Rands Seek understanding

The Cleanse

I’m in the midst of a media cleanse. This started before the election when I canceled my Washington Post subscription. Jeff Bezos can do whatever he wants with the Washington Post, and he’s 100% correct that I don’t trust large media organizations.

After the election, I removed all news sources from Feedly except the Atlantic because I find their writing informative and compelling.

A friend calls this turtling. Pulling your head inside your shell and hiding. It’s quite comfortable here. With most of my free time, I’m leveling a dragon Holy Priest in World of Warcraft. #ama

Next on the list is Twitter. Since it was sold and turned private, my engagement has been significantly lower, and my follower count has shrunk as the humans have moved off the platform, but quite soon, I’m deleting my account. My finger has been over the DELETE button for a few days, and I’ve wondered why. Two facts: First, there are thousands of folks with whom I share stuff there. I can see they are there via much reduced but real engagement. Second, I have just under 20k tweets since 2007 that, upon review, tell an interesting story… at least to me.

I’ve downloaded the complete archive, and I’m sad to say I’m about to create a bunch of 404 errors when my corpus of tweets vanishes from Twitter. Why? This is my content, and I don’t want whatever Twitter has become to benefit from its existence. I’ll share the archive here at some point, but for now, I’m cleansing.

Like FaceBook before it, Twitter turned into something else. They both, early on, felt like a means of connection. Unfortunately, building that social graph allowed these businesses to target you and your engaging, clickable content expertly. What was a means of connection turned into hot, juicy, bite-sized content. Over the past two decades, this practice has made us intellectually lazy because these media services are paid not on the quality but the quantity of service. More clicks, more engagement. Truth and facts. Optional.

And what was a clever means of connection turned into a raging stream of clickable things.

So, bye, Twitter. I’m late to the funeral, but better late than never. It was fun before it got terrifying.

While I am profoundly turtling and have little desire to see a path forward, I have two related observations:

First, the lack of healthy debate on most social media is one of the core issues with the platform. Humans must disagree, but these platforms do not provide a proper bi-directional medium (or set of tools) for these debates. It’s liking, then not liking, then yelling, then ALL CAPS, and NOW I’M UNFOLLOWING YOU and YES BLOCKING BYE.

Debate is a tricky act between two humans who can both speak, listen, understand, and possibly evolve. Two humans. Often, there will be more, but let’s keep it simple and assume it’s two. Both humans are required to do this, and in the primarily anonymous world of social media, it’s normal not to consider the other human a human. They are the last thing they wrote that you disagree with. There is no relationship; it’s simply the last thing they posted. And how do you feel about that post.

The stakes are higher in person. You have to stare at that human in the eye, especially after they say something you don’t like. So, what do you do? You can’t yell, you can’t ignore them, and you certainly can’t block them, so what is your move? Mine: seek understanding. Put on that empathy hat and try to understand why they’re saying what they’re saying. That’s the first step. There are many more — read the book.

The continual failure to do this in social media results in a growing echo chamber where the humans agree, and those who disagree are quickly voted off the island. Some of these echo chambers are low stakes. Think about your favorite sports team. Those fans are aligned on what’s important. Who needs debate? The only debate we care about is what $OTHER-TEAM we hate the most. Go $OUR-TEAM.

There are higher-stakes echo chambers, too. Use your imagination here.

Second, it’s not a short or medium-turn fix to what ails us, but I am curious about investing in local and independent news organizations. Large media organizations have to compete with social. They desperately need those clicks, and that means mimicking the patterns they see in social. The headline must engage in one second or less, or it will be forgotten. It’s an economy of attention, not understanding or truth.

Local media has taken it on the chin for decades because social media consumes advertising dollars. Local media has withered without that support, with remaining big media sources bending to social media engagement patterns. The idea of investing in local media news organizations is because they report on the events that happen in my neighborhood. This makes them more human to me. They have skin in the game because, like me, they live here. My problems are their problems, which means we have a solid foundation to start to understand.

How do I go about this investment? Where do I start?

I don’t know. I’m turtling. For now.

