Summary: This Is Day One: A Practical Guide to Leadership That Matters by Drew Dudley

• Drew Dudley’s “This Is Day One” challenges traditional leadership paradigms and invites you to embrace everyday opportunities to lead and make a meaningful impact.
• If you want to become a more compassionate and authentic leader, and are ready to redefine your approach to leadership, “This Is Day One” is your essential guide. It’s time to recognize your lollipop moments and start making a difference from day one.

This Is Day One (2018) challenges you to redefine and recognize your leadership potential. It provides a principled framework for developing performance-driving leadership values and behaviors that allow you to succeed while empowering others.

Introduction: A toolkit for developing consistent personal leadership skills.

On her first day at Mount Allison University, a young woman was intimidated by the noise and bustle of campus life. She was just about to go home and quit. But as she lined up in the queue of other freshmen, a student made a joke: he handed the guy next to her a lollipop and prompted him to make advances to the beautiful girl next to him. The whole scene was so awkward, you just had to laugh.

It was the author Drew Dudley who handed out the lollipop. For him, the episode was no big deal. But years later, the woman told him that his joke had convinced her that it was a bad idea to go home. A little lollipop had set off a chain of events that eventually led to her graduation.

This first “lollipop moment” illustrates the power of everyday leadership. And, whether we see it or not, small decisions can have a big impact. In this summary to Dudley’s This is Day One, we’ll explore personal daily behaviors that can empower change and help you become the person you want to be.

So, how do you become someone who makes a difference while staying true to yourself? It begins with establishing a personal leadership culture – the kind that reflects your reality and expectations. We’ll discuss leadership values, ask probing questions, and learn how to live every day as Day One.

You need a leadership philosophy.

Many leaders try to wing it. But to be a successful leader, you have to know your goals – only then can you develop a strategy. Without a plan, you’ll be flailing around, hoping to get lucky. So, if you’re serious about making a difference, you need to break down and identify your leadership values and philosophy.

Unsurprisingly, leaders with a philosophy are more successful. For instance, they score 135 percent higher on trust metrics. While there is no one-size-fits-all approach to leadership, developing a personal philosophy is a perfect place to start. By considering your values and goals, you create rules to guide your actions and help you make good decisions.

Deep value questions help you figure out what kind of leader you want to be – not what others expect you to be. Values guide our decisions, whether it’s about what to wear, watch, or study.

Have you ever seen The Truman Show? It’s a film about a guy who’s entirely unaware that his life is a TV show and everyone around him is an actor. Now, imagine you’re the protagonist and people are watching you for 30 days. Which values would you hope the audience identifies in you? Here’s a list – choose three of them: accountability, creativity, integrity, positivity, respect, and vision.

It might seem impossible to sum up everything you are into three parts. However, if you write down your values, you’ll eventually figure out what drives you. Note that these are only surface values. We’ll have to dig much deeper to get reality to match your perception.

Discovering values means considering what’s most important to you in any given situation. Say you’re trying to decide whether or not to take on a new job. You might accept it if it means being able to spend more time with your family. Other values that could come into play are authenticity – Are you being true to yourself? – and courage – Are you willing to take on a new challenge? In the end, only you can know your key values and how they’ll affect your choices.

If you want to be a good leader, you need to know who you are and what you believe in. A strong leadership philosophy is rooted in values. They help you align decisions with your priorities. Great leaders know they have to set a good example. So they don’t just talk about their values – they live by them.

Influential leaders share six core values.

Imagine what it would be like if all of your past actions, good and bad, were erased – and you didn’t have time to take things for granted or worry about the things you couldn’t change. You’d focus on today, ensuring everything you do aligns with who you want to be.

This is Day One.

It might sound scary, but starting over can be freeing. It lets you redefine yourself and gives you the chance to build the life you want. In committing to the Day One philosophy, you keep your mind on your goals and make steady progress toward them. Typically, you’ll bring these six key values with you.

First, leaders must make an impact. One way to cultivate impact is to recognize the leadership of others. Without this, it’s difficult to effect positive change. Show your trust and respect for people by identifying their unique leadership qualities.

Second, anyone in charge of something needs to have courage. Leaders must be willing to take chances and try new things, even if there’s a risk of failure. Why? Because you can’t learn and grow if you don’t take risks. Your methods become outdated and obsolete.

Third, true leaders empower others to believe in their own abilities and potential. They work to help others; as a result, they feel capable and valued.

Fourth, it’s vital to be able to make quick decisions in the face of a crisis. That’s next-day leadership. However, ensuring this doesn’t become your default position is more important. Day One leaders understand that their followers are essential to their success. They are committed to the personal and social growth of those around them. Growth keeps you from being stuck in next-day mode, where you’re reacting to change rather than being proactive.

