Category: Book Notes

Bird by Bird is one of my favorite books about the value of writing regularly. Anne Lamott weaves stories of her life with writing advice. Here are some of my favorite excerpts.

She said that sometimes she uses a formula when writing a short story, which goes ABDCE, for Action, Background, Development, Climax, and Ending.

More thoughts on structure. That’s a pretty easy to remember sequence. Can this formula work for writing an article? A lot of nonfiction books are collections of short narratives.

Maybe I can practice this sequence with that formula.

Action: Me writing furiously in various Dunkin Donuts through three months.

Background: Why am I trying to write? Why three months? Why Dunkin Donuts?

Development: Then I learn through repetition (aka hearing it on various podcasts) that writing is really in the thinking and organization.

Climax: Me thinking furiously in various Dunkin Donuts.

Ending: Glory. Riches. A few new Medium followers. And a realization that all three of these are the same things.

Perfectionism is a mean, frozen form of idealism, while messes are the artist’s true friend.

Once you accept that perfection isn’t necessary, you’ll start shipping. I’m not sure about the idea that you should ship while you’re still embarrassed. It’s good to apply to an entire product that you’ll iterate on. But it’s not like each of these posts will be read multiple times by individuals. I’ve got one shot in a lot of cases.

That said, I’ve been posting plenty of things that I’m embarrassed about looking back. But I listened to a podcast with Seth Godin and they talk about people who look at things and are embarrassed when looking back and those that are happy with it and don’t dwell.

If I didn’t write something for fear that I’d look back on it and shake my head at how bad it is, I wouldn’t write at all.

Writing has so much to give, so much to teach, so many surprises. That thing you had to force yourself to do—the actual act of writing—turns out to be the best part. It’s like discovering that while you thought you needed the tea ceremony for the caffeine, what you really needed was the tea ceremony. The act of writing turns out to be its own reward.

I’m experiencing this right now. After getting over the initial inertia, thinking through different systems, setting those systems up, struggling to learn the proper length to aim for in a day, and plenty of other hiccups, it’s starting to be very rewarding.

I used to look forward to the coffee in the morning. Queue. Action. Reward. Now I look forward to the writing. It’s become the reward.

(I still like the coffee too.)

“Do it every day for a while,” my father kept saying. “Do it as you would do scales on the piano. Do it by prearrangement with yourself. Do it as a debt of honor. And make a commitment to finishing things.”

I’ve been doing this every day. I don’t think it qualifies for “a while” yet. I don’t know yet what would be the writing equivalent of scales. Maybe writing a page under the same template each day. It is a prearrangement with myself. It does feel rewarding to honor a commitment I made to myself. And I’m appreciating the feeling of finishing. With each post and eventually with the collective whole of 100 posts.

A friend of mine says that the first draft is the down draft—you just get it down. The second draft is the up draft—you fix it up. You try to say what you have to say more accurately. And the third draft is the dental draft, where you check every tooth, to see if it’s loose or cramped or decayed, or even, God help us, healthy.

I’m too slow to get to the down draft and too often that’s as far as I get. Hopefully focusing on writing one thing each day will encourage me to get to the up draft and then the third draft.

I went to the dentist this week. It’s been six years and luckily¹ I had no cavities. There was a portion where I had no idea what was going on but the dentist would poke around and call out numbers. I asked and they were checking the separation between the tooth and gum based on how deep the instrument could go in. Anyway, each check was a little painful but sometimes it’s good to do that thorough check to find out where things might be breaking down.

There’s some other design or career analogy here. Oh yeah it’s about upkeep. Dental hygiene is made up of daily routines. You can’t floss for an hour at the end of the month to make up for things. You can ignore your daily routine then go to the dentist and get cavities filled, but it’s not the same as if you were just following the proper routine daily.

These are book notes for Save the Cat, by Blake Snyder. I paused about 30 pages in on my first read, about a year ago. I was reading Nobody Wants to Read Your Shi* recently, and Steven Pressfield mentions Save the Cat as a great resource. I picked it back up and finished it this time around. Here are some excerpts I enjoyed.

The number one thing a good logline must have, the single most important element, is: irony.

Save the Cat stresses the importance of loglines. Nobody Wants to Read Your Shi* talks about concepts in ad campaigns. Good concepts lead to lots of good ad copy that works as a hole. A logline helps keep a movie anchored.

Now that the posts are adding up, I’m thinking about the bigger picture of this 100 days, 100 posts project. What’s my logline? Considering irony is important. Maybe that stacking two crappy pages each day leads to something valuable. But you need to believe.

Hopefully I have a better logline when I’m 100 days in. Though that’s working backwards.

