It Doesn't Have to Be Crazy at Work

The third and currently final DHH/Fried book about work that I had long planned to read. In hindsight, maybe I should have skipped Remote and Rework. I’m fairly certain It Doesn’t Have to Be Crazy at Work is by far their most popular book, and it contains many things from the two earlier entries. It was noticeably more concise and to the point, and thus an even quicker and easier read. I said that most people should probably give the first two books a shot, but everyone should read at least this one. You won’t stop nodding your head furiously while reading. That said, I’ll now jump straight into the “annotated quotes” format again.

My annotations

Stress is passed from organization to employee, from employee to employee, and then from employee to customer. Stress never stops at the border of work, either. It bleeds into life. It infects your relationships with your friends, your family, your kids.

Very important life lesson. A healthy work culture benefits everything you do, at work and at life. Unhealthy work culture poisons everything, at work and at life. Kinda obvious, seeing how most of our lives are defined by our work.

Sitting in meetings all day isn’t required for success.

Amen. Don’t get me wrong, I love a good meeting. But hot damn, a good meeting is very hard work. And everyone in the meeting has to do that work. Which rarely happens (and I’m not excluding myself here, because just sitting through a meeting is infinitely easier than arguing why the meeting makes no sense in the first place), so a lot of meetings are a waste of time.

The opposite of conquering the world isn’t failure, it’s participation.

I wish the whole world was more about participation and less about conquering. So many things that are just a gigantic pile of shit these days are that way because in capitalism as we have it, participation is not enough, and conquering is the only thing that’s rewarded. It’s not enough for Facebook to be the biggest social network in the world, they also need to have Instagram and WhatsApp. It’s not enough for Spotify to have music, they also need to “conquer” podcasts. It’s not enough for Apple to have desktops, laptops, smartphones, tablets, and smartwatches. And an App Store. And a music store. And a movie store. And movie rentals. They also need a TV streaming service. And their own TV productions. And a music streaming service. And a gaming subscription. It’s not enough for Amazon to be the biggest online retailer this planet has ever seen, they also need to have AWS and WholeFoods, and Kindle, and FireTV, and Alexa. Don’t even get me started on Google. We’re already deep into the dystopian end times of mega corporations ruling our lives, they just have more familiar names than the theoretical villains in the movies.

Because let’s face it: Goals are fake. Nearly all of them are artificial targets set for the sake of setting targets. These made-up numbers then function as a source of unnecessary stress until they’re either achieved or abandoned.

Nothing shattered my belief in these kinds of “goals” more than seeing them abandoned again and again when they turned out to be hard to reach. And I don’t mean redefined, or postponed, but literally treated as if they never existed in the first place, after being relentlessly pursued as if they were the only thing that mattered in the universe for months.

Plus, there’s an even darker side to goal setting. Chasing goals often leads companies to compromise their morals, honesty, and integrity to reach those fake numbers.

I wish I could not confirm that, but by now I’ve seen that happen so often that it’s really hard to not be completely cynical about any morals or values that a company claims to have.

You can absolutely run a great business without a single goal. You don’t need something fake to do something real. And if you must have a goal, how about just staying in business? Or serving your customers well? Or being a delightful place to work? Just because these goals are harder to quantify does not make them any less important.

The most important goals are almost impossible to quantify in my experience. Trying to do so just wastes time and energy that would be better spent actually achieving those goals.

One thing at a time doesn’t mean one thing, then another thing, then another thing in quick succession; it means one big thing for hours at a time or, better yet, a whole day.

I’m always most productive, happy and energized when I do as few different things per day as possible. Most days I’m juggling between three and six things, which is quite exhausting, but slowly I’m getting better at managing that myself. What makes this so hard: The more things there are to do in general, the harder it is to focus on a single thing. And I do think that company culture plays a large part in how many things there are to do in general.

A while back I did some kind of internal tech support/triage, which of course was many more different things per day – but back then, that was almost my only duty. In that case I still considered “answering twenty different tickets for six hours” one thing, and it felt good doing that. There are jobs that consist of doing many small things after another, which is perfectly fine. In those cases, interrupting that main task of “handling the different things” is what should be avoided, e.g. a support person that’s also required to write project proposals and do reviews and has to switch between these three things constantly.

Ask people where they go when they really need to get something done. One answer you’ll rarely hear: the office.

That’s right. When you really need to get work done you rarely go into the office. Or, if you must, it’s early in the morning, late at night, or on the weekends. All the times when no one else is around. At that point it’s not even “the office”—it’s just a quiet space where you won’t be bothered.

A lot of my coworkers say they miss the office, and to some degree, I miss it as well. But I miss it as the social space where I meet colleagues and friends, not as a place where I can be particularly productive. No matter how you feel about remote work and office life, but I have never met a single person that hasn’t said something along the lines of the above quote.

