Goal Progress: November

December 1, 2020 • #

We had a hurricane blow up part of a week of productivity around here, but I still limped along with some middling progress on the year’s goals. I’m behind the targets this year late in the game, but I’m still happy with the results. I can still close the gap on the running target, at least.

I’ve been thinking about an idea Patrick O’Shaughnessy wrote about recently on “growth without goals” — setting up systems to be able to pursue and achieve personal growth without having hard numbers on a scoreboard. Using this site as a public accountability tool helps me to keep these top of mind for continued effort. I’ll have to give this some thought as we near the end of 2020 as to how I want to set up my personal growth systems for 2021. I’m thinking an evolution is in order that creates more space for discovery of new interests without interrupting growth in focus areas.

Activity Progress Pace Goal Plus-Minus
Running 588.6 miles 597 miles 650 miles -8.02
Meditation 1070 minutes 2607 minutes 3120 minutes
Reading 24 books 27.53 books 30 books -3.53

Reading seems like one that’s particularly absurd to quantify as num_books_read. The dimensions of depth and breath of a “book” are so all over the place that the metric approaches uselessness as a measurement. I’ve tried to avoid selecting material I choose to read around “managing to the metric”; the last thing I want is to end up reading 11 garbage quick reads just to hit an arbitrary number. The purpose is defeated if I were to fall into that trap.

One idea that comes to mind as I’m writing this is selecting target study areas to read about — something like choosing 4 or 5 topic areas I want to dive deeper in and measure to how many of those subjects I learn more about. A trackable tool to keep me honest would be useful, but I’m conscious of falling prey to simply managing what’s easily quantified.

With the downramp in the previous daily posting regimen, I’ve used that time mostly to catch up on a bunch of new ideas cooking in (and about) Roam, and put out a couple of newsletters, issues 4 and 5 of Res Extensa. (Subscribe here!)

It’s been fun to do so far. I’ve landed on this idea for the last couple of following a theme topic rather than a simple digest of links or interesting things. That could be interesting, but there are a lot of great “curator” newsletters out there already. Issue 4’s theme was legibility, from James C. Scott’s epic Seeing Like a State, and issue 5 looked at alternate timelines from a couple of different angles.

Weekend Reading: Digital Librarians, Tech Trees, and Alternate Histories in Maps

November 22, 2020 • #

📑 Chief Notion Officer

Julian Lehr is onto something here. All modern organizations are plagued with a problem of managing internal documentations. We have ample tools and keep squishing the problem from one place to another: wikis, search, tasks — it’s a game of whack-a-mole to find the right version of a document. He ponders at what size it makes sense to invest in a “digital librarian”:

A friend at Stripe recently suggested – half-jokingly – that we should hire a librarian to organize all our internal data and documentation. The more I think about it, the more I like the idea. Perhaps every company should hire a Chief Notion Officer once it hits 100 employees??

🌳 The Tree of Up

Up created a tech tree representation of their product and roadmap. Genius.

🌍 Intriguing Maps That Reveal Alternate Histories

Speculative maps of alternate historical timelines.

Everett 3.0

November 21, 2020 • #

Everett just hit the big 3.0 mark today.

Whenever I’ve asked him how old he’s turning over the last few weeks, the number has varied from 4 to 6. Clearly he wants to be up there with his sister. He’s changed so much as I look back on the status from a year ago — fully talking, self-sufficient to get his own things in most ways, doing full puzzles, drawing legible pictures. He’s really accelerated to catch up to where his sister was at the same age.

Sitting with Mario Sitting with Mario

While it’s not the same these days with planning kids’ parties, we’ve sort of adopted a tradition of the zoo on his birthday, or at least I’d call it one after doing it three years in a row. They had a good time as always.

When I watch video clips from February or March, it’s striking how much he’s changed since the start of this quarantine life. Of course we’re not totally quarantined now like we were in the March to July range, but still, he’s had a far-from-normal time for the last several months. He should’ve been in preschool at least at the start of the school year, but we opted to wait it out a little while. Hopefully we’ll send him back soon after the new year, if we can.

On his bunk bed On his bunk bed

He and his sister have become pretty attached-at-the-hip with one another during all this time together, though. They don’t know what to do when either of them is alone, but you’d never tell that from all the sibling spats you see when they’re together.

Let’s hope version 3.0 gets a more “normal” existence on his way to 4!

