Great advisors reveal your truth, not theirs

Giving answers is easy, and usually worthless

Photo by Blake Cheek

Being an advisor to other founders is a contradictory affair: Be helpful, but do not give advice. That is, I want to help you do your best work, but I don’t think I can or should do it by telling you what to do or think.

I obviously think I have value to add or I would not sign up to help. Well, maybe it’s not obvious; our industry is rife with advisors who attach their names and little else to projects. It’s true I’m motivated to join partly by the possible long-term reward, but mostly I’m helping because I enjoy it and am learning a lot.

While running Puppet, I was constantly confronted with a classic leadership struggle: How do I simultaneously help people improve their own answers, yet get them to do what I want? There are many who will say this is a false struggle, that I could have avoided it by focusing on empowering people instead of trying to get them to do what I wanted. Pfft. The literal definition of leadership is providing direction and getting people there, and that’s doubly so for a fast-growing startup where alignment is critical to execution. I spent a decade slowly, incrementally, getting better at this, but felt my incompetence as keenly at the end as I did at the beginning.1

Advising companies allows me to practice the empowerment-half of this skill without the other complications. Unlike when I was a CEO, I know I should not be setting direction or making decisions. My job is not to provide answers, but to help people do their own best work.

My only explicit training for this was when I was an organic chemistry lab tech in in college. My primary task was repeating questions back to the students: “I don’t know, which layer do you keep?”2 When I started dating my now-wife in college, she told me her friends were bitter that I would not give them answers. I knew my job. I was there to help them get an education, which required they did the work on their own. This has also been helpful experience for being a parent: “I don’t know, what is 12 times 9?”

Advising CEOs has similar constraints, but it’s a lot more open-ended, and has no answer sheet. In the lab, there was one right answer, it was always the same, and you could reason it out with the information at hand. Labs were also usually a day of work, maybe three days, and mistakes were pretty cheap, in the grand scheme of things. I don’t expect one of those students to track me down later in life and lay at my feet all of their struggles or successes. Most importantly, we were studying an objective space that I did actually know more about. When push came to shove, I knew the answers, and I could reason out anything that wasn’t obvious.

Helping CEOs is considerably harder. I’m rarely asked about questions that have a single right answer. No competent CEO would bother getting advice on an easy question, or one whose answer wasn’t important. Wrap into this the fact that I can’t possibly know the company as well as the person asking me the question.3 It’s inconceivable that I would often have answers available that the expert in the seat doesn’t.

That simplifies the challenge: Prod the questioner into getting to their own answer, no matter how much they complain. And they do sometimes get upset: I had a CEO exasperatedly demand what I would do, after a long session of forcing him to work through what he cared about, what he saw as the right answer. When I relented — only after he had already done all the hard work — he could see how thin and useless my answer was. By the time he’d decided what to do, he saw that what he learned from the process was at least as important as the answer, and my just providing a solution could never give that.

There is still some risk. I’m by no means a master of this technique. I know I have at times presented people’s options in stark ways, which sometimes felt like no choice at all. My own predilections, such as toward a consumer-style sales model, are hard to separate from any guidance I might provide. It’s honestly just hard to know sometimes whether you’re successfully getting someone to express their own implicit belief or leading them to agree with one of yours.

It’s a skill I expect to spend the rest of my life trying to master. But it’s worth doing, and I’m enjoying the learning process.

Helping CEOs instead of running my own company provides a kind of repeatable laboratory environment. I get to learn at the same time, though, because it’s much harder than being a lab tech.

It’s not enough to just parrot questions back. I spend my time listening closely and drawing out more information, then replaying back what I heard. Listening is a woefully underrated skill. I’ve been loving the opportunity to practice really hearing what people are saying, and trying to differentiate between the words they use, the meaning behind them, and their intent in saying it at all.

As you look for advisors, be sure you demand the same discipline from them. Don’t accept answers. They should hear you, understand your dilemma, and be able able to point out where you haven’t thought completely, or clearly.

A great advisor should provide light, not direction.

  1. If this whole definition of leadership annoys or offends you, I’d ask how you differentiate between leadership and management, and also how you expect a company to align around a direction without someone picking the direction.
  2. Nearly every experiment in organic chemistry involves using liquids to separate chemicals, where part of the solution ends up in an aqueous (watery) layer, and the other ends up in another layer, like separated oil and vinegar in salad dressing. One of those layers is now waste, and the other one has the chemical you’re working on. Don’t throw away the wrong one!
  3. This is another big difference from when I was the leader; I knew Puppet itself better than anyone, even if I could not know your specific area as well.

