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.

In our 94th episode, we talk about when Rands goes unhinged and why that is cathartic. Then, we talk about the plight of enterprise software users and why they are so unfortunate.

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

Manager at the first start-up. Solid guy. Significant experience. I know that I can learn from him. No doubt. All the correct operational 1:1 hygiene is there. We meet every week like clockwork; we fill the time, and I often leave with a healthy sense of productivity.

But sometimes… he talks. And wanders.

He’s a talker. He likes stories. He thinks out loud. Often, these stories are related to a topic he or I brought up, but often, they are entirely unrelated to the company, our work, or my job. Or are they? I’m not sure. He’s still talking, and while it’s a compelling tale, I think it’s for his narrative enjoyment rather than our collective professional well-being.

The failure case and the reason you are reading this is that once during storytime, I was seeking guidance, I was looking for answers to essential questions, and I was working to figure out how to make progress. I forgot the story he was telling, but I discovered a question, jumped in, and asked, “You mean I should do this?”

“Yes. Yes! Exactly. Do that — great call.”

So I did.

Two weeks later, I received an urgent and irate Tuesday night email from my manager, “Hey, what are you doing here? Why are you doing this?”

“You told me to.”

“No, I didn’t.”

I don’t yet have a deep analysis of why storytime guidance differs from work guidance. I suspect that because he was lost in the narrative, he is in a different part of his brain, which isn’t work; it’s the story. I do know that receiving contradictory guidance from leadership drives me bonkers. As a leader, your job is to illuminate, not obfuscate.

My solution in this scenario, which I’ve now used for over a decade, has three simple steps:

1. Prepare for the 1:1.
2. Capture thoughts in writing in real-time.
3. Post-mortem (document) the 1:1 immediately.

Preparation Artifact

Sometime before the 1:1, I spend five minutes writing down what I need from my boss this week. This can be a low-prep exercise where I yolo scribble my current set of worries, concerns, and questions. The content is less important than the fact that I’m preparing my brain for the 1:1. We are going to meet. This is what is important to me. With the initial concerns out of my head, I will then take a pass through my to-do list. Anything that I need to discuss that isn’t front of mind? Jot it down.

Do I share this list with my manager beforehand? Depends. My move is always to share any larger, complicated, or political topics the night before so that they can be pre-processed. I don’t always share all topics because it’s a conversation, it’s organic, and I want to give the conversation room to breathe. More on this in a moment.

Back to Reality

With my artifact in hand, my job is to steer the conversation towards these topics. I do this before storytime starts by declaring, “Hey, I have three topics I’d like to cover at some point.” This is easier if I’ve pre-sent the topics. Sometimes we do them right then and there (sweet), but sometimes they happen later organically as part of the 1:1. Read the room.

Now for a power move—it’s subtle. First, I bring the Preparation Artifact as a reminder of the topics or questions I have. I make sure he sees this act. Second, and here’s the move, when he says anything that sounds like a decision, task, or essential — I write it down.

This practice is for me, but it’s also for him. See, he might be in storytime mode, and while storytime might be his chosen means of delivering wisdom, he wanders. When I hear an essential thing, I pick up my pen, and I write it down. He sees this and remembers this isn’t a clever yarn told at the bar, this is work. This is reality. We are at work doing work things.

This practice is not a replacement for having a conversation. This does not absolve me from seeking real-time clarification; this is a quick reminder that we are doing work here. Infrequently, he sees me capture the decision and realizes what I might have heard, so he comes back to reality and clarifies, “This isn’t relevant to that topic. This is just a story.”

Oh.

The Tides of Trust

All done? Great, take three minutes to glance at my notes. Did I cover what I wanted? No? It goes on this list for next week unless it’s urgent. Did I capture all to-dos, thoughts, and next steps? No, write them down. Right now, I’m heading to another meeting, which is where I’ll forget critical bits the moment someone asks me a deliciously complex question.

This last step is essential because once I’ve written everything down, I often discover that what I heard is different from what I wrote down. The act of passing the thought through my fingers and onto the page forces structure onto the thought. Brains. I know, right?

Professional trust is like the tides of the oceans; it comes and goes. When trust was low between my boss and me, I’d send my read-out of the conversation as a mail or message. I am surprised how often the words he said differ from what I captured, and during low trust, he’ll respond and correct. This response means I need to send these follow-ups post 1:1. Three times with no response? The tide has returned along with truth. Good job.

Do That — Great Call

“You told me to.”

“No, I didn’t.”

In your career as a human working for other humans, this moment will stand out. You believe you did precisely what they asked, but upon completion, they question your work. The work you thought was precisely what they asked. For this specific scenario, I think my boss believed he’d figured it out, so it was OK to wander into story land.

At some point in your senior leadership professional growth, you’ll start to feel like you’ve got it figured out. The circumstances vary, but many years into your career, you’ll start to feel like you have satisfying answers to most questions, your projects will appear drama-free, and previously complex problems will appear familiar.

Good job. You’ve never figured it out. Ever.

Stories. Good stories are fun to write and to tell. You’re reading one right now. Stories can inspire you, point you in the right direction, but the leadership we need day after day is a conversation.

Dream a Bit. Nothing innovative was created by committee. You have to stumble on that odd idea at 3:15a and recognize that you’ve never seen it before. Maybe no one has seen it. Let it bump around your head a bit. Stare at it from a couple of different angles. Do whatever you do to let it stew, but pitch Jason at some point. Pitch him because he’s just as crazy as you, and he won’t shut it down because he knows what you know: innovation is a fight. He’ll raise an eyebrow when you make no sense, but he’ll still ask insightful questions. Keep talking with him. Soon, he’ll believe more than you.

