Two (hundred) crappy pages

This is it, the 100th post. It’d be great if I could end on a high note. Instead, this post will be a microcosm of the other 99. It’s going to be a hodgepodge.

I’m writing some of it longhand. How do some voice dictation1. I’ll write on the bus. I’ll write in the morning. I’ll write at a park somewhere on the way home. I’ll finish on my laptop and post it tonight2.

I wanted to have stats like total word count, cups of coffee consumed, where I wrote most often, and other meta things like that. Then I realized that’ll take more time than I have free today. I’ll even have a book excerpt. In The War of Art, Steven Pressfield talks about finishing his first novel:

But that moment when I first hit the keys to spell out THE END was epochal. I remember rolling the last page out and adding it to the stack that was the finished manuscript. Nobody knew I was done. Nobody cared. But I knew.

Nobody cares. But I care. Right now, I’m high stepping into the end zone. The game breakdown can start after I’m actually finished. You know what, we can start some of that now.

“He’s got a short memory. Bad page after bad page. Miss after miss he just kept at it.”


“He looked gassed at the end. Started paying more attention to the clock than to the blank page in front of him.”

“He lowered his “I Think” Rate through the season but barely moved the needle on Good Sentences Per Page.”

“Voice dictation got to his head. Ditched the old putter for some kind of belly stick and hasn’t learned to use it properly yet.”

“A specimen. His spine is perfectly fit to hunch into a chair for hours.”

“Deceptively quick.”

“Got a few minutes of access to him in the locker room. He just kept saying he heard different things on podcasts.”

Nobody knew Pressfield had finished his first novel. At least for one night. There aren’t trophies for everything, but you can at least relish in telling the neighbor.

Next morning I went over to Paul’s for coffee and told him I had finished. “Good for you,” he said without looking up. “Start the next one today.”

Tomorrow, I’ll reward myself with another blank page.

  1. (I’ll do some voice dictation.)

  2. Update: I ended up skipping the park. I wrote a little bit on the subway, which is just as representative of places I wrote during the past few months. And I’m currently finishing up on my laptop.

Sunday Journal Issue 07: Stumble and recovery

“I often like working with a hangover because my mind is crackling with energy and I can think very clearly.” — Francis Bacon

I heard that in Daily Rituals about Francis Bacon. So far it seems like artists before 1900 drank a lot and ate with no knowledge of nutrition. Not that there was a ton of knowledge to work off of at the time.

I involuntarily experimented with Bacon’s technique today. My conclusion: I don’t like writing with a hangover because I feel awful and can’t think at all.

There are allegedly benefits to a hangover. Not seeing them right now. I enjoyed Wait But Why’s explanation of the monkey mind. The instant gratification monkey steers us toward procrastinating. According to that article on the benefits, the hangover would put the monkey to sleep for a bit. What’s missed is that some other gibbon takes its place and bangs on your head with a wrench for a few hours.

Last week, I did a lot of catching up and was a little too happy with myself. I was finishing multiple posts in a day and I thought I could keep that up and finish the hundred posts early.

I took a few days off and now I feel like I’m stumbling to the finish line. For the last week I had some posts saved that I wanted to close out the project with. I thought I’d magically have more time to work on certain posts without actually scheduling the time.

I’m determined to finish in the next few days. I will not miss this deadline. Nobody’s watching. Nobody’s going to see if I reach the finish line on time or not. It still feels like it would take away all the work leading up to the day 100.

I finished reading The Ego is the Enemy. I saw Ryan Holiday speak live a couple months ago. Something that stuck out that I remembered while reading the book was the concept of Standards of Performance. It’s rooted in Bill Walsh and his time as the 49ers head coach. Here are a few of Walsh’s standards of performance from The Score Takes Care of Itself:

Exhibit a ferocious and intelligently applied work ethic directed at continual improvement.

Be deeply committed to learning and teaching, which means increasing my own expertise.

Honor the direct connection between details and improvement

Those come from a much longer list. Many of the items on the list, like these examples, also apply to much more than coaching a football team. I could do much worse than use these three standards to guide my future writing. Here’s another:

Maintain an ongoing level of concentration and focus that is abnormally high

I’ve been practicing meditation and my concentration and focus seem to be improving. I’ll also make sure to take care of the simpler things, like scheduling properly so I don’t end up trying to write with a hangover.

Whether or not anyone’s watching, it’s important that I know I got to the finish line on time.

Friday Links: Issue 09

This will be the last Friday Links post in my 100 Posts, 100 Days project. I want to write pieces that are more well thought out, and I’ll do that through more in-depth book notes posts. I also want to maintain consistency, so I’ll probably continue on with these Friday links.

Links and book notes will always give me a way to share things I find interesting. The built in structure of these links posts will make it easier to write consistently. That lets me have energy for the longer book notes.

I’ve been diving into Wait Buy Why lately and that’s where a lot of the motivation to write longer posts comes from. Tim Urban even gives direct advice on writing in the first edition of the Wait But Why mailbag:

  1. Don’t be a complete perfectionist, but don’t settle for writing you know isn’t working. Even if you’re experimenting, if something you’re trying isn’t working, try to figure out why, rewrite parts, start over and try a new approach, etc.—keep fiddling until it clicks. Each time you go through the hard, painful work of agonizing over writing that isn’t working and eventually get it to click, you become a better writer.

My next step will be working on figuring out what works. That advice is sandwiched between the other common thing you’ll hear: #1 write more and #3 read more. I’ve been writing and reading regularly. Now I need to be more thoughtful about what I write.

Last year, Fast Company also wrote a good breakdown of Wait But Why’s success:

This is all the more impressive considering there just isn’t a lot of content on Wait But Why. Unlike viral churn-and-burn content sites, which posts dozens of articles a day, Wait But Why has only published just over 80 articles in total. That’s an average of just one a week; 63 of them are pieces that stretch to over 2,000 words, with some reaching more than 3,000. The site’s slow schedule, which began as one post a week, is now more erratic. “After a post goes up, the next one might go up two days later or three weeks later,” Urban says.

Now that’s a schedule I can follow. I’m still thinking through exactly what I’ll try next but I’m thinking it’ll be down to one or two posts each week. Longer but not fluffier. Tim Urban provides a great place to start if I’m looking for examples to follow.