Because liking the person we go on a journey with is the single most important element in drawing us into the story.

He describes Lara Croft as “cold and humorless” in the movie version of Tomb Raider. On the other hand, we’d probably be happy following Mark Watney on any journey he decides to take. As far as writing goes, maybe I need to start thinking about being likable. That didn’t work in 7th grade… but it might work this time.

The theme of every Golden Fleece movie is internal growth; how the incidents affect the hero is, in fact, the plot.

One of the best things in the book is the different nicknames for concepts. Maybe I can do a small sketch for five different concepts in the book. Save the Cat (make your main character likable), etc.

Now look at The Matrix and compare and contrast it with the Disney/Pixar hit Monsters, Inc. Yup. Same movie.

The most immediately applicable part of the book is Blake Snyder’s 15-step beat sheet. As far as 80/20 goes, the beat sheet is the crucial 20% of Save the Cat. Snyder points out how different movies apply these beats. Some more than others, but they’re there if you keep an eye out.

A team updates the Save the Cat website, and I was happy to see that their beat sheet list is still updated. Here are a few of my favorites:

• Independence Day
• Game of Thrones — pilot episode
• The Martian: It has one of my favorite “Fun and Games” sequences in recent years

Pick some movies you like and check the beat sheet out for an idea of how all the concepts can be found in different movies.

“This sure isn’t like the time I was the star fullback for the N.Y. Giants until my… accident.”

That’s one of Blake’s examples of bad dialogue you want to avoid writing. As far as things I want to pursue: I’d like to write how Blake Snyder writes. Save the Cat ‘s fun to read. Plenty of people disagree with that, and I imagine they’re out writing very sophisticated screenplays. Doing a little bit of searching, I’ve learned that it’s a polarizing book. And people will go as far as saying it’s ruined movies in the past few years¹.

Blake Snyder passed away in 2009. It would’ve been great to hear what he thinks about the industry today and if any of the tips would change (I doubt it). He comes across really encouraging in his writing:

Would you blanch if I told you it was just a matter of turning the crank again and again until something happens? Because that’s all it takes. Just keep turning the crank. Any inroad, any one at all, is a gigantic leap forward.

Screenplays tell stories in fewer words than novels. They have to. The rules are set. You can self-publish a 1200 page behemoth at your leisure, but (for all intents and purposes) you can’t quite self-produce your 250 page screenplay.

Hollywood is filled with storytellers, and successful nonfiction writers know how to tell interesting, concise stories. I can learn a lot about applying these lessons, even if I’m not writing a screenplay. I’ll read his other two books later this year—maybe before this 100 days, 100 posts project ends.

In the meantime, I’ll be thinking about structure and storytelling² in my future posts.

These are book notes for On Writing Well, by William Zinsser.

But the secret of good writing is to strip every sentence to its cleanest components.

Good writing comes in the editing. I need to set time aside to deliberately practice cutting sentences down. In a past technical writing internship, I learned the importance of simple sentences. If people are following directions, extra words distract.

One assignment that’s stuck with me comes from a software documentation class¹. It was probably the first or second assignment. We were supposed to write directions for something we’re familiar with, like making a peanut butter and jelly sandwich. (Or maybe the entire class had to write steps for making a peanut butter and jelly sandwich.)

The next day, the teacher brought in the usual things for making PB&Js. He then took a random sheet from the stack and tried to follow the directions, of course following it word for word. Always failing. He demonstrated how you can cause confusion with too many words and too few.

Writers must therefore constantly ask: what am I trying to say? Surprisingly often they don’t know.

Asking this for every paragraph is good practice when outlining and writing a first draft.. Asking this for every sentence will help in editing and creating the second and third drafts. Asking this for every word is probably what separates good writers from the rest. Knowing the right answer separates the great.

What am I trying to say in this post? On Writing Well is a great book about improving as a writer.

I’m currently reading Save the Cat and Nobody wants to read your shi*. Both of them talk about underlying concepts in writing.

Zooming back, what am I trying to say in these 100 posts? Consistently working on something a little bit at a time (two pages a day) adds up.

Good writing has an aliveness that keeps the reader reading from one paragraph to the next, and it’s not a question of gimmicks to “personalize” the author. It’s a question of using the English language in a way that will achieve the greatest clarity and strength.

I’m currently using a gimmick in footnotes, but I think the footnotes are where I write things that are most alive. Maybe because they’re typically more personal thoughts. Somehow I need to bring that aliveness to the relevant points.

My vocabulary is okay. There’s a little bit of conflict there, because I want to expand the vocabulary of words I use. But then that gets away from the idea of writing how you speak. That’s the kind of writing that I enjoy reading. I mean, I’d probably say “has no bearing on” instead of “inconsequential”. I guess knowing which one to use when will come with experience.

