Decentralize Your Data

What does owning your data even mean, and can the Blockchain help?

Photo courtesy of Dennis Kummer

Congress recently required Mark Zuckerberg to defend his lifelong practice of mistreating your private information. Movements to give you control of this critical data took the opportunity to claim they can prevent future such breaches. Blockchain is the new solution in search of a problem, and personal data is in the crosshairs.

But can the blockchain actually help secure your personal data? What would that take? And seriously, what do people mean when they say we should own our own data?

It sounds nice. Too bad it won’t help. The problem is not “ownership” (whatever that even means in a world of infinite digital copies). It’s centralization. Having one person’s data is a small threat, only to that individual. Having everyone’s data is a national crisis.

By now we’re familiar with the huge amounts that Facebook, Google, Amazon, and apparently everyone except Apple have on us. But how did they get it? Mostly, we gave it to them, through using their products. What we didn’t give to them, we gave to someone else who then passed it on.

There have been massive breaches at Equifax, Facebook1, and many others. Even the general public is becoming aware of the real causes. Some of the the largest companies in the world exist purely to collect your information and sell access to you based on it. They might not sell your data, but they definitely sell your attention using it.

These are the problems you know about. Don’t worry; it gets worse from here. If you think your birthdate and pictures of your kids are personal, what about your DNA?

Anne Wojcicki is married to a Google founder, and she liked their data accumulation so much she started her own company to build a huge pile of even more personal data. 23andMe does not scrape the internet — or your cheeks — to get your DNA; no, people pay for the privilege of giving it to them. Yes, they offer a service in return, but do they clean house after? Hah! No. They keep it. (Hopefully somewhat more safely than Equifax does.)

What’s so wrong about there being a database of DNA from a big chunk of the population? Let’s ask the police.

You might not be afraid of the police. You should consider yourself lucky. I know anyone of color in the US is and should be. I know I am; I grew up on a commune, and policed raided us using helicopters and assault rifles in hopes of busting us for cannabis. I don’t mean to imply that hippies have been as systematically oppressed as African Americans (and certainly not in the south); just that I grew up with my own justified skepticism of exactly what that force was here for.

Even if you don’t fear the police, you should fear the consequences of DNA testing. The science behind most parts of DNA are absolutely rock solid2. The police work is another matter. Beyond outright fraud used to wrongly convict people, the messy world of testing DNA at crime scenes just makes it hard to get correct results. Juries inappropriately treat a complicated test as foolproof. It could be compromised anywhere from the crime scene to police handling to the lab itself. The failure rate even without fraud is high enough that I would not want to trust my life to it.

Not to imply that DNA testing is worthless; quite the contrary. It has been used to exonerate many people who were incorrectly imprisoned and put on death row. It’s not that it always fails, just that you don’t want to finding yourself gambling on it against life in prison.

But remember: This is just for cases where someone has a single person’s DNA. Like having just your fingerprint. What happens when someone like 23andMe has a whole database of it?

“If you didn’t do anything wrong, then you have nothing to fear.” Pfft. Yes, it starts with requests for the DNA of individual suspects, but it escalates to doing a database-wide search for DNA that matches. And by ‘matches’, we don’t mean, “is 100% guaranteed”, we mean, “eh, it’s pretty close”. A DNA “match” directed the police to someone they thought was a relative of a suspect, who was then brought in for questioning. So I guess as long as you’ve never done anything wrong, and aren’t related to anyone ever doing anything wrong, you’re fine. Right?

I feel so much better.

I had investors literally laugh at the idea that collecting this data introduced security concerns. They grew up at Google, so it’s not surprising they could not see centralization as a problem. Just like Equifax started out wanting to make it easier to get loans, and now they’ve got so much power you can’t get one without them.

There is a world of difference between giving someone your data, and allowing someone to include your data in a massive pile of it. Any discussion of the risks of data needs to acknowledge that.

Now we see our discussions of owning your own data don’t quite have it right. What we actually want is decentralization of data. We don’t want a single company to have access to this much information about huge groups of people.

And now you see the problem.

New technology can’t break Facebook’s business model. It can’t prevent Google from scraping every web site on the internet and identifying you by connecting everything. Whether you give it to them or not, they’ll know what you look like, where you live, and who you hang out with.

Most importantly, it can’t prevent people from sharing all that data with these services. After all, they’re getting something valuable in return, like connecting with friends and family. Or figuring out their family tree.

The problem is not the centralization. It’s the effectiveness of a business model built on centralization.

So anyone who comes to you and says “The blockchain will allow you to own your own data!”, ask them in return, “How will you make it such a joy to use that Facebook will go bankrupt?” And please, record the conversation, because I want to see them stammer.

This is fundamentally a product and design problem, but the technofuturists are treating it like a technology problem. “Oh, if only those college students had access to better cryptographic tools they never would have shared that data with Facebook!” 🤯 No. People will stop using Facebook, and 23andMe, and Google, when there are better solutions. And unfortunately, they need to work ten times better, not just a little bit.

So talk to me about the blockchain. I really do want to hear how you’ll use it to help people own their own data, and remove the incentive to centralize all of this data.

But talk to me of products. Of user benefits. Of business models built around all of this.

Because people have to want what you’re selling, and the only way to get that is to build something they want to use. Only then will they be able to own their own data.

This is the third article in a series of indefinite length on The Blockchain Without Blockchain

  1. Although technically not a breach, since their usage rules weren’t broken — that’s how little they respect your privacy.
  2. Although we’ve still got a lot to learn about the epigenome, so don’t think we’re done here.

Trusting more with the blockchain

Society is built on trust, and improves or weakens with it.

Photo by Nathaniel Tetteh

I know I have trust issues. I don’t need the blockchain crowd telling me.

Trusting is scary. We’ve all been burned at some point. But we can also look back and see trusting someone helped us develop, personally and professionally. None of us could be who we are if we had not learned this critical skill. Knowing where and how to trust is critical to growth, to life. It’s not even just humans — we can see this in our pets, our livestock.

A cynic might say that trust limits us. That if we only had less, we could do and be more. I’m not exactly known for looking on the bright side, but even I know this is wrong. Trust is the infrastructure for our experiences. Removing it flattens everything, not just limiting what you can do but limiting why you would do it.

Our problem is too little trust, not too much.

We know the stereotype of someone who does not trust. Someone outside of society. We know a person who cannot trust is broken in some way, missing something critical, in need of healing. Many of us also know the allure of not needing to trust, or be trusted. “Ah, to be independent, to owe nothing to anyone…”

This is the dream of remembered childhood. It was always a lie. We were failing to notice the work being done in our name, for us. It was a joyous lie, made more pleasant with the golden tinge of nostalgia. Grown, we miss the lie, we reach for it.

But deep down, we know: More than anything else, life is about trust.

Great companies have been built on this truth. eBay could only exist by creating trust between unknown parties.

Some look at this and see failure. “If only eBay had not needed trust…”

One of the Blockchain’s great claims is enabling commerce between people who don’t trust each other. Never mind that of course you still have to trust something — the code, the packaging of what you’re buying, the exchange, etc. You might scoff and say these are a given, but none of those things can be trusted in the current world of the blockchain. Never mind that commerce has always been done between people with little or no trust. That’s not what matters.

It is philosophical, psychological: Given the recognition that life is enriched by trust, and more riches require more trust, what do you do? Find a way to add trust to your life, or look for a way to get riches without it?

I can’t say the blockchain people are wrong. Maybe they really do need some kind of trustless commerce. I don’t know them. Well, other than the drug dealers. I know why they want this.

But in my life, for my problems? More trust is the answer, not less.

Ironically, the blockchain can actually help with that. Without changing a thing. Its boosters are right about its utility, they’re just wrong about why it works.

I don’t like to trust people with my data. People talk about wanting to own their data, being able to share bits with Facebook but not the whole thing. It’s a nice, if naive1, idea, but that’s not what I mean.

I don’t trust you to touch it. You’ll muck it up.