Ask for Help. Nothing innovative was created by a committee, but it does require a team. You can see the blast radius of your idea, but you need Laura because scale requires not just a team, but an understandable process to drive that team. You need help. Maybe it isn’t Laura, but it is most certainly someone who is definitely not you. In fact, the more they aren’t you, the better. The more their vision and values differ from yours, the higher the chance of success.

Set Clear Expectations. Nothing innovative was created without the team understanding the vision. Explain the vision; it’s better if it starts as a smaller, palatable, tractable idea. Walk through the pitch and the draft of the strategy. Ask Terrance. His tolerance for ambiguity is zero, and he will explain why we can’t set reasonable expectations with this pitch. Someone once said, “Feedback is a gift,” and they were right. By clearly setting measurable and objective expectations, we can start. The act of starting is more important than the vision being perfect.

Do Your Best to Exceed Expectations. Nothing compelling was created by a team meeting expectations. Once you’ve begun, you’ll see progress, but key decision points will show up, and you’ll need to decide: Do more? Do less? Cut our losses? Admit defeat? Ask Stewart. He is unencumbered by the constraints of reality. Stewart understands that the art of creation involves:

1. Being an expert on the situation in front of us. Do you know what experts sound like? They sound like they fucking know what they are talking about. Experts make the fakers sound like they just read the latest summarization of ChatGPT: vapid, empty, obvious, and sloppy data.
2. Ignoring the constraints of time and resources. Do you want to know how to piss off just about everyone? Ignore objective reality. Ignore the structure that gives everyone purpose. The question is: are you trying to build something new or not?
3. Diving into the problem with expert opinions and a plan that most folks don’t believe. Your degree of discomfort with this plan tells me everything I need to know, not just about its viability, but its potential impact.

Do the Work. Nothing compelling was ever built without many days of drama-free productivity. Ask anyone on the team. We do our best work when we can focus. The Drama People™ trade in drama, and sometimes we need them to highlight and address brokenness, but if the The Drama People™ are running the show, we’re not working, we’re worrying. You’re going to need Sarah — she has zero tolerance for drama. She’ll stare drama straight in the eye until it realizes its pointlessness.

Shit Happens. Deal with It. Nothing compelling was built by a team of talented people who didn’t deal with the shit. Yeah, I wrote shit. It’s a swear word. If this word makes you uncomfortable, I have more bad news. So much more than bad shit is going to stand between you and building the next thing. Ask Maria, she’ll tell you. She’s seen the shit and she knows better than most that bullshit kills culture, it promises unachievable insanity, and it is incapable of delivering the impossible.

Deal with it. No one believes you can do it; most everyone only believe what they have already seen, and if what you were trying to build was obvious, it would’ve already been done. The obstacles, the shit, are the clearest sign you are onto something. Repeat the loop. Ask for help, reset expectations, exceed those reset expectations, and prepare for more shit. It’s coming.

Admit You Are Wrong. Nothing compelling was created by people who didn’t fuck up. See, well, you actually screwed up. That was a bad decision, and it took us down an expensive and inefficient path to a dead end. You know how I know? Eliza told me, and, more importantly, I listened. Listen to the people you trust. You’ve been selling well-intentioned ego-based inspiration for a while now, and if you don’t listen to smart humans who tell you the truth, you will achieve an impressive nothing or, worse, a mediocre something.

Fearlessly Alter the Plan. Nothing compelling was created by people who didn’t change everything. It’s not just a bad idea and a dead end; it’s a deeply flawed strategy that can not succeed. This will feel like failure until you talk to Erik. He has no skin in the game, he speaks the truth, and, most importantly, he knows how to speak to you. This combination of attributes dispels the sense of failure and allows you to move forward. He’s not going to fix it; that’s your job.

So.

Dream a Bit. Nothing innovative was created by not trying again. Ask Jason again. He has time.

1. Vanilla. Someone decided. Good. No further questions. We can make progress now.
2. Educated. You ask why they decided, and they can clearly explain their reasoning. Not everyone might appreciate the decision, but they will be given the opportunity to understand.¹
3. Calculated. Not only can they explain the decision, but they have math! Wow, I’m super convinced now.
4. Instinct. They attempt to explain their reasoning, but they say “feel” a lot. A lot. Thing is, it feels right, so you don’t press.
5. Inspired. Now you press, and they can tell you want a clear rationale and justification, but none obviously exists. This decision is not meant to be understood; it’s meant to be appreciated for its poetry. It is 100% expected that inspired decisions are going to frustrate those seeking clarity; they are going to point at the lack of a clear explanation. “He doesn’t know what the hell he’s doing. It’s a guess.” It might be a guess, but it also might be art in the making.^{2 3}
6. Minimum Viable. My least favorite. Your investigation into their justification reveals that they chose a decision that was not designed to be good; it was constructed to offend the fewest humans. This is not leadership — it’s fear.
7. Delegated. Rather than doing the minimal work of even making a minimum viable decision, they gave the decision to someone else because — and I quote — “They are more capable of making this decision.” What they are actually saying is, “I would prefer that this human deal with the weight and consequences for this decision.” The good news: at least you got a decision.

Sometimes, they don’t decide. You push, you prod, but they won’t decide. No, they didn’t delegate, no, they didn’t wing it, they just waited and waited… kind’a maybe hoping the need for this decision would vanish. Technically, deciding not to decide is a decision, and that’s a choice, but it’s not leadership.