Hold on to your why

Founders need to retain their own mission while they build out the company’s.

Photo by Sharon McCutcheon

Managing a high-growth company is the hardest thing I’ve ever done. One big reason is that I only received problems that no one else could figure out. Some were organizational problems that should naturally route to the CEO, but a lot were functional issues that I was no more capable of solving than anyone else.

I eventually discerned a repeated pattern in solving these problems. At first I would just get a few issues. I’d muddle through — do a bit of research, ask for help, and sort things out. As we grew, more and more of my time would be spent on this one kind of problem. I’d become better and better at handling it, and just about the time I’d start feeling like I knew what I was doing, I’d realize, “Oh: There are people out there who specialize in this”. I could just hire someone to do it full time, and they’d be better at it than I ever would. Duh.

I’d then spend three months, or six, or twelve, hiring for the role, and bam, suddenly my time is freed up and I’ve got an actual expert in charge. Well, kind of. At this point I’m a self-taught semi-expert who does not buy into the orthodoxy of the role, and we’ve got a year of my weird solutions, so there’s a lot of friction as we sort out just how to add this new skill set to a growing org. But the point is, my time spent on this problem drops precipitously, and I no longer have much opportunity to put my new-found skills into practice.

Usually just in time for something new to come into focus.

This pattern — gain just enough expertise to hire someone — played out again and again, for me and for other founders I’ve talked to.

In some ways it’s thrilling. You get experience with all of the key areas at the company, and you’re always learning something new.

In other ways, though, it is soul-crushing. Over the eight years I managed Puppet while in fast hiring mode, I rarely got to spend time doing anything I was good at. Humans have a psychological need to feel competent, to feel like they are in control and know what’s going on. I don’t need this all the time, but please, just a little? Sometimes? Nope. Pretty much the second I started to feel like I understood something, I had to hire for it, and my problem changed from doing to managing.

After years of this, I knew just enough about everything to suck at it, but not enough to actually be useful to anyone.

Only as my tenure as CEO came to a close did I begin to see what I uniquely added to the organization. I began being comfortable not delegating certain problems, and felt justified in spending hours on something as an individual contributor, rather than seeking leverage in everything I did.

Only once this happened did I start to feel comfortable as a CEO. I wasn’t just routing problems, I was actually solving some of them. I was not spending 100% of my time in areas I was incompetent; just most of it.

I know the advice as well as you: Great leaders delegate, they empower. If you’re doing the work yourself, you’re not a real leader.

Bullshit.

Yes, building and running a team absolutely requires that you empower the team. But that doesn’t mean you don’t get to do anything yourself, that you hand everything off and have nothing left.

Just like everyone else, you, too, need a reason to show up, to stay engaged. You have to hold on to your own why.

If you don’t remember why you, personally, are in the job, then you’ll look up in a few years and realize it’s not there any more. You’ve moved too far from what gets you up in the morning, and suddenly you can’t do it. Or worse, the company has developed but you haven’t. You’re no better at the thing you want to master than you were when you started, because you haven’t been spending time on the problems you care most about.

Some of this is that you need a place of safety. I am a highly fireable person, and raising venture capital made for downright tenuous tenure. The less confident I was about my own strengths, my own value, the less safe I felt. And humans need to feel safe to do great work.

More than that, though, I needed a platform for learning. I was pursuing mastery, but of what, exactly? Of not mastering things?

I know other leaders really are master delegators, hirers, organizers, etc. But that was never going to be me.

I had to peel things back, really understand why I was there, what I cared about, what I wanted to be the best in the world at. And, really, what I was good enough at that I ended up in this place, running this company. Then, as the problems rolled by, I could be sure to push that forward just a little bit, even if my focus was on the organization’s needs, not my own.

The times I lost this sense of why I was there and what I was getting better at were some of my most depressing days. But the days where I could connect what I felt good at, what I spent my time on, and what the company needed from me were the best days.

I don’t think that’s any different for me, or for other founders, than it is for anyone else.

But all the discussions of leadership I hear leave this bit out: You’re a human, too. You have to provide the why for the whole organization, but every individual deserves to be able to translate that into what they do every day. Even you.

How to Neg a Founder

Is that a compliment, or an insult?

Photo by John Salvino

My experience growing and fundraising for Puppet was full of inspirational-sounding phrases that cut like a knife. Aggressive goals got praise for wanting to “build a real product” and “really scale this thing.” These are some of my favorites. And when I say “favorites,” what I mean is, I hate them. Deeply.

