How Will You Measure Your Life?

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These are my personal notes. I use them to remind future Brett what is important. As with all books I review, you can use my outline to determine if you should read this book. You will get something different out of the book than I did.


When attending his MBA reunions Clayton noticed people who were successful in their careers weren’t successful in their personal lives. Some of his classmates had even been jailed because of illegal activity. These weren’t the same people he remembered going to school with. He was curious what changed.

Clayton teaches a class at Harvard business school where students assesses businesses using certain ‘lenses’ or what Clayton calls, theories. They use these theories to forecast the future success of businesses.

On the last day of class Clayton uses the same methods to look at the students instead of businesses. They don’t focus on what a student hopes will happen. Rather, they allow a predictive theory tell what the future holds for each individual student.

Next to each student’s theory he writes the following questions and answers them utilizing the theory:

  • How can I be sure I will be successful and happy in my career?
  • How can I be sure my relationships (with my spouse, my children, my extended family, and my close friends) become a resources of enduring happiness?
  • How can I be sure I live a life of integrity — and stay out of jail?

Clayton wanted to extend this classroom exercise into a book in order to help us all understand how we can examine and improve our lives.

Chapter 1: Just because you have feathers…

A few examples are given to explain how theories solve problems. Clayton admits these theories alone won’t solve problem. Domain knowledge is required to solve any specific problem. Only when someone has domain knowledge, and a theory to view the problem with, can they determine the solution.

Theories however don’t map to problems neatly. There isn’t a one-to-one mapping of theories to problems. Usually, many theories apply to a single problem or situation. It’s up to the individual to figure out which theories apply and how to utilize them.

Section I: Finding Happiness In Your Career

What we think matters most in our jobs often does not align with what will really makes us happy.

Chapter 2: What Makes Us Tick

We, as a society, have used Incentive Theory — which is dictated by hygiene factors such as compensation and status — as a way to estimate our career happiness. This is the wrong theory to determine happiness. Motivation Theory — intrinsic conditions from the work itself — dictates what actually makes us happy.

In some careers however money is the motivator. For salespeople and traders money is literally the measure of personal success. But, for most of us tangible things won’t make us happy.

Motivation Theory suggests you ask ourselves the following questions:

  • Is the work meaningful?
  • Is this job giving me a chance to develop?
  • Am I learning?
  • Am I being recognized for the things I do?
  • Am I given responsibility?

Intrinsic values always outweigh financial ones.

Chapter 3: The Balance of Calculation and Serendipity

Motivation Theory alone won’t make you happy. A person can have a career plan, a deliberate strategy, but they also need to be open to emergent opportunities. You should identify things which don’t motivate you and iterate quickly. You should determine the right balance of hygiene factors and motivators.

Clayton outlines a tool created by Ian MacMillan and Rita McGrath called Discovery-driven planning that can help you do this.

Discovery-driven planning works like this:

Compile a list of all the assumptions which are made for a potential project. Rank-order them by importance and uncertainty. The top of the list has the most important assumption with the least certainty. The bottom of the list has the least important assumption with the most certainty. Once the list is compiled the company should identify ways to quickly and inexpensively test the validity of each assumption.

The Discovery-driven planning method can be used to qualify the value of a prospective job. Identify which assumptions have to prove true to be able to succeed at this job. Then, ask yourself the following questions:

  • Are the assumptions within our control?
  • Are the assumptions intrinsic or extrinsic?
  • Are we being realistic with our assumptions?

Finally, determine ways to swiftly and inexpensively test each assumption to see if they are valid.

Chapter 4: Your Strategy Is Not What You Say It Is

We lie to ourselves. A lot. What we tell ourselves our strategy is, isn’t our strategy. The way we spend our time each day dictates what our actual strategy is. Clayton gives examples where businesses accidentally focus on short-term goals rather than long-term goals.

People do the same thing.

People are quick to focus on immediate rewards from their careers rather than rewards from their personal relationships. Personal relationships take years to cultivate to receive any type of reward.

Where we choose to spend our resources — time, money, and energy — affects our short-term and long-term goals.

Section II: Finding Happiness In Your Relationships

High-achievers focus a great deal on becoming the person they want to be at work — and far too little on the person they want to be at home.