Modern-day offices have become interruption factories. Merely walking in the door makes you a target for anyone else’s conversation, question, or irritation. When you’re on the inside, you’re a resource who can be polled, interrogated, or pulled into a meeting.

I really don’t miss the office as a place to be productive.

We have all sorts of experts at Basecamp. People who can answer questions about statistics, JavaScript event handling, database tipping points, network diagnostics, and tricky copyediting. If you work here and you need an answer, all you have to do is ping the expert.

That’s wonderful. And terrible.

It’s wonderful when the right answer unlocks insight or progress. But it’s terrible when that one expert is fielding their fifth random question of the day and suddenly the day is done.

The person with the question needed something and they got it. The person with the answer was doing something else and had to stop. That’s rarely a fair trade.

The problem comes when you make it too easy—and always acceptable—to pose any question as soon as it comes to mind. Most questions just aren’t that pressing, but the urge to ask the expert immediately is irresistible.

That last sentence is such a critical thing. I still have to fight the urge to “just real quick” check something with someone. But it’s true: I almost never need a quick response. I need a reliable and high-quality response at some point. And so often things are not as quick and easy as first thought, so “real quick” is almost always a bad idea.

Now, if the sole reason they work there is to answer questions and be available for everyone else all day long, well, then, okay, sounds good. But our experts have their own work to do, too. You can’t have both.

This is something that always fascinates me – a lot of people seem to think that most other people have nothing else to do than to answer their questions. While in reality, most companies employ no one whatsoever whose sole purpose is to answer questions. I’ve literally had someone ask me if I was bored today as they hadn’t asked anything for an entire morning. And they were not joking, they were curious.

You can’t plan your own day if everyone else is using it up randomly.

Sadly, often the company culture is not helping here. Statements like “We’re a team, we always help each other!” make you feel guilty for protecting your time and own work. Most companies want it both ways: You have to always help everyone so things run smoothly, and you have to be able to plan your own work reliably. That is impossible and leads to burnout.

Have you looked at your own calendar lately? How many things did you put there? How many things did other people put there?

When you optimize people’s calendars for effortless carving, you shouldn’t be surprised when people’s time is sliced up. Furthermore, if you make it easy for someone to invite five other people to a meeting—because software can find the open slot that works for everyone—then meetings with six people will proliferate.

Did I already mention that I’m not a fan of most meetings?

Taking someone’s time should be a pain in the ass. Taking many people’s time should be so cumbersome that most people won’t even bother to try it unless it’s REALLY IMPORTANT! Meetings should be a last resort, especially big ones. […] If you don’t own the vast majority of your own time, it’s impossible to be calm. You’ll always be stressed out, feeling robbed of the ability to actually do your job.

I can confirm that, and really try only using meetings as a last resort these days. As a bonus, when using (digital) asynchronous communication, you get searchable documentation of that communication for free.

It’s easy to excuse this game of calendar Tetris with “But it’s just an invitation!” But nobody ever declines an invitation in good conscience. No one wants to be seen as “difficult” or “inaccessible.”

Indeed. The hard part about meetings should not be saying no to them, it should be creating them in the first place.

The expectation of an immediate response is the ember that ignites so many fires at work.

First someone emails you. Then if they don’t hear from you in a few minutes, they text you. No answer? Next they call you. Then they ask someone else where you are. And that someone else goes through the same steps to get your attention.

Ugh, this is so real it hurts to just read it. If you do this, I don’t like you. (In that moment.)

All of a sudden you’re pulled away from what you’re working on. And why? Is it a crisis? Okay, fine then! They’re excused. But if it’s not—and it almost never is—then there’s no excuse.

It really almost never is. I’ve been at my current workplace for almost five years now, and I think I can count the number of true emergencies with the fingers on one hand. I’ll need a few more hands for all the instances where people acted as if it was an emergency because they didn’t consider the consequences for me.

It’s getting better, but it’s a lot of work to get people to understand this.

[There’s] no reason everyone needs to attempt to know everything that’s going on at our company. And especially not in real time! If it’s important, you’ll find out. And most of it isn’t. Most of the day-to-day work inside a company’s walls is mundane. And that’s a beautiful thing. It’s work, it’s not news. We must all stop treating every little fucking thing that happens at work like it’s on a breaking-news ticker.

One way we push back against this at Basecamp is by writing monthly “Heartbeats.” Summaries of the work and progress that’s been done and had by a team, written by the team lead, to the entire company. All the minutiae boiled down to the essential points others would care to know. Just enough to keep someone in the loop without having to internalize dozens of details that don’t matter.