Though maybe not in terms of eating. He wrote a great Grub Street journal: Tim Urban Embraces the ‘Dark Late-Night Unhealthy Seamless Order.

There are two great champions of the DLNUSO, and one of them is pizza. Ordering a pizza any time after midnight and eating at least three slices is super-dark. No one is happy in that situation. And the other one is Chinese food. The main reason is: What kind of Chinese places are open at one in the morning to deliver? And it’s the most mysterious kind of food — no one knows what goes on in those kitchens. Who’s there cooking? It’s don’t ask, don’t tell, enjoy yourself.

I’ve had my share of days with multiple Seamless orders. Those aren’t typically good days. Urban enjoys avocados filled with different toppings. He also clearly enjoys writing. Probably to the point of it being something James Altucher describes as “super loves”:

Because you love those 20. But it’s BECAUSE you love them that they will always distract from the top 5 that you SUPER love.

I super love Writing. Podcasting. Comedy. My family. And the remaining businesses that I’m still involved in.

My top 5.

In that post, he describes Warren Buffet’s 5/25 rule. A few weeks ago, I wrote about the technique after hearing Angela Duckworth mention it in Grit. Altucher’s post is more interesting to read. Here are a few reasons why1:

  • He introduces the technique in a more interesting way

  • He gives the technique a straightforward name (“5/25 rule”) to refer to it by

  • He gives many more examples

  • He gives many very personal examples

His closing summary is really powerful:

“No” is how you whittle down and sculpt yourself into a work of art. “Yes” is how burn up and burn out.

I’m finishing up my 100 Posts 100 Days project this week. It was the first step for this blog. Over the next few weeks I’ll be thinking about what the next steps are. Scoping it down to the blog, I’ll evaluate what I loved during this project. I’ll have a better idea of what I want to say “yes” to so I can say “no” to everything else.

  1. Other than “He’s just a better writer”

Ego is the Enemy

Tim Ferriss often asks guests what book they’ve gifted the most. I never had an answer for that question (not that he’ll be asking me that personally any time soon). I can say now that I’ve gifted Ryan Holiday’s The Obstacle is the Way to multiple people. Holiday took Stoic philosophy—already written in relatively plain language—and showed how the lessons apply to modern life.

Holiday gave a good description on a podcast episode: The Obstacle is the Way teaches how to approach external challenges, and Ego is the Enemy lays out the internal challenges. We’ll face battles within ourselves during all phases of life.

I want to write full notes for Ego is the Enemy and its other sections: Success & Failure. I didn’t set time aside to finish that yet, but I want to make sure to include Ego is the Enemy in this 100 Posts, 100 Days project. So I’ll focus on the section most fitting to my current phase in writing: Aspire.

Posting daily for this stretch of time is a step toward my bigger aspirations of improving as a writer. If I listened to my ego, passion would be enough to get me there. It’s not. Passion doesn’t make you an outlier. It’s the work. It’s luck. Plenty of people have ideas. Plenty of people have passion. Having passion, ideas, and luck makes for a good mix. Putting the work in will make you successful. You can’t control the luck. So resolve to focus and appreciate the work.

Everyone would love to play a game for a living. Game day isn’t the work, though. That’s the flow state. That’s the fun part. A smaller percentage would love doing the practice it takes to earn the right to play a game for a living. It’d be great to send an audience into a ruckus with a comedy set. By most accounts, it takes night after night of bombing to get to that point. There’s almost always work to do.

The work won’t be easy, and that will be good for you. That’s how you identify what could be worth doing. If there’s something nobody wants to do, you can always start there. Doing the gritty work might be the cost of entrance to be around top performers. Being in that environment will accelerate your learning. The ticket in often looks like hard work.

So I’ll resolve to do the work. I’ll write these posts read by a handful of people. If that. I’ll earn the attention of my first ten by doing the work. The first thousand will be found on the same path, years down the road. Incredible success would require a few lucky breaks. In the meantime, I’ll get my reps in. I’ll be satisfied with the work. I’ll aspire.


I’ve been reading through Sprint. I remembered how much I enjoy reading things by the Google Ventures design team.

Book notes were the most valuable thing from this 100 Posts, 100 Days project.

  • Writing notes helped me think through what I learned from each book I read.

  • Notes gave me some built-in structure to follow. It was easier to get going on these posts.

  • Books provide thoughts from authors who have much more expertise on topics. I can pass on their knowledge as I learn to develop my own ideas.

I want to take my book notes posts a step further—with my own thoughts being a little deeper and with some designed layouts to make them more fun to read through. I was inspired by an answer in the Wait But Why mailbag:

5) While you’re experimenting with your writing, keep your mind open to all creative possibilities. The first 290 of the 300 blog posts I wrote in my 20s had no visuals. Only towards the very end did I try drawing something one night. And only then did I realize how much I liked combining hand-drawn visuals with my writing. That could have easily never happened, and if it hadn’t, Wait But Why would be an all-text blog today.

I’ll start with some kind of prototype. There’s a section in Sprint going over examples of different prototypes. Many aren’t constrained to a screen.

  1. You Can Prototype Anything

This statement might sound corny, but here it is. You have to believe.

At orientation at one of my old jobs, we were shown a 60 Minutes segment from 1999. It highlighted the design process at IDEO and how they prototyped a better shopping cart. A lot of ideas in Sprint have roots in IDEO and Stanford’s Reading through the case studies of design sprints reminded me of something I read in Bill Buxton’s Sketching User Experiences:

It is much easier, cheaper, faster, and more reliable to find a little old man, a microphone, and some loud speakers than it is to find a real wizard. So it is with most systems. Fake it before you build it.

Buxton expands this to a chapter called “The Wonderful Wizard of Oz”. He provides examples of prototypes going beyond digital prototypes on screen. One example involves a giant cardboard screen with people playing out a potential video.

Any of my success with writing things online started with this post about a personal design sprint (2014). Thousands of people read it. Not billions, or even millions, but it’s still cool to me. I’ll be thinking more about why that post was successful. A lot was luck (Jake Knapp shared it then Smashing Magazine shared it). But the content had value and for once I can take a few lessons from myself.

Front Page Sprint: Me in Keynote

This is a GIF of me working in Keynote for an hour. I exported the slides to jpg and am sharing it here. It’s very rough. Everything below this is just an image.

