Rework Review: 50 Ways to Start Succeeding in Business Today

There’s an ongoing joke with my co-workers about my obsession with 37 Signals. It’s probably not that funny any more because I’ve beaten it pretty senseless.

“37 Signals would say that…”

“What if we took a page out of 37 Signals book?”

“RUBY is THE GREATEST programming language ever.”

Never mind that I know next to nothing about programming.

I guess it’s just hard for me to ignore the success they’ve had as a company and the counter-intuitive way they’ve re-written business rules to achieve it. Over the last 5 years on this blog, I’ve used them as an example of why you can’t work at work,  how to guarantee people want to work for you, and the importance of alone time to accomplish creative tasks.

I first read their book, Rework, in 2009 near the start of my professional career, but now that I’m back in the start-up atmosphere, I wanted to re-read it with more experience and perspective.

Here are 50 of my favorite takeaways from the book:


1. On Learning from Mistakes:

What do you really learn from mistakes? You might learn what not to do again, but how valuable is that? You still don’t know what you should do next. Contrast that with learning from your success. 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.

Evolution doesn’t linger on past failures, it’s always building upon what worked. So should you.

2. On Planning:

Writing a plan makes you feel in control of things you can’t actually control.

You have the most information when you’re doing something, not before you’ve done it.

Figure out the next most important thing and do that.

3. On Growth (of your company):

Why is expansion always the goal? What’s the attraction of big besides ego?

Grow slow and see what feels right – premature hiring is the death of many companies.

4. On Workaholism:

Working more doesn’t mean you care more or get more done. It just means you work more.

Workaholics aren’t heroes. They don’t save the day, they just use it up.


5. On Starting:

What you do is what matters, not what you think or say or plan.

6. On Having a Backbone:

If no one’s upset by what you’re saying, you’re probably not pushing hard enough.

7. On Outside Funding:

“Cashing out” begins to trump building a quality business.

Spending other people’s money is addictive. There’s nothing easier than spending other people’s money. But then you run out and need to go back for more. And every time you go back, they take more of your company.

8. On Exit Strategies:

Your priorities are out of whack if you’re thinking about getting out before you even dive in.

When you build a company with the intention of being acquired, you emphasize the wrong things. Instead of focusing on getting customers to love you, you worry about who’s going to buy you.


9. On Constraints:

Constraints are advantages in disguise. Limited resources force you to make do with what you’ve got. There’s no room for waste. And that forces you to be creative.

10. On Simplifying Your Product:

Getting to great starts by cutting out stuff that’s merely good.

Most software is too complex. 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.

When things aren’t working, the natural inclination is to throw more at the problem. More people, time, and money. The right way to go is the opposite direction: Cut back. You’ll be forced to make tough calls and sort out what truly matters.


11. On Quitting:

It’s easy to put your head down and just work on what you think needs to be done. It’s a lot harder to pull your head up and ask why.

It’s easy to confused enthusiasm with usefulness. Cool wears off. Useful never does.

What can’t you do because you’re doing this? This is especially important for small teams with constrained resources.

12. On Interruptions:

If you’re constantly staying late and working weekends, it’s not because there’s too much work to be done. It’s because you’re not getting enough done at work. And the reason is interruptions.

[There’s *tons* of research on how “open” office environments are: disruptive, stressful, cumbersome, unproductive, adversely affect health, lead to resentment, less creativity, and  cause coworkers to feel distant and dissatisfied.]

13. On Good Enough:

When good enough gets the job done, go for it. You can usually turn good enough into great later.

14. On Quick Wins:

Momentum fuels motivation.

15. On the Importance of Sleep:

Forgoing sleep is a bad idea. Sure, you get those extra hours right now, but you pay in spades later: You destroy your creativity, morale, and attitude.

Creativity is one of the first things to go when you lose sleep.

16. On Estimates:

We’re all terrible estimators. We see everything going according to a best-case scenario, without the delays that inevitably pop up. Realty never sticks to best-case scenarios.

17. On Long Lists:

Long lists are guilt trips. The longer the list of unfinished items, the worse you feel about it.