Rands That's curious

Hold Your Breath

Hi. I’m stressed, too. Here are random thoughts on this from the beginning of November 5th, 2024 — election day:

  • Today, a convicted felon and failed businessman (six bankruptcies!) slash narcissist slash twice impeached politician who does not believe in democracy, who called for and achieved an armed insurrection, and who lies compulsively is the Republican nominee for the President of the United States.
  • While the presidency is at stake today, winning the presidency is only part of what is decided tomorrow. There are countless House and State elections, State Supreme Court, and other Statewide offices on the line tomorrow, which leads me to a strangely comforting thought…
  • There’s no scenario when it’s “over” later today. Whoever wins will face a passionate, well-funded, and motivated opposition who will spend the next four years attempting to win back what they lost.

Hmmm. This is just stressing me out more. Let’s try something different.

That’s Curious

If you ride a Waymo, they’ll flip you off.

Waymo is an autonomous vehicle available in San Francisco. No driver. All robots. I’ve taken ten rides so far, and it’s a coin flip if someone gives me the finger. There’s the folks on the street. Other drivers. Really, anyone might flip you off.

That’s curious.

With no judgment and pure curiosity, I suspect the reasons for the middle finger might include the following:

  • Anger with a service that will make a bunch of jobs irrelevant.
  • Abstract anger with the general idea of artificial intelligence and what it might present to the human race.
  • Fear. Pure fear of the unknown. We, as a species, have an impressive history of doing incredibly stupid shit because we’re scared.

Fear is natural. It’s equal parts rationality and irrationality. Shoved together instantly when you are quickly presented with a suddenly unfamiliar situation. It’s your brain flipping the high alert switch because you don’t know what to expect next, and the stakes appear high.

So you react. Fight or flight.

And then you flip off the robot car.

Cool.

There’s another emotion you can experience in a car, and that’s road rage. This is the moment you’re behind the wheel, and another driver cuts you off. In a second, you go from calmly driving down the highway to a vicious, rageful human bent on the destruction of this other.

In an instant.

That’s curious.

With no judgment and pure curiosity, I suspect the reasons for the rage might include the following:

  • Surprise, your calm drive to work was suddenly interrupted.
  • Anger at this anonymous whoever interrupted your calm drive to work and threatened your safety.
  • Finally, and full disclosure on this one, I did research here; you’re probably male and either already stressed about something else and/or have higher levels of impulsiveness and aggression on the road.

Understanding that, as a human being, you can have these real and immediate visceral reactions is essential because these reactions are being exploited daily1.

On Curiosity

I mostly ignored the mid-terms. I ignored it because most of the content generated that cycle wasn’t news; it was carefully constructed incendiary entertainment posing as news designed to get me to flip off someone. It was not designed to inform but to get me to react. Quickly and emotionally. No reason. Fight or flight. I chose flight.

This political season, I’ve been all in. Since last November, I have completed one small act each day. This can be a donation, or this can be an action like writing and editing this piece. At the outset, I had a blank slate regarding what I knew. I spent a lot of time understanding how political payment processing works. I built a remedial understanding of the critical issues in each swing state and read about the intricacies of voter suppression. Curiosity is a feedback loop. The more I learn, the more I can inform and target my actions. It’s delicious. Information is empowering.

And calming.

Elections have been gamified. The stories from major media outlets are designed to get you to engage and not to think. In fact, they’d much prefer if you forwarded that link with that clever headline to all your friends… who cares if you read it? We need the clicks. We need that sweet advertising revenue.

Campaigns run the same playbook, but they don’t need your clicks; they need your money, and that means they must convince you, scare you, and motivate you with an artisanally crafted crisis tailored to get you not to think but to flip off the robot car and then donate as frequently as possible.

The Big Lie

The only vaccination I know to the incessant barrage of memes, rage, and compelling lies is education. One of my daily acts has been educating myself. When someone makes a bold claim on the news or social media, I take the time to understand what they are saying and the history behind it. Many of these research adventures have led me to the darkest chapters of United States history, where I’ve learned that this group of oppositional humans has always existed. Its election deniers in 2024; in 1865, after losing the Civil War, unrepentant Confederates were sent to Washington as senators and representatives.

Congress refused to seat them and drafted part of the 14th Amendment “to perpetuate, as a constitutional imperative, that any who violate their oath to the Constitution are to be barred from public office.”