I skipped the storyboard step. It probably would’ve been better to has sketched out the full storyboard. Keynote is pretty fast but there’s still a long way to go for prototyping this. Something I always tell myself is that working in Keynote or anything else were making static mocks that it’s much much faster than it would be if I was trying to code it.

I wasn’t sure if I was even working on front page or if this was a very long post resembling a single page site. So some of the slides looks like one or the other.

I thought some of these modules were pretty cool. There could be some kind of flat map all The different places.

This is less a prototype and more just sketching with Keynote. It’s really just trying to get some ideas down. These next few there closer to along post rather than a front page.

I really want to get the book notes right. They’re probably the most frequent posts. If someone’s jumping from post to post then I would wager on that going to different notes rather than any of the other categories.

I had an animation of this. You would press the button to get the full dated list of posts. The front page is a very long content piece. With the option to see the list as it exists right now.

And that’s it. An hour wasn’t really enough to prototype, but it was good to see some ideas come out of this. Hopefully the final version is pretty cool and this becomes a fun look at the rough draft. I’m realizing just how much content I would want on this page. I have some writing to do.

The Serious Guide to Joke Writing

In The Serious Guide to Joke Writing, Sally Holloway shares exercises for comedy writing. I read it earlier this year. Here’s the directive I took away from it when I was Taking inventory of the books I read in the first half of the year:

Consider other perspectives.

I enjoyed the book and wanted to share some highlights. Sally talks about deliberately starting work on a joke and then leaving it to take a walk so that your brain can process it in the background:

If you’re not sure how wonderful this idea is then imagine if garden tools did background processing and, as long as you got hold of your spade and did some serious digging for half an hour, it would carry on digging after you had gone off shopping until it finished the job. Your brain is that powerful. Use it.

This is also a good way to tackle any problem1. Programmers can hammer away at a problem for hours. Then when they walk away for a few minutes and that’s when the solution hits them.

I’ve written before about whether comedy writing can be learned or not. Everyone’s funniest friends aren’t sitting in their rooms at night practicing. But that’s different from learning to write jokes and working on them. Professional comedians still get their reps in:

I admit my brain is attuned to joke writing, but I’m still putting time in. I run the subject through as many of my joke writing methods as appropriate. I like to do at least an hour a day (and more if I’m on a tight deadline). I break it up, do a bit here and a bit there.

Professionals are better at using the tools, but they still use tools and put time in. It’s the same as what Joe Toplyn says. It’s the same as what Simon Rich says. Rich also talks about the importance of my takeaway directive of considering other perspectives. He says Rugrats was a huge influence. Adults seem to be doing weird things, from the perspective of toddlers.

Here’s Holloway describing the exercise:

Think about it from the point of view of any objects or things or people that are directly or indirectly involved…

It’s part of a larger exercise of considering other perspectives. She says to describe things to an alien, describe them to a child, describe them to a foreigner. It’s another tool to use.

Even knowing how to use the tools, a professional doesn’t sit down, write ten jokes, then get ten great jokes out of it:

I say rubbish things, I say obscure things, I say puns a child of five could have written, and I say great things, but I needed to say all the other things to get there. So when students look at me that way I say: this is the process.

I believe in processes and systems. Like many other creatives, comedians create a lot of things and then whittle them down and refine. I’m not great at writing jokes yet. Or even good or okay at it. Still, I’ll work on it because I want to write things that are fun to read.

  1. Some people worry about meditation taking this kind of background processing away. With meditation, you learn to reign in the monkey mind. The gibbon might be manning the back burners. I’ll keep an eye on this as I learn to meditate.

Meditation: Take Ten

I started meditating a couple weeks ago. Going back through my posts, I also wrote about wanting to meditate a month ago:

There’s a chapter about meditation, which I really want to start practicing. I’ve done it maybe two or three times in my life. I listened to 10% Happier and thought it was one of the best audiobooks I’ve ever listened to. Then I didn’t meditate. Too many smart people meditate and there’s too much science backing it up to ignore it.

I listen to 10% happier again and also got a Headspace membership. Last week I finished up Headspace’s Take 10 series. It’s 10 sessions of 10 minutes guided meditation. Here are some thoughts after finishing. (For more about why I was beginning meditation, check out this post.)


I’ve seen an improvement in focusing on work. Meditation lets me practice recognizing when I’ve gone off track in thought. It’s helpful when working to recognize when I’m distracted. I pull myself back into work the same way I’d pull myself back into focusing on my breath.

In Deep Work, Cal Newport talks about practicing being bored:

To simply wait and be bored has become a novel experience in modern life, but from the perspective of concentration training, it’s incredibly valuable.

One of his examples is not pulling your phone out when you’re standing in line at the grocery store. I tried doing that for a few weeks after reading the book. It’s a useful idea that’s stuck with me. Meditation takes that practice another step.

Sometimes I meditated multiple times in a day. There seems to be a limit right now doing my. When I did two sessions that was really helpful. Three seems like too many.

The Headspace app is great. It takes the friction out of deciding what to do. There is a lot of series to pick from. There are series on focus and creativity, among others. You can’t jump from series to series without losing your progress.

I’m not sure exactly why but I’d guess it’s an exercise and not just jumping to the next shiny thing. They must have received enough complaints—they offer themed one-off ‘singles’ that you can do without losing progress in your current series.

Where I can improve

The app has some gamification, like recording your streaks. I like thinking I’m somewhat resistant to things like this, but it really hooked me this time. There were a couple nights where I was ready for bed and then realized I hadn’t meditated that day. To keep the streak going, I tried meditating while lying down ready to sleep. Not as effective.

As I mentioned, wasn’t having a lot of success with more than 20 minutes in a day. I want to practice until I can sit for 30 minutes. In 10% Happier, Dan Harris says his mom picked up meditation and was able to sit for 30 minutes right off the bat. He was both impressed and jealous. Seems like a pretty good goal to shoot for.


I’ll continue meditating with Headspace. It makes the rest of the day better. The app is nice because it feels like I’m progressing in some way. There are a couple more introductory series that I’m working through. After that, I’ll try the focus series and creativity series.