Whenever you can, divide problems into smaller and smaller pieces until you’re able to deal with completely and quickly.

18. On Making Tiny Decisions:

Big decisions are hard to make and hard to change. And once you make one, the tendency is to continue believing you made the right decision, even if you didn’t. Once ego and pride are on the line, you can’t change your mind without looking bad.


19. On Copying as a Formula for Failure:

The problem with this sort of copying is it skips understanding – and understanding is how you grow. 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.

20. On Decommoditizing Your Product:

Make you part of your product or service. Inject what’s unique about the way you think into what you sell.

Ex: A pair of sneakers from Zappos is the same as a pair from Foot Locker or any other retailer. But Zappos sets itself apart by injecting CEO Tony Hsieh’s obsession with customer service into everything it does.

21. On Picking Fights:

Taking a stand always stands out. People get stoked by conflict. They take sides. Passions are ignited. And that’s a good way to get people to take notice.

22. On Under Doing Your Competition:

Defensive companies can’t think ahead; they can only think behind. They don’t lead; they follow. Do less than your competitors to beat them. Solve simple problems and leave the hairy, difficult, nasty problems to the competition.

23. On Where to Focus:

When you spend time worrying about someone else, you can’t spend that time improving yourself. Focus on competitors too much and you wind up diluting your own vision.

Don’t allow the competition to set the parameters. You need to redefine the rules, not just build something slightly better.

It’s better to go down fighting for what you believe in instead of just imitating others.


24. On Saying No:

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 said yes to grows so tall you can’t see the things you should really be doing.

Use the power of no to get your priorities straight. You rarely regret saying no. But you often wind up regretting saying yes.

Making a few vocal customers happy isn’t worth it if it ruins the product for everyone else.

It’s better to have people be happy using someone else’s product than disgruntled using yours.

25. On Letting Customers Outgrow You:

We’d rather our customers grow out of our products eventually than never be able to grow into them in the first place. Adding power-user features to satisfy some can intimidate those who aren’t on board yet. Scaring away new customers is worse than losing old customers.

26. On Being A Good Product Even After They Get Home:

A product that executes on the basics beautifully may not seem as sexy as competitors loaded with bells and whistles. Being great at few things doesn’t look all that flashy from afar. That’s okay. You’re aiming for a long-term relationship, not a one-night stand.

You can’t paint over a bad experience with good advertising.

27. On Keeping Track of What Customers Want:

Don’t write it down. The requests that really matter are the ones that you’ll hear over and over.


28. On Welcoming Obscurity:

Obscurity helps protect your ego and preserve your confidence.

It makes no sense to tell everyone to look at you if you’re not ready to be looked at yet.

29. On Building an Audience:

When you build an audience, you don’t have to buy people’s attention – they give it to you.

Speak, write, blog, tweet, make videos – whatever. Share information that’s valuable and you’ll slowly but surely build a loyal audience. Then when you need to get the word out, the right people will already be listening.

30. On Out-Teaching the Competition:

Teach and you’ll form a bond you just don’t get from traditional marketing tactics. Buying people’s attention with a magazine or online banner ad is one thing. Earning their loyalty by teaching them forms a whole different connection. They’ll trust you more. They’ll respect you more. Even if they don’t use your product, they can still be your fans.

31. On Emulating Chefs:

As a business owner, you should share everything you know.

What can you tell the world about how you operate that’s informative, educational, and promotional?

32. On Emulating Drug Dealers:

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.

33. On Plastic Flowers:

Talk like you really talk. Reveal things that others are unwilling to discuss. Be upfront about your short comings. Show the latest version of what you’re working on, even if you’re not done yet. It’s OK if it’s not perfect. You might not seem as professional, but you will seem a lot more genuine.

34. On the Marketing Department:

Marketing is something everyone in your company is doing 24/7/365.

Marketing isn’t just a few individual events. It’s the sum total of everything you do.

35. On Becoming an Overnight Sensation:

You will not be a big hit right away. You will not get rich quick. You are not so special that everyone else will instantly pay attention. No one cares about you. At least not yet. Get used to it.

Once you have customers and a history, you’ll have a story to tell. But just launching isn’t a good story.


