The Diary of a CEO Summary – The Philosophy (Ch. 19–27)

The Diary of A CEO

Table of Contents

Book Name: The Diary of CEO: 33 Laws of Business and Life
Author Name: Steven Bartlett

The Diary of a CEO Summary – 33 Laws for Success by Steven Bartlett

What does it really take to build a successful life and business in today’s world? Steven Bartlett, entrepreneur and host of the world-famous podcast The Diary of a CEO, explores this in his powerful book: The Diary of a CEO – 33 Laws of Business and Life.

This isn’t just another self-help book—it’s a practical blueprint based on Steven’s own journey from nothing to building multimillion-dollar companies, along with insights from some of the greatest minds he’s interviewed. Each of the 33 laws reveals actionable lessons on mindset, leadership, wealth, and personal growth.

👉 To make this summary more reader-friendly and engaging, we have divided it into four sections based on the book’s original structure:

  1. The Self (Ch. 1–9) – Understanding and mastering yourself
  2. The Story (Ch. 10–18) – Shaping your personal and professional journey
  3. The Philosophy (Ch. 19–27) – Timeless principles for success
  4. The Team (Ch. 28–33) – Building and leading with impact

In this section, we’ll explore The Diary of A CEO – The Philosophy, breaking down its key laws with real-life examples and actionable takeaways to help you apply them in your own life.

Rule 20: A Small Miss Today Becomes a Big Miss Tomorrow

In The Diary of a CEO, Steven Bartlett emphasizes a crucial truth: tiny mistakes, when ignored, compound into major failures over time. Whether in relationships, business, or personal growth, overlooking small missteps often leads to massive consequences later.

The 1-Degree Shift That Changes Everything

Steven illustrates this with a powerful analogy: if a plane shifts its course by just 1 degree, it may land hundreds of miles away from its intended destination.

The same applies to life. Small issues—unresolved arguments, ignored habits, or neglected tasks—don’t disappear. Instead, they grow silently until they cause breakdowns in relationships, careers, and businesses.

The Role of Kaizen – Consistency Over Time

Earlier, we learned about the Kaizen philosophy: the practice of making small, consistent improvements over time. But the reverse is also true. Small, consistent neglects can create devastating results.

For example, a husband and wife might have a minor disagreement. If it’s not discussed, it lingers. Over months and years, resentment builds until the relationship collapses. On the other hand, small, consistent conversations—like weekly check-ins—can resolve issues before they grow out of control.

Real-Life Example – Preventing Big Crises

Steven Bartlett shares the story of a man named John who practiced a simple yet powerful discipline: weekly sit-downs with his partner. Instead of letting small frustrations pile up, they calmly discussed issues as they arose. This practice not only prevented conflicts from festering but also built long-term trust and intimacy.

In business, the same principle applies. A leader who ignores small inefficiencies—like poor communication in a team—may one day face a full-blown organizational collapse. Fixing small problems early avoids big disasters later.

Why Consistency is the Real Superpower?

Steven Bartlett reminds us that consistency is not glamorous, but it’s the foundation of all success. Small acts of maintenance, clarity, and discipline—done daily or weekly—protect us from the compounding effect of neglect.

As The Diary of a CEO Key Takeaways highlight:

  • Small actions compound into greatness.
  • Small neglects compound into destruction.

The choice lies in what we allow to grow.

The Diary of a CEO Key Takeaways from Law 20: A Small Miss Now Creates a Big Miss Later

  • Tiny mistakes ignored today can lead to life-changing failures tomorrow.
  • A 1-degree shift in direction can completely change your destination over time.
  • The Kaizen philosophy applies in reverse: neglecting small issues compounds into big crises.
  • Relationships, friendships, and businesses fail not from one big mistake, but from many small unresolved ones.
  • As Steven Bartlett explains in The Diary of a CEO, consistent maintenance, clarity, and open communication are the real tools for long-term success.

Rule 21: Out-Fail Your Competition

In The Diary of a CEO, Steven Bartlett emphasizes that the people and companies who succeed the most are often the ones who fail the most. Failure is not the enemy—it’s the tuition fee you pay for wisdom. Every failure contains feedback, and feedback becomes knowledge. When reapplied, knowledge turns into power.