Front page sprint: Crazy 8s

Continuing on with the sprint (part 1) for the front page of the 100 Posts, 100 Days, I did a few rounds of Crazy 8s. I finally broke in one of the Muji storyboard notebooks I picked up in Japan. Still can’t believe they were only about a dollar.

I refined some of the ideas that I came up with in the initial sketches. And I also doodled a few things representing some of the imagery I’d want to include in a post wrapping up the project. The imagery would show the tools I used, places I wrote at, and other things representative of writing during the past 100 days.

Couch to 5K: Sessions 1-6

I started running recently. Well, I started doing intervals of walking and jogging with ambitions to run. Eventually. I’m following the Couch to 5K plan. I’m using the first app that showed up in the App Store. so far I’ve been running on a treadmill before work.

I’m 6 sessions in, which is the first 2 weeks:

  • Week 1: 60 seconds of jogging, 90 seconds of walking, repeat for 20 minutes total

  • Week 2: 90 seconds of jogging, 120 seconds of walking, repeat for 20 minutes total

You start and end with 5 minute walks.

On paper it looks pretty easy and probably is for many people. I haven’t run in years and it was never really a regular part of my regimen. It can get hard during the later intervals but I find myself looking forward to running. That’s something I can’t remember feeling in the past.

Good things

  • I decided to start running with the intention of it being as much for the mental benefit as it was for the physical. That’s panned out. On days that I run I’ve felt like I’ve been better able to focus on work.

  • I’m approaching running with the right mindset. I tried running before and boredom took over in the past. This time, though, things will be better and it will be something that sticks. At the very least, I’ll see the Couch to 5K plan all the way through its 9 weeks.

  • I like the clarity of running with a program. When I tried running in the past I was just going out and failing to keep up with friends. Or I would set the speed on a treadmill and things would go well for a few sessions. I wouldn’t know how to change things to ramp up properly and then I’d just lose interest.

Things I can improve on

  • I took one day between weeks and didn’t feel great after the fourth session. I was feeling the ramifications of not taking a proper break before things ramped up. I understand how easy the programming is right now. It’s only going to get more difficult so I’ll need to be more careful to rest properly to recover for successive weeks.

  • I also took 3 days between sessions. That run felt great, but I want to aim for 2 day breaks at most. If I leave room for 3 days that’ll turn to 4 and that can snowball to where I stop running.

  • After my first day of running I felt extreme focus during work. It hasn’t come back since that first session and I’ll make sure not to chase that feeling. If it happens then that’s just a bonus. I’m happy with the smaller levels of focus and cognitive improvement I experience regularly.


  • I’ve been adding weight sessions throughout the weeks. I’ll be skipping leg day for a while. I’m sure there’s literature out there out there explaining why this is the wrong decision. I want my legs to be as fresh as possible during these earlier weeks.

  • I won’t use it as an excuse to house carbs. I’ve been eating piles of fruit in the past few days. There are worse things I can do but it’s not ideal. I don’t want to offset any good I’m doing by sabotaging myself in the kitchen.

Looking forward to where this will take me. I’ll try to check back in every 2 or 3 weeks, but will definitely write a recap after the 9 weeks are complete.

Sunday Journal Issue 06: Entering the final turn

I used the full utility belt this week. I wrote some posts long form, I did some voice dictation, I wrote with my Chromebook, I wrote at my desk, I wrote on the bus with my phone, I wrote notes about audio books, right now it’s about Kindle books, and I’ve been reading a hard copy book.

In some ways I’m shocked that I’ve gotten this far. I took the time to read a few older posts. They’re not worthless. there’s something there. and as a collective thing, I’m pretty happy with it how things are coming together. I’ve started thinking about what to do after I reach 100 posts. Like considering whether it’d be too show off-y to get a special hook for my apartment to hang the incoming Pulitzer Prize.

Navigation is top of mind. I doubt anyone is going to read the posts from beginning to end. They’re more likely to have interest in certain types of posts. I can see someone liking a book notes posts and trying to find all the books I’ve written notes up for. And then there are journal-type posts like this one. I can have something on writing, something on Fitness, something on meditation, etc. I can put some reading packs together. If you didn’t close this tab in disgust, you might like these other 5 posts.

It crossed my mind that I can try to code this in Jekyll. I have the insight to also see the black hole of tinkering that could turn into. There are WordPress plugins that automate this, and it wouldn’t be too hard to convert the entire thing to WordPress. Hey, another black hole. If I’m thinking MVP, I can just make more posts explaining the different hand-curated1 collections.

We’ll see when I actually sit down and see what I want to do for this.

Very late thursday night (Friday morning): I wrote a post with my voice, can you tell which one it is? Dictation could be a good way to do the initial brain vomit. You can get to two crappy pages awfully fast by speaking into your phone.

I wonder what the quality difference is for these two scenarios:

  • 15 minutes to dictate a very very sloppy first draft, 30 minutes of editing

  • 30 minutes to write a somewhat sloppy first draft, 15 minutes of editing

There would be a quantity difference as well—though that’s already into quality. If the quantity is higher through dictating but the amount of fluff is higher as well then that’s no good.

Actual Friday morning: Instead of writing, I just spent probably an hour messing with my monitor again. And it’s frustrating wasting time on these things that don’t really matter all that much. I just wanted to write this morning and instead I was messing around with resolutions, then an hour was long gone.

I have 21 posts left. I have 13 days left. This weekend will be important for banging out a few extra posts to make up the difference. There are some and drafts late so I’ll be able to work on those and I feel good about completing them. It be nice if I could get it down to one post per day in the final week so that my final we can really just follow the original schedule. So do that I will need to get to 10 posts with 10 days left. So I’ll have to do 11 posts in the next 3 days. When will the trains crash into each other?

I have an idea how I can get that done. I have enough ideas for topics. I have a large backlog of Kindle highlights. One of the lengthier parts of writing a book notes post is reading the book in the first place.


10-ish AM: I I’m in the coffee place in probably looks like I’m talking to myself. But I’m writing. I am dictating at least. I had an iced coffee with almond milk. Actually this microphone is not picking up when I want to say so I’m going to work on my Chromebook

I’ve got a free day, it’s way too hot out, so I’m going to do some major catching up to do some major catching up today. My goal is to get to 10 posts left in 10 days. This morning I’ll be editing some drafts. I’ll finish these posts then take a break to run.

