It’s hard to tell what drives each human. This is why my usual last interview question is a very blunt, “What do you want to be when you grow up?” I ask everyone regardless of the amount of experience because I want to see how they improvise and, often, a hint at their motivation.

I usually have a working thesis by the time we arrive at this final question. Ah, this person is motivated by accomplishment, great. Oh, this is a money person — that’s fine, coin-operated humans are very predictable, I find. Uh oh, I have no idea what motivates this person… dig more.

The need to understand motivation is required because your job as a leader is build a successful team that is full of individuals who want stuff. Compensation, opportunities, or just a quiet place to build. Understanding what they want is the start of understanding how to motivate them. If you don’t understand drive, you have nowhere to start.

While you figure that out, let me alert you to three drives that are going to consume a disproportionate amount of your time, frustrate your engineers, and erode your leadership credibility.

The Complicators

These humans like to fix stuff. The drive starts with the observation that a part of the system, product, or process is broken. Some credible engineers fear finding this brokenness, and then some light up because they now have a time to shine — let’s fix it!

Except they are The Complicator.

Sigh.

Let’s start with the positives.

• They did see the problem, and they are capable of fixing the issue.
• They are going to jump on the issue, start working, and give those watching confidence.
• They are going to sound like they are making progress, and all the cues confirm this progress.

… except they never finish.

The Complicator challenge: they love the solving part, but not the fixing part. Their desire to tinker exceeds the need to fix. What if I do this? Oh interesting. Flip that switch. Well, that’s delightful. I will flip that switch again.

Complicators create immense piles of mostly interesting stuff. Complicators will describe this stuff to you endlessly in detail — it’s almost as fun to talk about it as it is to tinker. Complicators might sound like they are close to a fix, but what you are hearing is their enthusiasm about this next tinker. When pressed for a timeline for a solution, the Complicator will firehose you with seemingly endless stuff they’ve tried and the near infinite ideas they have to try next. You will leave this conversation confused, but they will leave the conversation fulfilled.

The Complicator needs:

• A well-defined and measurable goal.
• A schedule.
• An understanding of a complete set of constraints.

When I see a Complicator spinning up the complexity, I find an operational human who can pair with them. Entropy Crushers are amazing at this and eat Complicators for breakfast.

Drama Aggregators

These humans crave energy. They trade in it. It starts down the hallway or in the Slack channel, where they discover a secret. What’s the secret? I don’t know, it’s a secret. With this secret in hand, these humans take the secret to a very specific set of people. Humans who:

• They trust (and thus are deserving of the secret),
• Add energy to the secret via the addition of conjecture and opinions,
• Are likely to take that secret, adapt it, and give it to others.

Sigh.

Let’s start with the positives:

• They did find the secret. The identification, collection, and distribution of semi-hidden information is a natural tax part of humans working together.
• I mean, they care, right? If they didn’t care about the company/team/product, they would peddle in gossip actively share interesting information.
• They sense something, and that something is important.

You are a manager in this scenario, and part of the management role is that you both have access to more information and a responsibility to share that information appropriately with your team. You will screw this up. The most common scenario is you are given Information X. You stare at Information X and determine “Not that important, actually,” and because of this perceived low importance, you forget to share at your next staff meeting.

The core issue: your quick assessment was correct, given the information you have at your fingertips. The issue is that when paired with other readily available information not in your line of sight, it is clear your assessment is wrong — horribly wrong¹.

Most of your team can intuitively sense information vacuums. It’s that slight eyebrow raise when the story… kind’a… doesn’t make sense. Some of them raise their eyebrow and move on, but not the Drama Aggregators. They sense the mystery, the intrigue. In fact, they already have a leading unsubstantiated theory why this information vacuum exists, AND BOY IT’S JUICY.

Sigh.

Drama Aggregators need:

• Information. Lots of it. Consistently. Proactively.¹
• A mirror. There are positive aspects to this behavior, but Drama Aggregators do not understand the aggregate cost of the drama they are aggregating. The lesson is not don’t do this; it’s to understand the implications of the drama you are aggregating.
• A job.

Yes. My snark is high with the Drama Aggregators. I’m working hard as I write this to shine a light on the positives, but when I find myself stumbling into a Drama Aggregated situation, my first unspoken thought is, “Don’t we have better things to do with our time?” If this situation is a result of a failure on my part¹, fine, I’ll take the hit, but when I discover the Drama, dig in, and find the swirl of noise, murky information, and emotion has no basis in fact, I’m furious frustrated. My average work day already has plenty of real firefighting, so why am I not putting out fake fires? At least the Complicator is doing something useful by trying to fix the problem.

I’ve hit that footnote¹ four times now, so you know the practice. It’s not going to eliminate the Drama Aggregators’ need for energy, but a strategy of overcommunication will fill information gaps. The reduction in these vacuums reduces targets for Drama Aggregators. Also, when they invariably spin up a High Drama regardless of your hard work, you can point at your communication furiously and remind everyone, there is little drama here.

The Avoiders

Lenny. Good engineering manager. We’ve been working together for over a year. We are built differently, so we stare at each other strangely now and then, but everyone is an adjustment. No issue here.

Year two of our working relationship, my staff meeting. I’ve identified a non-urgent, but long-term, important effort that one of my managers needs to drive. I clearly state the requirements and ask for volunteers.

Silence. Not surprised. We’ve all got enough work on our hands with Complicators making it complicated and Drama Aggregators viciously building unnecessary fires. I get it. However, if we don’t do my project, then we’re creating future avoidable pain for ourselves, so I say that — clearly — and ask for volunteers again.

Silence.

And then it hits me. Lenny has never signed up for anything. Lenny is working; he has a team full of engineers who are doing well, but when it comes to work outside of his clearly defined responsibilities, he doesn’t show up. So, after 30 seconds of silence, I give him the task. He squints, nods noncommittally, and a week later has stealthily reassigned the task to one of his peers.

Oh. The Avoider.

Let’s start with the positives. These humans:

• Understand what is and isn’t their work responsibility.
• Often serves as a healthy counter-perspective to your goofier ideas.
• Are really good at delegation. In every direction.

Of our three archetypes, The Avoider is the least a character attribute and also the easiest for you to address. Yes, they like working in their well-defined box that is their team or their product. “Not my problem.” Yes, like you, they do not like being told what to do; they prefer to be asked, but in this situation, the Avoiders don’t know what you are talking about.

In a healthy team, your team assumes your competence. This means when you say, “We should do X,” there are those sitting around the able, who don’t give X much thought; they assume, “Well, he knows, so let’s go.” I’m not talking about sycophants, I’m talking about teams who trust their leaders.

The challenge is that you start to get comfortable with people agreeing with you, so you do less work to frame your thinking. Your thought, they’ll figure it out, right?And sometimes you’re right, but sometimes this comfort turns into laziness. Your request isn’t a request; it’s a half-thought motivated by recency bias, and The Avoider has seen this before. No, thanks.

There are Evil Variants² of all of these archetypes, and a serial Avoider is one of them, but my working assumption for all of the non-evil variants is that they want to help. It’d be helpful if The Avoider requested clarification as opposed to avoiding, but he’s seen this trick before, and he’s not interested in wasting his or his team’s time in an effort he does not understand.

Regarding Slippery Humans

I had the robots run through the 900+ articles on this blog, asking the question, “How many labels for humans have I generated?” From 2002, there have been 90+ labels in 14 different categories³. To me, it started in 2003 with the Incrementalists and Completionists article. That work struck a nerve.

