the person who's close to you might say, "You seethe until you're ready to bring something up and it's really uncomfortable in the seething period." So it just gives you a little more self-awareness about how you actually handle conflict.

The other person might be a person who totally wants to talk about the conflict but wants to let it settle first and wants to also go through their own thinking process about what's important to them and might actually feel like they've resolved it themselves without having to have a conversation with you.

And if you're the person who's like, "Let's talk about it, let's talk about it, let's talk about it." And they're like, "I'm working through it myself." Now you have conflict over the conflict and it just turns into dynamic that's not necessary.

The act of writing out your thoughts is a direct aid to concentration, and tends to enforce the habit of choosing the best language. It gives clearness, force, precision, beauty, and copiousness of style, so valuable in extemporaneous and impromptu speaking.

One eminent speaker used practically no gesture; another was in almost constant action. One was quiet, modest, and conversational in his speaking style; another was impulsive and resistless as a mountain torrent.

While you might think turning a yellow spot into the sun is mainly about strong execution, it’s equally about inventiveness and vision. There are situations where I wouldn’t have been able to describe what the person ended up creating. I had a version of what “great” looked like in my mind—and they surpassed it in ways I wouldn’t have been able to articulate in advance.

Arielle because Balsamiq is a newsletter sponsor. She shared a story that’s an example of turning a yellow spot into the sun. Here’s what she said: “Something I did that completely changed my career in its early years: I kept a work journal. I noted down decisions I made as an IC and manager, decisions my managers made, the outcomes, the impact, and what I learned. I wrote down those "inside thoughts" we all have during meetings. I wrote down the advice I HATED and why, as well as the helpful stuff. I wrote down pivotal interactions with clients, peers, leaders, and direct reports. I wrote down specific phrases different leaders liked to use. It was almost scientific—I applied basic tactics I learned in science/psychology classes about field observation. I still reference that journal to this day.”

Most people in her shoes would have said, “I need a mentor. I need someone to teach me strategy. I need support. I need to ask execs to explain their decisions and get their feedback.” Not Arielle. Arielle took a little (i.e. the lived experiences she was getting on the job, like all her peers)—and she turned it into a lot.

There is no set of rules (beyond the first principles I cover here each week) to memorize. It’s the same foundational principles, like knowing your assets/levers/constraints, asking the question behind the question, thinking rigorously, etc.

Before you move on to the next shiny object, consider if you’ve really squeezed every last drop of juice from your current endeavor.

People celebrate the strategy at the beginning and the outcome at the end, but if you look more deeply, there was usually good decision-making and craft at each step, which layered up to greatness. That’s why turning a yellow spot into the sun isn’t only for dramatic projects. It’s equally about elevating stuff most folks think of as boring and small.

Keep an eye out for anything that makes you stop in your tracks, even small things. Note what makes it feel magical and add it to your mental swipe file.

When a statement is attributed to “a spokesperson” from a company or institution, the world doesn’t know who that spokesperson is. Only the reporter or writer, and perhaps their editors. There is an explicit lack of accountability attributing statements to an institution rather than to specific people. We even have different pronouns — it’s institutions that do things, but only people who do things. Who is the question.

This West Point / ProPublica near-fiasco has me reconsidering my skepticism toward The Verge’s obstinacy on this. It occurs to me now that The Verge’s adamancy on this issue isn’t merely for the benefit of their readers. Putting one’s name on a statement heightens the personal stakes. This is why it’s more than vanity to put your name on your work, whatever your work is — it shows you take responsibility for its validity

Some people are great at giving gifts. The kinds of gifts that dig into your soul and make you feel seen. I'm trying to become one of those people

Simon conspired with a friend who owns a 3D printer and designed and created a little desktop bear that can hold all of the nice things people have written about Bear. He then wrote each of these entries by hand (suffering only minor carpel tunnel) on sticky notes which the bear now carries like a human bear directional.

These are the kinds of gifts I want to learn how to give. Ones that make the receiver feel like they've been listened to and understood. That don't cost much money but are priceless at the same time.

Some good questions to ask: Can they show you some examples of past projects they've built in Webflow? Do some checking if their work looks good on smaller devices (Webflow cascades styles down from desktop, so mobile design can sometimes get overlooked) Are they using a class framework (e.g., Client-first, Mast, Lumos, or custom)? And are they comfortable building the site with a level of modularity that enables easy reuse of sections, components, and styles? This approach simplifies future design updates and makes it easier for your team to manage and expand the site after the handover. What's their approach to SEO in Webflow? What do they do to ensure performance and loading speed are optimized? Do they have a process QA and testing before launching a site? How do they handle client feedback and revisions? Do they have a process for educating you on how to use and manage the site they built?