Ultimately the product that any writer has to sell is not the subject being written about, but who he or she is.

This is getting pretty deep. I’ve never thought of selling myself as a writer. Well, I guess I’ve thought it’d be cool to earn money through writing. And I know he didn’t really mean “sell” in monetary terms. More just making people believe in a subject. And in turn, making them believe in me as a writer. This just got deeper.

Something from earlier is stuck in my head: my footnotes have the most aliveness. I’ll continue trying to figure that out. I think it’s because the footnotes give a sense of who I am.

One underlying goal when writing documentation is writing in a way where you can hide the seams between people. It’s written like code. You shouldn’t be able to tell who wrote it. If I want to succeed in any way as a writer, I need to start shooting for the opposite.

Clear thinking becomes clear writing; one can’t exist without the other.

Malcolm Gladwell estimates that finishing a book is probably 25% writing and 75% thinking about the writing. And it’s a cycle: learning to write clearly becomes learning to think clearly. That’s why you have to get the reps in. That’s why I’m trying to publish daily.

These are book notes for 59 Seconds by Richard Wiseman.

“He that has once done you a kindness will be more ready to do you another than he whom you yourself have obliged.” In other words, to increase the likelihood that someone will like you, get that person to do you a favor.

The quote in the excerpt is from Benjamin Franklin. Something I really like from Derek Sivers is his idea of “directives”. He reads a lot and sometimes his friends really just want a “Just tell me what to do” summary. 59 Seconds gives a “Just tell me what to do” summary of research. It gives practical, straightforward advice for many aspects of life.

In short, when it comes to an instant fix for everyday happiness, certain types of writing have a surprisingly quick and large impact. Expressing gratitude, thinking about a perfect future, and affectionate writing have been scientifically proven to work—and all they require is a pen, a piece of paper, and a few moments of your time.

I’ve written daily in the past, but I haven’t tried publishing daily. When wrote daily I would try to write gratitudes and affirmations. It was a very successful period in my life. So I believe they work. 59 Seconds presents the science of why. I’ve heard Tim Ferriss mention the 5-Minute Journal multiple times.

From a psychological perspective, thinking and writing are very different. Thinking can often be somewhat unstructured, disorganized, and even chaotic. In contrast, writing encourages the creation of a storyline and structure that help people make sense of what has happened and work toward a solution. In short, talking can add to a sense of confusion, but writing provides a more systematic, solution-based approach.

+1 for writing. In On Writing Well, William Zinsser says “clear thinking becomes clear writing”. The other way around, as this excerpt talks about, writing helps clarify thinking. Just another positive aspect of writing and it sure makes all of this seem worth it.

It seems that presenting weaknesses early is seen as a sign of openness.

Humility helps. You want to end on a good note. And you’ll probably want to start on a good note, too. But present weakness closer to the beginning than to the end and it can help paint the rest of what you’re saying in a positive light. It’s always nice to be confident you’re talking to someone who has nothing to hide.

Successful participants broke their overall goal into a series of sub-goals and thereby created a step-by-step process that helped remove the fear and hesitation often associated with trying to achieve a major life change. These plans were especially powerful when the sub-goals were concrete, measurable, and time-based.

Hey, hey. Let’s check these goals out.

Overall goal: Publish 100 posts in 20 weeks. Sub-goals: Publish 5 posts each week.

Zooming in. Overall goal: Publish 5 posts a week. Sub-goals: Publish each day with a 2-day buffer each week for planning and life.

Zooming out. Overall goal: Improve as a writer and increase comfort with sharing my writing. Sub-goal: Publish 100 posts in 20 weeks.

These are book notes for The Miracle Morning for Writers by Hal Elrod, Honoree Corder, Steve Scott, and S.J. Scott

I read The Miracle Morning last year and really enjoyed it. Of course, I woke up at 6am for a couple weeks after that and then it trailed off. But I still have kept some of the ideas from it about establishing a morning routine. I have a Kindle Unlimited account¹ and saw The Miracle Morning for Writers.

Affirmations are a tool for doing just that. By repeatedly telling yourself who you want to be, what you want to accomplish, and how you are going to accomplish it, your subconscious mind will shift your beliefs and behavior. You’ll automatically believe and act in new ways, and eventually manifest your affirmations into your reality.

My favorite advice on affirmations comes from Scott Adams, the creator of Dilbert. In his book, How to Fail at Almost Everything and Still Win Big, he explains how skeptical he was of affirmations. And essentially says hey, they work. (Here’s a blog post that’s a few years older than his book talking about mostly the same thing.)