Heck, I don’t even trust myself. Actually, I was never given that choice. My apps don’t trust me with my own data. They keep it hidden away somewhere, behind an API, in proprietary formats.

Their distrust is reasonable. I don’t know how the app works. The data model is hidden, the storage internal. Most importantly, they can’t tell if I mess with it, and they can’t fix what I break.

Things were in some ways better in the age of documents, but now our data is all hidden. We ask them to give us access, and they sometimes comply with simplistic APIs. But they do not trust us.

What if they did? What if I were allowed access to my own data? What if I could share it with you, my close friend, because I trust you with it?

I mean, not entirely trust. I’m not stupid. We’re not that close.

With the right tools, I could see what you did, understand it, ensure it all makes sense. You could change it, query it, hand it back to me, and I could validate the whole thing. Get the best out of your work, but keep safety lines in place.

Again, a cynic would say call this an example of eliminating trust. But is it?

Is the key to this new interaction really that I don’t trust you?

No. I don’t want just anyone to have my data. It’s for you. My close friend. Who I already trust. Mostly.

This change does not entice me to share with psychopaths, strangers, or, god forbid, the people I went to high school with. It provides just enough of a bridge that I’m willing to give you, my good friend, who I just met on the internet, rights that I’d otherwise hold back.

Of course I know this is not what blockchain people mean when they talk about trust. Meh. I’m not interested in making capitalism even less moral, less human. I don’t even want to hang out with the people who do. But I am interested in making data more useful. And I’m especially interested in connecting with other people.

And this certainly does that.

Now my applications can expose their insides. They can be slugs instead of snails.2 I can use the apps I love, but my tools can fill their gaps. I can script my way around their missing APIs and limited reporting. Heck, I don’t need their interfaces at all. Just because they’re provided doesn’t make them good, and I can get there faster using the tools I already know.

I can pick the best app, without committing to a long-term relationship. I can give you my data, take advantage of what you offer, and if I want to change later, I don’t lose everything.

There’s a great example out there: Github. If they went away tomorrow, I would lose almost no data I care about. They host, but do not control, my most important data: my source code. I get some utility out of they’re hosting it, but they don’t get special rights.3

Github actually created a new kind of trust relationship: Because its users can trust the data store, they began to trust strangers to contribute code. If I were using Subversion, I would have to give you all or no access; in Git, I can give you qualified access. Github calls these ‘pull requests’. “Yes, you can contribute code, but I get to read it first.” That enables a flowering of trust, potentially leading to a deep relationship. That path to complete trust is much narrower, much harder without this infrastructure of gradual trust.

You can choose whether to see this as more or less trust. You can’t argue with the new bonds created, the new groups formed, all through the help of tooling. Almost like how commerce starts with low-trust exchanges of money and can lead to deep and meaningful relationships.

What would a world look like if all of my applications had just as much, or as little, ownership of my data as Github does?

Of course, the apps won’t like it much. Their trusting me with my data also gives me power over it, where today I have none.

With enough usage, our expectations start to change. Given two otherwise equivalent accounting apps, wouldn’t you pick the one that trusted you? That gave you equal access to your data, simplifying automation and reporting?

I would.

This is the world I want.

This is the second article in a series in indefinite length on The Blockchain without Blockchain.

  1. Facebook does not have all of your data because you provided a massive dump at once; they’ve painstakingly collected it over the years, bit by bit. You can be sure they’ll store every little piece you selectively reveal to them.
  2. Honestly I don’t know if slugs are more useful, but they’re certainly more vulnerable. And I could not think of a better analogy.
  3. There is some data that only they have. This is a limitation in git, more than the plan of GitHub. E.g., my follower list is not in my repo, which is probably good, but it’s not anywhere else I can access, which is probably bad.

Blockchain without Blockchain

There is powerful technology hidden in the blockchain. Just strip out the parts everyone cares about

Image courtesy of MemeGenerator

People are very excited about the blockchain, convinced it’s going going to replace cash, or gold, or credit cards, or even the internet. I’ve even read claims that it’s the most important invention since little things like money and democracy. Starving through a failed attempt at utopia has taught me to align with the skeptics who point to the lack of proven use cases (other than fraud and crime), and with the pranksters who make fun of the claims of salvation.

That doesn’t mean I think it’s worthless.

The economic use cases (cash, gold standard, “sound money”, etc.) rest somewhere between unproven and conspiracy theory. None get any love from me. Just because I don’t respect the Austrian school of economics doesn’t mean I don’t understand it. They’re so stuck on their commitment to not learning from history that they can’t let go of the switch away from the gold standard. I am also not silly enough to think that the anti-government libertarians are in it for anyone but themselves.

I’m only here for the tech, people.

The world of the blockchain is in a state of flux. This is normal for movements, and especially so for the definitions of words to be shifting quickly. I experienced this directly as Puppet was helping to create the DevOps space. Today, when we say ‘blockchain’ we mean a specific set of features provided by the code underlying Bitcoin; some might add the requirement for smart contracts, as added by Etherium.

This definition won’t last.

I think that when we look up in five years, the word will mean something quite different. As the conversation inevitably shifts from hype about its universal applicability to finding practical use cases, I am convinced the term ‘blockchain’ will invert from its maximalist form, including all possible features, to a much more minimal form, defining a base set of functionality that is suitable to solving far more problems. Different implementations will layer features onto that base set, but all of these derivatives will be called ‘blockchain’ (which will soon have purists crying we’re not using the “real” blockchain).

It’s that base set of functionality that I’m interested in. I’m hoping the world’s excitement over the complete package can turn into momentum around a more flexible solution. What can we take away, and what can we do once we strip things down?

Let’s start with the most obvious thing we don’t need: Lack of trust. Free markets are built on trust, so it’s silly to try to build one that doesn’t. I just don’t run into many problems that can only be solved if I never trust anyone. Even writing that out makes me cringe.

I’m interested in power tools, user productivity, and helping teams, which inherently means I’m interested in people who know and trust each other. That isn’t to say data validation and simple synchronization are never helpful, but trust between people is not a problem. So take out that whole part of the story.

Next up is consensus. Let’s be honest: You don’t really want the world to have access to most of your data. And most of you who do, well, it probably doesn’t want to see it. This solution for deciding whose copy of data is right? I don’t need it.

That isn’t to say there aren’t important consensus problems; it’s just that the blockchain’s version of them is not useful to me. I do actually struggle with managing conflicts in my own work. I’m writing this essay on one of the six devices I regularly work from, and I obviously want it to transparently synchronize between the rest. I can dream about never having conflicts, but in the real world I need a simple way to handle them when they happen. That’s my consensus algorithm. If I use the Blockchain’s, then one chunk of work wins and the rest of the work gets thrown away. That might work well in some environments, but is obviously a non-starter for my personal work. Instead, I need an algorithm that gives me control over managing my own work streams.

I expect a blockchain hodler would flip at calling this a “consensus algorithm”. It’s not. It’s more like a tool for managing merge conflicts. If you buy into the blockchain, you’ve added a ton of complexity that can and should be handled by a person.

It’s not a big leap from managing conflicts between one person’s devices to managing conflicts within a team. This is still an important problem, one wrestled with by anyone building online collaboration tools, but requires nothing like the level of infrastructure built into the blockchain. After all, I trust myself. I trust my team. I like to be able to verify, but I’m more worried about mistakes and data loss than I am about intentional subversion of the system. And actually, the current solution is horrible for teams. It’s one thing for someone else’s work to cause yours to sit in a queue for a bit, it’s another thing entirely to have your code thrown away because someone is in front of you.

Taking out the trust-less consensus allows us to remove the worst part of bitcoin: Proof of work. This is how parties in a blockchain transaction fight to have their work accepted and others’ rejected. If they win, they are rewarded with a token, which is how they’re “paid” for their work.

We don’t need any of that.