That sounds like a pretty good way to deal with it. A while back my whole company was restructured with a huge focus on independence and autonomy for each internal unit, and ever since I have almost no idea what is going on anywhere else, even what people who sit in the same office and work on the same codebase as myself are doing. This is not only sad as you can’t celebrate the successes of others anymore, it has also often lead to problems and conflicts.

Companies love to declare “We’re all family here.” […]

We don’t need to bullshit ourselves or anyone else. We’re people who work together to make a product. And we’re proud of it. That’s enough.

I hate the family trope so much, it’s such dishonest and toxic bullshit. Sure, a lot of my coworkers are good friends, and some are amongst my best friends. But that’s it.

You don’t have to pretend to be a family to be courteous. Or kind. Or protective. All those values can be expressed even better in principles, policies, and, most important, actions. The best companies aren’t families. They’re supporters of families. Allies of families.

Corona was a tremendous test for how much a company cares about your actual family, and I personally don’t know any parents who were given the leeway that should have been given so they didn’t needlessly have to suffer.

You can’t credibly promote the virtues of reasonable hours, plentiful rest, and a healthy lifestyle to employees if you’re doing the opposite as the boss. When the top dog puts in mad hours, the rest of the pack is bound to follow along. It doesn’t matter what you say, it matters what you do.

That last sentence is especially important. Don’t underestimate your actions. No one cares about your words when your actions don’t follow suit. That’s one of the things that leadership roles in my professional life struggled with the most.

If you want them to stay home when they’re sick, you can’t come into the office sniffling.

I really hope it will some day become illegal to knowingly come into work while you’re sick. I’ve never been sick as often as I’ve been ever since I started my professional career.

When the boss says “My door is always open,” it’s a cop-out, not an invitation. One that puts the onus of speaking up entirely on the employees. […] Posing real, pointed questions is the only way to convey that it’s safe to provide real answers. And even then it’s going to take a while. Maybe you get 20 percent of the story the first time you ask, then 50 percent after a while, and if you’ve really nailed it as a trustworthy boss, you may get to 80 percent.

I’ve seen a lot of feedback tools come and go at my current place, as of now we seem to have settled on “It’s entirely your own responsibility to find the right ways to give feedback and improve things”. You can imagine how much honest feedback is given. It’s probably an inverse relation to how much discontent and vitriol is instead voiced in private.

The problem, as we’ve learned over time, is that the further away you are from the fruit, the lower it looks. Once you get up close, you see it’s quite a bit higher than you thought. We assume that picking it will be easy only because we’ve never tried to do it before.

Declaring that an unfamiliar task will yield low-hanging fruit is almost always an admission that you have little insight about what you’re setting out to do. And any estimate of how much work it’ll take to do something you’ve never tried before is likely to be off by degrees of magnitude. […] The idea that you’ll instantly move needles because you’ve never tried to move them until now is, well, delusional.

When presented with a question like “How hard can it be?” we used to answer “Pretty damn hard, actually.” but then accept being overruled instead of protesting and demanding that our expertise is respected. “Luckily”, we’ve now been burnt often enough that we do protest, and also more people have accepted that low-hanging fruit rarely are as low as you might think. It’s still something you always have to actively be on the lookout for, though, even in yourself.

Whoever managed to rebrand the typical open-plan office—with all its noise, lack of privacy, and resulting interruptions—as something hip and modern deserves a damn medal from the Committee of Irritating Distractions. Such offices are great at one thing: packing in as many people as possible at the expense of the individual.

I cannot overstate how much better it was having my own office at my first job. I enjoy banter in the office, sure. But that can happen at lunch or at random breaks. At my current job where I don’t have my own office I often used to sit alone in one of our conference rooms and even that made it so much easier to focus on my work.

When sales or service people, who often need to be loud and jovial on the phone, have to share accommodations with people who need long stretches of quiet, you’re not only destroying productivity, you’re fomenting resentment.

It’s absolutely insane to put people who need to use a phone for work and people who don’t in the same room. You might as well just burn their salaries.

In spaces like that, distractions spread like viruses. Before you know it, everyone’s infected.

Well that metaphor sure didn’t age well.

When someone takes a vacation at Basecamp, it should feel like they don’t work here anymore. We encourage them to go completely dark: Log out of Basecamp on their computer, delete the Basecamp app from their phone, and don’t check in. Go away for real. Be gone. Off our grid.

The whole purpose of a vacation is to get away. To not only be somewhere else entirely, but to think about something else entirely. Work should not be on your mind. Period. […] If you work full-time, when was the last time you actually got to disconnect full-time? Not for a weekend, but for weeks. When you didn’t hear from coworkers while away. When you didn’t feel any guilt or urge to check in and check up on work.

In that sense my last true vacation is more than three years in the past. I need a vacation, but unless I leave the country I’m having a hard time to get my mind off of work, and currently I’m not too keen on traveling.

