So much of what we do in work is thinking. Yes, developers type code onto the “page” and that code is what clients think they’re paying for. The truth is that they’re paying for you to make smart decisions.

Learning to make those smart decisions, with proper information, is what Paid to Think, by David Goldsmith, is all about.

So the big question is, what should you be thinking about? I promise that by the time you reach the end of this book, you’ll have a definitive (and possibly surprising) answer to that question, and you’ll also possess an abundance of tools that will enable you to convert your thoughts to realities. Paid to Think has been written so that you will know more precisely where to focus your energies and how to put your new found knowledge to immediate and practical use.

It’s Buried in Turtles

There is a great Dr Suess book called Yertle The Turtle. In this story, King Yertle is the ruler of all that he can see. Realizing that if he gets his subjects to form a tower he can see further, he gets them all to stand on each other’s backs with him at the top. Then it comes crashing down when one lowly turtle realizes he doesn’t have to stand for it.

Dr Suess is teaching us a lesson in greed, and while Paid to Think isn’t venturing into that realm, I kept thinking of Yertle.

The core issue with the book is that it’s got five steps for everything. Or 8 steps. Or 2 steps. Then inside each step, there is five sub-steps with three rules and four ways that you can adapt each rule based on a change in sub-step three.

I kept thinking all the rules and lists and steps and …. pages to print were a big pile of turtles. The deeper you went, the more turtles you found with more steps going on and on.

More than once, I’d be three pages of notes into step three to realize that I had no idea what step three was about and what it was all leading back to. So I’d read again, only to get lost on step three sub-step 2.

It got bad enough that it was all I could do to finish the book without skimming everything. Like that high school student reading with a fan pointing at the pages flipping them faster.

Further, I don’t think that a freelance business could do anything close to the “ideal” put forward in the book. In fact, I don’t think that most businesses that aren’t operating on a multi-national scale, could do it. I’d have to hire five people to do my work, and fill out all the sheets and stuff in the book to even be able to attempt most of it to the depth that Goldsmith describes.

With that out of the way, let’s look at some of the good that can be found in Paid to Think.

Enterprise Thinking

The main idea that Goldsmith is telling us about is Enterprise Thinking. This is simply his term for the thinking tools that he has. I never found a clear explanation of why Enterprise except maybe that you can’t do it unless you are in fact an enterprise.

He also talks a bunch about “cyclonic” thinking. This is simply his term to tell us that we jump around between the tools.

Many times he seems to use these terms mainly as a way to have his own intellectual property that he can sell to others. In fact, many of the thinking tools follow this model. He uses an established process and adds Enterprise to the front of it or “cyclonic” to it, and then calls it his own tool.

The idea that did resonate with me, being a Ready Fire Aim type, is:

You can never underestimate the value of thinking before taking action, especially when you’re about to invest labor, capital, time, and your reputation.

The Structure of Paid To Think

Paid to Think is broken up into four main groups of topics. Chapter 1 is laying the ground work of terms and ideas so that you can venture into the rest of the book and get less lost. Chapter two is all about getting you to question your assumptions and beliefs so you can see what might be holding you back.

The meat of the book is found in chapters three through fourteen. These are where you’ll find the thinking tools of Enterprise Thinking.

The final chapter, 15, is mostly inspirational. It’s telling you stories of how others have taken the thinking tools into their work and started to kick ass. It’s getting you to leave on a high note, so you’ll be more likely to put the tools into practice.

The Four Categories of Enterprise Thinking

According to Goldsmith, there are four categories that solid Enterprise Thinking makes up.

1. Strategizing

In the Strategizing category, you will learn the processes and tools you need to effectively develop targeted strategies that drive your organization forward.

2. Learning

Within the Learning category, you will gain an understanding of how to acquire new knowledge (more than simply awareness), enhance your global awareness, and watch your competition in ways that give your organization the edge it needs to survive and thrive now and well into the future.

3. Performing

…the Performing category addresses action itself: how you take action, how you engage in internal dialog to determine your next best steps, and how you reach organizational goals through other people.