We’ve already established we don’t need an automated, trustless process for deciding who gets to update the database (and we’ve concluded we don’t want conflicting just thrown away). As a result, this whole mechanism can just be removed. Good thing, too, because bitcoin is in the process of consuming all of the world’s natural resources in the name of never trusting anyone. This also simplifies the problem of scaling these databases. Bitcoin is stupid slow because its proof of work system is stupid slow. Remove that, and any iPhone can trivially record new data as fast as you want.

Now that we don’t need proof of work, we also don’t need, surprise!, the currency itself. In a trustless system, tokens are used to compensate the networks recording the transactions. This is now so cheap we don’t need to reward people to do it.

There you go. Now you’ve got the blockchain, except without cryptocurrencies, trustless transactions, consensus algorithms, or proof of work.

The blockchain without blockchain.

It’s important to note: It’s not that I think none of these features are ever useful in any case. It’s that none of them are necessary to get the most important features out of the blockchain, and each of them should only ever be added to a system if they’re truly needed. In most cases, YAGNI.

What can we do now? Well, obviously, now that we’ve removed so much functionality we can do a lot more. General purpose languages are more powerful than specialized ones, and a more flexible database is a more powerful one. The current set of blockchain features can really only be used for a narrow set of use cases, and even those seem to be more theoretical than actual.

What’s left?

A database. That’s what the blockchain always was anyway. It’s built on Merkle trees, which means you can validate every change back to initialization if necessary. This makes it kind of trustless: I can validate your work, rather than just trusting your word of what you did. This ability actually encourages me to trust you more with my data, though.

Check back later for more about what I mean.

This article is the first in a series of indefinite length. I’ll explore the consequences of this stripping away. I will also address some of the potential I see for full current blockchain feature set. I look forward to approaching this topic from a different direction.

The power of better tools

There is a solution to wage and productivity stagnation. Just don’t call it automation

Image courtesy of Washington Department of Transportation

I don’t know what the rest of the world thinks when they use the phrase ‘power tool’, but for me it’s visceral, literal. My experiences using them and watching them transform my family’s work permeated my time building Puppet. These power tools aren’t little plugins to expensive frameworks, they’re large capital investments that dramatically change your job.

I grew up building houses with my dad. The worst task he gave me was trying to paint a set of louvre doors for a closet while in high school; I had to flip the doors over every 90 seconds to catch drips getting through the slats. After three days of misery, my father relented and rented a paint sprayer, with which we finished the job the same day, at a much higher quality.

Around the same time, my dad would rent a pneumatic nailer for big framing jobs. By the time I finished college a few years later, that critical tool went from borrowed to owned and traveled everywhere with him. Initially used only for large jobs, most contractors now have multiple nail guns to cover framing, trim, and every other use case, and the air compressor needed to power it is as important as electricity.

It might not be obvious, but both of these are examples of automation. You replaced a very manual process — applying paint, or nailing things together — with a machine. If this were a factory, these days you’d call those machines robots, but because it’s a construction site, we just call them tools.

And these tools were expensive. Even with how much faster we finished that painting job, I expect it cost more to rent the sprayer than to finish the work manually, because of how little he was paying me. (This does ignore the soft costs of listening to me complain, which were likely high.) Even today paint sprayers and nail guns are often rented rather than purchased, because good ones cost a lot of money and aren’t needed all the time.

It’s no surprise that discussions of tools and productivity are easier to understand from my experience as a carpenter than as a sysadmin. There’s plenty of room for arguments about what is or is not a software power tool, but when it costs more than a week’s wages, it trails a bright orange cord everywhere it goes, and it can nail your hand to the wall while you’re standing at the top of a ladder1? It’s a power tool.

There’s a common story about what robots and automation do to people like my dad (and both of my brothers, who followed in his footsteps): It steals their jobs and ruins their lives.

What utter poppycock.

If you think of your job as driving metal spikes into wood, then a nail gun is a mortal threat. But if this is your value add, your biggest danger was never automation. My dad never sold his ability to join raw materials together quickly; he sold homes, he sold the opportunity to enjoy your house and family more. How did these new power tools affect that?

They were awesome. Painting and nailing are classic examples of menial, low-value work, and yet we spent most of our time on them. All of the differentiation we offered to our customers was packed into a narrow slice of work, because implementation took so much time and money. As we were able to bring more powerful tools to bear, the menial work shrank and larger portions of our time could be spent on design work, customer interaction, and tuning our customers’ homes.

Interestingly, my father’s next career step was even more pointedly about experiences enabled by tooling. He took a job with a state hospital in Tennessee, fabricating custom furniture for severely disabled patients. Suddenly he was using industrial sewing machines for upholstery, and partnering with medical professionals to design multiple beds for each patient, enabling them to be happier and more comfortable (and also avoid bed sores, thus saving hundreds of thousands of dollars per patient). Given the tragically minimal budget allocation for this kind of work, every dollar saved through automation and tooling directly delivered health and happiness to his patients.

It’s no wonder I see the value in power tools, that I am more conscious of the benefit they can deliver than the loss of low-value menial work.

I had a similar experience as I was building Puppet. I would meet executives and salespeople (I don’t know why it was always them) who would say, “Oh, automation? Great, you can fire sysadmins!” No. Beyond the obvious reality that I was selling directly to my users, who would never buy on the promise to fire their coworkers, that was just not why we were valuable.

Puppet gave people a choice between lowering cost but keeping the current service quality, or keeping your costs flat while providing a much better service. “Wait, making things better is an option? I didn’t know that!” Most companies were aware that their IT sucked, but they only knew how to measure and manage cost, so that’s what they did. Once you believed in the power to make things better, power tools turned out to be great investments for both the user and the buyer.

By letting people spend more time on the parts of their work they enjoyed, the work that makes them special, we also delivered higher quality experiences for their customers and constituents. “Spend less time firefighting and doing menial work, and more time shipping great software.” If the heart of your skillset is clicking buttons or responding to outages, Puppet might have been a threat to you, but our users knew where their real value was. We helped them spend more time there and less time on the boring, low value stuff. The sysadmins hated the work, the customers hated to need it, and the executives hated paying for it. Great, done, don’t worry about it.

When you look around the software market, though, power tools are out of style. There are big data companies building for the non-existent average user, minimalist companies building solutions that do little for almost everyone, and there are power tool companies of yesteryear still hanging around. There just aren’t that many modern software companies building large, clunky, expensive tools that just might cut your hand off if you’re not careful.

That’s partially why productivity has stagnated2. The world has not changed that much — some of the greatest improvements to productivity come from making large capital investments in tooling for your workers — but how we spend our money has. People balk at a $5k computer, when the Mac IIci would cost more than $13k in today’s dollars just for the hardware, yet was a powerhouse in desktop publishing. This is to say nothing of how the mobile app stores have driven down what people are willing to spend on software.

Yes, Adobe’s software is expensive, but it’s that price because it delivers so much value. If it didn’t, no one would buy it. Every large market should be so lucky as to have the collection of power tools that graphic designers get. It sounds crazy, but we’re suffering from not enough expensive software. Instead of building the most powerful software possible and finding customers who see its value, companies are building the simplest thing they can and trying to get everyone to use it.

There are bright spots in the industry, like Airtable and Superhuman. I’m hoping they help to shift momentum back to automating away the tedious work and enabling focus on what humans excel at.

More powerful tools improve your life, but they also make you happier even if you can’t buy them. They tantalize you, promising you great returns, if only you can come up with the cash. And they’re maybe just a little bit scary, warning you that buying them is not enough. You must master them.

  1. A friend of ours managed to do this when working alone in the time before cell phones.
  2. Yes, I might be being simplistic to make a point.

The Market Is Wrong About Your Problems

What Voltaire and the Flaw at the Heart of Economics Have to Teach Us About Software That Doesn’t Exist

Voltaire’s Candide juxtaposes an optimistic philosophy with unbelievable tragedy. He was angry at the 19th century philosophers who proclaimed that we lived in the best of all possible world while destruction and death unfolded around Europe on an epic scale.