Each of these labels is distinct in my head. They all started as an observation of another human, but I wasn’t seeing the entire human — it was this one habit. Characteristic. Behavior. The reduction to a colorful label makes understanding the situation approachable. Yes, The Old Guard. I know these people.

While mentally digestible, labels have historically bugged me for two reasons. First, they reduce a human to a label. This is the point of the label: to provide a name to the behavior, but when leading humans, there are no labels. Humans are complex. Humans feature sets of hard-to-predict behaviors that, when combined with other humans, only become more unpredictable. My labels might help a bit to understand one behavior, but the real work begins by stepping back and seeing the entirety of the human.

Second, and I haven’t reread all the personality articles over the years, but my impression is that my label schtick often conveys they are the problem. Sorry, as a manager, you don’t get to blame others on your team. It’s your fault. Yes, evil exists. Humans who are inexplicably hostile to the project or you. Who are acting purely in their self-interest. Who lie. Who deceives. You are accountable for all of them.

To understand motivation, you must understand drive. I wish all of these drives were productive and positive, but many are not. My discomfort with these drives is not an excuse to ignore them; in fact, they signal when I am required to do my most important work.

On the Pro Leisure Circuit, I’m spending a lot of time in random coffee shops. Cafe Dio in Los Gatos. Long-standing desk. View of the redwoods in front of my high school. Can recommend.

It’s been a while since I’ve documented what’s in my bag, but there have been several recent notable updates worth discussing, as well as a seismic bag shift, which is where we’ll start.

TUMI: Harrison Warren Backpack: I’ve been Team Tom Bihn for a long time. I recently purged the closet, and the pile of Tom Bihn bag-related detritus was impressive. The shift to Tumi was driven by the same design sensibility that drove me to Tom Bihn. As I wrote about, I have an existing bias against backpacks because of high school — lugging around bags of books in huge canvas monstrosities.

While Tom Bihn was my stalwart for years, it also started to look baggy to me. Roundish, lumpish, and just hanging on my back. On a post-pandemic trip to London, I walked into a Tumi store (a little drunk) and started talking backpacks.

Enter: the Harrison Warren.

On top of a very clean nylon and leather-highlighted design, the Harrison Warren offers less space. Pardon? You read that right, less space. No matter how diligent I am about what I put in my bag, I simply accrete stuff over time. A notebook, a book, a stack of papers, that thing I need to give to someone sometime. Stuff, stuff, stuff. Harrison Warren offers ample pockets, sleeves, and space for all my stuff, but it is not spacious. It is not designed to lug many pounds of random crap across the Continent which means I am required to be more stuff-thoughtful.

Equally important to the capacity is useful details. If you are considering a Tumi, you must go in and talk with the salesperson. The amount of consideration that has gone into a Tumi product is immense. They know you are an engineer, writer, or actor who needs quick access to their stuff at random times. Their bags are built for these humans, but unless someone explains these features… you’re going to think it’s just a pocket.

I’m coming up on three years with Harrison Warren, where I’ve been on hundreds of trips. Build quality — not an issue. He looks great.

ANKER: Prime Charger: Charging is a way of life. Each time I find myself with a dead device, I go on the operational offensive. What change do I need to make to ensure this never happens again? The short answer is: I have a backup of just about every critical device in my bag. There are two phones, a MacBook, an iPad, two AirPods, and so forth. Yes, this increases weight, but I DO NOT CARE. I AM NOT SHOWING UP IN LONDON POORLY EQUIPPED, OK?

Even with a healthy set of backups, all of these devices need charging. I was using this USB-C hub for years. Still, I was vaguely aware that different chargers provided different wattages, so I began investigating my vast array of white Apple charging bricks.

Let’s start with a vent: I am intimately aware of how much Apple cares about design, but it’s baffling how hard it is to read the text on these bricks¹. It’s designed to be unobtrusive, I get it, and most humans don’t care about how many watts are pumped through each brick, but when it matters, you sure do.

A charging primer:

• On top of the number of watts provided by your charger, there is also the amount of charge your device can accept. For example, your fancy new iPhone 17 Pro Max can accept 40W maximum, but your friend’s iPhone 17 can only accept 27W. Even with a much larger battery, the Pro Max will charge faster with the right charger.
• Lithium batteries charge on a curve with the first 50% being the fastest, 50-80% slowing down, and the charge to 100% taking relatively a very long time. For example, my iPhone 17 Pro Max takes 20 minutes to get to 50%, 41 minutes to 80%, and an hour and 31m to 100% with the best charger. You have two critical questions when your device is dead: how long until it’s working again, and how can I get the most charge in the least amount of time?

Again, most humans don’t care about all these details, which is fine. The issue is that most humans are grabbing that 20W charger out of their box of chargers and plugging in their device, and not knowing they are wasting a lot of time charging. If they’re plugged in all night, who cares? However, in a pinch, you can drastically affect the speed of the charge. We’re talking 47% faster on that first 50% charge. Huge.

Anker has been my go-to not-Apple device charger for many years. Their most recent Anker Prime Charger has a lot to like:

• Three USB-C ports at 140W each. (Yes, most devices can’t suck down this much power, but 140W covers everything you currently have and likely covers future toys you will have.) When two ports are active, it splits ~78W + ~76W. Three ports: ~60W + ~50W + ~35W. No USB-A. You don’t need it. You’re covered.
• More importantly to me, there is a display on this device that shows how many watts are being delivered via each port. Also, when you plug a device in, it smiles at you. Aw.

I had Grumbles build you a comprehensive cheat sheet of the Apple charging situation, comparing the 20W with Anker’s latest for all your Apple hardware. It’s illuminating — view it or grab the PDF.

UBIQUITI: Travel Router: The house is all in on Ubiquiti. I have a rack down in one of the closets, which powers a set of APs and cameras across the property. What was a messy mesh of Eeros was replaced with a rock-solid blanket of Wi-Fi and wired goodness².

Now that I’m on the Pro Leisure Circuit, my home network is also work. This means when I’m at my favorite coffee shop, it’d be very handy to have access to all my home resources. Ubiquiti already makes this pretty easy with Teleport VPN links, but with the Travel Router, they make it even simpler.

This small battery-less device connects with whatever untrustworthy Wi-Fi is available and, using Teleport/WireGuard (same thing, different branding), creates a secure tunnel back to your home network. When configured anywhere on the planet, my home Wi-Fi shows up just like I’m at home. The trade-off is a network performance hit from the encryption, but the peace of mind is worth it.

The Travel Router has not earned itself a place in the bag, yet. Two outings so far, and I’ve spent more time tinkering with the device rather than appreciating it. We’ll see.

The rest of the contents of the Tumi are presented with light commentary:

• MacBook Pro. The new one. Space Black. Yes, the Air is lovely, but I love the weight of the Pro.
• iPhone Pro Max — atomic orange, of course. iPhone 17 backup — just in case.
• iPad Pro 13 — mostly a content consumption device.
• A small see-through bag with back-up cables, converters, and stuff necessary to present.
• An orange notebook for random thoughts.
• Clif Bars. Because sometimes you get hungry.
• (5) Zebra Sarasa Gel .5. Best gel pen on planet earth.
• Altoids. Because toothbrushes are often distant.
• A Tide pen. Because I can be sloppy, and I like nice button-up shirts.
• A black Sharpie for when I need to yell.
• An iPhone MagSafe Battery — they stopped making these. I don’t know why. I’ll buy a Kuxiu S4 when it’s available. Stay tuned.