You don't need complex sentences to express complex ideas. When specialists in some abstruse topic talk to one another about ideas in their field, they don't use sentences any more complex than they do when talking about what to have for lunch. They use different words, certainly. But even those they use no more than necessary. And in my experience, the harder the subject, the more informally experts speak. Partly, I think, because they have less to prove, and partly because the harder the ideas you're talking about, the less you can afford to let language get in the way.

Informal language is the athletic clothing of ideas

I'm not saying spoken language always works best. Poetry is as much music as text, so you can say things you wouldn't say in conversation. And there are a handful of writers who can get away with using fancy language in prose.

But for nearly everyone else, spoken language is better.

After writing the first draft, try explaining to a friend what you just wrote. Then replace the draft with what you said to your friend.

The ability of generative AI tools to analyse huge datasets can also be used to help spark creative inspiration. This can help us if we’re struggling for time or battling writer’s block. For example, if a social media manager is looking for ideas on how to engage alumni on Instagram, they could ask ChatGPT for suggestions based on recent popular content. They could then pick the best ideas from ChatGPT’s response and adapt them. We may use these tools in a similar way to how we ask a colleague for an idea on how to approach a creative task.

We may use these tools in a similar way to how we use search engines for researching topics and will always carefully fact-check before publication.

we will not publish any press releases, articles, social media posts, blog posts, internal emails or other written content that is 100% produced by generative AI. We will always apply brand guidelines, fact-check responses, and re-write in our own words.

We may use these tools to make minor changes to a photo to make it more usable without changing the subject matter or original essence. For example, if a website manager needs a photo in a landscape ratio but only has one in a portrait ratio, they could use Photoshop’s inbuilt AI tools to extend the background of the photo to create an image with the correct dimensions for the website.

The phrase a picture is worth a thousand words has two popular origin stories. One version credits advertising executive Frederick R. Barnard, who attributed the phrase to an ancient Chinese proverb. The closest Chinese equivalent translates to “Hearing something a hundred times isn’t better than seeing it once.” In other words, the Chinese Origin was made up: “…the Chinese derivation was pure invention. Many things had been thought to be ‘worth ten thousand words’ well before pictures got in on the act;”

the true origin of the proverb is not Chinese but adspeak.3 It shows how the phrase has morphed into a commercial, facile cliche.

Letting images and pictures compete for supremacy reduces the complex relationship between images and words into a direct, quantifiable comparison. Words and images function differently

A few carefully chosen words can say what 1,000 stock images cannot. The right image can counter cynicism, closed-mindedness, or an automatic dismissal of a convincing argument.

Tell your audience how you interpret the image. What the image means.

Use images to complement, not repeat or overshadow, the text. Get rid of images that are just there to add color.

Stock images are clichés. Clichés can be easily turned on their head because of their simplistic topic. You want to communicate that you’re diverse and you end up telling people that you’re a company run by a minority. Or you want to communicate success, but the focus on two middle-aged white people ends up communicating their privilege.

Whether you like it or not, people will read into this picture as well and they won’t find a lot of valuable or advantageous information in it. It again mostly says: “This boring website thinks that I don’t see that this is a meaningless stock image.”

Pictures have an impact when they tell a story that only a picture can tell.

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.

The beginning is almost never the most compelling or important part. It's just the bit you thought of first, based on your subjective chronology.

Signposting what you're going to write about is good, but starting with an exhaustive list of definitions is extremely boring.

Invoking paleolithic people is an overplayed way to convince us your topic is cosmically important.

Openings need tension – paradoxes, unanswered questions, and unresolved action

Good openings propose problems, pose questions, drop you into an unfinished story, or point at fundamental tensions within a topic. Ideally within the first paragraph or two.

"Good writing starts strong. Not with a cliché ("Since the dawn of time"), not with a banality ("Recently, scholars have been increasingly concerned with the questions of..."), but with a contentful observation that provokes curiosity."A Sense of StyleStephen Pinker

Creating tension in non-fiction work is trickier because your story is (hopefully) constrained by reality. You are not at liberty to invent suspicious murders, salacious extramarital affairs, or newly-discovered-magical-powers to create tension and mystery. You have to deal with the plain, unexotic facts of the world.