The Success–Failure Equation

Thomas J. Watson, the legendary CEO of IBM, once said:
“If you want to increase your success rate, double your failure rate.”

Steven explains that before he even discovered Watson’s words, he had already been practicing this principle in his own company. He encouraged his team to take risks, experiment, and embrace failure as a natural stepping stone toward progress.

The world’s most innovative businesses—like Booking.com and Amazon (AWS)—didn’t succeed by avoiding mistakes. They experimented relentlessly, failed repeatedly, and refined their ideas until they struck gold.

Fast Movers vs. Slow Movers

Steven highlights that there are two types of companies:

  1. Fast Movers – These companies spot an opportunity, make a quick decision, and execute—even if it means failing several times before getting it right. Eventually, they find the winning formula.
  2. Slow Movers – These companies take months deliberating, overanalyzing, and waiting for certainty. By the time they act, the opportunity has already passed, and competitors dominate the space.

The lesson? Speed matters more than perfection. The companies willing to out-fail their competition become the market leaders.

The 5 Principles of Innovative Companies

Steven Bartlett shares five consistent principles that define the culture of companies that win by failing more than others:

  1. Remove Bureaucracy
    • Endless approval processes and rigid hierarchies slow down innovation.
    • The best companies empower employees at every level to experiment and make decisions without waiting for layers of management.
  2. Fix the Incentives
    • Teams need the right motivation to take risks. If employees are punished for failed experiments, they’ll stop innovating.
    • Reward effort, creativity, and learning—not just results.
  3. Promote and Fire
    • Promote leaders who encourage experimentation and bold decisions.
    • Remove those who suffocate innovation through fear, control, or excessive caution.
  4. Measure Accurately
    • Failure without data is just chaos. But when experiments are measured properly, every failed attempt teaches valuable lessons that lead to smarter decisions next time.
  5. Share the Failure
    • Don’t hide mistakes. Celebrate and share them openly so the entire team can learn.
    • This creates a culture where failure is reframed as progress.

Real-Life Example – Amazon’s Boldness

Think of Amazon Web Services (AWS). Initially, cloud computing was a huge gamble. Many analysts thought it was risky and unnecessary. But Amazon experimented, adjusted after early failures, and today AWS is one of the most profitable arms of the company—contributing billions in revenue.

If Jeff Bezos had waited nine months to “analyze” instead of acting quickly, Amazon would have missed the biggest tech wave of the last two decades.

The Diary of a CEO Key Takeaways from Law 21: You Must Out-Fail the Competition

  • As Steven Bartlett explains in The Diary of a CEO, failure is feedback, and feedback becomes power when applied.
  • Thomas J. Watson’s wisdom: Double your failure rate to double your success rate.
  • The most successful companies (Amazon, Booking.com, etc.) experiment, fail fast, and refine until they win.
  • Speed beats perfection—fast movers always outpace slow movers.
  • The five principles of innovation are: remove bureaucracy, fix incentives, promote the right leaders, measure accurately, and share failures.

Law 22: Think Like a Plan A Believer

In The Diary of a CEO, Steven Bartlett highlights one of the most overlooked truths: your Plan B often becomes the biggest obstacle to Plan A. He argues that the safety net we create for ourselves sometimes kills our hunger, focus, and determination to make our primary vision succeed.

Steven shares his own story—being a college dropout, disowned by his parents, living in a deprived area, and often scavenging for food. In those moments, he had no Plan B. The only option was to make Plan A work. This level of necessity became the fuel for his eventual success.

To illustrate this point, Steven recalls the true story of Nando Parrado, one of the survivors of a 1972 plane crash in the Andes Mountains. With no way back and no alternatives, Parrado and others were forced to push forward for survival—even if it meant eating the remains of fellow passengers. Their brutal reality shows the power of having no fallback option: survival demanded total commitment to moving forward.

Even modern psychology research supports this idea—when people have a backup plan, they unconsciously lower their effort toward Plan A. The brain feels less urgency to succeed, making mediocrity more likely.

We’ve all heard advice like “Don’t put all your eggs in one basket”. But Steven challenges this cliché. He insists that by spreading your focus, you dilute your energy and weaken your chance of extraordinary success. To truly achieve greatness, you must think like a Plan A believer—without distractions, without escape routes, and without compromise.