We might hear the claim that we live in the best of all possible words and scoff. Of course, we’re too enlightened to be such naïve optimists. But are we? Isn’t the belief tempting? Or even, doesn’t the behavior of those around you make more sense if you realize they believe this, at least a little bit?

Economists are theoretically rational, analytical, big picture thinkers, but at the root of modern economics is a belief shockingly close to Candide’s parody of optimism. They have what they call “The Efficient Market Hypothesis” (EMH), which roughly states that all assets are valued fairly. This is built off the idea that asset values in an open market are fair because they include all available information, and all the actors in that market are behaving rationally in regard to both the asset and the available information.

This theory tends not to trigger the cynicism that Voltaire does. Intuitively, it sounds not just right, but defined as so. Isn’t an open market essentially a mechanism for finding the fair value of an asset? It’s not so simple. And when it goes wrong, it does so spectacularly.

Modern economists cannot be as destructive as the great thinkers of the 18th century, whose big ideas justified eugenics and many other horrors. Just because they cannot as easily be used to justify mass murder does not mean they should not be accountable for the downsides of their obviously incorrect theory.

“No”, I hear you say, “the EMH is not wrong; it’s correct by definition.”

Economists have convinced us of what Voltaire was protecting us from: We live in the best of all possible markets, where all information is public and all assets are fairly valued. If the market does not value something, that it must actually be worthless.

But of course, if that were true Warren Buffet would not have become a billionaire buying stocks that were worth more than the market was paying, the finance industry could not have been built on advising clients about public stocks, and you’d have no need for lemon laws or other regulations that fight information discrepancies. Nor would Kahneman and Tversky have won the Nobel Prize for demonstrating that actors in an economic system behave anything but rationally, puncturing the EMH for good. Thankfully, this has forced the field to begin to grapple with its flawed underpinnings, but many modern beliefs are implicitly built around these bankrupt theories.

You might be patting yourself on the back right now for not being silly enough to draw Voltaire’s ire, but it’s baked into the value system of the world around you, especially if you live in the US.

  • The market moves from irrationally ignoring new technologies like the blockchain to irrationally dumping money on them, without any fundamental change to justify the shift
  • Investments are made based on proximity and serendipity rather than rationality and opportunity size
  • We tend to claim that the rich earned their status through hard work, rather than recognizing the role of privilege, inheritance, and luck in their status

Of course, not everyone in the market operates with such optimism, but each of us is biased in this direction. It affects our thinking whether we want it to or not.

“Ok”, you say, “even if I accept some people make optimistic investment decisions, what does that have to do with software?”

Great question. If we live in the best of all possible markets, where all information is public and all assets are fairly valued, then we can trust the market’s assessment of what software should and should not exist. Lack of software to solve a problem is a sign that it’s not worth solving.

If, on the other hand, our world could be better, or if our market is imperfect at valuing assets, then we can’t trust intuitive conclusions about where value resides. This is most true when it comes to valuing unsolved problems. It might be that a given problem has no solutions because it is not worth solving, but mundane reasons are more likely to be at fault.

Most great companies exist because they provided something the market did not know it wanted. Their founders encountered a flaw, and managed to build something great in the opportunity created by it. Henry Ford claimed if he’d have given people what they wanted it would have been a faster horse. The market knew how to value them, but not cars. Before Apple, the market did not value personal computers. Before Google, the market valued directories but not search engines. Before the iPhone, the market valued expensive phones for professional use but not personal.

These value statements were market failures, and their resolution generated billions of dollars for the companies resolving them. Now, of course, the market sees great value in what these founders have created, but not because the market is so smart; it’s because it can no longer fool itself.

It’s easy to grow despondent in the face of such obvious market failures. If the wisdom of the crowds, the great invisible hand of the market, can be so wrong, what hope does a lonely entrepreneur have? I take a different way.

I luxuriate in these misses.

They surround us. We bathe in them. Yes, many great companies have grown into critical market gaps, but even with all these successes, there are untold problems whose solution should be valued but is not.

Only once you reject the market’s flawed opinions about what matters, you begin to see nearly limitless opportunity. There are so many more unmet needs than there are perfect solutions. These are your opportunities.

Of course, just because the market dismisses a space doesn’t mean there’s a great opportunity there. It’s your job to know the problem, your customer, your user, your buyer well enough to draw your own conclusions, to develop enough certainty that you don’t need someone else to tell you what to believe.

Because that’s the real point: Trust yourself, not a bunch of paternalistic optimists.

Owning my writing

It’s the message, not the medium

I did more writing in 2017 than I ever have before, probably more than I had done in my entire life. I stated at the outset my desire to write in order to learn, and publishing regularly has delivered. More importantly, it forced me to capture and share many of the results of my R&D. The writing topics were primarily venture capital, the software startup ecosystem, and founder optimization, but one of my weaknesses is a drive to the meta, spending time on the tools and systems rather than the work itself. Unsurprisingly, this ground is as fertile in prose as it is in code.

I have done all of my writing on Ulysses, which has been a good tool. I do miss much of the power of Vim for managing text, but the usability trade-offs are usually worth it. Plus, Vim is not exactly strong on wrapped text. Ulysses’s most important capability for me is that it transparently syncs between my phone , both of my iPads, and all three of my computers (yes, I know). I can open any document on any device with no worries (given my iPads are on LTE, and thus can always download updates). Second to that is the ease of getting data out. I was able to text a 5k word document directly from Ulysses on my phone to two different people, because it converts anything to PDF and can send out via the share sheet. It publishes directly to most platforms, so I used it to post everything to Medium. I do wish its backend storage was more visible, so I could version control everything in git, but you can’t have everything.

The only time I ran into troubles was publishing my travel writing — I was copy/pasting photos from Apple’s Photos app into Ulysses, then publishing into Medium, and it turned out that no part of this process downscaled the photos, meaning each was about 20MB. This is fine when you’re on solid wifi, but not so good from a campground in Yellowstone. The primary reason I did not write during the second month of my trip is it was just too painful to publish. Ulysses really fell down here, because when it works, it works great, but when it fails it is miserable. I’d just sit and stare at my iPad for ages, with no visibility of failure or success until the very end, and it would often manage to upload the text but not the photos. The only fix for this was to delete the draft from Medium and try again. Not so great.1

Over the year I became concerned, though. I heard about Andrew Chen, who built a following on successive publishing platforms (e.g., Blogger), each popular and well-funded, only to have the companies disappear (because that’s what Silicon Valley does to most companies). He eventually realized that the only way to consistently reach those who were interested was via email; it’s never going away, subscriber lists are easily portable, and of course everyone knows how to use it. He had to move from letting a platform own his audience to taking control directly, and email was the only real way to do that.

I think Medium is pretty good, and at least for now it has no shortage of funding. Even last year, though, it made well-publicized efforts to retool its business, a clear sign that whatever it was doing before wasn’t working. It seems unwise to bet that a follower on Medium will have any meaning in a few years.

It just so happened that I ended the year with an experiment in their new business model. My series on Venture Capital, in partnership with NewCo, was published behind Medium’s paywall. While the experience was positive overall, and I got paid more for those pieces than I have for, um, all of my other writing ever, earning money isn’t my real goal in writing. Yet, paying writers is exactly what Medium has to figure out in order to attract the content and audience it wants. I appreciated the extra attention working within their paywall provided, but I came out thinking it’s unlikely to be the right path for me in the long term. My goal is to maximize the reach of my writing, and it’s more about the arc of all of it rather than a couple of heavy-hitting pieces getting the most attention, which means our respective goals are orthogonal at best, and in direct conflict at worst.

While I have not written about it, I spent a lot of last year fascinated by email, inboxes, and how we consume content. I’ve been a deep fan of RSS from the Bloglines days (Unread is my reader of choice these days), but RSS is mostly dead (thanks, Google!). The kinds of sites that produced great feeds back in the day grew too big for a hobby. They became either wildly profitable for a small team and thus got destroyed with ads and shitty content (hi Boing Boing!) or people had to back away because it was just too much. Mainstream publications like the NYTimes might still publish RSS feeds (I literally have no idea), but RSS is a poor fit for how much content they produce.