I didn’t know that. Now I do. We both do.

The biggest lie they propagate is devious and deflating. It’s the idea, the feeling, that there are many — more of them than you. They do this by being loud and outrageous, minimizing those they consider less. They want you to think they are legion because they know they are less. There are more of us than them. Not Democrats or Republics, but decent, kind, and thoughtful humans. I’m talking about people who want the best for others and are willing to do the work to help each other.

So, today. Vote, then stop watching the feeds. Turn off the TV, which is more entertainment than news. Don’t worry. The results will find their way to you. I guarantee it. While it does, take time to teach yourself something. Go deep. Call someone you know is stressed and ask them how they are doing. They’ll laugh nervously. That laughter, that’s stress transforming into relief. You helped. Briefly. Call another person? Sure. Do 15 minutes of your favorite exercise. Even better. Your brain does its best work when it’s working out; today, you need your best work. Tomorrow, too.

There’s no scenario when it’s “over” later today. Whoever wins will face a passionate, well-funded, and motivated opposition who will spend the next four years attempting to win back what they lost.

But there are more of us than them.

Now breathe.


  1. Oh, Waymo? They delivered absolute magic. Try it. It will exceed your expectations and give you a glimpse into a possible future where serious crashes are significantly reduced because 94% are caused by human error. There will be unforeseen consequences, upsides, and downsides, but as a super fan of progress, Waymo is on a short list of moments I know I’ve seen a compelling future. 
Writing Be ok with that

Your Writing

  • Less than 1% of your writing will be life-changing.
  • 3% will be trivial to write.
  • 4% will strongly resonate with others in a way you didn’t expect.
  • 5% will be quite good.
  • 15% probably should’ve never been published.
  • 26% will elicit a reaction you did not expect. Positive or negative.
  • 28% will become vastly better because you chose to edit.
  • 30% will start as one piece but finish as another.
  • 40% will be good solid writing.
  • 45% will do much worse than you expect when published.
  • 60% of your writing will never be finished. Be ok with that.
  • 100% of your writing is worth your time. 1

  1. Thanks to the folks at the Rands Leadership Slack for reviewing an early version of this piece. 
Rands Sort your voting plan

“I Am Very Concerned About This Election”

Good, me too.

Over on the Rands Leaders Slack, we are almost thirty-four thousand. Fun fact: in the 2020 Presidential Election, three battleground states, Arizona, Georgia, and Wisconsin, the margin of victory was less than 30,000. In Georgia, President Biden won by just over 12,000 votes.

It makes you think.

It’s an, uh, interesting time in United States politics. If you happen to live in the United States, I enthusiastically encourage you to firm up your voting plan. Check your registration, figure out how and when you’ll vote, do your research, be a leader, and show them how it’s done.

https://www.vote.org/ can help with all of this. Click on that link. Thanks.

If you’d like to take more daily action, join the Rands Leadership Slack, send me a DM that you’ve got a voting plan, and I’ll explain how you can get your hands on a couple of Rands stickers.

Happy democracy.

Tech Life An essential service

WP Engine / WordPress, Briefly

In the early days of this weblog, I was on MediaTemple using MoveableType for a good long time. Three things happened during these many years:

  1. MoveableType was mostly abandoned during this time. I’m sure well-intentioned folks were working on it (and it appears they still are), but the vibrancy of development had faded from my perspective at the time.
  2. MediaTemple (now GoDaddy) was similarly abandoned. They were happy to take my money, but the level of service had a marked decrease by the simple measure of the amount of time from when I asked a question about the service to when I felt the question was sufficiently answered.
  3. I became increasingly busy. The amount of time I could devote to the care and feeding of the site and hosting significantly decreased. While this made me sad as I have a deep desire to understand how things work, if I was devoting time to the site, it was writing.

Late in my tenure on MediaTemple, a good friend and noted WordPress enthusiast, Alex King, volunteered to move the site to WordPress. At the time, I was concerned about performance with a dynamically generated site — WordPress had an unclear performance reputation — but Alex convinced me. We agreed on a new design and moved to WordPress, and everything was fine. It was instantly obvious that WordPress had a vibrant development community, with the core software constantly being updated, unlike MoveableType. Publishing platform. Solved.