1:30 PM: I made good progress. I finished editing these posts:

In the afternoon, I’m hoping to start and finish a few more posts. They’re going to be journal posts:

  • Sunday journal: what you’re reading right now

  • Meditation: impressions after finishing the first series in Headspace

  • Running: finishing the first 6 sessions of Couch to 5K and why it’s been awesome and terrible (working title)

If I have anything left in the tank I’ll do a little more sprinting on the front page:

  • Crazy 8s: I want to think even further about what I can do on the front page to display the 100 posts when they’re complete

  • Prototyping: I want to explore things and do a screen recording session with either Sketch or Google Slides

5:00 PM: Instead of working on any of that, I wrote a post on a few passages I highlighted in Infinite Jest. Enjoyed writing it, mostly because I enjoyed going through all those highlights again.

Bought some clams and boquerones. Going to eat these then finish up the journal posts. (Oh, and start them.)

11:00 PM: Okay I started writing the Couch to 5K journal about running. After stopping for a few other important things, I got back to editing the post and finished it. Check it out. One of those things was stopping to watch most important running event there is: 100m at the Olympics.

It was looking a little bleak around halfway through. Wasn’t sure how things would look at the finish line. However, I’m back on track: 10 posts, 10 days. I didn’t finish the meditation journal or either of the exercises for the front page design, but at least I know what’s next in the queue.

Current total of all the posts is about 63,000 words.

  1. In the way those wacky museums of useless things still must have some kind of curator.

Book note on Infinite Jest: Quality

I watched the first season of Simon Rich’s Man Seeking Woman this week. There’s a clip where Josh is preparing his apartment and Infinite Jest is one of the books he arranges for display. I finished reading Infinite Jest around this time last year. (According to my calendar, my free time was primarily occupied with reading Infinite Jest and playing Counter-Strike: GO. Not a bad month.)

I was mostly reading the softcover but I picked a Kindle version up to read on-the-go. So I do have some things highlighted for the Kindle version:

“[…] He said she had a face that’d break your heart and then also break the heart of whoever like rushed over to your aid as you pitched over sideways grabbing your chest.”

I highlighted things that I thought were well written. In a sense, they’re sentences written in a way that I’d like to write. I know I’ll never get to David Foster Wallace’s mastery of English. (“Especially with that attitude! Never say never.” This is one of those actual nevers that’s just plain true.) If I can write anything even, say, 5% as good, I’ll be happy.

A good way to start is probably looking at some more things he’s written that I enjoy. It’s good to review for inspiration.

I picked some clothing up and began separating it by smell into wearable and unwearable.

I recently wrote about the phrase “Only emotion endures”. Something I enjoyed throughout Infinite Jest is how fun the descriptions are of ordinary activity. I know what sorting clothes by smell is like. It happens. It makes me think of underpacking for vacations. Or times where laundromat trips have been scheduled a little too far apart.

He was never what you’d call a ladies’ man. At parties he was always at the center of the crowd that drank instead of dancing.

It’s a great description. You get a broad sense of his physical appearance and his personality. It’s a deep look because you know someone that’s in the drinking-not-dancing crowd.

I’ve been reading Simon Rich’s work and enjoying the absurdist humor. Infinite Jest has its fair share:

Already carrying 230 pounds and bench-pressing well over that, Gately clocked a 4.4 40 in 7th grade, and the legend is that the Beverly Middle School coach ran even faster than that into the locker room to jack off over the stopwatch.

I’d like to know if a joke like that just came to him or if he had to work it multiple times and rewrite it. I have 170 other highlights in the book, and it was fun skimming the list. I’d like to write things that make people smile the way I smiled many many times while reading Infinite Jest.

Front page sprint: 20 minutes sketching

I’m starting to think about redesigning the front page of this site. At the end of this project, I’ll have 100 posts. I don’t expect that anyone will try reading all the posts. It’s a pool with green water and I wouldn’t expect anyone to dive into it.

However, if you arrive on this site through a specific post I’d like to make it easy to find similar posts. People might arrive on the front page to find out about this hundred posts in 100 days project. The front page should reflect the project as a whole. It should provide a compelling way to at least look through the titles and get a sense of what I was writing about. Then I can direct people to posts I think are generally most interesting.

Book stacks: A lot of posts are book notes. Hopefully, people read a book notes post and are interested in seeing other books I’ve read and written about. I want to make sure to handle this use case well. One idea I had was grouping related books that I’ve written notes on. One stack could be about Essentialism and Life Changing Magic of Tidying Up. That covers de-cluttering physically and mentally to focus deeply on important things.

This idea came from a time that I gifted a set of books to a friend. He was refocusing his career and I sent a few books that I read that I found helpful in the past couple years

Categories: Clearly not a groundbreaking idea. If I did categories, I’d like them to be presented in an interesting way.

Dated archive: There should still be some kind of dated archive to show the order that everything was written in. If I continue creating content beyond 100 posts, this would continue being a useful way to navigate the site.

Timeline: I really like this idea. Especially keeping in line with thinking the first hundred posts being a single collective thing. A timeline could create a good sense of what I was thinking at different times during the project. Even if I continue creating content for this blog, the first hundred can always stand as its own stand-alone project.


In Smartcuts, Shane Snow looks at seemingly overnight successes. Many people point out that overnight success is actually the result of years of hard work. However, tons of people put the same years of hard work in and don’t achieve the same level of success. A lot of times, wild success comes through putting hard work in along with taking a different route—a smartcut.

David Heinemeier Hansson created Ruby on Rails and is the co-founder of Basecamp. The 37signals blog has been an inspiration through my career. I appreciate what Basecamp’s leadership has done in highlighting the importance of work-life balance.

(If I had a sidebar: Basecamp comes from 37signals, originally a design agency co-founded by Ernest Kim. Ernest made Kicksology in the early 2000s. I’ve always been delighted by Basecamp having a historical connection to Kicksology. My friends would go to Kicksology to learn about the latest sneakers, and I would go to learn about the latest in HTML table layouts. The design holds up remarkably well 15 years later.)

Rails provides scaffolding for web apps. You could build on top of that scaffolding confident that smart people have made initial decisions for you. You might know better solutions for certain parts, but the defaults provided a great place to start.

“You can build on top of a lot of things that exist in this world,” David Heinemeier Hansson told me. “Somebody goes in and does that hard, ground level science based work. “And then on top of that,” he smiles, “you build the art.”