When I look around, it seems that the RSS feeds of ten years ago are now awesome newsletters. See how often your favorite sites talk about their newsletters vs their feeds. I’m pretty confident I’ve never heard a podcast ask me to sign up for a feed, but many casually mention their newsletters. (Well, to be fair, podcast feeds are just RSS, so in that sense it’s survived, but I think we can agree it’s a very different use case.) The market has moved.

This shift is not all peaches and cream. The superiority of email as a publishing mechanism has not brought with it a superior reading experience. Long form content from writers I follow does not belong in the same inbox as requests for coffee meetings, yet that’s where we are. (I asked the Feedly CEO if they would please please add newsletter subscriptions to their platform, and he could only say they were considering it. If you want to build the newsletter reading app, hopefully with an index of great letters to subscribe to, count me in as an early contributor.)

Even with its downsides, I’ve decided to move my writing to my own site via a newsletter-first publishing model. From now on, everything will be published first to that site and the newsletter (sign up now!). There will be exceptions, when publications offer enough exposure that I give them some period of exclusivity. I will also indefinitely duplicate each piece to Medium on a delay, to take advantage of the audience I already have there.

There are enough examples out there that I’m pretty confident this is the right long term answer, but it’s early enough that it feels like an unstable experiment. Like most, I love and hate email, and I am a bit bummed about the extra infrastructure involved in this system.

If you’re still an RSS person at heart, you can always just subscribe to the feed, and if Medium is your bag, at least for now you’ll be able to see everything there, too. Of course I can’t promise how this plays out in the long run — else it would not be much of an experiment — but you can bet I’ll work hard to find the right way to talk with the people most interested in what I have to say.

One note before I go: I could not have made this transition without the help of Mike Julian. He helped set up each of the services, mediated the hiring of a consultant to modify the site, and connected all of the services together. He’s got a great book on monitoring, and is available for consulting on monitoring and observability. I can’t recommend him enough.

Thanks for following on so far. I’m excited about another year of writing.

  1. It’s worth noting that Apple’s iCloud Photo Library did wonderfully here; I could upload every photo to my iPad, and it would sync when it had good data, and sit quietly when it did not. I love asynchronous protocols.

Why We Hate Working for Big Companies

Modern capitalism raises the flag of the free market while pitting centrally planned organizations against each other

It’s quite a journey from being born on a commune to raising more than $87m in funding at a software company. This journey forced me to wrestle with existential questions about my true beliefs, and how they intersected my life as an entrepreneur. One’s work is rarely a pure reflection of ideology, but companies need a clear and authentic strategy, which requires a tight alignment between company operations and the founder’s philosophy. I have discovered more about those differences between what I believe and the best ways to grow a corporation while studying economics — that is, how money is made and exchanged — than any other area.

A worldwide conflict between communism and capitalism defined the latter half of the twentieth century. The United States’ ideological battle was the central drama of my childhood, and it was with a combination of glee, pride, and “told you so!” that my fellow Americans watched the wall fall in Berlin, and the USSR dissolve shortly thereafter. I expect few would deny that the US is the standard bearer for capitalism.

Yet, there’s a flaw at the heart of this claim. While the United States operates as a free market economy, the key agent within modern capitalism — the corporation — works more like an authoritarian state. Given how much of our world is built around corporations, this truth and its impacts are critical.

I grew up apart from America’s passion for capitalism. In the era of Reagan, I was living on a commune. My parents did not earn money for their labor, and we didn’t have personal property. My family left the Farm when I was 8, and as I matured, my ideological roots were in conflict with the US’s nonstop pro-capitalism message. As I joined the workforce and eventually started my own company, I found myself attached to neither the communal roots of my childhood nor the Wolf of Wall Street world I moved into. I grew slowly in convictions, as I encountered problems in the course of scaling a company.

The first real conflict came when it was time to hire managers. I founded a company primarily because I did not thrive as someone else’s employee, so what led me to think others would? More importantly, anyone who has ever operated at the front line is aware of the severe costs imposed by the separation between the people who do the work and the people who make the decisions in hierarchies. Hiring managers was just going to make the company do worse, not better, right? Right?

I expect three of you are gleefully shouting, “Yay, holacracy!” right now, while the rest are confused and either offended or think I’m an idiot. I did consider a manager-less world, but a little research provided only examples of disaster, because the only available options just replace an explicit power structure with an implicit one. In other words, it’s still hierarchical with the founder on top, but now decision making is opaque and the system is easy to exploit because of the lack of controls (which looks surprisingly like the cult/commune I grew up in).

Those who are confused or offended by the idea that managers make performance worse would be informed by a deep dip in economics. One of the core principles of the free market is that central planning committees can never be as efficient or as effective as the people doing the work. By definition a free market economy lacks a decision-making hierarchy; the ‘free’ means every agent (individual or corporation) can decide for themselves, without needing permission from a manager above.

While there are many aspects of modern American capitalism I reject, this one I wholeheartedly support1. The downsides of a strong central executive were taught to me early.

Like many other communes, the one I grew up on routinely failed to feed its people — my parents speak with horror of the ‘wheat berry winter’, when we lived on little else. While his people were short on food, the founder of the Farm was off touring Europe as the 3rd drummer in a band, “bringing our message to the world”.

Thankfully none of us starved to death, but the failing was similar to what most communist countries experienced: The central organization could not feed everyone. For years, I assumed this was just incompetence, whether at the scale of the Farm or China. The truth was far more structural. Millions starved during the Great Leap Forward because the central organization was trying something impossible: Managing the productive output of an entire country. The Planet Money podcast tells a great story of how this central planning was walked back in China, but the general point here is that these communist countries did not just nationalize the means of production, they tried to centrally control all of it from within a small group.2

When people talk about communist countries not being a free market, this is what they mean: They tell the farms what crops to produce and in what quantity, rather than letting them decide for themselves. China even went so far as to dictate what hours a farmer should start and stop working, and then directed managers to ring a bell for transition times to control every little group of farmers. Anyone who’s ever had to punch a clock into a rigid, dysfunctional hierarchy is likely getting painful flashbacks about now.

It should be immediately obvious why this fails miserably: The distance between the central planning committee and the farmer is so great that good decisions are nearly impossible. It’s nearly impossible for critical feedback to make it from the edge, where the farmers are working, to the central planning committee in time to affect decisions, and then for those decisions to make it back to the edge in time to be useful. The podcast linked above also points out how unmotivated the farmers were under this regime, cutting productivity even further. Those who have studied lean manufacturing, agile development, and DevOps are likely seeing parallels here.

The result was catastrophe. When a corporation is painfully inefficient it loses money and might have to do layoffs, but when a country fails at growing food, its people starve to death. I don’t mean to imply that central planning was the only cause of famine under communist rule — there were political operations that led to mass starvation, just like in the West — but learning more about these helped crystallize what I do truly prefer about capitalist models. It also converted the phrase ‘the free market’ from a catchy slogan into something meaningful to me.3

The most important feature of free market economies is that each person within them is able to make independent decisions in their own best interests4. If you’re a farmer, you can decide what to grow, how much to grow, and when to work to develop your crop. Heck, you can even choose not to be a farmer any more. Success is merely dependent on your finding a buyer for your work at a price you can tolerate. Any given year might not be perfect, but your decision making gets better over time as you learn to respond to customer demand.

This pattern is easy to understand in any system where the people doing the work make the decisions. If you’re a jeweler, you can decide what to make, how much to sell it for, and what to spend your time on. Same if you run a small restaurant, lead local tours, or are a one-person shop doing house remodeling. It’s a free market, where you can charge what the market will bear, and you can quickly and efficiently respond to its whims, ensuring that you are getting the best use of your time.