The one that I heard most often made me want to walk out of the room. I’d pitch an investor while fundraising, and he (always he) would say: “So you’re going to try to turn this into a real company, eh?” As if being my full time job for years was somehow not real. As if you are the arbiter of truth, not my customers. Or me.

If you want to make an entrepreneur feel small, you really want to piss them off, try to inspire them this way. I assume most people who used it thought they were complimenting me, impressed that I was taking this big step or something. But it was a sure fire way to trigger my defenses. When you diminish the work I’ve done so far, it’s hard to see you as a potential partner. I quit my full time job five years ago, and have missed out on hundreds of thousands of dollars of earnings, but asking you for money is what shows I’m serious?

I’m convinced at least some investors did it on purpose, as a form of negging — trying to position themselves as an authority and me as someone who needed their help and wisdom. “That’s pretty cute. Why don’t you get some help from the professionals?” I’m good, thanks.

I know most people didn’t mean it that way, though. Their worldview is just so skewed that if you haven’t raised a ton of money, you’re not really trying. They can only conceive of success if it looks a specific way. You literally cannot succeed unless you do what they do, what all their friends do.

If you’re an investor, advisor, or executive, take a deep look at how you talk to founders. Are you truly complimenting them, or actually diminishing their work? Are you presenting yourself as the arbiter of success, even while you think you’re saying the other person has done so well?

If you’re a founder, know that you don’t have to take it. No one else gets to define success for you. There’s always an in-crowd, but by definition the best results come from being outside of it. Even if you decide you need their money, you don’t have to accept their framing.

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.

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.

Where does your work live?

Most of our software is confused about what job we’ve hired it for

I’ve really enjoyed playing Zelda: Breath of the Wild, but my life has been changed more by one of its reviews than by the game itself. The review had a unique view on what made the game so great. It contrasted Zelda to other games — Destiny, for example — saying that while others tended to distribute gameplay across multiple areas (e.g., in Destiny, the radar is a critical part of the game), Zelda really focuses the game into the main screen where you walk, glide, ride, and fight.

The review (which I unfortunately cannot find, because of the quantity of posts online that all use similar words) called this “where the game lives”. I love what this phrase evokes. I absolutely loved the game Borderlands, but I was deeply frightened of ever finding out how much time I spent at its store screen, because item collection and management was such an important part of the game. A lot of its fun was specifically from the collection, rather than the playing, but that meant a large chunk of the game lived in the store, as opposed to out in the world.

Most of our software could use a similar dissection.

Like Destiny and Borderlands (which are both great, and quite similar), the tools we use show a surprising distance between what they help us do and what we’ve hired them for. If I may be permitted to steal from this review, this distance is a sign that our software is confused about where our work lives.

To pick a counter-example, I’m writing this post in Ulysses. People who choose this software laud its simplicity, which makes it easy to focus. What they really mean is, all you can do with it is write. There’s almost no formatting, very little organization, very little anything but writing. The work lives in the writing. (My first draft was written on an ipad, which further simplifies that focus.)

Contrast that with any task or project management tool. My wife and I are in the middle of planning a bunch of camping, and we’re using Trello to organize many of the options. What is Trello’s opinion about where the work lives?

Last time I looked, my wife had three browser windows open, each with about fifteen tabs. She’s also working in RoadTrippers (Pro, natch). To get this work into Trello is a process of copying, pasting, writing copy about why you pasted it, and then using Trello to file it so you can find and manage it later.

In this operation, where does the work live? It’s scattered across maps, calendars, browsers, and applications like RoadTrippers. Does Trello know that? Does it agree? How does its opinion of where the work lives affect its utility? Brief introspection leads us to conclude Trello has no idea where the work lives, and the humans using it are entirely responsible for connecting the two.

Here’s a simple exercise for anyone using a task tracking app: Envision yourself going into that app and just marking everything done, even though you obviously haven’t done the work. It hurts to even consider, doesn’t it? Your brain has absorbed that these tasks are representations of work, and it’s your job to match the representation to the work, because you know the tool won’t do it for you. When you mark something done, of course nothing goes out and does the work; you’re just lying to your software about the state of the world. And it has no idea! This disconnect is what leads to an allergic response to the idea of marking work done in software that is not yet done in the real world.