36. On Doing it Yourself First:

Never hire anyone to do a job until you’ve tried to do it yourself first.

You may feel out of your element at times. You might even feel like you suck. That’s all right. You can hire your way out of that feeling or you can learn your way out of it.

37. On Hiring:

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

38. On Passing on Great People:

Pass on hiring people you don’t need, even if you think that person is a great catch.

39. On Familiarity and Hiring Slowly:

You need to be able to tell people when they’re full of crap. If that doesn’t happen, you start churning out something that doesn’t offend anyone but also doesn’t make anyone fall in love. You need an environment where everyone feels safe enough to be honest when things get tough.

40. On Years of Experience Irrelevance:

There’s surprisingly little difference between a candidate with six months of experience and one with six years. The difference comes from the individual’s dedication, personality and intelligence.

How long someone’s been doing it is overrated. What matters is how well they’ve been doing it.

41. On Delegators:

With a small team, you need people who are going to do work, not delegate work.

42. On Remote Work:

Geography just doesn’t matter anymore. Hire the best talent, regardless of where it is.

[They feel so strongly about remote work, it became their next book – Remote: Office Not Required]

Damage Control

43. On Speedy Customer Service:

People are used to platitudes about “caring” that aren’t backed up.

Even if you don’t have a perfect answer, say something. “Let me do some research and get back to you” can work wonders.

44. On Putting All Employees on the Front Lines:

Listening to customer is the best way to get in tune with a product’s strengths and weaknesses.

The more people you have between your customers’ words and the people doing the work, the more likely it is that the message will get lost or distorted along the way.

Don’t protect the people doing the work from customer feedback.


45. On Culture:

Culture is the by-product of consistent behavior. Culture is action, not words.

46. On Temporary Decisions:

Don’t make up problems you don’t have yet. Most of the things you worry about never happen anyway.

Optimize now and worry about the future later.

47. On Skipping Rock Stars:

Instead of thinking about how you can land a roomful of rock stars, think about the room instead. Rockstar environments develop out of trust, autonomy, and responsibility. They’re the result of giving people the privacy, workspace, and tools they deserve. Great environments show respect for the people who do the work and how they do it.

48. On Diversions:

When everything constantly needs approval, you create a culture of non-thinkers.

People need diversions. It helps disrupt monotony of the workday.

49. On Sending People Home at Five:

You want busy people. People who have a life outside of work. People who care about more than one thing. You shouldn’t expect the job to be someone’s entire life – at least not if you want to keep them around for a long time.

50. On Sounding Like Yourself:

When you’re writing, don’t think about all the people who may read your words. Think of one person.

Speaking of culture, here’s a quote from David Heinemeier Hansson in their first blog post of 2014 – “Healthy Benefits for the Long Run“:

We ultimately want 37signals to have the potential of being the last job our people ever need. When you think about what it’ll take to keep someone happy and fulfilled for 10, 20, 30 years into the future, you adopt a very different vantage point from our industry norm.


There’s actually more than 50 ideas here that you can use to start improving your business today, but if you think that gives you a reason to skip the book then you’re making a mistake.

Top performers read books. Here’s what two of the smartest people I know have to say on the subject:

Ramit Sethi:

Here’s a good rule of thumb I use: Any time I wonder, “Should I buy that book?” I DO IT.

A book is years of an author’s life compressed into 200 pages for about $10-$20. There is almost no better value. If you pick up just ONE insight from a book — and apply it — you can change your life.

Ryan Holiday:

Human beings have been recording their knowledge in book form for more than 5,000 years. That means that whatever you’re working on right now, whatever problem you’re struggling with, is probably addressed in some book somewhere by someone a lot smarter than you. Save yourself the trouble of learning from trial and error–find that point. Benefit from that perspective.

The purpose of reading is not just raw knowledge. It’s that it is part of the human experience. It helps you find meaning, understand yourself, and make your life better.

There is very little else that you can say that about. Very little else like that under $20 too.


I try to review many of the non-fiction books I read on this blog, but I share interesting articles, quotes, mental models and more with my exclusive e-mail subscribers. You can join them by providing your e-mail address in the form below.