This was a powerful organizing principle for a long time. The history of human commerce developed largely this way: One person, or as many people as could fit in one shop, would turn labor into a product, then find a buyer for it. Most large-scale efforts were organized by the state of the time: Monarchs and the landed gentry, who were the only ones capable of marshaling enough resources to build palaces, roads, and other large construction projects.

This began to change in the 17th century when corporations like the Dutch East India Company were able to deliver massive windfalls to investors by pooling money and using it to extract resources from colonies. There was a step change in the 19th century, as corporations went from generating wealth to building and owning infrastructure. It’s one thing to outfit a single ship for a year-long voyage, yet another to maintain railroad schedules across the United Kingdom, or run a telegraph network around the whole US. These aren’t just short-term money-making exercises, they’re long-term commitments with big capital outlays and large returns over years and years.

We still live in a free market economy, but it’s not one Adam Smith would recognize. Instead of individual or small operators, ours is composed almost entirely of corporations. Really big corporations. And these companies, they use the same kind of central planning that we so despise in communist systems. I know. I’ve done it.

By the time my company got near 500 people, we had a multi-week planning process, where the leadership (i.e., me and my lieutenants) set out top-level goals, built a top-down plan to accomplish them, then drew information from the front line to see where it needed change. We called this a bottom-up plan, but it was only bottom-up from the perspective of numbers — how much money we’d have, what our costs were, etc. — rather than from the bottom of the organization. We could see no way to have a system where the people doing the work built a plan for the organization. Even thinking about it now, my reaction is, “How would they know what my goals are?”

That’s the kind of question you can only ask in an authoritarian state, not in a free market economy. My goals became my company’s goals, and the only real way to ensure people worked toward them was providing a plan. You might argue that a corporation should focus on shareholder value, but that doesn’t help make decisions about what the company should actually do.

Great leaders find a way to listen to everyone in the company, but in the end, leadership is about making decisions. That’s essentially the definition of the word. And we all know leaders who did not bother to listen, or just did not need to in order to be great; today’s most vaunted tech leader, Steve Jobs, was famously disrespectful of the opinions of others, yet made a lot of world-changing decisions (not all for the better).

This is exactly why working in a big corporation is so stifling. If you’re in a small company, the executives are close enough to the front line that it’s more like working in a tribe, but in a big company, the leadership is so removed from whose who do the work that executive teams operate like the politburo we so decry in communist countries. Certainly the bureaucracies are no more enjoyable or forgiving.

I find it both ironic and painful that my inability to work for someone else resulted in my creating a company that involved a lot of smart, capable people working for someone else.

I wish I had a solution. If this were an easy problem, its solution would already be pervasive, because the benefits are massive. Just in terms of efficiency, we’ve seen how much better the free market is than planned economies, but it also has a hugely positive impact on quality of life. People are happier when they’re in control.

I know the solution is not more freelancing and contract work, which America’s corporations are addicted to. That’s the worst of both worlds: The exploitative nature of capitalism with the inefficient bureaucracies of communism. Transactions on the free market work because they’re good for both sides, but most people only accept part-time contract relationships today when they have no other real choices.

Holacracy certainly isn’t the answer. It’s fundamentally flawed because of its implicit power structure — Tony Hsieh still runs Zappos, even if he does not use a central planning committee to do it — but the biggest problem is it makes no mention of economics. Without a clear system for scoring the transactions (i.e., money) it’s impossible to build a free market.

This problem of how to handle economics within a non-hierarchical company might lead some to think of using blockchain tokens as an internal currency. This is impossible today, beyond the fact that the world of blockchain is mostly about fraud and black market sales. The biggest problem is that we have no idea how to value most of the work people do. I mean, we might know that what a developer should get paid for a year’s work, but how much is that work worth? The majority of the work done in modern corporations is incredibly hard to value, which is partially why companies are so inefficient and make so many bad decisions.

That brings up an even bigger problem — companies today hire workers to make money from their labor. In other words, they generate profit because they pay their employees less than they’re worth. If everyone could trade their labor for exactly the amount of money it was worth, the corporations that employ them would have a much harder time making money. Instead, in modern corporations the shareholders and the executive team — again, the central planning committee we so despise — make the majority of the money, while the front line does all the work and makes very little. This is true even at the big tech firms; software developers might be well paid relative to hotel workers, but they’re paid a pittance compared to the founders and executives. This might speak to why we have no solution yet — free market corporations would tend to reduce concentrations of wealth, which would be terribly disruptive to the current system.

Like I said, I don’t have a solution. But at least now I know what makes the current system so painful, and it gives me some hope that we actually can come up with a better answer. I know I’ll be working harder in the future to manage the downsides of what we have today.

  1. Although I might stress the “well regulated” part more than most modern economists.
  2. Of course, capitalism is just as capable of killing its citizens, whether through starvation or lack of health care.
  3. Note that I’m not taking the capitalist side of the cold war here; while Americans were decrying the oppression of the Soviets, we were actively clawing back progress on civil rights and knocking over democratically elected governments. This article is about principles, which political regimes rarely show a great track record in following.
  4. But not so independent that you should be as pathological as Ayn Rand.

Abandoning Trello

On the value of change and focus

I have been a passionate advocate of Trello almost since the day it came out. Visualizing the work is incredibly powerful, and its use of priority by ordering is so obviously better I could not imagine using anything else. I have brought Trello into companies, and caused hundreds of people to use it. Recently, though, I stopped using it in key functions, moving my personal tasks into Things and other work into the applications that own it. It started as an experiment, but quickly snowballed into a full transition as I realized how much better it would be for my core use cases.

I am a productivity junkie, from GTD to Deep Work, and while I know the tools aren’t the work, they’re one of the fastest and easiest ways to change a system, bringing new perspective and abilities.

I initially adopted Trello for managing my personal tasks. From there, it slowly spread to group and company use cases, and by the time I left Puppet in 2016 it was baked into our core business operations.

I had considered switching away from it for my personal tasks a few times, because it’s been obvious for years that it was not a fit for how I managed and processed my life’s flow of work. Where I had always taken great pride in my productivity system, I could no longer muster the discipline it required, which meant it was extraneous process and I was also failing to do my job. I sank so low that I began sending person to-do items to my inbox. shudder However, my life as CEO was busy, yet not really built around task execution, so it was never worth the cost of the tooling change. Or so it seemed.

While I abhor tooling changes for their own sake, sometimes you just have to experiment, and when I had a run of open space I decided it was time. Even if other places were worse, I was better off spending time elsewhere to get out of my funk than I was continuing to stare at this board that just wasn’t working for me.

As I looked to move away from Trello, I wanted to switch to OmniFocus, but the timing is wrong. I recently downloaded the current version, but it reminded me why I stopped using it years ago: It asks too much of me1. The biggest disconnects were the need for contexts, and the inability to set priority by dragging items around. It looks like the impending next version will be a great compromise for me, but I can’t use it until it arrives.

As I began moving tasks into Things, I was slowly reminded what it was like to have my task app be, well, an app. Before Trello I used Asana, at a time when its mobile experience was just a badly packaged web page. It’s been years since I had the pleasure of working with someone who bothered to build for the platforms I used. What a difference it makes.

Processing this small but meaningful change took over my brain for the rest of the day. I could not let go of the transition, but I also could not stop thinking about its consequences. “Thinking” is being too generous. I had not seriously looked outside of Trello for years; all of my habits and instincts are built within its constraints, its physics model. That meant wide open opportunity to construct whatever world I wanted, but also the need to do so, and embarrassing mechanisms for getting in and out. Creating a quick task in Trello is most easily accomplished by sending myself an email, which tells you how seamless the core experience really is. Telling Trello of work to be done in another application usually required custom applescripts to connect the two (e.g., creating message:// urls).

The keyboard’s change in utility keeps hitting me. I did not realize how rarely I used Trello shortcuts for their sheer disagreement with my hands. Well, partially, they were insane — ‘c’ archives cards, where I kept thinking it would create them, and repeating mistake kept my hands off the keyboard — but also, they were just different. I keep visualizing myself sitting at Things, fingers poised over the keyboard, in a world that makes sense to me. It’s pleasant.