4. Forecasting

The Forecasting category shows you how to gain a future-oriented mindset necessary to forecast tomorrow’s trends, opportunities, and challenges to better ensure a strong and healthy future for your organization, your career, and your life.

Goldsmith says that all four categories are connected. You’ll jump through them and around in them with “cyclonic” thinking.

Then he introduces us to the 7 Crosses of Enterprise Thinking.1

7 Crosses of ET
1. Cross functional – works in every department
2. Cross level – works senior to junior
3. Cross Industry
4. Cross Sector – private/public/IPO
5. Cross Cultural
6. Cross Time – historical or present day
7. Cross Life – work and home

This is another fault starting to show in the book, or at least showing again. The forward to the book makes such huge bold claims about how it will transform everything in your business and life, that I have no idea how any author could ever live up to them.

The 7 Crosses feel the same way. Goldsmith is saying that his system is the best for…everything all the time. That’s a huge claim to make, and one that’s contrary to the mental model theory2.

With a mental models approach, you’d ensure that you have tools from Paid to Think, and many others. Then you’d apply the best tool for the job. In fact, you’d make sure that you can apply at least two mental frameworks to it. If you can’t, you either don’t have the mental tools to dig in, or you don’t understand the problem with enough depth.

Our Limiting Beliefs

The beliefs we have limit us. They limit us in subtle ways. We start to see success, and then sabotage ourselves without thinking about it3.

One of the core contentions around what limits us as managers is that we’re managers, not leaders. Leaders lead from the field. Managers sit back in a cozy room sending people out to do their bidding.

When managers entered the scene, leaders moved from their on-the-field command positions to the seclusion of the executive office, rendering many (though certainly not all) decision makers out of touch with the realities that challenged their organizations.

This is faulty because so many managers are then out of touch with the realities of the work. In a recent Freakonomics episode4 they discussed this idea in as it pertains to CEO’s. Does an outside CEO or an internal one that came up through the ranks perform better.?

The data says that the internal one does, and at a cheaper cost. There isn’t even a contest between the two models in fact. Internal people who understand the culture and the goals of departments, win hands down.

These external CEO’s also often put way too much faith in a revolutionary idea instead of constant improvement.

Many decision makers put a lot of pressure on themselves to come up with the next killer idea, believing that they have to wow customers, prospective employees, or other stakeholders in order to win sales, key talent or other advantages for their organizations. But you don’t always have to reel in the ”big fish” to enjoy great rewards. In fact, more often than people realize, great rewards don’t necessarily come from earth shattering factors. Instead, they are oftentimes the result of minor factors that cause us to win or lose “by a nose.”

While this section does an okay job at getting us to question some of the beliefs we have, there are much better books out there. Like, The Big Leap. If you’re looking to question your assumptions that may hold you back from success, read that instead.

Now, we’re on to the third section of the book and what should be the meat of it. The thinking tools of Enterprise Thinking.

Category 1: Strategizing

Goldsmith says that the order of the thinking tools doesn’t matter, but this is a book, and thus it’s consumed linearly and you have to pick one to start with. So, we start with strategizing.

This is also where we start bogging down in the steps and sub-steps and rules and three ways that you might make an exception to rule 5a.

I’m only going to highlight the few parts that I found useful. The rest is so buried in a stack of turtles that I can’t make sense of most of it.

What is Your Challenge?

An excellent strategy executed poorly is still better than a poor strategy executed well.

One of the keys to thinking, in general, is not trying to rush it. When I start my new notebook, I take a few hours to think back through where I’m at and where I want to be.

During the strategizing process, any time you feel the urgently to push forward quickly, slow down and harness those urges instead.

Rushing will result in a weaker strategy. A weaker strategy will harm your success. The part that I’ve come back to a number of times, and helped me reframe my problems in my business, is his method for finding your challenges and seeing if they are the most important single thing you can be working on.

It starts by writing down a single statement for your challenge. Note the word challenge, because it can be a problem or an opportunity. Using challenge helps make it more agnostic.

Then you walk through a number of questions to help you figure out if this is really the challenge or a symptom of the challenge.