With all of these items in this bag, it weighs just under six pounds. There’s an international variant of this bag build out, which includes international converters as well as additional backup cables, because somehow other people need these items more internationally.

The best part? This bag is sitting right there. It’s ready to go whenever. Will I need all that stuff? Rarely. Will I grin when out of nowhere someone needs an extra phone? I will. Will I slowly become the guy at the conference who can help you with whatever? Yes, I am that guy.

When I explain that Claude Code has changed my relationship with developing software completely, I’m under-exaggerating… if that’s even a thing.

This off-the-cuff piece started as a unposted social update that read:

Watching Claude Code adeptly use every type of Unix command shows me that a) you can do anything in Unix, b) my higher-level operating system mostly hides this functionality from me, c) I am extremely lazy, and d) I am immensely curious.

An Introduction to Pansy Rain

This morning it’s going to start to rain — a lot. As previously described, I deeply enjoy tromping around my forest in the rain, fixing drainage, and pulling sticks from stuff. More importantly, I am deeply curious about how the weather works. This is curiosity motivated by an immense fear of climate change and a desire to understand clearly what will occur this week. And why.

Years ago, I started posting a short paragraph to a group chat filled with fellow mountain Dads. It was a three or four-paragraph affair about what was going to happen with the weather in the coming week. No one requested this lightweight and trying-to-be-approachable blurb. It started and stopped during the rainy season in Northern California, but over time, I continued through the summer, starting to track heat events, air quality (see fires), and fog.

Here’s the one from last week:

Welcome back, Winter. We missed you. Rain, lots of it this week. Chance of pansy rain tonight, but I wouldn’t count on it. Looks like we’re in for a solid inch-plus on Tuesday morning through Wednesday evening, but the show starts on Saturday night. Solid chonky rain through the end of the week and into next. Weirdly, the first storm is coming from Hawaii (wet), but the big weekend fronts are coming from Alaska. This latter rain is going to hang.

See? Approachable? My initial goal was that anyone could quickly read this blurb and plan for their week. Ah, yes. Rain on Tuesday. I will plan accordingly.

The friendly tone and brief amount of content might lead you to believe the construction was equally brief. It’s not. The initial flow was:

• Fire up Wunderground’s 10-day forecast. This deliciously informationally dense chart is my go-to initial stop for all things local weather. It includes rain, cloud cover, chance of precipitation, accumulated rain, and wind speed — and a lot more.
• Compare against Windy.com. Windy has similar information to Wunderground, but includes stunning maps that include a mind-boggling amount of different layer visualizations. The goal was to compare data from Wunderground to what Windy reported, which tended to provide better rain forecasts from my local microclimate.

It started as 30 minutes of work, and it grew to over an hour of research. As I received light positive feedback for the posts, I started to research data on local streams and reservoirs, along with other fun facts I discovered during my research.

Then the robots showed up.

An Introduction to Chonky Rain

This morning. Just this morning. Here’s what I’ve done with Claude Code:

• Pulled snapshots from my local weather station to backfill my storm tracker, which is a feature I built last night to track before, during, and after snapshots of storms. I wanted to see all storms (8) from this season, so I had the robots look at historical data, find the storms, and then backfill using my local weather station and open data sources (Weatherlink, Open-Meteo, Valley Water, and others)
• Found an issue with the data where I was fixing a sensor issue, which caused a data spike. Smoothed the spike.
• Comparing my local readings with other data sources; refined a multiplier I use to account for my microclimate.
• Updated creek data to include week-over-week change, so I get a better sense of how water is flowing down those mountains, into the reservoir, and then into town.
• Moved all this data into the Sunday report mail that I use to write my four-sentence approachable blurb.
• Oh yeah, as I write this piece, the robots and I are now planning what we’re going to track during the Summer. Fire alerts, air quality, and fog monitoring.

This morning’s work builds on an existing set of scripts that run early every Sunday morning to track:

• Weather observations and color for the coming week.
• Current conditions from my local weather station.
• Last 7 days of rainfall.
• 10-day forecast.
• Local reservoirs week-over-week change.
• The first version of my storm tracker functionality.

I am perfectly capable of building any part of the above system. I am capable of finding the services that provide the information, signing up for an API, understanding the API, building code to call that API, generating a report, and sending that report as an email. Done it a lot. Made a successful career of it, too.

I’ve written none of the code for this weather project. I’ve signed up for some API keys, but mostly what I’ve done is tell Claude Code what I’m looking to do and let the robot figure out what API we need, how to use it, and then suggest different ways we can report this information.

Extremely Lazy and Immensely Curious

When I go through these types of robot-related productivity rants, someone invariably unhelpfully volunteers, “Well, this is a good way to get really dumb.” What this someone is suggesting is that because I am doing none of the work involved in building the thing, I will not intellectually profit from the exercise.

In a world where I hadn’t spent several decades building software, I would partially agree. The lack of domain experience could mean I trust whatever the robot’s built at face value, but — just like humans — the robots make mistakes and often straight-up lie. Been dealing with those situations for a bunch of decades, too. It’s not a problem, it’s how humans (and robots) work.

Yes, I am extremely lazy. I’ve developed a set of habits that support this laziness. Where’s the best affordable Italian restaurant in Greenwich Village? Ask Noah. He knows, and he responds quickly. How should I think about this emotionally charged and complicated people situation? Ask Julia. She knows, and she can view complete emotional chaos dispassionately. Which API should I use to monitor fog? Ask the robots. They don’t know, but they know how to know.

Am I sad as I watch the robot expertly craft semi-familiar Unix commands to perform all the weather-related wizardry? Nope. I learned to delegate to humans a long time ago. It was hard to give up the Legos to someone else, but this forced me to learn other lessons. How to ask others to help. How to clearly make requests. How to listen to their responses to see if they heard. Hearing them. Watching how they work and when they ask for help. Learning how to taste the soup. Discovering lies. Fixing them. Remaining immensely curious and always learning how to communicate better.

Here’s this week’s weather blurb. Written by me:

At this second, it’s partly sunny at the house, but just wait. It’s coming. Around noon today, chonk-i-ish rain begins and continues through Monday. Let’s say two inches today and three inches tomorrow. Sweet. Short break on Monday night, but another inch on Tuesday and a drizzle on Wednesday before we dry out a bit, but more next week. Might be chonky.

(Two inches last week at Chez Rands, Lexington Reservoir up 2.5% on the week, twenty-nine inches for this rain season so far.)

I worked for each of these humans. They either hired or promoted me. I worked for them for many years. As is my way, I’ve vastly altered the details of each human, but the core issue I describe is the core issue. Also, each of these humans is very smart. No dummies.

Here are their introductions:

An Introduction to The Artist

They hired me. I could tell via the interview process that, like me, they were an introvert. The interview was awkward. Long pauses. Odd questions. No feedback. I got the gig because everyone else who interviewed told me I was a fit, but whether they thought I was a fit or not, I will never know.

First day on the gig. I was sitting at my desk, and they walked into my office, hands in pockets, stood in the door, and asked, “How was your first day?”

… because someone told them that is what you do with new hires.