MediaTemple was the next issue. Without warning, MediaTemple shut down my site because the now unused MoveableType site had been hacked in a manner I still don’t understand. No warning, and they blocked my access so that I couldn’t debug the issue. Worse, the only way to unlock the site was to pay MediaTemple money for a site cleansing, which I eventually did, during which they found nothing.

I started looking for a new service provider, and WP Engine showed up as a credible vendor after I spoke with WordPress knowledgable humans. I don’t remember what I was paying for MediaTemple, but WP Engine felt like quite a bit more. I went back and forth with myself and finally decided, “I am willing to pay for good service so I can just write.”

I vividly remember the migration to WP Engine not because it was flawless, but because when I had issues, I pinged WP Engine tech support, and they responded almost instantly and competently and the chat was not over until I told them that we’d resolved the issue1. This professional, high-quality tech support level has remained unchanged for many years, and I’ve remained on WP Engine.

Since my move to WP Engine:

  • I can’t recall a single outage. I have been sitting here staring out the window of this train for twenty minutes and can’t recall a single outage.
  • I’ve added several new paid services to my account.
  • I am mostly unaware of what is going on with maintaining my site. I upgrade WordPress and plugins when upgrades are available, but mostly I write and publish content, which is — ya’know — where I want to spend my time.

WP Engine. Not cheap. I don’t care. As a lifelong user of online services, I have a hard-earned and well-defined rubric regarding what I’ll pay, which reads, “I will pay a premium if you are doing what you say you are going to do — all the time.”

I can’t comment on the WordPress v. WP Engine kerfuffle. It seems like a long time coming; it is super complex and increasingly heated. Drama usually means profound misunderstanding.

I can confidently say:

  1. I appreciate the hard work of many humans who invest unfathomable hours into WordPress and the vibrant WordPress plugin ecosystem. I eagerly pay for many of these services.
  2. WP Engine provides a valuable and essential service, delivering WordPress to me and my readers, for which I also happily pay. I pay for many online services and would rank WP Engine’s quality, reliability, and support in the top 10%.

As an eager user of the software and the services, I hope they’ll find a fair and symbiotic resolution.


  1. One issue I had during migration was that WP Engine did not allow a few plug-ins that I was using on MediaTemple. One was an old link checker that would go through old posts and find old links. WP Engine’s justification for disablement was, “This is resource intensive,” which made sense at the time. 
Management I am eagerly listening

Poets and Police

I was doing this talk, which I’d done dozens of times before. Good, well-practiced deck. I was speaking to CTO-types (current and aspirational) as a favor to a friend. This was a monthly morning coffee chat for this crew, and they invited folks like me to speak. It was on a weekday morning near Slack in downtown San Francisco.

No problem.

Practiced talk, small group, low stakes. I was editing the title slide to update the location and name of the event. No practice necessary; again, I’d done it before.

The piece was based on this piece called Stables and Volatiles. The brief pitch. Stables are those who happily work with direction and appreciate that there appears to be a plan and the calm predictability of a well-defined schedule. Volatiles are the opposite. Read the piece; I like it.

Finished quickly. I was told this was more about a discussion than a presentation. Fine with me. Q&A tells me precisely how well the deck landed, and I’d done this talk enough to believe the Q&A would be rich. Healthy banter. It started that way. Questions about my first stint at Apple and whether well-known people were Stables or Volatiles, but then Leo in the Back Row lost his shit.

“This is bullshit. It’s a false dichotomy.” Leo, the CTO in the Back Row, was pissed about my presentation. For those without ChatGPT at the ready, a false dichotomy is “the fallacy of presenting only two choices, outcomes, or sides to an argument as the only possibilities, when more are available.”

After some back and forth, I told Leo, the CTO in the Back Row, that, like most of my writing, I liked to describe humans in stark, clever ways. This often took the form of a “THIS or THAT” black-and-white structure, but I was 100% clear that the answer to humans was a hard-to-define grey area. My job was to get you to think, not to define every possible configuration of human behavior.

I’d delivered that answer before, and it worked, but Leo, the CTO in the Back Row, was having none of it. He was still angry and — now, I am guessing — because I’d wasted his time. He was promised a structured model, and I delivered confusing poetry.

