36 Lessons from ReWork by Jason Fried

Phil Santos
10 min readMay 30, 2016

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The rules for a new entrepreneurship.

1. Learning from mistakes is overrated

“Contrast that with learning from your successes. Success gives you real ammunition. When something succeeds, you know what worked — and you can do it again. And the next time, you’ll probably do it even better. […] That shouldn’t be a surprise: It’s exactly how nature works. Evolution doesn’t linger on past failures, it’s always building upon what worked. So should you.”

2. Planning is guessing

“Writing a plan makes you feel in control of things you can’t actually control. […] Plans let the past drive the future. They put blinders on you. ‘This is where we’re going because, well, that’s where we said we were going.” And that’s the problem: Plans are inconsistent with improvisation. […] Sometimes you need to say, “We’re going in a new direction because that’s what makes sense today.’”

3. Make a dent in the universe

“To do great work, you need to feel that you’re making a difference. That you’re putting a meaningful dent in the universe. That you’re part of something important. You want your customers to say, ‘This makes my life better.’ You want to feel that if you stopped doing what you do, people would notice. […] What you do is your legacy.”

4. Scratch your own itch

“The easiest, most straightforward way to create a great product or service is to make something YOU want to use.”

5. Draw a line in the sand

“As you get going, keep in mind WHY you’re doing what you’re doing. Great businesses have a point of view, not just a product or service. […] A strong stand is how you attract super fans. They point to you and defend you. And they spread the word further, wider, and more passionately than any advertiser could. […] Strong opinions aren’t free. They’ll turn some people off. They’ll accuse you of being arrogant and aloof. For everyone who loves you, others will hate you.”

“When you don’t know what you believe, everything becomes an argument. Everything is debatable. But when you stand for something, decisions are obvious.”

6. Build half a product, not a half-assed product

“You just can’t do EVERYTHING you want to do and do it well. You have limited time, resources, ability, and focus. […] So sacrifice some of your darlings for the greater good. Cut your ambitions in half. You’re better off with a kick-ass half than a half-assed whole. […] So start chopping.. Getting to great starts by cutting out stuff that’s merely good.”

7. Start at the epicenter

“When you start anything new, there are forces pulling you in a variety of directions. There’s the stuff you COULD do, the stuff you WANT to do, and the stuff you HAVE to do. The stuff you HAVE to do is where you should begin. Start at the epicenter. The way to find the epicenter is to ask yourself this question: ‘If I took this away, would what I’m selling still exist?’”

“So figure out your epicenter. Which part of your equation can’t be removed? When you find it, you’ll know. Then focus all your energy on making it the best it can be. Everything else you do depends on that foundation.”

8. Ignore the details early on

“When we start designing something, we sketch out ideas with a big, thick sharpie marker, instead of a ball-point pen. Why? Pen points are too fine. They’re too high-resolution. They encourage you to worry about things you shouldn’t worry about yet, like perfect shading or whether to use a dotted or dashed line. You end up focusing on things that should still be out of focus.”

9. Making the call is making progress

“When you put off decisions, they pile up. And piles end up ignored, dealt with in haste, or thrown out. As a result, the individual problems in those piles stay unresolved. Whenever you can, swap “Lets think about it” for “Let’s decide on it.” Commit to making decisions. Don’t wait for the perfect solution. Decide and move forward.”

“When you get into the flow of making decision after decision, you build momentum and boost morale. Decisions are progress. Each one you make is a brick in your foundation. You can’t build on top of “We’ll decide later,” but you CAN build on top of ‘Done.’ “

“You don’t have to live with a decision forever. If you make a mistake, you can correct it later. It doesn’t matter how much you plan, you’ll still get some stuff wrong anyway. Don’t make things worse by overanalyze.”

10. Be a curator

“It’s the stuff you leave out that matters. So constantly look for things to remove, simplify, and streamline. Be a curator. Stick to what’s truly essential. Pare things down until you’re left with only the most important stuff. Then do it again. You can always add stuff back in later if you need to.”

11. Sell your by-products

“When you make something, you always make something else. You can’t make just one thing. Everything has a by-product. Observant and creative business minds spot these by-products and see opportunities.”

12. Launch Now

“When is it safe to let people have your product? Probably a lot sooner that you’re comfortable with. Once your product does what it needs to do, get it out there.”

“Don’t recognize this approach for skimping on quality either. You still want to make something great. This approach just recognizes that the best way to get there is through iterations. Stop imagining what’s going to work. Find out for real.”

13. Reasons to quit

“Here are some important questions to ask yourself to ensure you’re doing work that matters:

  • Why are you doing this? What is it for? Who benefits? What’s the motivation behind it?
  • What problem are you solving?
  • Is this actually useful?… Sometimes its fine to play a bit and build something cool. But eventually you’ve got to ask yourself it it’s useful, too. Cool wears off. Useful never does.
  • Will this change behavior? Is what you’re working on really going to change anything? Don’t add something unless it has a real impact on how people use your product.”

14. Meetings are toxic

  • “They’re usually about words and abstract concepts, not real things.”
  • “They usually convey an abysmally small amount of information per minute.”
  • “They drift-off subject easier than a Chicago cab in a snowstorm.”
  • “Rules for meetings:
  • Set a timer. When it rings, meeting’s over. Period.
  • Invite as few people as possible.
  • Always have a clear agenda.
  • Begin with a specific problem.
  • Meet at the site of the problem instead of the conference room. Point to real things and suggest real changes.
  • End with a solution and make someone responsible for implementing it.”

15. Good enough is fine

“When good enough gets the job done, go for it. It’s way better than wasting resources or, even worse, doing nothing because you can’t afford the complex solution. And remember, you can usually turn good enough into great later.”