I feel weird recommending affirmations to people, because I felt weird doing them. I also think they really worked. Reading the section on affirmations in The Miracle Morning for Writers was a good reminder. Most would agree that setting goals is important and reviewing them is crucial to reaching them. From what I could tell, affirmations work because they’re a way to explicitly review your goals on a regular basis.

²You often hear that we got to the moon with computers that were about as powerful as graphing calculators. We³ didn’t set a course for the moon and then put the shuttle on rails. The computer constantly calculated and adjusted back in the proper direction. Affirmations allow you, every day, to quickly check course and make sure you make the small adjustment.

You’re working on a section and realize you need to research a fact, so you hop on Google, and then you think of something related to social media. Next thing you know, you’ve spent the last 15 minutes watching cat videos on YouTube.

The internet is a black hole. Given enough time, starting anywhere I’ll end up at the 2001 Slam Dunk Contest. I bought a Chromebook to try and avoid distractions. It still has a web browser⁴ so of course that entire black is available and I need to be careful.

Some things I’ve been trying to avoid distraction that are effective:

• Writing longhand in a composition notebook (This is also why reading on a Kindle is nice)
• Turning wi-fi off
• Setting a timer
• Giving up

I’ve been trying to separate writing from things that aren’t writing:

• Outlining and then finding corresponding excerpts before adding thoughts and expanding on them
• Finding corresponding links
• I put TKs everywhere⁵ when I can’t remember a name or want to look something up later — I started doing this when I watched this playback of someone writing an article about Google draft progress.

To quote Bill Gates, “Most people overestimate what they can do in one year and underestimate what they can do in ten years.”

Okay, so I’m not going to dig into whether he actually said that or not. There’s a similar quote that I can’t find the proper attribution for either, “People overestimate what they can do in one day and underestimate what they can do in a year.” I guess you can only believe in one of those sayings.

People pack their days to the brim so that any time they’re doing something it feels like they might be better served doing something else. Then they don’t find time to write, work out, or work on whatever other project they know is important. And you can forget the importance of consistency. Writing for half an hour a day adds up significantly over a year. I’m doing this project because I know that if I keep at it, I’ll have a body of work. It might not be worth reading, but it’ll be there. And it’s a step in the right direction.

Does a writing location really matter? I think it does. Where you decide to write has a direct impact on turning it into a permanent habit.

I’ve been trying to find a location for writing. Anywhere-but-at-home seems like the general location. But I think it’d be good to pick one of these coffee places nearby to make it a permanent habit.

He recommended that instead of starting with a novel, a new writer should take an entire year and produce 52 short stories, one for each week. In Bradbury’s view, it’s impossible to write 52 bad short stories.

This goes back to creating things on a regular basis and knowing the amount of work you can do in one year. Over this year, I’ll be writing 700 Crappy Pages, the sequel to 52 Bad Short Stories to Tell in the Dark.

The problem is this: When you start and stop a dozen projects, you’re not completing a single thing. In fact, you’re teaching yourself that it’s okay to quit whenever a project becomes challenging or boring.

Real artists ship. It’s satisfying to finish things. Unfortunately, it happens to be satisfying to start things too. You get that rush starting things and announcing goals to the world. The same payoff isn’t always there, though. Finishing is hard. Being able to share something of that helps others is in most cases better than keeping to yourself.

There’s always a slog where you know how far the end is or you might not even see the end in sight at all. Then there’s a slog when you can see the end but it’s not quite as close as it appears. It’s important to push through all of this. When it gets challenging, that’s probably where you’re starting to learn the most.

In Happy Money, Elizabeth Dunn and Michael Norton explain the best ways to spend money to increase happiness, based on behavioral science. I really enjoyed it and have been trying to apply the lessons ever since I read it. Here are some I enjoyed:

Research shows that experiences provide more happiness than material goods in part because experiences are more likely to make us feel connected to others.

I’ve tried putting this into practice as an adult. I really value travel, will gladly save up for a trip, and never regret it. That said, it’s nice having a down jacket and experiencing not freezing to death walking to work.

We are happy with things, until we find out there are better things available.

Most people recognize this. The harder part is turning those feelings off. There’s always more. Always. I still struggle with this. Sure, this down jacket is warm, but they look warmer in the Canada Goose. And if I get that, then I’ll want the one with OVO stitched on it. And so on.

People who spend more of their money on leisure report significantly greater satisfaction with their lives.

It’s important to be deliberate about leisure and relaxation. Just like it’s good to schedule time for relaxing, it’s good to set aside money for leisure. It’s good to step back from the day to day stress and consider why you’re putting yourself through it in the first place.