They are The Artist. Burdened with creativity, all the vision. You could see it in the things they built. Inspired. Somewhere along the way, someone decided to make them a manager. Direct reports. The hope that the art they created would scale with the number of humans.

The challenges were many and diverse, but the core issue is the value of the things this manager was capable of creating, which blinded everyone else to the fact that they were reading books about being a manager, following the rules, but either not caring about what good looked like being a manager or not knowing.

“How was your first day?”

I told them. I walked through each 1:1 I had (five), shared my first very raw impressions (many), and asked them what they thought. The reason I knew someone told them to ask me about my day was that they had absolutely no clue what to do with my assessment of the day. Blank stare. They either didn’t understand or didn’t care. I couldn’t tell which.

Introducing, The Dictator

They promoted me. It took a couple of years of hustle, but they went for it. First meeting in the new role, and we’re in the basement for what is called a product review. Engineering, product managers, and designers. Small affair. Happens when it’s clear we’re at an impasse. A large enterprise customer is threatening to bolt unless we solve a critical feature issue. Not a lot of people — everyone here can contribute significantly.

Product kicks off the discussion with a timeline and three fact-filled slides. Framing the conversation. Small clarification questions, but everyone has been briefed beforehand, so we get to the heart of the problem. Cutting to the chase: it’s a design issue. We had the right requirements, we built it correctly, but our design is wrong. It is confusing the customer. The good news, Design is on it — Design vetted the deck with engineering, and they’ve got solid proposals. This meeting should be a formality, but the Dictator is here.

When we reach the discussion portion of the meeting, the Dictator starts asking questions. Does this mean this? Yes. Have they seen that? They have. If the feature is supposed to do this, why does that happen? Well, I’m glad you asked. We have… and that’s when it happens.

No, no, no, I know you have a proposal, I want to litigate some more. This back and forth goes on for an hour. Several of us attempt to redirect back to the proposal and do not succeed. Soon, we’re at the whiteboard designing a new feature, and the punchline is: the feature is wrong. It’s clumsy at first glance and bad when you’ve thought about it.

And no one says a thing. We leave the meeting, having agreed on building a feature that anyone who has read the deck knows is wrong. And we built it.

And last but not least, please welcome, The Knife

They promoted me, too. I’m not quite sure why.

After it happened, it took a month before we had a 1:1. I would get random requests for information or suggestions, but mostly I ran my show as I saw fit. When the 1:1 showed up on my calendar, I was one part relieved, one part excited, and one part nervous.

I walked into their office, and they were on the phone. Pointing at me to sit down. They were talking to finance people, and my recollection of the vibes of that call is The Knife thought the world was about to end, like that weekend, and they needed to act quickly to protect their assets. (Note to reader: the world did not end that weekend. In fact, while it might feel otherwise, it still has not ended.)

I sat for twenty minutes of a thirty-minute 1:1 listening to all the details regarding the end of the world, wondering why they had huge bulk boxes of granola on the floor, and then they were done.

I don’t know what we talked about. Not a clue. Not even going to invent anything because all I remember is that they pulled a hunting knife out of a drawer in their desk and started talking about something. Not the world ending, not about the granola, and not about the knife they were examining, twirling in their hands.

It wasn’t threatening. I was not in danger. It was just fucking weird.

Our Mind-Blowing Interlude

Ok, forget you read those introductions.

If you and I were at a bar and I explained the respective track record of The Artist, The Dictator, and The Knife in their respective roles, you would consider them good at their job. If I further explained objectively what they had done for their respective teams and companies in terms of generating shareholder value, you would vigorously nod, “Yeah, these are successful humans.”

It’s stronger than that, I can confirm that these are wildly successful leaders.

I can further confirm that each were very bad managers.

Let’s start with my belief that a manager’s job is to tell you where you are, and a leader’s job is to tell you where you are going. With this simple definition, The Artist, The Dictator, and even The Knife, as we’ll see, were strong leaders. They knew where we were going.

An easier way to understand the difference is that leaders are stronger at strategy and managers are stronger at operations. When do you need which? Depends an an endless set of factors, including team size, their place on the organization chart, company culture, and many more. The thing to remember is your boss likely leans strategic or leans tactical.

Let’s continue with the fact that you are going to end up with a bad manager at some point, and it’s not your job to change them — you can’t. In fact, the more senior the leader, the less you’ll be able to influence them.

Let’s finish with the fact that while I despise many of the traits of these humans, I learned essential lessons.

Ok, now remember those introductions.

They Are Bad Managers Because…

The Artist is bad because they don’t value humans. It’s not the part of the equation they care about. Maybe introversion? But mostly because they’re an artist, and what artists care about is the art. Not the essential humans who build the frame, find the right paints, brushes, and make sure The Artist can work in a clean, well-lit place. That’s just noise.

My approach with The Artist was education. I believe they understood the motivations and intent of other humans, but because they were so focused (and rewarded for) the art, they did not spend the time to understand the consequences. They did not appreciate why a team that understood the mission, how they were going to achieve it, and how each individual could meaningfully contribute made for better art.

I started with verbal explanations of complicated human situations. I got blank stares, so I started to write before 1:1s. When the stakes were high, I stared hard at the situation and wrote and rewrote the situation, my assessment, and my recommendation — over and over. The Artist saw the work, recognized how much work I was putting into explaining situations they were ignoring, and sometimes they’d engage. Sometimes not.

The Dictator is bad because this dictatorial approach was everywhere, not just in the basement. Our 1:1s started with less than 30 seconds of pleasantries before they started the rant. It was the dictatorial rant about the most recent interesting problem, and, wow, they had opinions. My initial job was to hold on for dear life.

My approach with The Dictator was one of the most important lessons I’ve learned. Yes, The Dictator used their position to bully the conversation, but I couldn’t deny that The Dictator cared deeply about the problem in front of us. The Dictator stared hard at the problem, the challenge, the opportunity, and they saw a single detail.

The Dictator cared deeply and had no time for anyone who did not share this belief.

In the next product review, I went hard on pre-game. I reviewed the deck, found the gaps, and had them filled. I spent 1:1 time with the product manager, and I walked around downtown San Francisco with the designer to hear the backstory. When The Dictator did The Dictator thing and started to shove the conversation in a useless direction, I told them, “This path has been explored. We understand this is a flawed direction, and here’s why.” I don’t remember what we were litigating, but I vividly remember the burning look on The Dictator’s face, Oh. You care, too.

This changed nothing about The Dictator’s approach. It still felt like a constant battle, but by doing the work of caring deeply, the battle was not one-sided. Yes, this is not how you treat humans, but this is how I developed my habits to see situations where my job was to be an expert.

The Knife is… just bad. Back to the beginning, no dummies here. This is an intelligent person, and they did a good job leading a team, but they had absolutely no business attempting to manage one.

Education didn’t work. Verbal explanations weren’t brushed aside; they listened, but then they responded… about something else. Written attempts went unread. Caring deeply didn’t work either. Seeking common ground… trying to reverse engineer what this human cared about was like trying to thread lukewarm lemon Jell-O through a needle.

The Knife could lead. When they spoke to the team about topics totally unrelated to the problems ahead, we somehow learned a lesson. Our 1:1s remained bizarrely off topic. Sometimes they called with random requests that I barely understood, but I acted on them.

But the lesson was stay the hell out of the way. Let them do their work, however inscrutable.