Real-Life Example

Think about entrepreneurs like Elon Musk. When Musk invested everything into Tesla and SpaceX, he admitted he was prepared to sleep on the factory floor if things went wrong. There was no fallback. That relentless dedication made both companies industry leaders.

The Diary of a CEO Key Takeaways from Law 22

  • Plan B is a Distraction – Having an alternative weakens your drive to succeed in Plan A.
  • Necessity Fuels Success – When you have no choice but to succeed, you push beyond comfort zones.
  • Commitment Over Comfort – Full belief in one path brings clarity, focus, and resilience.
  • Failure Builds Strength – Without an escape route, even failure becomes a stepping stone forward.
  • Be a Plan A Thinker – True success demands undivided belief in your primary goal.

Law 23: Don’t Live Like an Ostrich

In The Diary of a CEO, Steven Bartlett admits one of his biggest mistakes—behaving like an ostrich instead of a lion. The “ostrich effect” refers to our natural human tendency to bury our heads in the sand and avoid facing uncomfortable truths.

The Ostrich Effect: Why We Avoid Discomfort

As humans, we are hardwired to shy away from pain, discomfort, or bad news. Steven explains that:

  • We avoid health check-ups until a diagnosis forces us to act.
  • We don’t open our bank accounts when we know we’ve overspent.
  • We ignore cracks in our relationships until they turn into irreparable breaks.

Research supports this. A UK survey of over 1,000 board members revealed that CEOs are often removed for denying reality, mismanaging change, tolerating low performance, or refusing to act. Avoidance creates bigger disasters in the long run.

Steven also warns that people who feel “invisible” in their organizations or relationships are the most at risk of falling into the ostrich trap—especially in the face of innovation, change, or uncomfortable truths.

How to Avoid Becoming an Ostrich?

Steven highlights a key insight from Nir Eyal: people don’t just seek pleasure—they are primarily motivated by avoiding discomfort. This applies everywhere—whether in business, relationships, or personal growth.

For example, instead of confronting a partner about recurring issues, many people let problems linger. Over time, those unspoken truths explode into bigger conflicts.

To counter this, Steven shares his 4-step method for handling discomfort and avoiding procrastination:

Step 1: Pause and Acknowledge

Stop running. Recognize the discomfort instead of pretending it doesn’t exist.

Step 2: Review Yourself

Ask what role you’ve played in creating the situation. Honest self-reflection is critical.

Step 3: Speak Your Truth

Have the difficult conversation—whether with your team, partner, or yourself.

Step 4: Seek the Truth

Don’t just rely on your assumptions. Look for facts, data, and perspectives that reveal the real picture.

Real-Life Example

Think of companies like Kodak. Once a photography giant, they ignored the digital revolution because facing that truth was uncomfortable. By burying their heads like ostriches, they missed the future and eventually collapsed. On the other hand, Netflix embraced change early by shifting from DVDs to streaming—even though it was uncomfortable at first.

The Diary of a CEO Key Takeaways from from Law 23

  • Avoidance Creates Bigger Problems – Ignoring issues only makes them worse over time.
  • Discomfort Is a Signal – Growth requires leaning into, not away from, what feels hard.
  • Relationships Need Truth – Unspoken issues in personal or professional life eventually explode.
  • Steven Bartlett’s 4 Steps Work – Pause, Review, Speak, Seek.
  • Be a Lion, Not an Ostrich – Face reality with courage instead of denial.

Law 24: Turn Pressure Into Your Privilege

In The Diary of a CEO, Steven Bartlett explains that comfort is slowly killing us—mentally, physically, and emotionally. Growth rarely happens in comfort zones; it happens under pressure. This chapter teaches us how to change our relationship with stress and transform it into a source of strength.

Pressure Is Not the Enemy

Tennis legend Billie Jean King once said: “Pressure is a privilege – it only comes to those who earn it.” Steven agrees and stresses that pressure itself is not good or bad—it’s our perception of pressure that defines its effect.

Research confirms this. People who believe stress is harmful are more likely to suffer health problems and even die from stress-related causes. On the other hand, people who view stress as a natural challenge experience better performance, stronger health, and greater resilience.