Stripe's Content Strategy

November 17, 2020 • #

Morgan Mahlock wrote recently about the promise of Stripe Press, Stripe’s book publishing outfit:

Within the legacy publishing industry, Stripe’s young publishing press is refreshing - it is Sutherland’s electric cover art on a dusty, tired bookshelf. An Authoritative Look at Book Publishing Startups in the United States by Thad McIlroy states, “Book publishing has never been a technology-adept industry; indeed it is historically technology-averse. This is a challenge for the (minority of) startups targeting existing publishing companies.” Stripe Press is different because it was born from a technology company. It is a strategic asset because it allows Stripe to shape and share influential knowledge with its interconnected ecosystem of entrepreneurs, businesses, authors, and technologists.

Her post gives a good summary of why Stripe Press is exciting for the book publishing industry. The catalog only sits today at 10 titles, but I believe 4 those were released this year. The pace has been increasing, but they keep elevating the quality bar.

Stripe Press

They’re not only attracting original works like Nadia Eghbal’s excellent Working in Public (2020), but also breathing new life into notable books from the past. Both Martin Gurri’s Revolt of the Public (published in 2014, one of my favorites this year) and Donald Braben’s Scientific Freedom (2007), to name two examples, saw relatively small initial publishing runs. The editorial staff over at Stripe is doing amazing work to bring these books back into wider circulation using a spotless curatorial eye for the noteworthy and influential.

Stripe Press is, of course, producing excellent books for us to read, and giving authors writing about technology a channel for getting their work out there. But it’s also a marketing channel for Stripe.

Content marketing, my favorite of the marketings

I have a soft spot for quality content. The best content marketing doesn’t feel anything like marketing. Its value is so deep you don’t even think about what you’re giving in return to its creator.

The tech companies of the last 20 years didn’t invent content marketing, though our scene talks about it more than any other. Even Ben Franklin used a content marketing play when he published Poor Richard’s Almanack as a way to promote his printing business.

The scene is now full of companies that embrace the multichannel returns they can drive through quality, helpful content. A few favorites of mine:

Not only does Stripe do a stellar job at the traditional CM channels — blog, help guides, developer documentation, email — they went farther than anyone and became a book publisher1.

What differentiates Stripe as a publishing house from the HarperCollinses or Hachettes is that it’s not their core business, but a component that drives other parts of the business. Direct sales revenue is only 1 channel of value they’re deriving from putting this catalog in print. Stripe sees their Press group as a content marketing strategy, especially to raise global interest in technology, pushing their mission to “raise the GDP of the internet.” At the most tactical level, the Press catalog increases interest in tech, creates more founders, who then start companies that become Stripe customers.

Stripe flywheels

I linked a while back to Max Olson’s excellent post Advantage Flywheels, which presents a great framework for analyzing the causal loops that power businesses. Irrespective of Press, Stripe’s built a fantastic advantage with feedback loops combining in powerful ways. Using Max’s same architecture of flywheel archetypes, I took a stab at drawing out what Stripe’s machinery looks like, with its products in blue:

Stripe's flywheels

At its core, Stripe serves developers who build applications which expand in usage and generate financial transactions.

Spinning off from those central inputs and outputs are several flywheels that create momentum that feeds back into the core business. Radar does fraud detection, which improves with masses of transaction data. Billing and Sigma are tools that improve finance management and reporting. Atlas helps founders incorporate and get started, thereby generating more customers for Payments, Issuing, and more. That’s where I see book publishing fitting into the machine: as a mechanism to expand the TAM for internet businesses.

Press is unique in this regard for a tech content strategy. Normally something like a blog, video channel, or newsletter would be tied more directly to the “more developers” nexus, but for Stripe, book publishing is playing a longer game. Even though this feedback loop has a long time delay (publishing a book won’t make a new founder overnight), I believe it’s a powerful one. The best strategies serve more than one function; Press is a brand builder, a recruiting tool, a direct revenue driver (from book sales), and most importantly, a way to increase the number of people interested in technology over the long term. Founder Patrick Collison himself described this exact strategy in response to a Hacker News thread:

The vast majority of Stripe employees (and there are now more than 1,000) work on our core functionality today. But we see our core business as building tools and infrastructure that help grow the online economy. (“Increase the GDP of the internet.”) When we think about that problem, we see that one of the main limits on Stripe’s growth is the number of successful startups in the world. If we can cheaply help increase that number, it makes a lot of business sense for us to do so. (And, hopefully, doing so will create a ton of spillover value for others as well.)