Things like:

  • Is this only one challenge (no ‘and’ in it because that’s two challenges)
  • Is it a problem now, or am I dwelling on something that already happened?
  • Did I write down what I think is the solution?

There are a few others, but it was the third one that I keyed on. My problem right now is lack of sales. But when I started the work I wrote down that it was “not enough people know me”. My thinking was that if more people knew me, I’d make more sales.

But, that’s not true. Lack of sales could be because of a few things. I could have terrible products. I could have poor on page marketing. It could be that not enough people are familiar enough with my content.

Going through the work to define my challenge had me start surveying my readers about content. Next, I’ll dig into my on page marketing, and learn about how to do that best for products. Then, with those two items solved to the extent I can perfect them, I can dig into what I thought my original problem was.

The final great step of this was the “what-would-it-take” question. I asked myself “What would it take to know that my products fit my market.” Then I started to develop a survey. I’ve started to introduce early versions of my products to members so I can test and refine them.

Decision makers find that asking what-would-it-take questions gives them more, better, and different macro tactics from which to choose. As a result, they put themselves and their organizations in stronger positions to achieve their Desired Outcome and they avoid costly preventable mistakes

This question is similar to one I’ve heard Tim Ferris talk about. He asks himself “What would this look like if it was easy?” Then he uses his leverage to make sure that even if things crash, he’s got a fairly easy ride or at least options to get the work out where and how he wants to get it out.

This single idea and work on reframing was the best concept in the whole book. If you’re going to read Paid to Think, find this section and then you can stop.

The Rule of Two

In Star Wars mythology, there is the Sith Rule of Two. There can only ever be a master and an apprentice. This stopped the fighting amongst themselves until at some point the apprentice was strong enough to kill the master and become the master.

We see a similar, bad, dynamic with so many projects. We see 9000 things on our plates and no way to handle them all. This is where Goldsmith puts forward his second great idea, the Rule of 2.

You can only ever work on two projects at a time. That’s two major projects. You’ll still have emails to return and meetings to go to, but only ever two major projects. If you violate this, you’ll be overloaded.

Too many projects overload people with too many thoughts, details, and activities, which ultimately leads to decreased performance levels, like an instance where an individual is working on a spreadsheet, becomes interrupted, loses his or her train of thought, and makes a small error in calculation that could snowball into disastrous results later.

This has changed how I build out my quarterly plans. No more trying to push forward three books. I pick one and if it goes fast enough, I move onto the next one.

On top of that, I can have one client project. That’s it. Two main projects at a time the rest I need to say no to because they’ll only harm my overall output. If I need the income, time to start charging more because I can only handle one at a time.

Alongside this idea of only ever working on two projects is the idea of only ever scheduling part of your day.

A good rule of thumb is to schedule no more than 60% of your day, because planning is not an exact science, and you never know what interruptions, unforeseen opportunities, problems, and other unexpected activities can encroach on your schedule

This flies a bit in the face of people like Cal Newport, who schedules every minute of his day. According to Goldsmith, you should only ever be scheduling 60% of your day. The rest is for dealing with the things that will throw you off track.

You see a similar idea in The 12 Week Year5. In that book, they recommend you put a few buffer blocks into each day. The buffer blocks are around so that you have space for life/work to happen without feeling like you’re getting behind.

There is more under the turtles

In the rest of the book, Goldsmith talks about his method for developing new products which has three steps.

  1. Ideation – get the ideas
  2. Elimination – filter them
  3. Development – get them going

Yes, each step has many sub-items and exceptions to the rules. No, you can’t keep track of what they are.

He wrote a whole chapter on establishing alliances in business and differentiating between what an alliance is and is not. In general, if the people you’re working with don’t benefit from the upsides they have a hand in, they’re not partners they’re vendors.

Goldsmith dives into technology but uses so much jargon as to make the starting almost impossible to understand. He also falls into what Cal Newport would call Any-Benefit thinking. This is the idea that if there is some benefit, we should be pursuing the idea. We don’t weigh the negatives that make come with the new ideas and techniques.