Making Pressure Your Privilege

Steven highlights a study shared in the Harvard Business Review, which revealed that people who adopt a “stress is enhancing” mindset perform better at work and enjoy improved wellbeing. To help us reframe pressure, Steven outlines a 4-step process:

Step 1: See It

Acknowledge pressure instead of denying or avoiding it. Name it clearly so it loses its power to paralyze you.

Step 2: Share It

Discuss your stress with someone you trust. Sharing reduces the weight it carries in your mind.

Step 3: Frame It

Reframe pressure as a signal that you’re doing something meaningful. Remember—it exists because you’ve chosen a path worth pursuing.

Step 4: Use It

Channel pressure into action. Instead of resisting it, harness its energy to fuel focus, determination, and persistence.

Pressure Can Save Your Life

Steven points out a universal truth: humans naturally choose the easy path, but easy choices often create long-term problems. Hard choices, on the other hand, build resilience, character, and opportunities.

For example, someone avoiding the pressure of exercise may find comfort today—but risk chronic illness tomorrow. In contrast, embracing that daily discomfort leads to long-term vitality. As Steven says, “Hard is the price we pay today for an easy tomorrow.”

Real-Life Example

Consider Navy SEALs in training. Their infamous “Hell Week” is designed to push soldiers beyond their mental and physical limits. While it looks brutal, those who survive develop a lifelong resilience that helps them thrive under real battlefield conditions. The same principle applies to entrepreneurship, leadership, and personal growth—pressure is a privilege that shapes us into our best selves.

The Diary of a CEO Key Takeaways from Law 24

  • Pressure Is Neutral – It’s not good or bad; it’s how we frame it that matters.
  • Your Beliefs Shape Stress – Viewing stress as harmful makes it harmful; seeing it as empowering makes it a tool for growth.
  • Reframe Discomfort – Pressure means you’re doing something meaningful and important.
  • Follow Steven Bartlett’s 4 Steps – See it, Share it, Frame it, Use it.
  • Hard Now, Easy Later – Embrace difficult choices today for a better tomorrow.

Law 25: The Power of Negative Manifestation

In The Diary of a CEO, Steven Bartlett introduces a counterintuitive but powerful idea: instead of only visualizing success, we must also anticipate failure. This practice, known as negative manifestation, isn’t about being pessimistic—it’s about identifying the red flags, risks, and obstacles that can stand between you and your goals.

Why Startups Fail: Asking the Right Question?

Steven shares that most startups fail in their early stages not because the idea is bad, but because founders rarely ask the right question:
👉 “Why will this idea fail?”

Instead of blindly chasing optimism, Steven encourages leaders to embrace realism by spotting the dangers ahead. He shares that his first business venture failed partly because he didn’t examine the possible pitfalls in advance.

The 5 Common Biases That Blind Us

Steven highlights five psychological biases that distort our judgment and often lead to failure:

  1. Optimism Bias – Believing everything will turn out fine, even without evidence.
  2. Confirmation Bias – Seeking only the information that supports our beliefs.
  3. Self-Serving Bias – Attributing wins to skill but blaming losses on external factors.
  4. Sunk-Cost Fallacy – Sticking with something just because we’ve already invested in it.
  5. Groupthink – Going along with the crowd instead of challenging flawed ideas.

These biases can blind us to reality, making us ignore potential risks until it’s too late.

The Power of the Pre-Mortem Technique

Instead of waiting for failure and doing a post-mortem, Steven recommends a pre-mortem—a proactive exercise where you imagine failure in advance and prepare for it.

Here are the 5 steps Steven uses:

  1. Set the Stage – Gather your team and explain the process.
  2. Fast Forward to Failure – Imagine your project has failed spectacularly.
  3. Brainstorm Reasons for Failure – List all possible causes, from poor execution to external risks.
  4. Share and Discuss – Collaborate and refine the most likely reasons.
  5. Develop Contingency Plans – Create backup strategies to address each potential risk.

This method helps leaders spot blind spots and increase their odds of success.