Stripe’s long been known for it’s writing culture, so I suppose it’s also not surprising that a company of readers and writers would want to make books.

When you pop the hood on a strong business like Stripe, you’re always likely to find interesting systems dynamics — multiple outputs feeding other inputs. It’s fascinating that an old, traditional business like publishing could be done in a novel way like this. They’re positioned to bring in new innovations for authors (and readers) that they haven’t scratched the surface on yet; it’s still just paper books. If there’s room for innovation in writing books, Stripe will find it.

  1. I have to wonder here how much the Collison brothers’ bibliophilia plays a role in the decision to launch a publishing house. Can’t be coincidental. 

Fulcrum Field Day

November 9, 2020 • #

A fun aspect of working on a business product with a product-led growth strategy that you get to use the your product for in your personal life. I’ve used Fulcrum for creating personal tracking databases, collecting video for OpenStreetMap, and even documenting my map collection.

There’s no better way to build an empathetic perspective of your customer’s life than to go and be one as often as you can.

Last week our team did an afternoon field day where the entire company went out on a scavenger hunt of sorts, using Fulcrum to log some basic neighborhood sightings. 42 people scattered across the US collected 1,230 records in about an hour, which is an impressive pace even if the use case was a simple one!

Data across the nation, and my own fieldwork in St. Pete Data across the nation, and my own fieldwork in St. Pete

It’s unfortunate how easy it is to stray away from the realities of what customers deal with day in and day out. Any respectable product person has a deep appreciation for how their product works for customers on the ground, at least academically. What exercises like this help us do is to get out of the realm of academics and try to do a real job. With B2B software, especially the kind built for particular industrial or domain applications, it’s hard to do this frequently since you aren’t your canonical user; you have to contrive your own mock scenarios to tease out the pain points in workflow.

The problem is that manufactured tests can’t be representative of all the messy realities in utilities, construction, engineering, or the myriad other cases we serve.

There’s no silver bullet for this. Acknowledging imperfect data and remaining aware of the gaps in your knowledge is the foundation. Then fitting your solution to the right problem, at the right altitude, is the way to go.

Exercises like ours last week are always energizing, though. Anytime you can rally attention around what your customers go through every day it’s a worthy cause. The list of observations and feedback is a mile long, and all high value stuff to investigate.

A Reverse Dunkirk

November 6, 2020 • #

In Erik Larson’s book The Splendid and the Vile, he tells the story of Britain during the Blitz of 1940-41.

In May of 1940, a strategic lapse by the Germans allowed the British to evacuate 330,000 Allied soldiers from the French coast in the famous Dunkirk evacuation. An assemblage of 800 mostly-ragtag vessels were able to slip those hundreds of thousands through air and u-boat attack to safety across the Channel.

There’s an anecdote in the book that I’d never thought about before, with respect to Britain’s response as they prepared for what they thought would be an inevitable amphibious invasion.

Here’s Larson:

One thing Churchill did not address in his speech was an underappreciated element of the Dunkirk evacuation. To those who cared to look, the fact that more than three hundred thousand men had managed to cross the channel in the face of concerted aerial and ground attack carried a darker lesson. It suggested that deterring a massive German invasion force might be more difficult than British commanders had assumed, especially if that force, like the evacuation fleet at Dunkirk, was composed of many hundreds of small ships, barges, and speedboats.

Wrote General Edmund Ironside, commander of Britain’s Home Forces, “It brings me to the fact that the Bosches may equally well be able to land men in England despite [RAF] bombing.”

He feared, in effect, a reverse Dunkirk.

With how successful the British were with a haphazard troop movement with mostly civilian boats, imagine what Germany could’ve accomplished moving a powerful (and much larger) invasion force in a dispersed fashion along the Kent coast? Moving inland through rural areas to regroup and move on London? If Germany knew in the summer of ‘40 how ineffective the Blitz air raids would be, maybe it would’ve happened?

How I Plan My Week with Roam

November 4, 2020 • #

For years Todoist was my tool of choice for task management. When Roam came on the scene for me earlier this year, I’d seen pretty compelling methods from the #roamcult for how to manage todos inside of Roam with its TODO feature. It was an intriguing idea: such a fast and simple way to capture things without leaving the current frame.

But it took me a while to go all-in on Roam for tasks. Todoist was so embedded in my muscle memory, especially with its accessible web and cross-platform mobile apps and its excellent quick-entry “Quick Add” flow from the desktop. It was going to require a lot to make the switch to a different system, and one that’s wildly different from the way any other task management app works.