I have a lot of work in Trello. Basically everything I’ve recorded in the last 4 years about what I could or should do is there, and it’s been the platform for organization all of that information. I’ve always been pragmatic, so even when I built it I would not have said it was the “best” answer, just that it worked at that time for my use cases.

Now I am questioning everything I’ve done recently — not to ask if I’ve made a mistake, just wondering what the world would look like if I had done that work differently. Are there projects languishing from sheer friction, that would suddenly become easier if migrated?

The answer in at least one other case is ‘yes’. I had a Trello board for managing all of my writing ideas, and I had a standard right-to-left workflow from idea to writing to done. I just never really used it. Instead, I did all of the management of writing in the same place I did my actual writing: Ulysses. I built a workflow from folders2 instead of lists3, and eventually I realized that the Trello board was hurting, not helping. The ideas I put in there languished, and Ulysses is just as good at capturing a sentence or two about a post as it is for writing the entire thing. The board is now closed, and my writing is in the same place as all of the work needed to manage it.

Tools do not make the difference, but tools can make a difference. A thing can go from undoable to tractable with a small change in tools, just as a math problem can go from impossible to trivial if you flip the equation around a bit.

I know Things won’t work for many of the use cases I have in Trello, partially because it’s so obviously a single-person tool, and much of my work does not have a home I can move the organizational work into. E.g., I have a list of lists in Trello of all of the day trips I could consider taking around Portland, and I can’t think of where I’d move that. I don’t know where those other problems get solved now. Maybe they don’t change.

But I know my standards have been reset. I know I made a mistake letting myself sit in one tool for years, unhappy but unwilling to invest in the change. It’s a wonderful feeling to be looking at the world through new eyes again.

  1. To be fair, I also stopped using it in the days when it took 45 seconds to open the app on an iPhone, because that’s how slow the data synchronization was.
  2. Which they call ‘Groups’.
  3. Really, are they any different?

Great design is ruining software

The arrival of the smartphone has convinced the world of the value of great software design, but it’s not all good news

The smartphone has reached more people and delivered more value faster than any technology ever seen. Much of the world has had to adapt to this arrival, but software design suffered the greatest reckoning. As the smartphone ascended, developers finally adopted reasonable design principles, realizing that they could not pack every feature ever seen into the smartphone experience. This recognition of the value of design — and especially, minimal design — is a good thing. Mostly.

I could not be happier that the industry finally accepts that there are principles of design, and there is a practice and discipline behind building great software. It’s great that we’re seeing more focused software that does little, but does it very well, rather than the previous age of the GUI when software attempted to own large parts of our lives by doing anything and everything. For a long time, Microsoft Word was used by nearly everyone who had a computer, and their strategy was to ensure no one ever had a reason to choose something else by building every feature anyone might ever need; their toolbar was the canonical example of never saying no.

The smartphone changed all that. Those rows of icons would fill the screen on a phone and leave no room for typing, and of course, no one would use them anyway because of how different the usage patterns are. As people realized they could no longer just throw in the kitchen sink, they began hiring (and listening to!) actual designers, and those designers have been steeped in the culture of Dieter Rams and the minimalism of the Bauhaus movement, which is awesome. Mostly.

Unfortunately, the phone caused everyone to focus on the final design principle of Dieter Rams (“Good design is as little design as possible”), without apparently remembering the nine that came before it, or why they were earlier in his list. I get it; the design constraints in a phone are intense, and it might not be a good idea to minimize everything, but it sure is easy.

The consequence of this mobile brutalism is a new movement building simpleton tools: Software that anyone can use, but no one can become an expert in.

Trello is a great example. I adore Trello. I think it’s great software, and it’s clearly a success by any measure. However, for all that I’ve relied on Trello daily for years, I feel no more an expert than I did just after starting to use it. It’s not because I haven’t tried; it’s because there’s no depth. You can pretty much plumb the product in a couple of days.

That’s fantastic for getting new users up to speed quickly, but deeply frustrating after a couple of weeks. Or months. Or years. Compare that with Vim, which I still use for all of my code editing, yet it’s so complicated that most people don’t even know how to quit it, much less use it. I’m not going to claim its lack of user friendliness is a feature, but I will defend to the death that its complexity is.

Apple’s Notes is the ultimate expression of this trend in text editor form. It’s a fine text editor. I know some people have written huge, impressive programs in similarly simplistic editors like Notepad on Windows. But I personally could not imagine giving up keyboard navigation, selection, text munging, and everything else I do. The fact that complicated work can be done on simplistic tools speaks to the value of having them, but in no way invalidates the need for alternatives. Yet, on the current trends, no one will even be trying to build this software I love because they couldn’t imagine two billion people using it on a smartphone.

I think it’s fair to say that that’s an unfair standard, and even a damaging one.

I miss the rogue-esque exploration that tool mastery entails. It’s not that I want tools to be hard; I want them to be deep. I want to never run out of ways to invest in my tools. I don’t want to have to swap software to get upgrades, I want to upgrade my understanding instead.

But I look around my computer, and everything on it was designed for the “average” user. I was not average as a CEO with 40+ hours of meetings a week while receiving more than 200 emails a day, nor am I average now as someone who spends more time writing than in meetings. There’s no such thing as an average user, so attempting to build for one just makes software that works equally poorly for everyone.

It is a rookie mistake to conflate the basic user who will never plumb the depths of their tools with the expert user who will learn every nook and cranny of your software. It is a mistake to treat the person who sometimes has to solve a problem the same as a person who spends 80% of their time working on that problem.

I don’t want to be an expert in all of my tools — for all that I take thousands of photos a year, I don’t think I’m up for switching to Adobe Lightroom — but for those tools that I spend the most time in, that most differentiate me, I want the opportunity for true expertise. And I’d happily pay for it.

Back in the days when computer screens were tiny, there were plenty of stats that showed that paying for an extra screen would often give people a 10% or more boost in productivity. I know it did that for me. As a business owner, it was trivial to justify that expense. Monitors cost a lot less than 10% of a person’s salary, and don’t need to be replaced every year. Heck, the whole point of the automation company I built was to allow people to focus their efforts on the most valuable work they could do.

Yet, when it comes to software being built and purchased today, to the tools we use on a daily basis, somehow our software ecosystem is failing us. There is no calendar I can buy that makes me 10% better, no email client available that I can spend five years getting better at.

It’s great that people are finally making software that everyone can use, but that’s no excuse to stop making software for specialists, for experts, for people who could get the most advantage from that extra 10%.

Please. Go build it. I know I’ll buy it.

Putting OKRs Into Practice

The true story of trying to put Google’s planning system into use

When Google was less than a year old, they began using a planning system presented by legendary venture capitalist John Doerr of Kleiner Perkins. When I went to put it into practice at Puppet in the early days of growing the team, things were not as easy as they appeared. Success involved creation of a complete solution, not just a description of the documents you need to create.

When I went to try to use the system as described by Doerr, I had multiple questions it didn’t answer. Just to start with, when and how do you make and update these OKRs? It’s great to say you should have this recording of your goals, but I could easily come up with multiple conflicting mechanisms for developing it, none of which are obviously better:

  • The CEO could develop them independently and deliver them to the team
  • The executive team could develop them collaboratively
  • They could be sourced from the front-line team

None of these is obviously right or wrong, and of course, neither are they sufficient explanations for how to do it. Do you do it one sitting? Multiple revisions? How long should you spend on it? How often should you update them? Can you change them mid-stream if your situation obviously changes? There’s a lot left to the reader. You can say it doesn’t matter, but of course, it does, and even if you’re right, you still have to pick one. Why go through the effort of describing the output but skip the whole process you used to create and maintain it?

Here’s how we did it.