Real-Life Example

Tech companies like Google often use “pre-mortems” before launching big projects. For instance, before rolling out Gmail, engineers simulated what could go wrong—security issues, server overloads, or user rejection. By addressing these risks early, Gmail went on to become one of the most successful email platforms in history.

The Diary of a CEO Key Takeaways from Law 25

  • Negative manifestation is proactive, not pessimistic—it’s about anticipating risks before they derail you.
  • Biases blind us—optimism bias, sunk-cost fallacy, and groupthink can lead to poor decisions.
  • Pre-mortem is more powerful than post-mortem—solve problems before they happen, not after.
  • Steven Bartlett’s 5-step method: Set the stage, imagine failure, brainstorm causes, discuss, and plan contingencies.
  • Resilience comes from preparation—the more risks you foresee, the stronger your path to success.

Law 26: Your Skills Are Worthless, But Your Context Is Priceless

In The Diary of a CEO, Steven Bartlett reveals a powerful truth: skills alone don’t determine your value—context does. Two people with the same skills can be paid completely different amounts depending on where and how those skills are applied.

Skills vs. Context

Steven explains that society often labels people based on their profession: lawyer, accountant, dentist, or social media manager. But these titles can be misleading. What truly matters is where you apply your skills.

For instance, a social media manager working for a small business might earn an average salary. But the same manager, with the same knowledge, working in a billion-dollar tech company, can command exponentially higher pay because the context amplifies the value of their work.

When Context Multiplies Your Value?

Steven highlights industries like AI, cybersecurity, and fintech, where software developers and programmers are highly sought after. These professionals often earn far more than their counterparts working in traditional IT or basic web development—despite using the same coding skills. The difference lies in the industry context and the problems they’re solving.

Real-Life Example

Take the story of Aeron, who started his career in IT governance. For the first 2.5 years, his work was valuable but limited in recognition and pay. Later, he transitioned into the server industry, where his skills were suddenly worth much more. Eventually, he moved again into advanced IT sectors, where the challenges were greater, but so were the rewards. Aeron didn’t reinvent himself—he simply reapplied the same skills in a more valuable context.

This is Steven Bartlett’s core point: you don’t always need new skills; sometimes you just need a new environment.

The Bigger Lesson

Your value isn’t fixed—it’s dynamic. By placing yourself in industries, companies, or roles where your skills solve more urgent, complex, or high-value problems, you multiply your worth without necessarily working harder or learning something new.

The Diary of a CEO Key Takeaways from Law 26

  • Skills alone don’t define your value—context does.
  • Same skills, different pay: A software engineer in fintech can earn double compared to one in traditional IT.
  • Reapply, don’t reinvent: Sometimes changing industries creates exponential growth without new training.
  • Steven Bartlett’s insight: Your worth is tied to the environment in which you apply your knowledge.
  • Action step: Audit your current context—ask yourself if your skills could be more valuable elsewhere.

Law 27: The Discipline Equation – Time, Death, and Control

Discipline is often seen as something complicated, but Steven Bartlett in The Diary of a CEO breaks it down into a simple equation. The essence of discipline lies in how we manage our limited time on earth and how we allocate it toward the things that matter most.

Understanding Life’s Limited Clock

Steven highlights a sobering fact: the average life expectancy in the U.S. is around 77 years. If you are already 30, you have lived roughly 10,950 days, and about 17,228 days remain. No matter how successful or wealthy you become, you cannot extend these days beyond what is naturally given.

This means that the way you spend your time will determine everything—your success, health, happiness, and relationships. Whether you achieve your ambitions or fall short depends less on talent and more on discipline in managing this limited resource.

Time as Betting Chips

Steven Bartlett uses a powerful analogy in The Diary of a CEO: think of time as betting chips in a casino. Every hour of your life is represented by one chip. Once you place it, you can never take it back.

For example:

  • You might spend 1,33,333 chips on sleep.
  • Another 50,554 chips might be lost to endless scrolling on social media.
  • 30,000 chips go into eating and drinking.
  • Around 8,333 chips are spent in the bathroom.

That leaves only about 200,000 chips (roughly 8,000 days) to actually build your dreams, nurture your family, develop your skills, travel, and live a meaningful life. Suddenly, every single hour matters.