Leo, the CTO in the Back Row, was the Police. And the Police don’t like poetry.

Guess What, Leo

I have another false dichotomy for you: the Poets and Police.

Poets:

  • Finish things. Usually.
  • Use rich language to describe abstract situations.
  • Believe well-formed, highly descriptive ideas make the world an understandable place.
  • Are fine with ambiguity because they understand it’s all just shades of grey.
  • Fall in love with ideas. They’ll fall in love with a single choice word.
  • Like to use the word “feel” because feelings are distilled intuition expressing themselves as inspiration.
  • Love thoughtful compliments.

Police:

  • Finish things. Wow, they finish things.
  • Crave well-defined structure and rules.
  • Believe rules make the world an understandable and measurable place.
  • Hate ambiguity because it provides no direction.
  • Deeply enjoy both debating and enforcing those rules. They believe this is how you make future measurable progress.
  • Will debate a single word that is out of place until clarity is achieved. (Poets do this, too.)
  • Are excellent at measuring anything with metrics. Are unlikely to believe unmeasurable truth.
  • Never use the word “feel” because feelings are irrelevant to getting the job done.
  • Appreciated well-defined accomplishment.

Two things.

First, as a Poet, I know I am describing the Police from my perspective. Police will profoundly disagree with many of the attributes I describe. I am eagerly listening.

Second, yes, this article is similar to my much earlier piece on Organics and Mechanics, but I feel it’s stronger writing.

Third, I am making up a third thing. To annoy the Police who were keeping count because that is how we Poets roll.

Success is Both

As a self-declared Poet, I can confidently describe the Police because it is a job requirement that develops strong working relationships with these essential humans. I need them because the Police do the challenging work of keeping the trains on time. This isn’t simply holding conductors to a schedule but also maintaining the trains, taking care of the track, and ensuring we have a qualified staff of humans to do all this work. Oh, and how about a budget? How are we going to afford all of this? Someone needs to build a credible business plan for this train company so we can afford to keep the trains on time.

As a self-declared Poet, we also need to understand the aspirational goals of this train company. I also understand the importance of consistently sharing this vision with everyone. I know we need to listen because we need to understand how the company feels. I’m adept at organizing teams of humans with differing ideas and skills. It’s an endless puzzle that I enjoy attempting to solve. I love celebrating our victories. I feel our failures deeply, but I know that with the Police, we will learn from these failures.

Listen. Leo. The CTO. You there — in the back row. I get why you’re mad. See, while we differ in how we view the work, we are the same regarding what’s essential. We want the team to succeed, and we want them to advance. I’ve learned some of my favorite moves watching you work, Leo. I’ll work hard to try not to waste your time with too much poetry if you work hard to understand that poetry is part of how we describe and achieve the impossible.

Management Leaders tell you where you are going

Words on Founder Mode

I’ve worked at three successful start-ups and one failure. I’ve also worked at post-IPO successes such as Borland, Netscape, and Apple, which means I’ve seen a lot of different founders who, if you measure success financially, were quite successful.

My backstory aside and with deep respect, most founders fail. You’ve heard of the stories of sucessful founder because they’ve become famous (or infamous). However, the majority of start-ups fail. No one tells and retells the stories of these companies because they never launch. No one became rich or famous. It is their defining characteristic. In his recent essay, Paul Graham talks about the successful founders. However, it’s not “Founder Mode,” it’s “Successful Founder Mode.” Lumping all Founders together would mean we should — statistically and more descriptively — call this “Failing Founder Mode,” which is neither clever nor inspirational.

As a person deeply in love with naming things, I like the framing of Founder and Manager Mode because it’s clever and instantly useful. If you’ve been reading me over the years, you’ve noted I’ve begun to detest the term manager for some of the reasons Graham highlights: unfamiliar with the details, management at a distance, lousy hiring, and siloed decision-making. I’ve gravitated towards the word leader both because I want to make it clear any motivated human can execute the skills of a good manager — leadership comes from everywhere — and, more importantly, I believe managers tell you where you are. Leaders tell you where you are going. It’s a philosophy thing.