Chapter 5: The Ticking Clock

Businesses succeed when they are short on money. With abundant capital companies invest in the wrong things because they don’t focus on profitability. Small companies have the single focus of profitability to survive. They place bets which have long-term benefits but no immediate reward. Personal relationships are the same way. To have good personal relationships we need to invest in them long before we can reap any rewards from them.

Chapter 6: What Job Did You Hire That Milkshake For?

The most fulfilling relationships are those where we have made the most sacrifice.

Rather than focusing on what we want out of relationships we should be asking ourselves what can I do for them. Businesses create products and services by hiring companies to do a job for them. We hire our spouses to do a job for us and they hire us to do a job for them. Successful marriages are a result of servicing our spouse’s needs rather than our own.

Husbands and wives who are most loyal to each other are those who have figured out the jobs that their partner needs to be done.

Chapter 7: Sailing Your Kids on Theseus’s Ship

The theory of capabilities determines when something should be outsourced and when it should not.

  1. Assume the capabilities of your supplier will change and determine what they are striving to do.
  2. Determine what capabilities you need to succeed in the future. Your capabilities must stay within the company or you risk your own future.

Capabilities are the resources, processes, and priorities one has. Resources are the what, processes are the how, and priorities are the why.

Self-esteem comes from achieving something important when it’s hard to do.

Your children learn their values from the people around them. If you are the main person they are around they will learn their values from you. If you have outsourced some of your responsibilities they will learn their values from the outsourced.

Chapter 8: The Schools of Experience

The Schools of Experience theory: People who have experienced the problem first hand are better than those around the problem. Failure is a requirement of gaining experience. We learn from our failures not our successes.

We should provide an environment for our children to fail which will set them up for future successes. Only when they fail do they learn beneficial life skills.

Chapter 9: The Invisible Hand Inside Your Family

A culture is the unique combination of processes and priorities within an organization. A culture is created not by what you say, but by what you do. Others will see what you do, and if you are influential or in an influential position, they will mimic you. Culture is what a person does when no one is watching them.

Your company and your family have a culture whether you wanted one or not. You should be deliberate with the culture you create. Creating a deliberate culture is hard. When a problem is handled differently than your culture dictates, immediately address it. This constant reinforcement needs to continue happening, until it is automatic.

Left unchecked long enough, ‘once or twice’ quickly becomes a culture.

Keep enforcing your cultural value.

Section III: Staying Out of Jail

Full versus marginal thinking is the theory which enforces living a life of integrity.

Chapter 10: Just This Once…

Why is it that big, established companies that have so much capital find [new] initiatives to be so costly? And why do the small entrants with much less capital find them bot be straightforward?
The answer is in the theory of marginal versus full costs. Every time an executive in an established company needs to make and investment decision, there are two alternatives on the menu. The first is the full cost of making something completly new. The second is to leverage what already exists, so that you only need to incur the marginal cost and revenue. Almost always, the marginal-cost argument overwhelms the full-cost. For the entrant, in contrast, there is no marginal-cost item on the menu. If it makes sense, then you do the full-cost alternative. Because they are new to the scene, in fact, the full cost is the marginal cost.

This theory applies to choosing right and wrong. To lead a life of integrity means always living by the general principles you create. It’s easy to find the exception to your general rule and do something differently just this once. As the saying goes, “The path to hell is paved with good intentions.”

You can’t apply the rule just some of the time. You need to apply it all of the time. Resist temptation and stick to your morals.

100 Percent of the Time is Easier than 98 Percent of the Time… Decide what you stand for. And then stand for it all the time.


Don’t leave the purpose of your life to chance. There are three parts of choosing a purpose to your life.

  • Likeness — What do you want to become? Before painting a painter will make a rough sketch of what they intend. This is what you intend to be.
  • Commitment — The world will attempt to break the Likeness you choose. You have to commit to the likeness regardless of what happens.
  • Metrics — Choose things to measure the progress you have towards your likeness. This allows you to calibrate your life towards the Likeness you chose.

Unlike listening to the world for emergent opportunities, your purpose must be deliberately chosen and pursued. How you get to your likeness is where you listen for emergent opportunities.

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