The Discipline Equation

Steven Bartlett frames discipline as an equation that connects three unavoidable forces:

Discipline = Death × Time Allocation × Intention

  1. Death reminds us that time is finite.
  2. Time Allocation shows that where we spend our hours determines our outcomes.
  3. Intention means that without a clear purpose, our chips are wasted.

When you combine these factors, you realize discipline isn’t about forcing yourself but about being deeply aware that your time is limited—and using it consciously.

A Real-Life Example

Think of someone who dreams of starting a business but spends most of their evenings binge-watching shows or endlessly scrolling on Instagram. Over five years, that’s thousands of wasted hours—chips gone forever. On the other hand, someone who dedicates even just two hours daily to learning, networking, and building projects accumulates over 3,600 focused hours in five years. That’s nearly the equivalent of a university degree earned by sheer discipline and consistency.

This shows that small intentional bets of time compound into massive life outcomes.

The Diary of a CEO Key Takeaways from Law 27

  • Time is your ultimate currency. Treat every hour like a betting chip that cannot be regained.
  • Discipline is awareness. It’s not about restriction—it’s about aligning your hours with your priorities.
  • Death is the motivator. Knowing your time is finite helps sharpen your focus.
  • Intention multiplies impact. Purpose-driven allocation of time ensures that even fewer hours can create great results.
  • Small daily investments add up. Consistent use of your chips builds the life you want.

Law 28: Focus on Who, Not How

In The Diary of a CEO, Steven Bartlett shares a powerful truth: the fastest way to build extraordinary companies, organizations, and projects is not by learning how to do everything yourself, but by finding the right people who can.

Most entrepreneurs make the mistake of thinking success depends on their personal ability to master every skill—whether it’s marketing, finance, operations, or technology. In reality, true success lies in asking: “Who can help me?” instead of “How can I do this myself?”

The Power of People Over Personal Effort

Steven Bartlett explains that CEOs and founders are ultimately judged by two abilities:

  1. Hiring exceptional individuals who bring specialized skills.
  2. Creating a culture where those individuals collaborate in ways that make the team greater than the sum of its parts.

This is where the magic equation comes in: 1 + 1 = 3.

When you find the right who, you don’t just add skills—you multiply impact.

Why “How” Slows You Down?

When you focus on learning how to do everything yourself, you face two big problems:

  • Time drain: You can’t master multiple crafts without sacrificing speed.
  • Lack of excellence: You might be “good enough,” but rarely world-class.

Instead, by asking who, you leverage the expertise of others who have already mastered the skill—and free yourself to focus on vision, leadership, and growth.

Real-Life Example

Think about Elon Musk. Musk didn’t personally build Tesla’s first batteries or write all of SpaceX’s code. Instead, he found the right whos—engineers, scientists, and innovators—who could execute his vision at the highest level. His genius lies in finding and empowering the right people, not doing it all himself.

On a smaller scale, imagine a local entrepreneur who dreams of starting a bakery. If she spends all her energy trying to master accounting, marketing, and website design on her own, she will burn out. But if she hires an accountant, partners with a marketer, and works with a web designer, she can focus on what she loves most—crafting delicious products and building customer relationships.

The CEO’s Real Job

Steven Bartlett reminds us in The Diary of a CEO that leadership is about vision and people. Great CEOs don’t try to be the best at everything—they create an environment where the best people can thrive.

Your job as a leader is to:

  • Define the vision.
  • Find the right who.
  • Build a culture that inspires excellence.

The Diary of a CEO Key Takeaways from Law 28

  • Ask “Who,” not “How.” Growth comes from finding the right people, not doing everything yourself.
  • Hiring is leadership. The quality of your team defines the quality of your company.
  • Culture is a multiplier. Great leaders build systems where 1+1 = 3.
  • Delegation accelerates growth. Free yourself from “how” so you can focus on the bigger picture.
  • Success is shared. Behind every great CEO is a team of skilled, motivated people.

👉 This law is a reminder that you don’t have to know everything—you just need to know who does.

The laws in The Philosophy remind us that success is rooted in principles that give life structure and meaning. Yet, no great achievement is possible without people. In the final section, The Team, Steven Bartlett shifts focus to leadership, collaboration, and building high-performing groups that can turn vision into reality.

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