The Essential Lessons

As essential lessons go, stay the hell out of the way doesn’t feel particularly helpful, but this is not the lesson.

Everyone is an adjustment. The person you need to be with your boss, their boss, your team, and everyone else is slightly to significantly not you. You will need to adapt how to prepare, how you communicate, and how you act with each of them. Some adaptations are trivial and familiar, but others require you to find a different perspective to help build new habits. Yes, one would hope your leader knows when to manage, but you don’t pick your bosses; you decide who you are with them.

I don’t like fish.

“But Rands, have you tried…”

Yeah, I tried that. I don’t like fish.

“Wait, wait, wait, what you need to try is…”

Tried that, too. A couple of times. I don’t like fish.

“Rands, you haven’t had good fish.”

Yeah, I’ve had good fish. Many times. Girlfriends, good friends, bad friends. They’ve all taken a swing at my “don’t like fish” thing, and they’ve all failed. There was that time I thought I liked fish, but that was the six Sake bombs I drank at the Hard Rock in Vegas while consuming aforementioned good fish. In this state, I would’ve raved about a stale white bread half-eaten bologna sandwich I found on the floor of the casino.

I don’t like fish.

I don’t like productivity systems, either.

“But Rands, have you tried…”

Yeah, I’ve tried that. I’ve probably tried it a couple of times. I’ve also tried every other system, too. Complex ones, simple ones. My professional life contains a vast graveyard of productivity systems, notebooks, and processes. Friends, dear friends, have built businesses around productivity software. God bless them. Each time we meet, I’ll buy them a round of drinks and toast their success, but we aren’t talking about productivity software.

I hate it.

Hey so.

I am, once again, testing a productivity system. We have clearly established that I am a productivity system hostile, and I am clear that it has vastly more to do with me than with any single productivity system.

The Tool Rule

You are dependent on a set of tools to get work done. These include mail, Slack (or a Slack-like yard sale of mediocrity), a calendar, some robots, and a productivity tool, which might be a fancy digital productivity system or it might be a piece of paper full of unchecked boxes.

Let’s start with Rule #1 regarding these tools: if the work to maintain the given tool is greater than the perceived value it creates, I will ignore or stop using it.¹ This is the failure state for most productivity systems. I become frustrated because the work does not justify the value. The details here are important.

Software-based productivity tools make it simple to capture and create ginormous lists of tasks. What starts as a list of ten critical tasks instantly bloats to 50+ in just a few days. How does one cope? Tags! Buckets! Sub-tasks! Colored prioritization! Deadlines! It’s an endless list of hacks designed to give you convenient ways to slice large lists of work. However, the addition of each mechanism created more smidge of work you need to consistently perform in order to keep your to-do list fresh and relevant.

Deviously, the act of performing this additional maintenance initially gives you the impression that you’ve completed a task — that you’ve done work. You haven’t. I mean, yeah, if my entire job was to maintain a productivity list, well, cross that off the list, but the whole point of a productivity system is to give you time to work. A productivity system is doing its job well when you aren’t using it because it’s created time for you to get work done.

Productivity system maintenance is a fact of life, but when the act of maintenance becomes an onerous task unto itself, I get productivity rage. I either passive-aggressively slowly stop doing the work over time or I rage quit the whole damned application, grab the nearest Post-It note, and start over.

Again.

“Rands, you’re doing it wrong. You just haven’t had good fish. You should…”

Stop. Just stop. I have. I did. I did again. It didn’t work. For me. Decades of doing it. So much rage. I hate fish.

Sorry about coming off hostile. I’m hostile with myself. I’m disappointed that after three decades of constant work, I struggle with building a system that consistently supports my style of work. I’m hostile… with myself.

So maybe my productivity should be hostile?

The Feature No One Would Use

I have a new system in place, which I’ll describe more in a moment, but here’s the initial inspiration:

No one would ever turn this feature on, but I’d like my productivity system to automatically delete — without warning — to-dos that are older than 30 days, have no status updates, and have no due date.

The idea was simple. Any item on my to-do list that is older than 30 days with no recent activity or due date would automatically — without warning — be deleted.

There is wisdom behind this feature that no one would use, and it’s based on the fact that my ability to prioritize at the moment a task arrives is hot garbage. Important to note that I don’t know this at the moment because you are in my face right now asking for what is clearly the most important thing and you are aces, so, of course… of course, I am going to prioritize your thing as urgent.

It’s not urgent. It’s urgent to you, and I’ve got mad respect for you, but your task is objectively not that important, and I’m not going to know that until time has passed. We’re doing other things now, and days later we’ll separately remember your ask for me and immediately recognize the passionate moment in business, but the task is irrelevant.

Irrelevant. Sitting there in my productivity system du jour, tagged as important, colored in red, with the note: “Maria needs this immediately.” She doesn’t need it. I shouldn’t do it. With the reasonable passage of time, I am capable of two pieces of analysis:

1. I’ve had time to understand the request fully. It has a more defined shape and scope in my head. I have intuition when the task is first provided to me, but it is usually imprecise.

2. I’ve also had time to see all the other things on my plate, so I can calmly, relatively compare this ask to the other forty-eight items on my list.

However, rather than having to do all this reflection, why not have the productivity system remove the irrelevance all by itself? I can feel your discomfort with this concept across the Internet, and I share it. What if it’s actually an important task and my prioritization is hot garbage?

Here’s the funny.

When I started writing this article, I intended to pitch you on a fully paper-based system. A single piece of paper that captured all my work and home tasks. Work on the left. Home on the right.

Revolutionary, right? Paper-based task list. Here was the trick: I required myself to rewrite the list each day. Often twice. The rewrite forced me to examine each task and first make sure I was clear about what the task was, and then, more importantly, quickly ask myself, “Is this actually important?”

I was in love with this system for a total of three weeks. I liked the act of the rewrite, I appreciated the forced re-caching and re-prioritization of all the tasks, and I felt good when I revisited an item and judged it: “Nope”. After almost a month, the list was getting longer, and I could sense myself approaching the Rands Productivity Rage Threshold™, but then the system broke down completely in a moment.

I left my paper list at home.

Easy recovery. Just get someone at home to send me a picture of the list and perform the rewrite. Solid.

But I left it at home again two days later. Too much work. Fragile.

So, I rage-quit another productivity system. Again.

Let’s Remember Mail

Are you still struggling with your email inbox? I’m not. It’s been years. And the fact that I conquered email after decades of productivity frustration was at the front of my mind. The thought: “If I can design a set of habits that tamed email, then I can do the same for a productivity system.”

Before I enumerate my mail habits, let’s go back to our very first rule: if the total work to maintain a given tool is greater than the perceived value it creates, I will stop using it.

The mail rules:

1. All irrelevant emails are addressed immediately.

The spam robots have mostly solved the firehose problem, but they don’t cover all irrelevant emails. It is stupidly trivial to sign up for email while traipsing around the Internet. I do it all the time, usually when purchasing from a new vendor who tucks a clever double-negative into their request to send me mail as part of a purchase. I blame myself. However, the moment I see this mail appear in my inbox, I act. I act immediately. I unsubscribe instantly. I hate fish. If this is a subsequent mail after I’ve already unsubscribed, I aggressively block. Right away.

