Notes on “It Doesn’t Have to be Crazy at Work”

Peter Wildeford

Jun 22, 2022 — 9 min read

“It Doesn’t Have to be Crazy at Work” by Jason Fried and David Heinemeier Hansson is a brazen ad for working at Basecamp, the company founded by the book’s authors. But if you can get past that, it has some good advice for those managing companies and designing how companies ought to work. And if you’re not in a position where you are designing a company, it gives you ideas for what to push for where you do work or what you should consider looking for when you look for your next job.

However, this book is not that helpful if you're a regular worker (non-executive) and you're looking for ways to make your work less crazy, since many of these suggestions will not be something within your power to implement. Something to look for in your next job I guess. (Have you thought about working at Basecamp?)

Also I'd point out that not every idea in the book is a winner in my mind and I certainly have some disagreements with the authors. In these notes I just aim to summarize what I find as the key takeaways of the book, from my understanding and as applied to my personal context (running a non-profit not a for-profit), rather than try to present my all-things-considered view on how best to run a company.

Why is it crazy at work?

So why is it crazy at work? Fried and Hansson cite two main reasons:

the work day is sliced into tiny fleeting moments due to many distractions
there is an unhealthy obsession with growth at all costs

Instead, the alternative mindset is to focus on protecting people’s time and attention, having reasonable expectations, and providing ample time off. This alternative lifestyle is async and independent.

Think of your company’s work experience as a product that you are selling your employees and figure out how to make your company attractive and advertise the idea of working at your company (hint: write a book about how great it is to work there).

Focus on doing good work and being fair with your customers and your employees.

De-slicing the Work Day

Protecting employee time and attention is the most important thing for getting good work out of a reasonable 8 hour work day.

8 hours is enough time to fly from New York City to London, but such a flight feels so much longer than a typical 8 hour work day. Why? Because it is continuous and uninterrupted. That’s not what our work day feels like.

An uninterrupted hour lets you do good work, but a typical work hour is more likely to be 20 minutes on a phone call, 10 minutes with a colleague who taps you on the shoulder, 10 minutes on your desired task, 10 more minutes being interrupted by a work conversation near your desk, and then 10 minutes on your desired task. All the context-switching and distraction breeds an inability to focus and get things done and makes people frustrated and short-tempered.

What causes these issues?

The open-plan office is an incredibly expensive distraction machine, surrounded by distracting sounds and where you can be very easily interrupted
Meetings are costly. A meeting with eight people for one hour doesn’t just take one hour, it takes eight hours.

A lot of these topics are very similar to the ones brought up by Cal Newport in “Deep Work” (see my notes on this) and “A World Without Email” (see my notes on this) and I encourage you to turn to those guides for more details and solutions.

In my notes on “A World Without Email” I mention the distraction-urgency trade-off where it is costly to distract someone but still valuable to get their input on something when you are blocked - Basecamp claim to have solved this trade-off by having subject-matter experts use office hours.

Ending Hustle Culture

Basecamp avoids setting goals (other than being profitable) because goals have a dark side: they promote an unhealthy hustle culture that doesn’t let anyone take a break and they potentially promote compromising on ethics (e.g., hit a revenue target by making it harder for customers to request refunds). Also, long-term goals tend to produce a false sense of security in the face of a quickly changing world and put pressure on the company to not change their plan in the face of something changing.

It’s important for the boss to model this change in culture. As the boss, off-hand things you say or do are taken seriously. If you want your employees to have work-life balance, you need to have work-life balance too.

Here are some cool things that Basecamp does (cue the ad)

Work remotely
Work 40hrs/wk normally and not more than that
Work 32hrs/wk during the summer (three day weekends)
One month paid sabbatical every three years
Everyone who has been at the company for more than a year not only gets vacation time but gets $5000 to put towards their vacation
Work on shipping a feature (doing a single defined piece of work) within a defined six-week sprint followed by two weeks of more open-ended exploration and figuring out what to do on the next sprint.
The deadlines for the sprint are fixed and instead the scope of the project is decreased to fit the sprint if it looks like targets will not be met.
People write status updates instead of spending time in a status meeting.
Updates about what the teams are up to are communicated to the entire company in a regular newsletter rather than through constant updates with too many details.
Everyone with the same role is paid the same amount and there is no salary negotiation.
They don’t have bonuses but instead just lump it into total compensation, since bonuses tend to become expected things. (Though it looks like, per their current “Benefits and Perks” page, they do now offer bonuses.)
They don’t have stock, but they distribute 25% of annual growth in profit to employees (kinda like a bonus?). And if the company ever is sold, 5% of the sale price will be distributed to employees (now 10% per their current “Benefits and Perks” page).
$1000 per year continuing education stipend - for any skill, even if not work relevant (e.g., learn how to play the banjo).
$2000 per year charity match.
Local monthly community-supported agriculture share (fresh fruits and vegetables at home).
A monthly massage (at a spa, not at the office).
$100 monthly fitness allowance
Their offices have library rules (quiet, very limited interruptions).
Write up ideas prior to presenting them so that people have adequate time to think and review the idea.
Don’t deploy on Fridays.
Work on projects in teams of three (two programmers and one designer).
Keep meetings small, usually at most three people.