You can probably afford some kind of leisure right now. And you can take take it a step further than a trip to a movie by following these guidlines:

The experience brings you together with other people, fostering a sense of social connection.

The experience makes a memorable story that you’ll enjoy retelling for years to come.

The experience is tightly linked to your sense of who you are or want to be.

The experience provides a unique opportunity, eluding easy comparison with other available options.

Pick experiences that are: shared, memorable, personal, and unique. (“Well I’ll never have the chance to do this again” leads to spending $20 more on odd things the further away you are from your comfort zones.)

By consistently asking yourself how a purchase will affect your time, your dominant mind-set should shift, pushing you toward happier choices.

Growing up, I never ever ever thought I’d pay to have my laundry done. I never did a thorough cost comparison or anything like that. It didn’t seem to be stupid. It just never crossed my mind that I’d need to do it. Or want to.

Then I moved to New York. And I found a sublet in Chelsea. The building’s basement seemed like there was a mouse army setting up a siege on the cockroaches on the other side of the wall. It happened to be where the washing machines were. I wanted to stay far far away from that.

That’s a little extreme, but even now in an apartment where things aren’t a horror movie, I’ve continued using drop off service. For probably $10 more than it would cost do it myself, I can buy two hours of my life back.

Note: This was originally posted on Design Sprints.

Communication is an important soft skill for product designers. In Discussing Design, Adam Connor and Aaron Irizary discuss the importance of critique in the design process.

A lot of communication within a design team comes in the form of critique. Adam and Aaron explain how to deliver and receive critique. (For communicating with PMs and engineering, I’ve really enjoyed another book: Articulating Design Decisions by Tom Greever.)

You can improve as a designer by delivering useful feedback to other designers. The same way teaching is a great way to solidify knowledge, delivering useful feedback requires you to think about different aspects of design and organize your thoughts.

What kind of critique is useful? Let’s take a look.

Critical thinking

I love Dribbble — it’s a positive place on the internet, and that’s a great thing. However, it’s not the best place to look for effective critique. Adam and Aaron’s three key elements to effective critique can help explain why:

“1.) It identifies a specific aspect of the idea or a decision in the design being analyzed.”

People complain that Dribbble feedback isn’t useful for finding flaws and improving design. “Good job” and “Great work!” aren’t specific at all.

“2.) It relates that aspect or decision to an objective or best practice.”

A lot of time, the work shared on Dribbble is a detail shot or some other form of a very small part of a larger project. There isn’t enough shown and sometimes there isn’t an objective at all to relate critique to.

You should be basing design decisions on objectives and best practice. When starting out, it’s good to lean on best practices to build out something that mostly works. It’s okay to stray away from best practices if your solution works better for a project objectives.

When critiquing, think about design aspects that are going against objectives or best practices. Otherwise you might simply be saying that your arbitrary choice is better than their arbitrary choice.

“3.) It describes how and why the aspect or decision work to support or not support the objective or best practice.”

Good critique requires effort on both ends. Presenting something while also explaining all the factors involved — constraints, timelines, background info — takes effort. Parsing this info and fully understanding the problem being designed for also takes effort.

Combined, this is probably why there’s not a hugely popular community for useful design feedback. If people took the time to do that on Dribbble, it wouldn’t be a light, fun place to go to. It wouldn’t be Dribbble.

Feedback that doesn’t nail these three elements might fit into another category. Let’s take a look.

Reactions and directions

Discussing Design describes three types of feedback: reaction-based, direction-based, and critique.

Reaction-based feedback includes the quick emotional responses you’ll often get when showing something for the first time. “Nope.” and “Good work!” are examples. You can tell how useful feedback is by asking the following questions:

“…are the people from whom you’ve asked for feedback reflective of your design’s actual audience? Are they looking at it the same way your potential users would? Does this reaction divulge anything specific about any of the design decisions you’ve made so far or their effectiveness?”

With reaction-based feedback, the answer to these questions is usually “no”.

If you leave a meeting with a list of changes, that’s direction-based feedback. It answers “yes” to some of the above questions, so there’s a time and place for it. But it can be an issue:

“Similar to reaction-based feedback, direction-based feedback without any explanation indicates nothing about the effectiveness of your decisions in meeting the design’s objectives. Sure, if the person giving you feedback is the one who will ultimately approve the design, she might supply you with a to-do list that you could act upon to get her approval, but getting that approval and creating an effective design are not necessarily the same things.”

Sometimes you might hit the three elements of critique and it still won’t be useful. How come? The timing might be off.