I act on every item in the list. Progress, however small, occurs, and my list signal improves. It took months to get my Inbox into high signal shape, but the combination of the robots keeping the spam out and my aggressive unsubscribes has left my Inbox with blissfully high signal. This is actually our next habit…

2. All relevant emails are acted on. Without fail.

If a mail has passed through the robots and my block list, it is likely a mail I care about, whether it’s a mail to me, a newsletter I enjoy perusing, appointment confirmations, account updates, delivery notifications, or other essential emails. After digesting the mail, I will choose one of three actions to perform on each email:

1. Delete.
2. Respond.
3. Schedule for Later. WARNING WARNING DANGER DANGER

DELETE: This is pretty easy and equally satisfying. Goodbye mailing list. No, I am not interested in this robot-generated job inquiry. Delete. Mistakes can be made here, yes, I didn’t see this was from an actual human, and you bet I am a world-class skimmer, but more often than not, this mail deserves to die.

RESPOND: Trickier. This is going to involve work, and I’ve got to make a quick call. Do I have time to respond, or should I do this later? The difference between “it will require solid think time for me to respond” and “It’s easier for me to do this later” is subtle, but after years of self-reflection, the difference is obvious. Informed laziness. I glance at the mail, and I can instantly size the amount of work required. It’s either more work than I want to do at the moment or — and this is the devious one — it’s not instantly obvious to me how to make progress or respond, which makes the perceived work much larger and unattractive.

So now I mostly default respond. Kicking and screaming. I respond. God, I hate fish.

LATER: Slippery. If I’ve done an honest mental assessment of Respond, Later is a valid choice. There are very good reasons to schedule a response for Later, such as the complexity of the topics or the need to consider a response deeply, but Later compounds. One Later — not a big deal. One hundred Laters is an immense pile of work, a compounding management task that will eventually prevent you from doing actual work.²

I’m happy to report that the above list of actions consistently applied to my inbox has resulted in endless months of inbox zero. There are days when I get a little behind, but most nights I go to sleep with nothing sitting in any inbox.

The Productivity Rules

With the mail rules in mind, the Productivity versions are familiar:

1. Understand & Prioritize.
2. Commit.
3. Later.

UNDERSTAND AND PRIORITIZE: Similar to mail, each task can represent significantly different amounts of work from minutes to days³, and I need to understand that work before I commit. Remember Maria’s task from the above? The sky-is-falling-one marked RED and URGENT. Well, it’s been three days, and I haven’t heard a peep from Maria regarding this allegedly important work. With respect to everyone who walks into my office with an emergency, my job is not to confuse urgent with important. I won’t say this to your face, but I’ll write it down here. Yes, I alerted Maria that this does not seem that important, yet, and yes, she agreed.

Every morning, every task is passed through my is this important to complete filter. If there are tasks where I am stuck, my half-move is to spend 30 seconds editing or rewriting the task. The act of passing the task through my fingers either gives me perspective or reshapes the task to be more understandable. For tasks that I’ve Latered a lot, this editing pass is especially important because it’s currently written in a fashion that makes it disposable.

COMMIT: With a cached understanding in my head, I decide today or not. If it’s today, it stays right where it is. Things allows me to move tasks to the evening, which is mostly “This is a home task, and I’ll do it when I’m home” commitment. Not for today? You know the drill…

LATER: Ok, not today, but when. Same buckets as above: tonight, near future, or distant future. Wait, I’m still trying to figure it out. I can’t commit nor schedule, so let’s move it to the Someday bucket⁴.

Same warning as above, it’s easy to punt a task to later, so this part of the process involves the most thinking. In the hostile productivity software I’m invariably going to vibe code, I want to see two bits of data for each task: days since the task was created and the number of times this task has been rescheduled. I do this in my head, but I know I lie to myself. I know I have very little clue that this task has been here for over six months and has been rescheduled dozens of times because there is either something interesting to me inside of this task, or there is a threat, a consequence to not completing it.

Remember the productivity truth: you will find less and less signal in an ever-growing list.

The scheduling bit is 100% the same as mail: today, a date in the near future, a date in the distant future, and, if I’m brave, never. You should probably read this footnote⁵.

I’m Hostile with Myself

I don’t actually hate fish. It’s a bit. I’ve learned over the years that folks have this intriguing reaction when they learn I don’t like fish, so I lean into it.

“You don’t like fish?”

“I don’t, and do you know why? Fish pee in the ocean.”

It’s a bit.

But, yeah, I don’t really like the taste of most fish. Someone once told me that I’m a “super taster” and that fishiness taste that everyone hates in old fish? Yeah, I taste it sooner than most folks, so BOOM — I work that into the bit. “Folks, I’m a supertaster, and I know when fish is bad before you!”

Mostly, I am disappointed that I find what others consider to be a delicacy to… taste like salty old sadness. Neither do I hate productivity systems, but I need my productivity system to be hostile.

I’m a stimulus-driven creature. New productivity tools (or any new tool) come with a wave of enthusiasm, but that enthusiasm fades with time, and when it fades, I still have all the same work to do. Without my enthusiasm, I will quickly develop habits that start laborious and then become ludicrous.

Also, sans enthusiasm, I go through the motions on other habits. *Yeah, yeah, yeah, I need to do this… can I do the bare minimum? Move to tomorrow and done, right? I want to work on something interesting. This gets the task out of my way, but this eventually creates a pile of moderately important tasks that I am forever moving from now to later. Without a constant pruning function and without critical thought, I start pushing a pile of tasks that I never finish and only increase with time.

The system collapses, and the cycle continues. I become hostile with myself.

It’s not the tool or tool features (or the fish). It’s entirely me and my ability to have the stamina to follow a reasonable set of habits. Stop blaming your tools for the fact that you’re lazy.

That’s it

No tags, no colors, very few rules, no priorities. This temptation applies to a great many knobs and dials that Things provides, but each time I consider one of these features, I ask myself: Do you want to complete this action for every single task in your future? It’s not three seconds it takes to add a tag, it’s three seconds multiplied by the next 1000 tasks. That’s almost an hour of my time. Still interested? Ok, how much closer does adding this habit get us to Rands Productivity System Collapse?

This morning in Things, I have 38 tasks. It’s a Saturday, and I haven’t triaged that list at all. Let’s do that now.

Ok. That took two minutes, and I’m down to 24. These are 24 tasks I am intending on doing today. The ones moved were a combination of: stuff I completed last night, tasks I am scheduled to do later (either Monday — beginning of work week or Saturday — beginning of weekend). I will likely only complete half of these tasks during the course of the day, but come the evening, the goal is always the same: a blissfully empty list.

Your job is to push through the work. To find the essential work that creates the most value. For every action that creates an additional signal in your to-do list, there must be an opposite reaction that removes something else. Your most valuable asset at work is your time.

And the Bigeye Tuna Pizza at Yellow Tail in Vegas is excellent. I highly recommend it.

In our 95th episode, we again talk about the value of exercise. Lyle paddles an outrigger, Rands used to play hockey, but now he bikes, and we compare peak heart rates. It’s a thriller.

Enjoy it now, or download for later. Here’s a handy feed or subscribe via Overcast or iTunes.

I wrote a piece a long time ago about The Wolf. It’s my personal take on the mythical 10x engineer, except that they aren’t a myth. They exist. I’ve seen them. Many of them.

The article was popular. With hindsight, I determined two populations cared about the piece and one who did not. One was the “I want to be a wolf” crowd, and the next was the “How do I create a culture that encourages Wolves?”