[It] happens in organizations all the time. A single snarky remark can cascade into a storm of collective snark in the same way that a single spark can ignite a forest fire. And, implicitly, when you let it happen, it becomes okay. Behavior unchecked becomes behavior sanctioned.

It can be very hard to say “Hey, I really think we shouldn’t use ‘retard’ as a pejorative. I know you don’t mean it that way, and we all sometimes say things impulsively.” – even when it’s not in an actual conflict but just banter at the foosball table. But that’s the right time to do it, because it is ten times harder to say something later that day or week when a slur like that is used for the third time. “Why didn’t you say something sooner?”, “But he said it too!”, and whatnot. I’m grateful to be in the position that my coworkers are not only open to these things but actually on the lookout themselves. Despite that it’s still hard to speak up for me, because so often I don’t say something right away and let the issue grow bigger than it needs to be, both on its own and in my mind.

We kinda knew it wasn’t right, but we didn’t stop it. Which just made it that much harder when we finally decided enough was enough.

Unwinding the new normal requires far more effort than preventing that new normal from being set in the first place. If you don’t want gnarly roots in your culture, you have to mind the seeds.

Very true, and also one of the main reasons why I’m very hesitant to not doing things properly in the first place. A dirty hack is the new normal quicker than you can type “We’ll improve it afterwards”.

[I]n business, you may have to make multiple major decisions monthly. If every one of them has to be made by consensus, you’re in for an endless grind with significant collateral damage. The cost of consensus is simply too much to pay over and over again.

Easily the single best thing about our work culture is that we strongly utilize consent for decision-making. Consensus is nothing but pain and suffering.

You just can’t bring your A game to every situation. Knowing when to embrace Good Enough is what gives you the opportunity to be truly excellent when you need to be.

We’re not suggesting you put shit work out there. You need to be able to be proud of it, even if it’s only “okay.” But attempting to be indiscriminately great at everything is a foolish waste of energy.

While I agree wholeheartedly, the problem here is that people have very different opinions about what’s “okay”. I know that I’m a perfectionist and often let “perfect” be the enemy of “good”, but I strongly believe that I have a pretty good handle on it by now. What I struggle with is how to handle situations where someone else’s “okay” is miles away from my “not acceptable”.

Time-management hacks, life hacks, sleep hacks, work hacks. These all reflect an obsession with trying to squeeze more time out of the day, but rearranging your daily patterns to find more time for work isn’t the problem. Too much shit to do is the problem.

The only way to get more done is to have less to do.

Saying no is the only way to claw back time.

Saying no is also incredibly hard, as already mentioned above.

If the boss is constantly pulling people off one project to chase another, nobody’s going to get anything done.

“Pull-offs” can happen for a number of reasons, but the most common one is that someone senior has a new idea that Just Can’t Wait.

These half-baked, right-in-the-middle-of-something-else new ideas lead to half-finished, abandoned projects that litter the landscape and zap morale.

Yet another thing I wish I wasn’t as intimately familiar with. To be fair though, the focus on autonomy that came with our restructuring helped a bit in this aspect.

We’d come up with a new design that moved the stuff around a bit too much to make room for something better, and all we’d hear is “WHAT DID YOU DO TO MY APP! I LIKED IT JUST HOW IT WAS! CHANGE IT BACK!”

The standard playbook in software is to dismiss users like that. Hey, this is the price of progress, and progress is always good, always better. That’s myopic and condescending. For many customers, better doesn’t matter when comfort, consistency, and familiarity are higher up on their value chain.

I enjoy ridiculing people who are against change out of principle as much as the next guy, but this is a very valid point. Change just for the sake of change is bad as well.

Here’s something that should be obvious: People don’t like to have their grievances downplayed or dismissed. When that happens, even the smallest irritation can turn into an obsessive crusade.

Imagine you’re staying at a hotel, and the air-conditioning isn’t working right. You call the front desk to mention it, and they say, oh yeah, they know about that, and someone is going to come fix that next week (after you’ve left). In the meantime, could you just open a window (down to that noisy, busy street)? Not a word of apology, no tone of contrition.

Now what was a mild annoyance—that it’s 74F degrees when you like to sleep at 69F—is suddenly the end of the world! You swell with righteous fury, swear you’ll write a letter to management, and savage the hotel in your online review.

Jean-Louis Gassée, who used to run Apple France, describes this situation as the choice between two tokens. When you deal with people who have trouble, you can either choose to take the token that says “It’s no big deal” or the token that says “It’s the end of the world.” Whichever token you pick, they’ll take the other.

Excellent way of putting it. It baffles my mind how many companies get this wrong when doing support. It’s not limited to that, though. The same applies for internal feedback as well – with just one disregarding response an issue can instantly multiply in severity, because now it’s not just about the issue anymore, it’s about how issues are dealt with.