I’d like to say that Trello was just a bad example, but I think all task tools share this confusion. Bug trackers and project management tools are specialized examples of this, and they obviously have no idea where the work lives. If I’m writing code, all of the work is done in my text editor, in files on disk, and maybe in my testing tools to ensure the work is done and done right. I then go somewhere entirely different to mark the work done. Why? Shouldn’t GitHub know it already? Why do I have to explain it? The answer is because these trackers think tracking is the work, when of course, the work is the work.

It’s no better in personal tools. I just started using Things 3 for my own tasks, nearly all of which end up being expressed in email or calendars, yet Things 3 has no conception of either. It has no idea where my work lives, and expects me to put out all of the effort necessary to connect them.

Speaking of email and calendars, they have their own role in this conversation.

Email is interesting. Everyone hates it, because it’s so important to everyone that we use it constantly, yet this animosity is a result of its utility and criticality. In other words, people hate it because it works so well. But when you’re doing email, what work are you actually doing?

I’m not sure I know. You’re communicating. But usually, you’re communicating about some other kind of work, like a document, a meeting, or some kind of activity that takes place outside of the inbox. A well designed application will remove the need for communication via email — Google Docs is a great example of this. Its sharing and commenting features have allowed many discussions to move from email to where the work is, in the document itself; their addition of suggestions has doubled down on focusing on the work, rather than talking about the work. (Note that this is completely different from Slack, which advertises that it gets rid of email, by which it means it moves the conversation, not that it does a better job of bringing the work into the software.)

Of course, how do you have Google Docs tell you someone commented on your document? Email. 🙂

What about calendars? Why do calendars exist? As a tool, where does their work live?

I am thankful to have had to try to explain to a friend my position on this, otherwise I’d think it was easy to understand. It’s so counter to how people work today that a relatively obvious truth is impossibly counter-intuitive: calendars are about how I spend my time.

When using a calendar, the work is what you actually do. You, a person, out the in the world. That’s what the calendar is about. Its job is to ensure you do the right things at the right time, with the right people, in the right place. It’s about doing, not documenting, managing, or notifying. You can put something in a calendar and not do it, or do work that’s not in the calendar; any of us would say, obviously, that it’s what you do that matters, not what the calendar says. Merely creating an event has no effect, and thus no value; it only matters if it then affects your behavior. The work lives in what you do. But does your calendar make even the slightest attempt to directly manage how you spend your time? What would that even look like?

To pick a small example, my calendar apps seem to not care what city I’m currently in, or where I’m physically located. Isn’t this weird? The tool whose primary job is to manage where I am physically located makes no attempt to represent or take into account the core fact it is meant to control. It still dumbfounds me.

Yes, they can tell me in real time when I should leave for a meeting based on travel time (as long as travel involves driving, rather than walking down the hall to a conference room), but they can’t say, “Given that on Tuesday you’ll be in Portland, working from home, you should block out travel time to get downtown to lunch and back”. That is, they can alert me in the moment, but they can’t do their core job — reserving time to ensure I’ll be doing the right thing in the future. Because they can’t do this, I have to create those blocks myself, else I’ll find myself choosing between skipping one appointment or being late to another. The whole point of a calendar is to manage time, but in this simple example they fail to ensure I will have space to transition my corporeal existence between physical locations. Shouldn’t that be step one, rather than an exercise left to the human?

I also reserve time for tasks I do alone every day, like working out and writing. I do this primarily to ensure it gets done, rather than because those times are special (although I do get a bit jittery now if I don’t write first thing in the morning). There’s no way to explain to my calendar what I’ve actually blocked that time out for, and thus no way for it to respond to whether I’ve done it or not, even though my computer knows if I’ve done my writing, and my watch knows if I’ve worked out. Wouldn’t it be great to see your calendar dynamically rearranging your day because it noticed you missed your workout?

My calendar is confused about what work I’ve hired it to do, and therefore does not know it needs to look in those places.

We’re so used to the idea that our software represents the work that we seem to have lost hope that it will actually help us do it. Most of the tools we use are entirely disconnected from the work they’re supposed to help us with. Marking something done does not do it, deleting email does not indicate communication has happened, sitting at your computer while your calendar says you’re writing does not produce text. The representations are not the work, yet we forgive our tools for only dealing in representations, not actual work.

I don’t know if that reviewer was right about why Zelda: BoTW is so great. I can’t even imagine what all the software I use would look like if it were built around where my work lived, rather than merely being used to model and manage it.

What I do know is that our software can and should be built to help us do the jobs we’ve hired it for. But because it is confused about why we use it, what we do every day is lower quality, less fun, and just downright confusing.

This also shows just how much opportunity there is to improve the software we use on a daily basis.