It’s less clever and symmetric, but I would define these two modes as: “Founder Mode” and “Scale Mode” because one of the many things you need to do as a successful start-up is scale. Landing managers is one of those tactics, but it’s just one essential investment you make as you scale. Other tactics are equally important. Focusing on managers as the thing that makes you a larger successful company gets you… more managers. Gross.

My observation from three successful start-ups, three post-IPO starts where the founders still ran the show, and one failure: the founders were all eccentric humans. In a hypothetical room full of humans, which included these founders, you would eventually notice their behavior or conversational pattern. You would single them out in your head because the hair on the back of your neck stood up and wonder, “What… is going on there?” My one start-up failure? The founders? By the book, MBA types. Standard vanilla leadership. Trust me, you’ve never heard of them or the start-up.

Graham hints at some of the attributes of Founder Mode but mostly says it’s not as well-defined. It is. Founder Mode is the culture of a company, and a culture is defined by the character of the founders. Here are the values I’ve discovered over and over again working with these humans:

  • The whole team is involved in the details. Anyone can argue about the product because everyone works to be a product expert.
  • Everyone does the work. The stratification of responsibility is a red flag not just in rapidly growing team, but any company. Everyone files bugs because everyone uses the product. Yes, there is job specialization, but there is also a belief that we are equally accountable for the product.
  • An organization chart doesn’t tell you who can speak with whom; it tells you who is accountable for what. It’s a map. Not a power structure.

And finally, hire leaders, not managers.

Management I know you can do this

Late Again

Awkward.

Seven of us now. Sitting around the table. Five minutes since the start of the meeting. We’ve used up our chit-chat allowance and wonder if you will show.

In the scheme of things relevant to a company’s success, showing up late to a meeting is not the end of the world. When it happens a lot, when it’s always the same person and that human is a leader, I have a severe tick when it comes to this human. Here is my chain of increasingly frustrated and snarky reasoning:

Here’s my inner dialog:

  • Do you know that you are late?
  • Do you understand why you are consistently late?
  • Do you understand the total cost of this lateness? It’s the room full of humans waiting for you, plus the repeat of the information they’ll need to hear when you arrive.
  • Do you understand the subjectively immeasurable credibility hit you take each time this happens?

With that out of my system, let’s get to the heart of my concern. If you understand the problem and further understand the cost of this behavior, why is it continually happening?

Many meetings are predictable. Look at your calendar first thing in the morning. Is this an achievable set of work? No double bookings. Good. Do you see where you are likely going to be time-constrained? You’ve got a meeting you must attend that always runs long — ok, move the meeting after it. You’ve got one meeting on the opposite side of the campus? Ok, build in travel time and adjust the calendar as necessary.

Some meetings are not. Day has started, and the universe is throwing you curveballs. It happens. A reliably stable meeting ran long. Did you tell the next meeting to move on without you? Wait, you need to be there? Ok, move to the next available slot — quickly and alert attendees. Loudly. An important meeting landed in the middle of your everything? Ok, what needs to shift? Shift it. Loudly and promptly.

But it just keeps happening. Five minutes late to everything. Too much on the calendar, too many curveballs. You are in a constant state of stress, and this is where I will stop us for a second to state the obvious.

There are leadership types who believe this level of busy is correct. They believe a key part of the job is this level of stress and scurrying hither and fro. Some humans find a modicum of pride in this state. You know, the meeting doesn’t start… without me.

To all the serial show-up-laters who meet this criteria,

You are a failing leader.

Strong words. You thought your consistent five minutes late was a quirk. A minor operational error, but in my book, it’s a strategic flaw because you are not identifying and fixing the fundamentals. There are so many minutes in a day, there are only so many meetings you can personally attend, and these are knowable quantities. Failure to address these fundamentals means you are not growing as a leader.

Who can go instead of you? No one? Why? What is so essential about you? Experience? Really? How does one gain experience? You give others the same opportunity that someone else gave you. You ask them, “Can you attend this review?” They look panicked, so you tell them, “Here is the essential context you need. These three things will likely happen; here’s what I do when they occur.” They look less panicked, and you finish with, “I know you can do this.” They grin. Nervously.

Delegation. This is one solution. There are many more, but I’m not listing them because it is your job as a leader to identify the problem that ails your team and be accountable for properly and permanently fixing them.

So you can show up for a meeting on time.