I’ve been a fan of what DHH and Jason Fried are preaching for several years now. In case you’re not aware: They are big proponents of remote work and healthier work attitudes. Besides being vocal Twitter users and bloggers, they have published three books about those topics. What I enjoy about their tweets or blog posts is mostly seeing that other people share my mindset and thoughts — but I don’t learn all that much new or make groundbreaking discoveries. It seems that I’ve always been quite progressive in my own views about work. That’s why I never read any of their books so far. An entire book, just for getting some affirmation? I didn’t even read many books at all up until a short while ago.

But now I do, and as the pandemic has made these “new work” topics more relevant than ever, I decided to dive in after all. I started with Rework, which they published back in 2010. They describe the book as “the perfect playbook for anyone who’s ever dreamed of doing it on their own. Entrepreneurs, small-business owners, and artists who don’t want to starve will all find valuable guidance in these pages.”

I’m neither of those, but I do work at a small-business where speaking your mind and “being the change you want to see in the world” is encouraged. So my perspective towards the content might be different, but I’ve thought about most of it a lot. The book was interesting, though I didn’t gain any major new insights. Nonetheless, never before have I highlighted so many passages for quoting them here later.1

So before finishing this post with a few of those passages and some thoughts about them: I think reading the book was time well spent (it’s not very long anyway). Even if you’re already as radical in your opinions about work as I am, it never hurts to be reminded of the reasons for it.

But more importantly there is a ton of people who are still stuck in “the old ways”, for lack of a better term. To me, that’s the real target audience of this book, because most aren’t stuck by choice. They simply never considered there might be an alternative way of thinking about work, and that’s exactly what DHH and Jason Fried are offering.

My annotations

The most common excuse people give: “There’s not enough time.” They claim they’d love to start a company, learn an instrument, market an invention, write a book, or whatever, but there just aren’t enough hours in the day.
Come on. There’s always enough time if you spend it right. And don’t think you have to quit your day job, either. Hang onto it and start work on your project at night.
Instead of watching TV or playing World of Warcraft, work on your idea. Instead of going to bed at ten, go to bed at eleven. We’re not talking about all-nighters or sixteen-hour days—we’re talking about squeezing out a few extra hours a week. That’s enough time to get something going.

I really stumbled over the “just do it at night” part. Even with the disclaimer about all-nighters at the end, I’m not sure they’d formulate this the same way today — which to me signifies a positive movement of goal posts since the book came out.

While I don’t disagree with the notion that “not enough time” is an excuse you tell yourself, I can’t help but also say that it’s really tough. It often takes a lot of energy to just squeeze out a few hours per week for blogging. For the past few months I’ve also been working on a software side project with a friend. We’re slowly getting to something that feels at least beta-ready, and it is a fun, instructive and rewarding experience. But at the same time it’s yet another thing in my life where I have to carefully balance everything as to not let myself get overwhelmed with pressure and guilt for not doing enough.

How often do you think a quick trip to the grocery store will take only a few minutes and then it winds up taking an hour? And remember when cleaning out the attic took you all day instead of just the couple of hours you thought it would? Or sometimes it’s the opposite, like that time you planned on spending four hours raking the yard only to have it take just thirty-five minutes. We humans are just plain bad at estimating.
Even with these simple tasks, our estimates are often off by a factor of two or more. If we can’t be accurate when estimating a few hours, how can we expect to accurately predict the length of a “six-month project”?

I’d go as far as to say I’ve become an enemy of estimates. At my work, they regularly are the source of pain and suffering, frustration, blame, guilt and all kinds of useless negativity. They give you the illusion of being able to plan things which you simply can’t. You spend an awful amount of time to come up with estimates that still don’t feel right in the end, and even worse: won’t matter the slightest when push comes to shove. If something is important, it will be done regardless of how long it takes. Why not just focus on the question of importance in the first place then?

And a quick suggestion about prioritization: Don’t prioritize with numbers or labels. Avoid saying, “This is high priority, this is low priority.” Likewise, don’t say, “This is a three, this is a two, this is a one, this is a three,” etc. Do that and you’ll almost always end up with a ton of really high-priority things. That’s not really prioritizing.
Instead, prioritize visually. Put the most important thing at the top. When you’re done with that, the next thing on the list becomes the next most important thing. That way you’ll only have a single next most important thing to do at a time. And that’s enough.

Assigning different priorities is just as useless as guessing estimates. We always say: “When everything is important, nothing is important”. It’s a pretty difficult thing to handle when your organization does not have a single source of truth for importance and you get requirements from many different people/departments, who obviously all consider their needs most important.

Accounting is a department. Marketing isn’t. Marketing is something everyone in your company is doing 24/7/365. Just as you cannot not communicate, you cannot not market:

  • Every time you answer the phone, it’s marketing.
  • Every time you send an e-mail, it’s marketing.
  • Every time someone uses your product, it’s marketing.
  • Every word you write on your Web site is marketing.
  • If you build software, every error message is marketing.

I wish the entire world realized this a lot more. Instead of trying to brainwash and spy on us all the time, why not just spend that time and energy on a better product, better website, better support, better communication?

A “fun” anecdote about error messages in software: We once built an internal tool that massaged a lot of data twice per day and then wrote it into a cache. End users would only see/use this cached data, because otherwise the tool would have been unusably slow, and they didn’t need super current data anyway. However, the data massaging takes five to ten minutes, during which time the previously cached data is already gone, and end users only see a “data is being generated” message. Thinking that end users would likely never see the message due to the time of day when the cache is being generated, we made the message “funny”. If an end user actually managed to see it, it would only be for a few minutes anyway, right? Well, as it turns out, there is a second possibility for the end user to see that message, other than hitting the exact time of regeneration by chance. In fact, if the regeneration just fails for some reason and no newly cached data is generated, the user sees nothing but that fucking message. The funny, funny message that tells them with a smirk that the data will be there soon. Instead of a helpful hint about where and how to ask for help when a tool they need to do their time-critical job is completely broken for half a day.

Culture is the byproduct of consistent behavior. If you encourage people to share, then sharing will be built into your culture. If you reward trust, then trust will be built in. If you treat customers right, then treating customers right becomes your culture.
Culture isn’t a foosball table or trust falls. It isn’t policy. It isn’t the Christmas party or the company picnic. Those are objects and events, not culture. And it’s not a slogan, either. Culture is action, not words.

We actually use our foosball table.2 It’s not just there so we can list it in our job benefits, in fact I’d probably rather not even mention it there due to how cliché it is. But I agree, it has not much to do with culture. Culture is that my team asks if everything is okay when I seem down, and that I’m not afraid to share I’ve had a rough week with random panic attacks thanks to depression.

Actions speak louder than words, which is something I’ve painfully had to learn in several relationships. The last sentence from the above quote hits the nail on the head. When I’m frustrated with culture at my workplace, it feels like being in a dysfunctional relationship. You are being told one thing, but experience something else all the time. For me, this discrepancy (i.e. not acknowledging actions, but instead repeating words that don’t fit those actions) usually makes it even worse.


  1. The experience of using annotations/highlights on the Kindle is just mind-bogglingly bad. Maybe if you only buy Amazon’s own DRM-ridden ebooks they do a better job with it, but I had to resort to a calibre-Plugin to export my annotations/highlights to the PC and be able to copy&paste them. I’m honestly considering getting an iPad again, just for being able to better highlight things and take notes when reading. ↩︎

  2. Well, used it. Thanks, Corona. Haxball just is not the same. ↩︎