Your job becomes much harder if you pick topics with no tension, problems, or puzzles within them. To paraphrase Williams, it is more of a failure to pose an uninteresting problem, than to poorly articulate an interesting one

Your interest in the topic is your best directional clue for finding the tension or interesting paradox. Your urge to write about the thing hopefully comes from a place of curiosity. You have unanswered questions about it. It feels important or consequential for unexplained reasons. You think you've seen things in it other people haven't. Pay attention to that interest.

Problems are a destabilising condition that has a cost for a community of readers that needs a solution. Destabilising condition is just a fancy word for “change” here – a change in the status quo. Put another way, a problem is an expected turn of events, that has undesireable consequences, for an audience who will care about it, that we want to explore solutions to.

Williams is speaking to a community of academic writers in his book. They're trying to present scientific and research problems in plain, objective language, which isn't necessarily what we want to do with narrative writing like blogging or personal essays. We have a little more liberty to put interesting padding around the change, consequences, and solution, such as telling an opening anecdote, or drawing readers in with characters, rich details, and sensory descriptions.

Williams suggests we try to state our problem and then ask a series of so what?'s to get at the underlying problem

For your writing to be worth reading, you need to be exploring something of consequence for someone

When McPhee writes, after first immersing himself in his raw material (field notes, interview transcripts, official documents) for weeks, he then draws a structure for the work. The structure lays out the major themes and scenes he'll work through, in the order that will make them most compelling and coherent.

Developing a structure requires navigating the tension between chronology and theme. Chronology is what we default to, but themes that repeatedly appear want to pull themselves together into a single place. The themes that really matter should be in your opening. Even if the moment that best defines them happens right before the end of the timeline.

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.

There are four signs your idea has legs:People pay you money: Several people start to pay for your product, ideally people you don’t have a direct connection toContinued usage: People continue to use your prototype product, even if it’s hackyStrong emotion: You’re hearing hatred for the incumbents (i.e. pain) or a deep and strong emotional reaction to your idea (i.e. pull)Cold inbound interest: You’re seeing cold inbound interest in your product

Every prosumer collaboration product, including Figma, Notion, Coda, Airtable, Miro, and Slack, spent three to four years wandering in the dark until they stumbled on something that clicked.

When I am in good hands I open myself to a state of curiosity and appreciation. I allow myself to suspend preconceived notions. I give you freedom to take me where you want to go. I immerse myself in your worldview and pause judgement.

That trust doesn’t come easily. As an audience member it’s about feeling cared for from the moment I interact with your work. It’s about feeling a well-defined point of view permeate what you make. If my mind was changed, I must have been in good hands.

I know I am in good hands when I sense a cohesive point of view expressed with attention to detail. I can feel it almost instantly. In any medium. Music, film, fashion, architecture, writing, software. At a Japanese restaurant it’s what omakase aims to be. I leave it up to you, chef.

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

Experts suggest spending several days without setting alarms and just waking up when your body naturally wants to, which you can try over a three-day weekend.

The more you go back and forth between early and late bedtimes, the more likely you are to struggle to fall asleep when you need to.

reward yourself for waking up early on a Saturday: Plan a morning walk, brunch or a call with a friend, or watch your favorite TV show while you eat breakfast.

The Learn In Public movement has encouraged thousands of people to write, speak, draw, or otherwise pick up what mentors put down, with the end goal of lifelong L(N*P) growth in personal knowledge and network. A key part of this strategy is maintaining your own Digital Garden. A Digital Garden is your very own place (often a blog, or twitter account) to plant incomplete thoughts and disorganized notes in public - the idea being that these are evergreen things that grow as your learning does, warmed by constant attention and fueled by the unambiguous daylight of peer review. It is in part a trick for creators to play on themselves: For perfectionists who stress over shipping anything less-than-polished and therefore never ship anything, it is a license to trade off self review for peer review and increased velocity. Many report both improved quality and quantity of output after giving themselves the permission to do this.

People with audiences do of course have some obligation to not do them a disservice, else they don’t deserve that audience. However this doesn’t mean that they must do exhaustive due diligence and be authoritative in every context - there needs to be space to experiment, grow, and quite frankly, be ignorant and wrong.

I will “steelman” arguments - the opposite of “strawman arguments” - instead of picking on the weakest piece of their argument, I will confront head on their best argument by seeking first to understand before trying to be understood.