“How do I become a Wolf?” Wolves don’t know they are wolves. They don’t care about the label or the unique conditions that surround them. Wolves are the result of the work, not asking the question. Wolves don’t ask to be wolves; they are.

“How do I create a culture that attracts or encourages Wolves?” I have slightly helpful advice here. First, I’ve seen Wolves in every type of company. Tiny, medium, and huge. Enterprise, consumer, ad-tech, and pure services. Every single one had Wolves in their engineering-friendly companies. That’s your job — building a culture conducive to engineering.¹ After that. Nothing. Don’t talk about 10x engineers at your All Hands. Build a safe, healthy, distraction-light, and drama-free environment where builders focus on building. That’s where engineers do their best work.

And the third important population. Wolves, the population, did not read this piece. Yes, I shared the piece with the Wolf I was thinking of, and he nodded and said, “Yup,” and returned to the project in front of him. Wolves don’t care if they are seen or not. Wolves are entirely focused on the self-selected essential project in front of them because they decided it was worth their time and important to the company.

A Wolf Factory

I have tried and completely failed to build a Wolf-like role within two different companies. I used different approaches and different framing in each attempt, but each was a failure. Existing Wolves were, at best, distracted from their work and, at worst, left the company because they felt like I’d forced them into management. Disaster. Another time, I created an entirely new title, which was my definition of the responsibilities of a Wolf. Learning from my prior attempt, I left the Wolves out of the process except for a gentle heads-up regarding my intent.

The result of the second attempt was a handful of fake Wolves stumbling around attempting to do Wolf-like things. They’d carefully read my role description. They worked hard. And they pissed off just about everyone around them because while they were respected, they were now acting with unearned privilege.

At my next company, four months into the gig, a random meeting with Richard showed up on my calendar. He was an engineer on one of my teams. I’d never spoken with him outside of a group setting. No title for the meeting. No heads up. Just a meeting.

Richard showed up right on time. Nervous. Random, disposable chit chat before he got to the point:

“Yeah, so. I’ve been really worried about the quality of the code base, so I haven’t done any of my work for the past two weeks because I’ve been building a testing framework to pressure test the worst part of the code base. Can I show it to you?”

He did. Punchline: never seen anything like it. Jaw to the floor. Not going to tell you why. It’s his secret to tell.

Picking my jaw off the floor, I calmly asked, “This appears amazing. How can I help?”

“My manager is getting mad because I’m working on this versus a feature. I think this is much more important.”

“I see. Let me see what I can do.”

I did very little to support Richard. At my next 1:1 with his manager, late in the meeting, I made an off-the-cuff comment about Richard’s testing framework, “Looks promising.”

I did not:

• Suggest to his manager that this work was more important than his feature work.
• Come up with ideas on how to help load balance the engineers so Richard has time to work on his side project.
• Get others interested in his effort.

All of these activities did occur because good work speaks for itself and Wolves are entirely motivated by good work. Richard eventually (reluctantly) demonstrated his project to others, and they all had the same jaw-dropping reaction. They stepped in to help on the spot and made it even better. Someone else chose to help with some of the feature work, so that just got done, albeit a little late. All of this signal eventually got to his manager, who was now paying full attention to the effort.

Could I have accelerated this effort? Yes, but when it comes to Wolves, my job is to stay the hell out of the way.²

The Hell?

One of my managers discovered — months later — that Richard had pitched me on his project and also that I’d briefly mentioned my impression to his manager. They were confused. They’d watch this rogue project appear out of nowhere, gather steam, and eventually become the cornerstone of our testing strategy.

Confused, “Why didn’t you do more for an obviously helpful effort?”

I responded, “I was not required to help make this effort successful. I was aware Richard was a Wolf long before he walked into my office. I’ve seen many. My job was not to help nurture this effort; my job was stay the hell out of the way. The work was going to be successful without me; he’s a Wolf. More so, the organization, seeing how this engineer works, is actually more important than the success of this essential project. Richard’s ability to help will be amplified in the future by others recognizing this ability.”

Still confused, “But what about the process? We do things a certain way for a reason.”

Pause.

“Process is how we get things done at scale, but we’re also innovating. We’re bringing new work into the world. At key moments, process has an unfortunate side effect of crushing innovation unintentionally. My job here is to identify the work and explain why management staying out of the way is the correct strategy.”

“And you didn’t ask, but the reason I swear slightly when I say this is because managers need to hear this. The job is a privilege, but many managers confuse the privilege with the desire to know, act, and help with everything. They believe that is their job, but very often, their job is to know when to do absolutely nothing.”

Many, many years ago, at my childhood house in the Santa Cruz mountains, I grabbed a shovel and started to dig a hole.

Why? Unclear. I was six or seven. I’d seen what my Dad could do with a shovel, so one afternoon…. I started digging, and by the time evening approached, my Dad walked out, “So, wha’cha doing there?”

At the time of the hole intervention, I’d been at my hole digging for a couple of hours, and while that sounds like a lot of time, I was only two or three feet deep in a hole maybe the size of a picnic table. The removed dirt was tossed carelessly in every direction.

“I’m digging a hole.”

“I see that. Wha’cha planning on doing with that hole?”

No real answer at the ready. Like pulling a stick from a stream, I was mostly enthralled with the act of digging a hole. I dodged his question, “Yeah, I think I’m going to need some wooden columns here at some point. Ya’know, to hold the ceiling up when I get that far.”

Dad, “Uh huh.” The hole was three or four feet deep — barely above my knees. And it was getting dark.

I continued, “And I am worried about moisture…. ya’know? Dripping from the ceiling.”

Dad, “Yeah. I get that.” Barely to my seven-year old knees.

The digging continued for another hour. I’d discovered blisters (no gloves) and also dirt was now falling back into the hole with each shovel-full (no solid dirt extraction plan), but my Dad stood there the entire time. Question continued:

Dad: “Maybe we should get you a wheelbarrow? You could move the dirt into the ravine.” I ignored him and kept digging.

Me: “Dad, do we have a wooden chest? Where could we keep my stuff in the cave? Like a treasure chest?” Dad, “I’m sure we could figure that out.”

You think you know how this story ends, and you’re mostly correct. We covered my picnic-table-sized shallow hole with a piece of plywood to “make sure no one falls in.” My plan was to finish digging the following day, but I have no memory of that picnic-table-sized hole after that night. I’m sure I visited it the next day, but the interest had vanished.

I don’t remember this story because of the picnic-table-sized shallow hole; I remember this story because of my Dad. He walked out of the house and found his young son digging a random hole on the property. No plan, poorly equipped, but enthusiastically digging. He stood there asking questions, not judging. Supporting the dream.

Just letting me gleefully dig.

He taught me that no one knows where inspiration comes from — only that it’s fragile, invaluable, and fleeting.

Come winter in the Santa Cruz mountains, the rain runs down the hills. When the rains start, I throw on my rain gear, grab my shovel, and tromp around the property. My goal: make sure the run-off creeks and streams run unimpeded and in a better direction.

At the beginning of the season, this is work. There’s almost a year of fallen detritus in these small run-off creeks. Leaves, sticks, and branches. Often, small plants have grown. Sometimes I leave them, sometimes I remove them. During that first rain, the detritus clogs the usual run-off streams, which is where I show up. With my shovel in hand, I quickly shovel the detritus away, and the water runs down the hill.