Roam Weekly Planning

I eventually took the plunge, moved all my pending tasks over to a Roam page from Todoist, and started to come up with a process. I was first just managing tasks from a giant temporary “Inbox” page, but over time I learned better how I wanted to fit them in with the advantages of a Roam-based daily workflow.

Though the switch to Roam for task management gives up some useful abilities with dedicated favorites like Todoist or Things, the gains with managing tasks alongside the rest of my knowledge graph are well worth the trade-offs. Most task management tools have way too many features for my needs, anyway. Here are just a few things I love about this process so far:

  • You can insert todos in context — Being able to quickly slot todos anywhere is beautiful. As you’re writing other notes specific to projects, meetings, phone calls, articles, or anything else, you can Cmd-Enter and add something right as you’re thinking of it. This method ends up being a solid “ubiquitous capture” flow similar to what you’d do with Todoist or OmniFocus inboxes.
  • The [[TODO]] page, pinned to the sidebar — This lets you quickly dredge up all of your todos regardless of where you scattered them. Use this plus filters to drill in to specific areas. A solid “inbox” equivalent to process your todos into other places.
  • Add tags to filter for context — If you’re familiar with [GTD’s contexts](https://evomend.net/en/what-not-gtd-context/ “Contexts in), you’ll recognize this. I add tags to tasks so I can filter for all [[TODO]] tagged #Email, for example. Now let’s go over how I plan out my week with Roam.

My Weekly Process

At the beginning of each week, I start out by creating a new page for the week ahead, dated starting on Mondays. So this week’s page is [[📆 Weekly Plan: 2020/11/02]]. I just focus into the search bar and type it out.

For the page template I start out with sections for Weekly Goals and Daily Goals. The first I treat like a general holding area for tasks I want to work on in the upcoming week, and the latter I include a block for each day. Then I manually add in the dates for each day with Roam’s /date picker slash command (/today and /tomorrow can also be useful here, if relevant)1. To make all of this faster, I use a TextExpander snippet to automatically insert the basics. Typing rcwp stamps in my basic template2:

- # Weekly Goals
    - 
- # Daily Goals
    - Monday: 
    - Tuesday:
    - Wednesday: 
    - Thursday: 
    - Friday:

When I started down this workflow path, I initially thought it’d be annoying to have to set up a new page each week. But so far it’s actually been valuable to force a start-of-week planning session to think through what I want to get done. Usually on Sunday nights I’ll go in and make the Weekly Plan page, then pull up my [[Projects]] page, [[Blog Ideas]], [[TODO]], or even my page from the previous week to look for all of the various tasks I might want to focus on.

Using the sidebar helps a lot here. I’ll pop open other pages with a Shift-click, then drag over todos I want to work on under the Weekly Goals section. If I want the todo to actually stay where it is and not move it to the Weekly Plan page, I use Roam’s Alt-click and drag to bring over a block reference instead of the entire block itself. This is a neat way to keep todos in the right place, but have a reference to them in your task plan. There’s an example of this in the video below, where I’ve got a trip planning project page with tasks on it that I want to stay there, but still see in my weekly view.

Once I’ve got a batch of tasks entered under the week, I’ll start queueing them up into their appropriate days. Some things have deadlines or due dates I’m trying to manage to, so need to get done at specific times. Others I’ll just leave in the Weekly section until I know when I plan to do it. Regularly on weekday mornings I’ll go to my plan and pull in what I want to get done that day. It’s a living document until the week is over, a part of my morning routine to go to this page.

My favorite thing about this process is how it manifests your tasks on the Daily Notes page. Because the Daily Note automatically displays references to any page that includes that day’s date, you get a slick little embedded list of the day’s tasks. The Daily Notes view is my default working mode during a typical work day, so this is an excellent place to have all of those queued up activities available on the same page where I’m taking meeting notes and the like.

Tasks embedded in Daily Notes

Areas for Improvement

After about 2 months committed to this process, it’s pretty solid for me. I’m not missing as much from my old workflow as I thought I would, and I’m enjoying the benefits of Roam’s graph structure too much to reconsider now. Plus the potential is high that the lightning-fast Roam team will add improvements to all this.

Todoist’s Quick Add is something I’d love an equivalent for somehow in Roam. The Capture mobile entry web app that Roam has isn’t bad, but it’s not that fast for adding new items quickly while on the go. To fill in this gap now I’ll usually just throw things into a sheet in Drafts which gets processed later back at my desk.

