Book Notes: How Will You Measure Your Life?

Nick Gray
Nick Gray
Jul 11, 2017 · 6 min read

This is one of my new favorite books.

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I first read this book on a beach during bikini boot camp in Tulum. Ideal life situation 10/10

Here are my favorite highlights:

The Book’s Purpose

  1. How can I be sure that my relationships with my spouse, my children, and my extended family and close friends become an enduring source of happiness?
  2. How can I be sure that I will live a life of integrity — and stay out of jail?

Importance of Planning

Power of Theory

Reactive vs Proactive

Creating Your Strategy

  1. Priorities
  2. Balancing plans with opportunities
  3. Allocating your resources

What is Strategy?

Rather, it is a continuous, diverse, and unruly process. Managing it is very hard — the deliberate strategy and the new emerging opportunities fight for resources.

Evolving Strategy

93 percent of all companies that ultimately became successful had to abandon their original strategy — because the original plan proved not to be viable.

Resource Allocation and Strategy

“To understand a company’s strategy, look at what they actually do rather than what they say they will do.” Andy Grove

Individuals prioritized things that gave them immediate returns — such as a promotion, a raise, or a bonus — rather than the things that require long-term work.

Strategy: Summary

Factors of Motivation

  • Hygiene factors
  • Motivation factors

Hygiene factors are things like status, compensation, job security, work conditions, company policies, and supervisory practices.

Fun fact: The opposite of job dissatisfaction is not job satisfaction, but rather an absence of job dissatisfaction.

Motivation factors include channeling work, recognition, responsibility, and personal growth. Feelings that you are making a meaningful contribution to work arise from intrinsic conditions of the work itself.

New ideas: What has to prove true?

Time Management

  • I’ve had to force myself to stay aligned with what matters most to me by setting hard stops, barriers, and boundaries in my life.


The larger and more complex a company becomes, the more important it is for senior managers to ensure employees make, by themselves, prioritization decisions that are consistent with the strategic direction and the business model of the company.

It means that successful senior executives need to spend a lot of time articulating clear, consistent priorities that are broadly understood throughout the organization. Over time, a company’s priorities must be in sync with how the company makes money because employees must prioritize those things that support the company’s strategy.

Never Outsource the Future

Ship of Theseus / Theseus’ Paradox


The path to happiness is about finding someone who you want to make happy, someone whose happiness is worth devoting yourself to.

Sacrifice deepens our commitment.

Children and Parenting

  • The two fundamental jobs that children need to do are to feel successful and to have friends — every day.
  • Children will learn when they are ready to learn, not when we’re ready to teach them.


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

Family Org as Business

Growth vs Profitability

  • When the winning strategy is not yet clear in the initial stages of a new business, good money from investors needs to be patient for growth but impatient for profit.
  • Once a viable strategy has been found, investors need to change what they seek — they should become impatient for growth and patient for profit.

If a company has ignored investing in new businesses until it needs those new sources of revenue and profits, it’s already too late. It’s like planting saplings when you decide you need more shade.

Henry Ford Quote on Technology

If you need a machine and don’t buy it, then you will ultimately find that you have paid for it and don’t have it.

Staying Out of Jail

Life is just one unending stream of extenuating circumstances.

It’s easier to hold to your principles 100 percent of the time than it is to hold to them 98 percent of the time.

Nick’s Conclusion

“Management is among the most noble of professions if it’s practiced well.”

My friend Nina Simon suggested that we read this during our long weekend retreat at Bikini Bootcamp (related video).

More Information


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