Critique Timing

Connor and Irizarry provide a good rule of thumb for when to critique solutions:

“For example, the best time to critique a solution is after it is 20 percent baked but before it’s 80 percent baked.”

When you’re in that 20%–80% sweet spot, it’s good to receive critique often. Discussing Design refers to “Dailies” done at Pixar. I went to the bookshelf (read: searched my Kindle) to check out what Edwin Catmull had to say about Pixar Dailies in Creativity Inc.:

“The first step is to teach them that everyone at Pixar shows incomplete work, and everyone is free to make suggestions. When they realize this, the embarrassment goes away—and when the embarrassment goes away, people become more creative. By making the struggles to solve the problems safe to discuss, then everyone learns from—and inspires—one another. The whole activity becomes socially rewarding and productive. To participate fully each morning requires empathy, clarity, generosity, and the ability to listen. Dailies are designed to promote everyone’s ability to be open to others, in the recognition that individual creativity is magnified by the people around you. The result: We see more clearly.”

Engineering won’t have time to incorporate design improvements after the 20%–80% sweet spot. Before the sweet spot, it’s better to continue creating without stopping for critique. How come? Each task requires a different mindset.

Mindsets: Creative vs. Analytical

Many writers write and edit separately because they require different mindsets. One mindset is creative and the other is analytical. Adam and Aaron discuss how these different mindsets apply in design and critique:

“When designing something, the brain operates as a toggle, switching between creative thinking — where individuals are generating ideas or assembling parts of ideas — and analytical thinking — where they are determining whether what they’ve designed so far is in line with what they are trying to achieve. Experienced designers, artists, engineers, and others have learned how to be deliberate in controlling when to make this toggle, periodically pausing their creative work to take a step back and critique what they have so far.”

Discussing Design lays out some techniques to facilitate effective critiques.

Design Studio

In the Google Ventures design sprint methodology, diverging and deciding are separate steps.

Teams generate as many ideas as possible with mind maps and Crazy 8s. At the end, participants select the best ideas based on the objectives.

Discussing Design describes a similar technique called Design Studio. They mention Todd Zaki Warfel adapting the technique from other design disciplines to the digital world. Back to the bookshelf, here’s an excerpt from Warfel’s book, Prototyping: A Practitioner’s Guide:

“In the world of architecture and industrial design, a design studio is a process, not just a physical place. This process is taught in every respectable architecture and industrial design program. You’ll be hard pressed to find a design studio class in computer science.”

“In studio classes, you design or prototype and present to your peers. Your peers critique your work, highlighting the strengths and areas that still need some work.”

Adam and Aaron describe a three-charrette activity to quickly go through multiple rounds of design and critique. Like Crazy 8s, it involves timed sketching. Their activity goes like this:

• 8 minutes for six sketches of different concepts
• 8 minutes for iterating on their strongest idea
• 20 minutes as a team to sketch one idea

Sum Up

Here are some key takeaways from Discussing Design:

• Quality: Objectives and best practices are your guiding light for effective critique.
• Timing: Critique is most useful when it takes place during the 20%–80% sweet spot.
• Mindsets: Creation and critique require different mindsets and should be separated.

Embracing critique and following these principles will help you be more effective in delivering and receiving critique.

Note: This was originally posted on Design Sprints.

In Founders at Work (2007), Jessica Livingston, founding partner at at Y Combinator, interviews 30 startup founders.

The Steve Wozniak interview alone is worth the price of admission, but it also happens to be posted free in its entirety on the book’s website. Check that out to get a sense of the questions, answers, and how thorough each interview is. (Put another way: the book is very long and also very good.)

The companies were founded from the 1970s to the 2000s. The interviews take place a few years after the dot-com crash, and slightly before iPods, phones, and internet communications devices became a single thing.

There were a lot of “Ohhh yeah” moments—the nostalgic kind, not the Macho Man kind. And they sort of come in two forms: 1.) memories from the founder stories where I could remember how that technology impacted me—90s things like Hotmail and WebTV were real fun for me, and 2.) memories from “present day” 2007 before mobile took over the world—like Digg driving heavy traffic to sites.

pg had this to say in an old HN thread about the book:

“Startups are basically comedies.” I highlighted a ton of things and picked a few to share—let’s start with some scenes from pg’s own comedy.

Paul Graham — Cofounder, Viaweb (and some investment firm)

Years ago, working out of an apartment wasn’t quite as accepted. Here, Paul Graham talks about trying to look legitimate when, you know, business people visited.

When that first giant company wanted to buy us and sent people over to check us out, all we had in our so-called office was one computer. Robert and Trevor mostly worked at home or at school. So we borrowed a few more computers and stuck them on desks, so it would look like there was more going on.