With a framework in place you can focus on the things specific to your idea. If we had infinite time it be fine to Tinker. But we don’t so focus is important. Once you know the goal then you can work towards it and also keep an eye out for any lateral moves so you there Astor.

Siegel cared more about his long-term journey than his short-term paycheck; she screened every offer through the lens of, “Will this help Jimmy get SNL one day?” He said “no” to television sitcoms, “no” to acting jobs that might take him too far away from SNL.

Great lesson on focus and an abundance mindset. It depends on where you are in your journey but you don’t have to say yes to every single opportunity. It’s important to learn to say no to those good-not-great opportunities. Having an end goal in mind makes that filtering more straightforward.

One of the ideas in Smartcuts that stuck with me was the value of calculators early on in math education:

The overwhelming majority of academic research about calculators indicates that leveraging such tools improves conceptual understanding. By learning the tool (calculator) first, we actually master the discipline (math) faster.

Tooling has become so important in web development. When I learned HTML, I made a page that had a single sentence and I was fascinated that I could just change the text. It’s different today.

WIth the right tools, you can put together a very basic app in one day. A novice won’t know exactly what’s going on underneath the hood. Still, the end product is more interesting than a page with a single sentence.

Let’s say you had one month to learn something, you could 1.) learn CSS from the ground up or 2.) jump into learning a CSS framework. Learning from the ground up, you’d probably have a good understanding of CSS. However, you probably couldn’t put a layout together as robust as what you would get through a framework.

Success is measured by your goal. If your goal is building something quickly, it might be better to use the framework and spend the majority of time talking to users. If your goal is to become a web developer, the ground-level understanding is more important.

Rails grew popular quickly because it helped developers build things quickly. Authentication is taken care of, where writing this yourself would take an eternity with no experience.

The most popular Rails resource is probably the Michael Hartl tutorial. He introduces tools early on. Tools which you’ll eventually use if you want to make anything production-ready. In that book, learning Ruby is the means to the end. In that case, the discipline is building something useful with Rails.

Smartcuts also covers the power of constraints.

Constraints made New York City an architectural marvel. Manhattan Island’s narrow shape forced the city to build up, to rethink and renew; it impelled architects to reinvent stone buildings into steel skyscrapers.

Started reading through Sprint and it reminds me how important constraints are for creativity. My current constraint is one page each day. One of the best things I took away from design sprints is learning how to time block creative activities. You hit the end of a block and continue moving on with what you have.

You just have to be ruthless about moving on. The end result of the process is more important than polishing during any single step.

Moving on can be difficult if you’re working alone. With no outside facilitator, you just need to trust your plan and know that following the system will work. That said, it takes a few attempts to make sure the system works in the first place. When you see success with the system then you’ll build up belief in it.

I’ve iterated on my system for writing daily posts. There were many small failures along the way, but I trust it now. If I want to finish a post in an hour or two, I can do that.

The next step is taking what I’ve learned in creating a system for quantity and begin creating a system that helps me improve the quality of writing. I’ll keep my eyes open for a smartcut along the way.

Choose Yourself!

Some of my posts have been written around things I hear on James Altucher’s podcast. I enjoyed his book Choose Yourself!. I like his outlook on life. Altucher has had it all and lost it all and got it back and lost it all again. A few times over. His background is diverse and his time making media websites in the 90s is fascinating. He’ll mention making Mobb Deep’s original website the way I’d say, “Oh I picked up this bag of gummi sour snakes at the corner store on the way here.”

When I say I like Altucher’s outlook on life, a lot of that has to do with his grasp of what’s important for happiness. I liked how he described what he calls the currency of unhappiness:

I don’t like the word purpose. It implies that somewhere in the future I will find something that will make me happy, and that until then, I will be unhappy. People fool themselves into thinking that the currency of unhappiness will buy them happiness.

A lot of times it seems like blocks of unhappiness lead to happiness. There’s an idea that it’s worked in the past, So we can do that again. It’s important to realize it’s not the only way, though. A lot of the factors in life that contribute to happiness are achievable now. Not everything is at the next milestone.

He also has a pretty good sense of what it takes to be great at something. He’s been successful in multiple fields: creating businesses, chess, the stock market, and now writing and podcasting. Here are a few of his tips regarding where to find inspiration for something you’re trying to master:

Study the history of the form you want to master. Study every nuance. If you want to write, read not only all of your contemporaries, but the influences of those contemporaries, and their influences. Additionally, draw inspiration from other art forms. From music, art, and there again, go back to the influences of your inspirations, and go back to their influences, and so on.

This reminds me of Smartcuts. A lot of breakthroughs come from lateral thinking. Normal practices in one field applied to other fields can produce effective results. Meditation principles applied to productivity leads to deep work. It’s focusing on the present.

We might not have wormholes at hand but all of us time travel every day. You can cherish memories and look forward to future plans. If those thoughts are given a negative shade, you might be worried or anxious. Here’s what Altucher recommends for helping that:

All you have to do is stay in the present. When you catch yourself upset about the past or worried about the future, say to yourself, “Ah, I’m time traveling,” then STOP. That’s what meditation is.

I’ve been practicing meditation and am quickly learning how important it is to be able to catch yourself in your thoughts. If something is bugging you then you’re better able to be deliberate about accepting that and putting it out of mind for good. Reading The Obstacle is the Way, things clicked for me in realizing just how much is out of our control. And energy that would be spent worrying about those things can be applied productively somewhere else.

I used to think a lot about what I could have done differently. In college, I didn’t get into the computer science department. That killed me. Then it lingered for a lot longer than it should have. At a certain point I realized how grateful I was for experiences and people in my life. If I went back, I might not have them. Not that I wouldn’t be happy. My major example is that I don’t think I would have ended up in New York. I think I’ve experienced more and learned more living here than I would have if I took a different route.

Everyone also worries about the future to some extent. The key is to recognize that you’re worrying then identify what you have control over. If there aren’t steps you can take to improve the situation, then it’s probably out of your control and, again, that energy can be applied positively elsewhere.

I’ve been better about being present in the past couple years. It’s important and building better relationships and in focusing on work. I haven’t entirely stopped time traveling, but I try to make sure it’s the positive kind. If it’s negative time traveling, I think of what I’m grateful for or I figure out what I can do right now.