16. Long lists don’t get done

“Start making smaller to-do lists too… Long lists are guilt trips. The longer the list of unfinished items, the worse you feel about it.”

“Prioritize visually. Put the most important thing at the top. “

17. Don’t copy

“You have to understand why something works or why something is the way it is. When you just copy and paste, you miss that. You just repurpose the last layer instead of understanding all the layers underneath.”

18. Say no by default

“It’s so easy to say yes. Yes to another feature, yes to an overly optimistic deadline, yes to a mediocre design. Soon the stack of things you’ve said yes to grows so tall you can’t even see the things you should really be doing. “

“Start getting into the habit of saying no — even to many of your best ideas.”

19. Don’t confuse enthusiasm with priority

“The enthusiasm you have for a new idea is not an accurate indicator of its true worth. What seems like a sure-fire hit right now often gets down-graded to just a “nice to have” by morning. And “nice to have” isn’t worth putting everything else on hold.”

20. Don’t write it down

“How should you keep track of what customers want? Don’t. Listen, but then forget what people said. Seriously.”

“The requests that really matter are the ones you’ll hear over and over.”

21. Emulate Chefs

“They cook, so they write cookbooks. What do you do? What are your “recipes”? What’s your “cookbook”? What can you tell the world about how you operate that’s informative, educational, and promotional? This is our cookbook. What’s yours?”

22. Go behind the scenes

“Give people a backstage pass and show them how your business works. Imagine someone wanted to make a reality show about your business. What would they share?… [Customers] will feel a bond with you and see you as human beings. They’ll see the sweat and effort that goes into what you sell.”

23. Press releases are spam

“If you want to get someone’s attentions, it’s silly to do exactly the dame thing as everyone else. You need to stand out.”

“Instead, call someone. Write a personal note. If you read a story about a similar company or product, contact the journalist who wrote it. Pitch her with some passion, some interest, some life. Be remarkable. Stand out. Be unforgettable. That’s how you’ll get the best coverage.”

24. Drug dealers get it right

“Drug dealers are astute businesspeople. They know their product is so good they’re willing to give a little away for free upfront. They know you’ll be back for more — with money.”

“You want an easily digestible introduction to what you sell. This gives people a way to try it without investing any money or a lot of time.”

25. Marketing is not a department

“It’s the sum total of everything you do.”

26. The myth of the overnight sensation

“Dig deeper and you’ll usually find people who have busted their asses for years to get into a position where things could take off. And on the rare occasion that instant success does come along, it usually doesn’t last — there’s no foundation to support it.”

“You have to do it a long time before the right people notice.”

27. Do it yourself first

“Never hire someone to do a job until you’ve tried to do it yourself first. That way you’ll understand the nature of the work. You’ll know what a job well done looks like.”

“You’ll also be a much better manager, because you’ll be supervising people who are doing a job you’ve done before. You’ll know when to criticize and when to support.”

28. Hire when it hurts

“Don’t hire for pleasure; hire to kill pain.”

29. Hire great writers

“Being a great writer is about more than writing. Clear writing is a sign of clear thinking. Great writers know how to communicate. They make things easy to understand. They can put themselves in someone else’s shoes. They know what to omit.”

30. Test drive employees

“Hire them for a mini project, even if it’s for just twenty or forty hours. You’ll see how they make decisions…. You’ll get to judge them by their actions instead of just their words.”

31. Take a deep breath

“When you rock the boat, there will be waves. After you introduce a new feature, change a policy, or remove something, knee-jerk reactions will pour in. Resist the urge to panic or make rapid changes in response. Passions flare in the beginning. That’s normal. But if you ride out that first rocky week, things usually settle down.”

“So when people complain, let things simmer for a while. Let them know you’re listening. Show them you’re aware of what they’re saying. Let them know you understand their discontent. But explain that you’re going to let it go for a while and see what happens. You’ll probably find that people adjust eventually. They may even wind up liking the change more than the old way, once they get used to it.”

32. You don’t create a culture

“You don’t create a culture, it happens. This is why new companies don’t have a culture. Culture is the byproduct of consistent behavior. “

“Culture is action, not words.”

33. Decisions are temporary

“ ‘But what if…?’ ‘What happens when…?’ ‘Don’t we need to plan for…?’ … Don’t make up problems that you don’t have yet. It’s not a problem until it’s a real problem. Most of the things you worry about never happen anyway. “

“Besides, the decisions you make today don’t need to last forever… Optimize for now and worry about the future later.”

34. Skip the rock stars

“Instead of thinking about how you can land a room full of rock stars, think about the room instead. We’re all capable of bad, average, and great work. The environment has a lot more to do with great work than most people realize.”

“Rockstar environments develop out of trust, autonomy, and responsibility. “

35. Don’t scar on the first cut

“Policies are organizational scar tissue. They are codified overreactions to situations that are unlikely to happen again. That are collective punishment for the misdeeds of an individual. This is how bureaucracies are born… Policies are only meant for situations that come up over and over again.”

36. Inspiration is perishable

“We all have ideas. Ideas are immortal. They last forever. What doesn’t last forever is inspiration. Inspiration is like fresh fruit or milk: It has an expiration date.”

“If you’re inspired on a Friday, swear off the weekend and dive into the project. When you’re high on inspiration, you can get two weeks of work done in twenty four hours.”

“Inspiration is a now thing. If it grabs you, grab it right back and put it to work.”

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Phil Santos

A music and nightlife philosopher. Author. Join my Newsletter on music, wellness, and community building. https://philsantos.substack.com/welcome