Multiplayer abilities were something I never took advantage of in Todoist, but are a key piece of any work (or even family) project management usage. Roam’s recent additions in support of multiplayer look promising here, but that hasn’t been relevant to me just yet. Multiuser project management (that tools like Asana excel at) is a beast in itself to solve.

Managing dates isn’t as smooth as in most task management apps, but there are some advantages I really do like. For any task entered anywhere in your graph, you can add a future date to it and have it magically appear in Daily Notes references that day to jog your memory. A feature that no task management tool other than OmniFocus ever supported, but I’ve wanted ever since, is the idea of a Start Date. With that you could put in something you want to remember, but for later, put “in 90 days” next to it and it would disappear until resurfacing then. It was a great way to put in things you know you needed to remember, but don’t need to continue seeing in your list for weeks until it’s relevant. Dating your todos like the above is similar in concept: tagging them with a date 3 months out will make them pop back up when they need to be considered.

The Future

From what I’ve seen in Twitter discussions about the incoming Roam API, I’m hopeful that its hyperactive developer community will jump right into building applications on Roam for workflows like this. A dedicated, customizable app specifically for task management built on the “Roam platform” would be a phenomenal tool worthy of driving its own second-order revenue for a developer. Thinking about David Crandall’s piece on the prospects of Roam as a service layer, there’s so much potential for it to power its own developer marketplace.

In the next post I’ll go over my current workflow for using Daily Notes. It’s an interesting companion to this process of task management.

  1. If I was fancier I could probably add this logic to my TextExpander snippet, but adding dates manually doesn’t bother me. 

  2. This setup will look familiar if you’ve seen Nat Eliason’s Effortless Output course. I also found this Alfred workflow with a similar template. 

The Forest Cube

November 2, 2020 • #

There’s a YouTube channel I linked a couple months back called “Modern Self Reliance” where a group of guys built an off-grid cabin. In a new series, they’re adding a neighboring cabin in the form of an 8’x8’x8’ cube, for others to hang out on the property. It’s an excellent series so far. I love how they harvest materials from the property itself (like the cabin’s cedar posts) or salvage things from past projects to do the builds. Looks like a ton of fun.

Part 1:

Part 2:

Part 3:

Goal Progress: October

November 1, 2020 • #

October is over already?

At this rate, it’ll be New Years in no time flat.

Anyway, let’s check in on the 2020 goals:

Activity Progress Pace Goal Plus-Minus
Running 534.25 miles 543 miles 650 miles -8.90
Meditation 1070 minutes 2607 minutes 3120 minutes
Reading 23 books 25.07 books 30 books -2.07

I made middling progress in areas, like some better runs in the first couple of weeks. Felt good to have some overachieving progress. But then we did a week out of town up in Georgia last week, and my plan to do some trail running didn’t become reality. Between schoolwork (Elyse was still remote-learning from the Georgia countryside), rain, and a surprise tropical storm, much outdoor activity was a challenge, to say the least. We did get in 1 hike, but 5 and 3 year olds aren’t that compatible with long excursions.

I went a full 7 days without running, the longest gap in probably 2 years. While it wasn’t necessarily intentional, it’s probably good for health to get some air space there every now and then.

On the reading side, I finished Stephen Fry’s Mythos, which is his reimagining of the greek myths. I listened to the audio version which is read by the author himself, and if you know any of Fry’s work, you’ll know this is the proper way to consume this book. An outstanding rendition of the tales, more accessible than Edith Hamilton’s Mythology or something like Ovid or Virgil classics.

Ross Douthat’s The Decadent Society was both thought-provoking in its claims, and occasionally frustrating by its pessimism about the state of western culture. I tend to agree with many of Douthat’s views on his “4 horsemen” of decadence: stagnation, sterility, sclerosis, and repetition. I’m skeptical of, but open-minded to, the theories of technical stagnation that you read about in the works of Peter Thiel and others. There’s a compelling case to be made that something is going wrong, and Douthat has an interesting take on where he thinks the issues lie. My skepticism is less around the presence of decadence, decay, or drift than it is around the severity of the issues. It’s a worthwhile and provocative read. Along the same lines I’d highly recommend Yuval Levin’s takes on institutional decline in his book A Time to Build from earlier this year.

Subscribe here to receive my newsletter, Res Extensa, a digest of my latest posts, links, and updates. Currently bi-weekly.