It really does sound like a sitcom. And the fun doesn’t stop there. Here, he talks about power going out in Cambridge. After running the generator indoors and deciding it was too loud (not, you know, too dangerous), they put the generator in the street and ran an extension cord:

It was running through our office at chest height and you could kind of twang it and it would go “boinnnnnggg.” Then we started the gas generator up in the street and that was just about bearable, so we ran the servers on that for a couple hours until the power came back.

pg: scrappy. Founders at Work has a lot of stories involving hardware: servers getting overloaded, learning to use a shrink-wrapping machine for CD distribution, servers going offline so someone could drive it somewhere with a T3 line, etc.

Steve Perlman — Cofounder, WebTV

When I mentioned “Ohhh yeah” moments, this was a big one for me. My cousin had a WebTV and so whenever my family visited his we’d use that to browse the web. And I have no idea what we’d even look at. At night we’d use his dad’s computer to play TetriNet.

With so many people connected in the Valley, founders also share early-day anecdotes from companies that aren’t their own. Here, Steve Perlman talks about Apple and dialog boxes:

The following is not something from my personal experience—it’s a story told to me by the Mac team—but they said that, when they first did the dialog boxes for the Lisa, instead of saying “OK,” it said, “Do It.” They found that people were reluctant to click on that, and they couldn’t figure out why. Then, once they had a test subject there who just wouldn’t click on it, they said, “Why didn’t you click on that little button there?” He said, “I’m not a dolt. Why would I click on that?”

So they changed it to “OK”. Don’t be a dolt, test with your users.

Mark Fletcher — Founder, ONElist, Bloglines:

A lot of common themes run through the interviews. They’re things you hear about all the time about startups and building products. Here, Mark Fletcher talks about finding a problem to solve:

I started ONElist because I wanted to start a mailing list for my parents, and at that time you had to download software and you had to have a computer connected to the Internet. It was just really difficult for an average person to put together a mailing list. So it was the same thing. I guess my advice is: solve a problem that you have, first and foremost, and chances are, other people may have the same problem.

How do you find a good problem to solve? Solve your own. Ben Trott and Mena Trott, founders of Six Apart, created Movable Type because there wasn’t a great existing solution for Mena’s rapidly growing blog. Stephen Kaufer built TripAdvisor after trying to plan a trip and finding the end steps of booking had solutions, but planning where to go and stay wasn’t a great experience.

Another theme Mark Fletcher talks about is iterating:

So just get something out there. If you find really early versions of ONElist or Bloglines on archive.org, the websites are horrible. They are crap, they don’t have any features, they just try to do one thing. And you just iterate because users are going to tell you what they want, and they’re your best feedback. It’s critical just to get something out quickly. Just to start shipping and then you can iterate.

Founders at Work was published before The Lean Startup when lean methodologies and MVPs weren’t so widespread. Some of the concepts surely existed, but others wouldn’t work when releases were months or years apart. Charles Geschke, cofounder of Adobe, talks about Xerox in the 70s, “They said, ‘Oh wait a minute. At Xerox it takes us at least 7 years to bring a product out.’” Not to mention iterating after that.

Joshua Schachter — Founder, del.icio.us

The variety of people and companies profiled is great. Some grew to thousands of employees, some stayed small, some were funded, some were bootstrapped. Some bordered on ruin and others say things along the lines of “I don’t know, it actually went pretty smoothly!”

Here, Joshua Schachter talks about building del.icio.us in his spare time:

I could come in and look at it, figure out what I’m doing, do it, and be done for the day in 15 minutes. So if I could get one thing done a day, I was happy.

I love this. Success comes through a lot of paths and it’s good to see that something millions of people found useful was built in (sometimes very) small chunks of free time.

Stephen Kaufer — Cofounder, TripAdvisor

Again, a lot of companies built things we take for granted now. I booked a trip to Spain with some friends last year and, along with other sites, TripAdvisor was part of that. Still it was this whole production to plan out.

I can’t imagine planning without those resources. Stephen Kaufer talks about planning a trip before TripAdvisor and learning an island wasn’t all that great through a chat room. Here, he talks about finding content for TripAdvisor:

Then we hired people to read every single travel article we could find on the Net, and classify that article into our database, and write a one-line summary. It’s a fairly significant effort, and people that we talked to said, “You’re nuts. You’ll never finish.”

Do things that don’t scale.

Ron Gruner — Cofounder, Alliant Computer Systems; Founder, Shareholder.com

The most entertaining stories are the most ridiculous. Ron Gruner shares a story about an 800-number mixup. A company printed millions of annual reports with the wrong 800-number for the shareholder’s call. Reprinting wasn’t an option, so Ron Gruner and his team had a few days to figure out how to take that number over.