I appreciate that Altucher doesn’t proclaim he’s a guru or anything like that. His suggestion is to see other have done, including himself, and take the lessons from that. Then try them out yourself to see what works.

The Choose Yourself Guide to Wealth

James Altucher followed up Choose Yourself! with The Choose Yourself Guide to Wealth. The books are similar, with Altucher sharing what he’s learned through his experiences. Guide to Wealth is focuses more on careers and starting businesses.

The same thing happens with the idea muscle. Somewhere around idea number six, your brain starts to sweat. This means it’s building up. Break through this. Come up with ten ideas.

Coming up with the ideas is one thing. Building them and sharing them is another.

In How to Fail at Almost Anything and Still Win Big, Scott Adams explains the concept of skill multipliers. Some general skills that can be applied to you whatever your expertise is that will separate you from the bulk of the pack. Leaders in any field always have some of these skill multipliers.

James knows the importance of one of these multipliers: public speaking. You have to be able to share your ideas. His advice for who to observe and learn from? TED speakers? Nope. Stand-up comedians:

Comedians are the best public speakers and are up against the most brutal audiences, so you must study them. Learn from them.

Comedians iterate. In interviews, when comedians are asked about how they got to where they are, most say they got used to failing in front of live audiences. It’s the best way to test material. Not that it becomes pleasurable in the moment—bombing is still bombing—but they learn not to dwell on it.

One of the best stories in the book is about Gene Wolfe, who found success iterating on the machine that cooks Pringles (this excerpt isn’t from the book, it’s from an interview with Gene):

LP: Along those lines, is it true you invented the machine that makes Pringles potato chips?

GW: I developed it. I did not invent it. That was done by a German gentlemen whose name I’ve forgotten for years. I developed the machine that cooks them. He had invented the basic idea, how to make the potato dough, pressing it between two forms, more or less as in a wrap-around, immersing them in hot cooking oil, and so forth and so on. And we were then called in, I was in the engineering development division, and asked to develop mass production equipment to make these chips. And we divided the task into the dough making/dough rolling portion, which was done by Len Hooper, and the cooking portion, which was done by me, and then the pickoff and salting portion, which was done by someone else, and then the can filling/can sealing portion which was done by a man who was almost driven insane by the program. Because he would develop a machine, and he would have it almost ready to go, and they would say “Oh, instead of 300 cans a minute, make it 500 cans a minute.” And so he would have to throw out a bunch of stuff, and develop the new machine, and when he got that one about ready, they’d say “make it 700 cans a minute.” And they almost put him in a mental hospital. He took his job very seriously and he just about flipped out.

Once he was done iterating on potato chips, he pivoted his career. One page and one day at a time. From Guide to Wealth:

Gene has been an adult for almost 25,000 days. He writes a page a day. A page is about three hundred words words. A paragraph or two. Can you do that? Twenty-five thousand pages. About eighty books’ worth of pages. Gene ended up writing fifty published novels, including many best-sellers and award winners. He didn’t get stereotyped and stuffed into that Pringles can, as dead as the chips he created.

Lately I’ve been going back through what I’ve written for this 100 Posts, 100 Days project. Sometimes I can’t fully remember writing certain posts. It’s more content than I want to go through in one sitting. That speaks to successfully creating quantity, which was the goal, knowing quality would probably suffer. It’s rewarding to see it come together. The next step is shifting the focus to quality.

The Miracle of Morning Pages

Before I started the 100 posts in 100 days project, I was experimenting with morning pages for writing every day. I found it really good, but it could take a while. I didn’t read Julia Cameron’s The Artist’s Way, but I bought the supplement: The Miracle of Morning Pages. My biggest takeaways from this were that the rules are more strict than most people usually following it do.

First thing upon waking up

You want to capture your monkey mind immediately. The intention isn’t to create new content that’s shared with people. The real reason to do morning pages is to get the junk out of your head to generate clarity. The content isn’t the point, the practice is.


Cameron stresses the importance of doing morning pages longhand. Longhand translation to actual words differs of course, but it’s safe to say you’d fit more per page when typing. If you type your morning pages and actually get to three typed pages, that’s a lot more content than you’d get handwritten. Again, though, the content is the point. So I can see where going longhand could generate completely different results.

Toss them out, burn them, etc.

I struggled with treating morning pages as non-permanent things. I’d never say I’m a minimalist but I’ve always tried to keep clutter down in my apartment. I think it’s a holdover from living in 7 different places my first year in New York. Even if a stay was only a few days or a couple weeks, I still had to move everything.

On the other hand, I’m a digital hoarder. What if something good is in the morning pages? Just let it go? I guess there’s that idea that if it’s really important then you’ll remember it. And that it’s practice in seeing that good ideas aren’t a finite resource. You’ll always think of more.

Absolutely stop when done

You’re supposed to get to 3 pages and stop. No more and no less. It’s enough to get to clarity and move on with your day. That doesn’t mean you have to stop writing entirely. It just means morning pages need to be separate from writing that you do that’s going towards your novel or articles or whatever that may be.

Book note on The Creative Habit: Excuses

In The Creative Habit, Twyla Tharp shares her journey and gives guidance on building a habit of working on your creativity. One of the key things is getting over some of the fears and excuses you might have for starting and sharing something creative:

  1. People will laugh at me.

  2. Someone has done it before.

  3. I have nothing to say.

  4. I will upset someone I love.

  5. Once executed, the idea will never be as good as it is in my mind.

My real fear is that people will cringe when they read things I write. I can deal with people laughing at me. It seems like I’ll have to go through both if I want to learn how to get people to laugh with me.

I’m not the first person to blog, and I’m not even the ten thousandth person to try posting every day. In a lot of cases I know that because I’m pretty much taking the exact same premise or method.

I don’t have a fear of having nothing to say, I’m not even worried that I won’t have anything good to say. I know I won’t have anything good to say on some days. The point of establishing a habit is to to keep working through those days because they’ll add up and I’ll learn to start creating something good.

I’m not too worried about upsetting someone I love. I’m not doing any kind of tell-all and I’m not hiding any of this from anyone. My girlfriend was one of the first people I told about this project and she’s been very supportive. Same with my brother and a couple close friends I’ve shared this project with.