The internet allows customers, patients, clients, patrons, and other stakeholders to tap into your organization’s products and services at times and locations that are convenient to them. Newer phone technologies give people the flexibility to do their work ta just about any place in the world with an Internet connection, as if they were sitting in offices.

He does come back around with a one-off sentence to evaluate the real benefit of new technology, but it’s passing in the midst of a whole lot of rah-rah for new technology.

One great idea in the midst of his discussion on technology, is making sure that your staff have the right tools in place to do their work.

Give your staff the necessary resources and guidance to learn how to use a new technology and to integrate it into their daily work life: time, training, new tools, etc.

It brought to mind one job where I had a computer that would take 15 minutes to start. Then 5 to start Photoshop and each tool action took a 15 – 20 seconds to do anything. It was impossible to meet any realistic expectation of producing work in a timely fashion and my boss was mad at my lack of productivity.

You could lament the time it took, but make sure that you have given your people the tools they need and the training to use those tools. Far too many problems aren’t with the people. The tools aren’t allowing them to do the work they are trying to do.

Category 2: Learning

The second category of thinking tools deals with learning. What to learn when and how to learn it effectively.

We are overloaded with daily opportunities to learn. It starts early, from the time we read our morning newspapers, it ends late, after we’ve watched the late night news before bedtime, and we’re hit all day in between with digital feeds and streaming news reports. Then there are the magazines, books, people, seminars, and training sessions that we seek out as a way of concentrating our focus on specific topics of information. But at the end of our continuous daily cycles of learning, do we really have that much useful and valuable information at our disposal?

Yes, all the tools provided mention “cyclonic” thinking. We’re developing intellectual property here people.

Goldsmith does provide a great differentiation between knowledge of something and awareness of it. You might be aware of a new technology, but have little to no knowledge of it. He uses the idea that you don’t let someone aware of heart surgery perform the surgery. You want someone with first-hand knowledge.

As you’re looking to gather knowledge, make sure that you’re giving more weight to those sources with first-hand knowledge that’s current. People that have less knowledge or experience that’s long old, get less weight.

Paid to Think also exhorts a business to have a learning mentality throughout the positions.

When everyone on staff adopts a learning mentality and seeks out awareness and knowledge from a variety of sources, their increased awareness and knowledge banks multiply the potential of your organization.

Unfortunately, telling us that we need to have a culture of learning is where Goldsmith stops. There is little concrete advice on how to build that environment in your workplace.

When it comes to global awareness, Goldsmith has a few tools that amount to being aware of how global events can affect your business. I worked for a canoe shop that saw the war effort in the US ramping up in the early 2000’s and rightly deduced that carbon and kevlar would be in demand for military applications.

They purchased a decade’s long supply of it at lower prices and then spent the next number of years using the tried and true materials no one else could get at a formerly reasonable price. They invested in finding and trying new materials because they had a long runway to perfect things before the shipped them to customers.

This is the type of global thinking and learning Goldsmith wants us to be making.

There is much more content before the end. Notice I didn’t even talk about some parts of the Enterprise Thinking model from the beginning. Specifically, I’m not mentioning performing and forecasting.

These sections mostly repeated tools you learned about already in the book but added another three tweaks to the already existing five steps, three sub-steps, with four adjustments.

It was so bogged down; I couldn’t pull much out of it despite trying to read parts two or three times.

Should You Read Paid To Think

There are a few core great ideas in Paid To Think. The reframing work is great. The rule of two is awesome. When you encounter issues with staff, making sure that they have the right tools to do the job is great.

But…oh my goodness is so much of it bogged down in lists and steps and sub-steps.

Read the first bit, then when you’re done just be done. Don’t bother reading the book. It strikes me as more a quest for pushing intellectual property of the author than a way to effectively give tools to the size of business I run.

Get Paid to Think on Amazon

  1. Yes you can already see the turtles stacking up as we go deeper and deeper. 
  2. I wrote about decision making and mental models, and you can find 113 of them at Farnam Street
  3. A great book about your limiting beliefs is The Big Leap, by Gay Hendricks. I reviewed it here
  4. Becoming a CEO, Freakonomics Podcast 
  5. Here is my review of The 12 Week Year