Startup Days

Starting by reading John Doerr’s original presentation, even though it’s relatively thin. In summary, you should have three to five top-level objectives, and each of these should have a couple of key results associated with it. Together these constitute a company’s Objectives and Key Results, or “OKRs”. These should then cascade down to the rest of your team, so that each team and person has OKRs. This is a useful high-level tool for communication and focus, even in small teams. (Note that I’ll use ‘goals’ and ‘objectives’ interchangeably here; far more people use the shorter term in practice, and we treated them equivalently.)

At Puppet, we spoke of an operational rhythm, which is essentially the set of repetitious tasks we run and the cadence we execute them on to keep the business working. But the OKR system as presented includes no operational rhythm, no indication that people are involved in creating these goals or that doing so takes any time. So we invented our own rhythm:

  • As early as possible each period, the management team meets to decide the company OKRs. This started out as a 45-minute meeting that just recorded the goals that were in my head, but evolved over years into a two-day offsite where the leadership team first acquired a shared understanding of where the business was and what we needed to do, then built the goals from there. In retrospect we should have put in these longer days earlier; your team should frequently think deeply about what you should be working on, rather than just running all the time.
  • The rest of the company has some time to build its OKRs from the top-level goals. Initially this was a couple of days, but it eventually morphed into a couple of weeks.
  • These cascaded goals are then used to modify the company OKRs if needed. (In other words, we supported a merged top-down and bottom-up planning model.) This is when management would learn if our view of reality was materially different from that of the people at the front line.
  • At the end of every period, the management team records how we did against our goals. Again, this began as just writing down the score, but grew to become a more complete retrospective run by a project manager. This meeting it at most a couple of hours long, and just includes the leadership team.

When we began this process, we wanted short-term goals, so we ran this cadence eight times a year; thus, we called our planning periods “octaves.” As we matured and could think and execute in a more long-term fashion, we reduced this to quarterly.

I think this system is sufficient for most companies of 15 to 250 people. Some companies might grow out of this at relatively few people, whereas others might scale very well with it. I expect most people could scale this system successfully by gradually increasing the amount of time spent on each session, with more time in deep discussion, and also by assigning a project manager to run it. I ran the whole process until we were probably 250 people, which was a mistake that took too much of my time, resulted in too centralized of an organization, and limited our effectiveness because I suck at project management.

Note that these are pointedly not plans; that is, they are not step by step instructions for how to achieve a goal. We’re declaring what we want done, but not how we expect to do it. This is both a blessing and a curse. On the one hand, it provides a lot of freedom for people at the front line to figure out the right way of accomplishing something, but it also leaves a gaping hole in your organization. At some point, someone has to actually do the work, but where in your operational rhythm does a team translate goals into a plan for accomplishing them? Do you make that time? We didn’t until far too late, and it mattered.

Scaling

As we scaled the company and this system, we found a few critical gaps.

The biggest one is obvious enough that I cringe now just thinking about it. You would never try to build a product without being clear on who would do the work and, of course, you shouldn’t try to accomplish your company’s goals without assigning each objective and key result to an individual, yet our initial version (and the one presented by Doerr) had nothing to say on people. At some point we added the requirement that every objective had a name assigned to it, which was a huge change for us – and a really positive one.

The lack of accountability for each goal was exacerbated by the fact that we didn’t have any mechanism for in-quarter check-ins on the goals. We’d frequently only find out at the end of a quarter that a goal was going to be missed, when it was far too late to do anything about it. So we built a weekly operations review (“ops review”) where we reviewed progress against the goals. This meeting is a predictive exercise, not a status statement. Goals are green if you expect to accomplish them on time, even if you’re still two months away from the deadline. We mostly focus just on the areas we don’t expect to hit, which allows us to invest early in correcting our execution or changing our expectations.

It’s worth reiterating, because this was so hard to get people to understand: The goal of the ops review was not to describe the status of each goal; it was to build a shared understanding of whether we were likely to achieve our goals and then build an action plan to resolve the predicted misses. The majority of people entered that meeting with a belief that they needed to justify their paycheck, and it took a lot of education to get them to understand the real purpose.

This addition to our rhythm was pretty awesome. In one move, it basically eliminated the firefighting that had driven so much of our execution. We still had fires periodically, but they were actual surprises, not just sudden surfacing of old information, or realizing at the end of the quarter that a goal never had an owner.

The downside of the ops review is that it’s expensive (it necessarily includes a lot of top people at the company) and it takes a lot of work to make this kind of meeting worthwhile every week. I got the idea for this meeting from the excellent American Icon, about how Alan Mulally turned around Ford. A long, weekly operations review with his senior team was one of his key tactics. My team often complained that weekly was too frequent, but if a company as big as Ford was responding weekly to the conditions on the ground, shouldn’t a small startup be at least that responsive?

Around this time, we integrated the budgeting process into the planning process. It’s important to recognize they’re different — you should build the plan you want then find a way to budget for it, rather than building a budget for your departments then letting them decide how to spend it. It’s important that your should be good at both, though, and it was around this stage we started to develop the budgeting skill and learning how to integrate it into planning. That was painful, to put it mildly.

As we scaled, the company goals tended to get expressed in terms of departmental targets within sales, marketing, engineering, etc. When we were small, this seemed like a feature because it had natural lines of ownership, but as we grew it became clear it was a critical flaw. It’s important to translate plans to people and teams, but this was dysfunctional. It discouraged people from building goals that relied on other teams, and thus encouraged silos in the company. Talk about a failure mode. When we added names to each objective, we rebuilt the whole process to be structured from the top down around company goals rather than team goals, which allowed us to crack this departmental view and force shared goals and collaborative execution.

We also eventually added a layer of OKRs above our annual goals, giving us a roughly three year time horizon. These became crucial in sharing and deciding what the priorities were for a given year.

What might come next?

The above roughly describes the system as it stood when I stepped down from Puppet in 2016. It was obvious at the time that we were in need of another step-change in capability in our planning system, but the new CEO took responsibility for driving that. By the time I left, we could see many opportunities to improve what we were doing.

The big one is that we needed to push all the local knowledge about this process into code. We were using multiple different formats and tools, because different meetings require different interactions, and it was too difficult for most people to track what was happening, where, and why. For instance, our source of truth for the OKRs themselves tended to reside in Trello, but it’s a poor fit for storing updates and presenting the predictions of whether a goal would land. I couldn’t imagine trying to run a report on quantitive goals based on Trello data. Thus, we ended up storing the weekly updates in spreadsheets, which are exactly as powerful and readable as shell scripts. It meant we couldn’t trust most people to update the data, because the document was so complicated. I would have loved a single source of truth that anyone could use. In addition, I wanted to have an app automatically pull any data from original sources so I didn’t have team members doing manual work that could be automated (I mean, duh, Puppet is an automation company).

I also wanted a significantly better retrospective process that truly helped us improve the business by laying bare how our wonderfully laid plans went wrong. We were good at the work of looking back and being transparent about where we were, but there was a lot of room for improving how we tie that work to how we operate.

Lastly, I hate that our goals were built around quarters. I think having a cadence for building and validating plans is critical, but it’s silly that this cadence got translated into the timelines for the goals themselves. It often implied that each of our goals would take exactly a single planning cycle. Some obviously do — we have quarterly sales targets that we need to hit during exactly a quarter — but many of our top-level objectives were shoehorned into a quarterly system. I’d much prefer a Kanban-style on-demand planning system that would allow us to have a high-fidelity plan for what we’re working on now, and a quality backlog for what we’ll do as goals complete.

Conclusion

I’m not convinced it matters much what planning and execution system you use, but I’m utterly convinced you should have one. In the end, it’s merely a team-wide mechanism for developing, communicating, and tracking what you’re trying to achieve. It’s obviously important to have goals. I think most of us would agree you should, in some way, share those goals with the team so everyone is working toward the same ends. And, of course, your goals tomorrow should probably be somehow related to your goals today. (This is surprisingly hard.)

If you don’t have one yet, you could do worse than building an operational rhythm from what we built at Puppet. You’ll have to work through a lot of initial discomfort as you translate vague words into technical terms whose meaning is widely agreed upon around your team. But it’ll be worth it.