Because of privacy issues, the paging company wouldn’t give up their customer’s details. Ron shares their solution to this privacy issue:

Then Josiah Cushing, one of the college grads I had hired, during our staff meeting said, “Ron, why don’t you try hiring a private detective?”

The guy who owns the number agrees to transfer the number over as long as they pay for his pager subscription for a year. And a subscription for his wife. “We’ll make it two years.” Not much of a price to save an entire company.

And then there’s the “Ohhh yeah” moment of remembering that pagers were a thing.

If you have any interest in startups or technology, Founders at Work will have something you’ll like. In a few years, maybe it’d be cool to see a sequel with today’s companies. “Our site was getting hammered. We had to spin up more Heroku workers.” Maybe not.

Note: This was originally posted on Design Sprints.

I don’t read particularly quickly, but I finished Austin Kleon’s Show Your Work in a single sitting. It’s great for identifying what work is worth sharing and getting inspired to share it more frequently.

Here are the book’s ten main points and how they apply to me, design, development, prototyping, and my plans for this site.

You don’t have to be a genius
This is very good for me.

Think process, not product
I’m glad I really enjoy prototyping. It’s part of the process and leads to a better end result. On the other hand, it’s important to remember it isn’t the end in itself.

The idea of focusing on the process falls in line with other things I’ve read about work and learning. It becomes a cycle. When you learn to enjoy the process, you’ll improve and as you improve you’ll enjoy the process more. This gets you past dips and leads to better end products.

I forget where I heard this, but someone pointed out that people overestimate what they can finish in a day and underestimate what they can get done in months or a year. This can make it hard to start something big because you don’t think you’ll be able to finish it. But if you show up every day it adds up.

Share something small every day
After a few years of having a Dribbble account, I finally posted one thing. But I’ll start sharing more there. For all the flak it gets about comments being “Good job!” well, is that so bad?

It’s probably not the best place if you’re looking for serious critiques to improve things. But a design community with positivity as its core is, well, a net positive.

Open up your cabinet of curiosities
I’ve been linking to things on this site but I’m thinking of changing the format for sharing links. The ongoing link blog is sort of dead. Long live the newsletter.

Tell good stories
Austin Kleon talks about how art sometimes isn’t immediately interesting until you learn the story behind it. But something seemingly mundane with a good story is interesting because the story is interesting.

In that sense, I can look at the design sprint posts as stories explaining how certain prototypes came to be. I love reading other design process posts. Here are a few that come to mind:

• The Making of Tiiny
• OneShot, a one week design case study
• Designing Search for Rooms

I can’t get enough of these. They’re good stories.

Teach what you know
I try sharing what I know about Framer, Origami, and Form. Even with varying skill levels with each tool.

I’ve listened to Ben Orenstein’s Giant Robots podcast for a few months now. Learning and teaching come up as topics regularly in episodes. He encourages blogging every day:

Write about what you’ve learned so far. Don’t make the excuse that you’re just a beginner. Imagine someone who is two months behind you and write for them.

Recent beginners can be better at helping a novice because they just went through the same issues. Experts can lose that perspective. A huge benefit of it is that it really solidifies your own knowledge. Through teaching, you organize your own knowledge and identify the gaps that can be improved.

I’ll continue writing and putting videos together as I learn.

Don’t turn into human spam
My greatest fear. I was an over-sharer through high school and college. Then pulled it back in the past few years. And now I’m slowly ramping it up. The best way to avoid turning into human spam is to create interesting things. If spammers sent out a bunch of stuff people loved and found value in, well, it wouldn’t be spam.

Learn to take a punch
I wrote a Material Design post last year and was pretty excited that people were reading it.

Then one person tweeted it was “boring as hell”. It’s fine, I was ready for that jab. But then some designers I really respect favorited the tweet. So it was like the jab was chained into an E.Honda special.

This reminds me of one of Pasquale D’Silva’s tweets: “A glitch in many designers is the lack of ability to detach emotion from criticism.” It’s been really helpful to remember that criticism is free feedback.

Sell out
I’d love to. I’m putting affiliate links in book note posts and that’s about it so far. I read a lot of books and won’t be writing notes for all of them. It’d be great if it could pay for a better microphone or something of that sort.

In the meantime, I’ll stay focused on creating useful content.

Stick around
The first thing I wrote about design that anyone really read was about a personal design sprint. I’ve written a long piece about once every month or two since then. I want to keep it up. But I also want to start writing shorter things. Which is why I started designsprints.com.

I’ll stick around.