At my company (Rethink Priorities, cue our ad) we do (1), (2), (4), (8), (9), (10), (11), and (19). Maybe we’re a great place to work too!

Appendix: Favorite quotes

One enjoyable part of the book is that the writing is very pithy. Here are some of my favorites:

But what if you have a question on Monday and someone’s office hours aren’t until Thursday? You wait, that’s what you do.

As a general rule, nobody at Basecamp really knows where anyone else is at any given moment. Are they working? Dunno. Are they taking a break? Dunno. Are they at lunch? Dunno. Are they picking up their kid from school? Dunno. Don’t care.

"But how do you know if someone’s working if you can’t see them?" Same answer as this question: "How do you know if someone’s working if you can see them?" You don’t. The only way to know if work is getting done is by looking at the actual work. That’s the boss’s job. If they can’t do that job, they should find another one.

At many companies these days, people treat every detail at work like there’s going to be a pop quiz. They have to know every fact, every figure, every name, every event. This is a waste of brain power and an even more egregious waste of attention.

Whenever executives talk about how their company is really like a big ol’ family, beware. They’re usually not referring to how the company is going to protect you no matter what or love you unconditionally. You know, like healthy families would. Their motive is rather more likely to be a unidirectional form of sacrifice: yours.

Balance is give and take. The typical corporate give-and-take is that life gives and work takes. If it’s easier for work to claim a Sunday than for life to borrow a Thursday, there ain’t no balance.

Have you heard about those companies whose benefits include game-console rooms, cereal snack bars, top-chef lunches and dinners, nap rooms, laundry service, and free beer on Fridays? It seems so generous, but there’s also a catch: You can’t leave the office. These fancy benefits blur the lines between work and play to the point where it’s mostly just work. When you look at it like that, it isn’t really generous—it’s insidious.

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.

Following group chat at work is like being in an all-day meeting with random participants and no agenda. It’s completely exhausting.

Our deadlines remain fixed and fair. They are fundamental to our process—and making progress. If it’s due on November 20, then it’s due on November 20. The date won’t move up and the date won’t move back. What’s variable is the scope of the problem—the work itself. But only on the downside. You can’t fix a deadline and then add more work to it. That’s not fair. Our projects can only get smaller over time, not larger. As we progress, we separate the must-haves from the nice-to-haves and toss out the nonessentials.

It’s critical that the scope be flexible on the downside because almost everything that can take six months can also be done in some other form in six weeks. Likewise, small projects balloon into large projects all the time if you’re not careful. It’s all about knowing where to cut, when to say stop, and when to move on.

Another way to think about our deadlines is that they’re based on budgets, not estimates. We’re not fans of estimates because, let’s face it, humans suck at estimating. But it turns out that people are quite good at setting and spending budgets. If we tell a team that they have six weeks to build a great calendar feature in Basecamp, they’re much more likely to produce lovely work than if we ask them how long it’ll take to build this specific calendar feature, and then break their weekends and backs to make it so.

Normal comes on quick. First it starts as an outlier. Some behavior you don’t love, but tolerate. Then someone else follows suit, but either you miss it or you let it slide. Then people pile on—repeating what they’ve seen because no one stepped in to course correct. Then it’s too late. It’s become the culture. The new normal.

There are many reasons to be skeptical of best practices, but one of the most common is when you see someone deriving them purely from outside observations about how another company does it: “Top 10 best practices for how Apple develops products.” Has that person worked on a product development team at Apple? No. They’re simply coming to their own conclusions based on their own assumptions about how they think things work. Unless you’ve actually done the work, you’re in no position to encode it as a best practice.

Furthermore, many best practices are purely folklore. No one knows where they came from, why they started, and why they continue to be followed. But because of that powerful label—best practice—people often forget to even question them. Someone much smarter than us must have come up with them, right? Everyone who follows them is experiencing great success, right? If we aren’t doing well by them, it’s got to be our fault, right? Most of those rights are probably wrongs.

"Whatever it takes!" It feels good, doesn’t it? It’s hard to find three words loaded with more inspiration, aspiration, and ambition than “whatever it takes!” It’s the rallying cry for captains of industry and war generals alike. Who wouldn’t want to be such a hero and a leader? But you’re not actually capturing a hill on the beach of Normandy, are you? You’re probably just trying to meet some arbitrary deadline set by those who don’t actually have to do the work. Or trying to meet some fantastical financial ‘stretch goal’ that nobody who actually has to do the stretching would think reasonable.

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.

Don’t shuffle 12 things so that you can do them in a different order, don’t set timers to move on from this or that. Eliminate 7 of the 12 things, and you’ll have time left for the 5. It’s not time management, it’s obligation elimination. Everything else is snake oil.