As far as not reaching the expectation I have set in my mind, you can beat that by setting the bar very low. Not a great strategy for long-term goals. The long-term goal is to have a hundred posts in 100 days knowing that will get me a good practice. However, it requires a lower bar for each post. And there has to be some kind of balance. My rule that I’ve stuck pretty close to it is to not have cut out those that are two or three sentences just the post for the sake of posting.

Some days I haven’t had a full hour and it’s not enough time to really polish anything of length. In the future, if I’m writing one-day posts I’ll aim to create shorter posts. Otherwise I’ll take multiple days to give myself time to write something of substance.

Friday Links Issue 08: More Rich

Simon Rich Picks His 9 Favorite Obscure Saturday Night Live Sketches He Wrote

With FXX’s Man Seeking Woman returning for its second season last Wednesday, we asked the show’s mastermind Simon Rich to look back on his years as a Saturday Night Live writer and pick the most obscure sketches he penned.

Another set of links, another Simon Rich interview. I read Ant Farm this week, which has some pieces from when he was editor of the Harvard Lampoon. They’re not as polished as the stories in his latest book, and it’s inspiring.

It’s not exactly like looking at work in progress. It’s not a discarded legal pad, but it’s a look into how his storytelling has evolved. In Ant Farm, you’re dropped right into a scene, with the title and a couple sentences explaining the context.

In Spoiled Brats and The Last Girlfriend on Earth, he weaves those jokes into a larger narrative and the payoff is better.

I got a Hulu account to watch his show Man Seeking Woman, and it takes the storytelling even further. Elements of his short stories are put into the scenes, or sometimes brought wholesale into a scene.

Each scene could stand alone as a single sketch but they’re all part of a larger narrative. You get attached to characters. Again, the payoff is even bigger.

Even if that kind of writing ability is decades away for me, it’s great to see the steps he took to get there.

How I Used a Vacation Timer to Write a Book (or, Why I Shut Off the Internet at 9PM)

For years, I tried to start a daily writing habit. See, I had this crazy idea to write a book, and I knew I’d need a lot of time and practice to get it done. But with kids and a full-time job, there was no way I could find big blocks of time during the day.

My trouble lately has been trying to get out of the bed in the morning instead of reading a lot of Internet. I don’t actually have all that much trouble using the laptop at night.

Waking up early isn’t the problem, but reading internet right away is. Maybe I can put my phone in an electric safe and then connect that to a vacation timer.

I can also daisy chain it to all the cardboard cutouts to stave off the wet bandit.

Why Self-Help Guru James Altucher Only Owns 15 Things1

It was around 10 a.m. on a sun-drenched summer morning, and James Altucher, perhaps the world’s least likely success guru, was packing his worldly possessions, about 15 items, into a small canvas carry-on bag. “If I were to die, my kids get this bag,” Mr.

I’m a big fan of James Altucher. I like this idea that biographies are a good way to learn. Not everything will work for everybody, and there’s no point in trying to follow footsteps completely. A lot of luck comes in the play. But you can cherry pick different things as long as you make sure that you try them out and review of that working for you.

I’ve recently started his idea generating system. And it’s giving me a lot of ideas as it should. But it’s true that once you get to ideas seven or eight it starts to get hard and thinking hard to get the last two to finish up at 10 is good daily exercise for your brain. And whatever the creative muscle is.

The Best Fictional Basketball Shots Ever

I pose to you a simple question: What is the most impressive fictional basketball shot that has ever happened? Think of a movie or a TV show or a music video or anything, really, in which you saw fictional basketball being played. Think of all the shots that happened during those scenes.

Shea Serrano is one of my favorite writers. I would love to write things like this. His writing has a distinct voice. It’s just plain fun to read.

  1. I should note that I got this link through Tim Ferriss’s 5-Bullet Friday newsletter. Which of course is where I stole this idea of creating Friday links posts in the first place.

Spark Joy

In Spark Joy, Marie Kondo explains further how to apply the principles from The Life-Changing Magic of Tidying.

When I was a kid, my parents would have different levels of clean. The highest for me and my brother to strive for was “party clean”. Aka guests are coming over. We’d clean and clean then tell our dad we were ready for inspection, which we never seemed to pass the first time through. Probably the entire point of the whole thing, looking back.

When cleaning my bedroom, I’d do fine until I hit the pile of Game Players and EGM magazines. If I read Spark Joy back then, I probably would’ve been very confused, then finished cleaning faster, treating magazines like books:

To avoid wasting the entire day reading them, the trick is never to open them. Check for joy by simply touching them.

When I visit my parents’ house, a handful of those videogame magazines are still on the bookshelf. Right below the World Book encyclopedia and the teen and children supplemental books. I’ll have to confirm the next time I’m over, but I’m sure touching them would spark joy.

I really like this tip for dealing with food scraps:

Consequently, my kitchen never smells like raw garbage. So what do I do with the kitchen scraps? I keep them in my freezer. I set aside a corner of the freezer for kitchen scraps and, after thoroughly draining them, I plop any fruit and vegetable peelings, chicken bones, etc., in a bag as I cook. Twice a week, on regular pickup days, I remove the bag of scraps.

I do a C-minus version of this. I don’t usually have much actual food in my freezer so it’s usually just empty containers from Seamless deliveries from the week. Or last two weeks. Or…

Anyway, she also takes labels off of as many things as she can:

The more textual information you have in your environment, the more your home becomes filled with noise.

My pet peeve is when people leave stickers on TVs and laptops. Those would probably drive Kondo up the wall. She takes things a step further by removing labels from laundry detergent and other household bottles.

The book also has some advice for the digital world. In particular, photos:

Since the advent of the digital camera, people take endless photos but rarely look at them more than once.

I took the time to organize my photos and have found that I look at them a lot more. While I can’t bring myself to delete large swaths of photos, I did some organizing locally then uploaded them all to Google Photos.

Probably one of my favorite products1 of the last five years. Can’t recommend it enough if you were like me, used an SLR and other cameras along the way until phones caught up and now you take so many but never want to plug the external hard drive in to look at the old photos.

Until there’s technology to magically handle all the other piles of clutter in life, it might be a good idea to follow some of the guidelines in Spark Joy.

  1. Disclaimer disclaimer disclaimer