I like to solve problems, and the act of fixing creeks directly links effort to a satisfying outcome.

The Thing About Water

Here’s what you need to know about water running down the hill. It’s going to do its thing whether I’m tinkering or not. The combination of gravity and the stubborn erosion provided by water means a creek will slowly be carved into anything, regardless of my good intentions. Think the Grand Canyon… except way smaller.

During the early rains, when a year’s detritus is sitting on the ground getting in the way, there is a critical blockage that does matter. Mountain roads. The ideal state is that water runs alongside the road to the nearest outlet or drain, which redirects the water under the road and into a stream that eventually flows into a lake or ocean. When the run-off next to the road is blocked, it can either go around the blockage or, and this is the problem, run across the road.

In heavy rain, this cross-the-road blockage scenario can be an issue. See, water is just going to do its thing. Problem is, on this new side of the road, water hasn’t been running, so it’s making up a new path dictated by gravity. This newly directed flow merrily crosses the street, finds the lower part, and runs down the hill. Sometimes, usually, this is a non-issue, but sometimes the run-off on the wrong side of the road quickly erodes the new side of the road.

In a big storm, what starts as blocked run-off can turn into a failed road.

Except there’s me. With my shovel.

Having spent days of my life cleaning run-off creeks, I’ve triaged a lot of clogs — small and large. A moderately sized blockage on the side of the road looks like a big mess. You’ve got the backed-up water, in front of that, a huge mess of leaves and other floatables, and in front of that, you’ve got the dam. This is the problem. It’s a collection of sturdy sticks and branches that have combined into a wall, which, when combined with the soft, floating leaves, is now blocking a majority of the run-off and forcing the redirect.

My shovel and I used to attack these blockages from where the water flows in, but I’ve learned over the years that the better way is to attack from the “dry” side of the blockage. Why? Because quite often, there is a lone stick or branch that is 90% of your problem. This is the one key object that started this entire blockage situation. Yes, the majority of the problem comes from everything else latching onto that one stick, but…

Sometimes…

Not every time…

You pull a single stick, the dam breaks, and the water starts flowing. That moment — stick out, water flowing — stayed with me.

The Stick Thesis

I’m late on my New Year’s post. Some of my favorite posts show up in January. Fresh starts. Full of potential. Blank slates. It’s why New Year’s resolutions feel timely.

I sent a draft version of my New Year’s post to the leadership newsletter, but I don’t think you’ll ever read that piece. The pitch was about selecting a New Year’s resolution that had immensely satisfying feedback loops. Failure to find this feedback loop means your New Year’s resolution will be a dabble. 30 days of inspiration following 30 days of degradation. A good resolution must give an immense sense of accomplishment and satisfaction.

The hard question is: how does one find these satisfying feedback loops? I had two observations on this topic as I tugged and pulled a redwood branch from the base of a dam blockage on a nearby road, which resulted in an immediate fix to the flow.

First, “Gosh, this is fun. I could do this all day.” The act of helping is immensely satisfying to me.

Second, for every potential New Year’s resolution that has been bouncing around my head for the past two months, what was the stick at the base of the dam? Exercising every day. Yes, swell idea, but what am I actually trying to fix? What’s driving the perception of the need to exercise? It’s not just staying in shape; it’s that as I age, I want the next fifty years to be as compelling as the first.

My stick thesis is simple: your habits will only change if you seek the single stick, the blockage, the core problem that is blocking everything else. Seeing that stick not only gives you a place to start, but the discovery will better motivate you when you yank it, and the water starts flowing.

Happy New Year.

Who doesn’t love a hack?

A hack. A clever bit of knowledge that, when used, provides disproportionate return on investment. The fact that it costs you little to nothing to use and deploy a hack isn’t irrelevant. You understand the work involved in discovering and refining what others call a hack. You call it knowledge, and knowledge is processed experience.

That is part of the joy of a hack. It’s your relief that, whew, I don’t have to do all the work to enjoy the reward. Our ability to both create and share hacks is fundamental to our species. We share hacks as gifts in how we play and how we work.

Think about the first hammer. Someone somewhere, a very, very long time ago — probably accidentally — figured out that when you lashed a stone to the end of the stick, they suddenly could clobber the crap out of stuff. CLOBBER BASH WHACK. This is so much easier than hitting stuff with my hands…. hurts a whole lot less. Also, kind’a fun, right?

All this clobbering did not go unnoticed. Nearby others quickly recognized this exponential value of stone lashed to stick, figured out how to build one themselves, and commenced their own clobbering, bashing, and whacking. THIS IS FUN.

This is Fun

My current most productive Claude Code workflow for developing the randinrepose.com weblog — it’s a WordPress joint — involves a long-running Ghostty session:

• I used to have Claude Code build scripts for me to perform tasks, but I realized scripts are actually a time-saver of the past. I can ask Claude Code to do many of the common activities, including: Google Analytics queries, theme tweaks, and plugin development and management. Yes, sometimes I build a script, but more often than not, my one-off requests are readily fulfilled by robots calling available APIs. Worth noting that Claude Code is frequently developing scripts on its own, but I’m mostly unaware of this.
• Whenever I complete a task, I have the robots update a file called worklog.md. This Markdown file is a log of everything that I’ve done with the site since I started this process two months ago. This file is checked in along with everything else into GitHub.
• Finally, and more recently, I’ve learned of claude.md, which is a markdown file Claude Code loads at the beginning of the session. This file is a home to core principles I want the robot to follow (Ask clarifying questions), critical dependencies in the project (I use external typefaces, they are slow, I understand and accept this), build and deployment reminders, known issues, readily available tools, and much more. Claude Code loads this at the beginning of the session and suddenly knows, well, all the hacks we’ve developed over the past two months.

Each of the prior three bullets is a result of the robots doing something frustrating. The primary issue is blowing away the context of what we’re working on and having to remind the robot of the hack. Yes, you can copy files to production. This is how. Yes, I know that performance is slower because of remotely loading fonts. Yes, we’ve already tried other approaches, and they didn’t perform.

It’s a series of hacks I’ve developed not only because I keep catching the robots in errors, but also because I deeply understand how software is developed. Robot mistakes look mostly like the mistakes we humans make, and I’ve made a career out of sniffing out and fixing mistakes big and small.

The Hammer Hack

Most of the initial reactions I’ve seen to the first use of AI are pure wonder. How did it know? How does it do it? If it can do this, what sorcery can it perform? Pure wonder is usually followed by terror, too. How did it know? How does it do it? If it can do this, what other sorcery can it perform?

Watching a robot do work you thought was the domain of we humans is wondrous and alarming. Watching someone with no experience build, draw, or create something via robots for the first time is a joy. Watching them attempt to finish that building, complete that drawing, or put a bow on the creation quickly devolves into a study in frustration. These previously delighted humans quickly realize they don’t have the language or the experience to explain their intent or their goals, so the robot hallucinates their intent. This turns into a frustrating communication pain spiral where the creator becomes increasingly frustrated, and the robot becomes increasingly unhelpful and apologetic.

There are two populations I see using the robots. An excited group of humans who believe these tools are going to magically build for them, even though these humans have no experience in this craft. Unless these humans take the time to understand how to build, the results will be incomplete or mediocre.

The other population knows a hammer doesn’t build anything for you; it just makes the act of building easier. Understanding the act of building doesn’t make your product good; it’s the experience of building and deeply understanding what you want to build that makes it great.