Fifth, a leader knows how to rise above the chaos and keep their cool – to elevate instead of escalate. They treat everyone with respect and show class, no matter what. They know small acts of kindness can make a big difference, so they go out of their way to be kind. If you want to be a respected leader, act with class.

And finally, it’s important to have self-respect. This isn’t the same thing as being narcissistic or egotistical; it’s having a healthy appreciation for yourself. Paralympian Stephanie Dixon has competed in Athens, Sydney, and Beijing. She’s won 17 medals and set five world records despite having one leg. Stephanie tells a story about wearing a prosthetic leg to school. It irritated her, slowed her down, and caused her pain. However, she believed she should keep wearing prostheses to please others . . . until she realized she was prioritizing their needs over her own. Stephanie now uses crutches and lives authentically as a result. Leaders who respect themselves inspire others to do the same.

These six values contribute to both personal and professional success. Furthermore, the ripple effect from embodying these values benefits countless other people too. So, now that you’ve learned the key values, let’s look at how to embed them into a Day One leadership culture.

Develop your personal leadership culture.

Culture influences our behavior. When someone violates a cultural norm, the reaction is swift. For example, in 2022, singer Harry Styles was chastised for his unconventional fashion choices. Similarly, people who don’t follow Covid’s mask-wearing rules are often publicly shamed. While it may be tempting to dismiss customs as something over which we have no control, the truth is that we can shape our own culture.

When it comes to developing a personal culture of leadership, pay attention to your actions. The key is to keep asking questions. You can use a peculiar phenomenon known as the question-behavior effect to ensure repeated positive behavior. This phenomenon compels you to evaluate your actions and change them in the future if needed. Knowing that your actions reflect your values enables you to generate the powerful momentum needed to achieve your most significant goals.

Let’s pick a value – for instance, impact. You can define impact as “a commitment to creating experiences that make others feel better after interacting with me.” Next, you need to embody your definition in the form of a question. Ask yourself, What have I done today to recognize someone else’s leadership? By framing the question like this, you leave little room for yes-or-no answers. But we’ll go into more detail on forming leadership questions later.

Prioritize and commit to answering the impact question every day for a week. Search for leaders from the past and present. This could be anybody – a coach, teacher, parent, or even a warmhearted hot dog-vendor. Day One is a pledge to create experiences that make others feel good about engaging with you. So, create another value question and use it as an opportunity to demonstrate your Day One leadership culture on a daily basis.

Ask the edge-of-the-bed question if you want to grow.

Great leaders aren’t perfect. They don’t have all the answers. Sometimes, the best way to shine is to reflect the light of others.

Imagine your child is about to leave the nest. It’s the last night they’ll sleep at home, and you’re sitting on the edge of their bed to say good night. They ask you a question: “What single life lesson has had the greatest impact on your happiness?” What would your answer be?

Use this edge-of-the-bed question to elicit people’s stories. You’ll gain knowledge while helping others identify what they can teach. It’s a great way to learn about leadership – and it’s a constant reminder that we can find it anywhere.

Take a few minutes at the end of each day to reflect. Ask yourself, What did I do today to increase the chance that someone would learn something? What will boost my productivity tomorrow? Plan and work hard to keep growing at a healthy rate. Edge-of-the-bed questions motivate and reward us, reminding both parties why we matter.

OK, now it’s your turn to create your edge-of-the-bed advice. Make a list of 30 life insights that you believe could help others. To start, think about the advice you’ve gotten that has helped you in the long run. How would you explain it?

Think about the backstory: Is there a takeaway? What problems does the advice help people avoid? What new perspectives might it create? As you review your list, core values will emerge.

Almost every insight you gain comes from something you did or failed to do. From this, you can reverse-engineer your values. Consider each insight for a moment, and then complete this statement with your value: If someone followed this advice, they would do a better job embodying . . .

Mining your best and worst days helps match reality with perception.

Think about the two worst moments of your life. The times you fell short – when you were the furthest away from how you see yourself. It’s not usually a place you want to visit. But do it anyway! Grab a piece of paper. Rather than expressing how you feel, explain what happened and why you feel that way. This quick exercise will help you delve deeper into your core values.

Now write down your two happiest life moments. It could be when you achieved something remarkable or showed strength in the face of adversity. How proud are you of the two situations you’re most pleased with?

You’ll likely realize the disappointment in the first scenario results from deeply violated personal values.

As previously discussed, leaders must create and identify core values. These principles will guide everything you do, from communicating to making decisions. Keep asking yourself questions on a daily basis to ensure your actions reflect your values – and to remain committed to progress. This is how you train for Day One leadership.

To identify the core values of the worst and best moments you identified earlier, finish the following sentence: “If I take this insight to heart, I will [insert your value here] better.” Four important values will immediately become clear – because strong encounters like these expose our true selves.

Summary

To put your leadership values into action, ask yourself specific and action-oriented questions about your life and work. So, for example, instead of asking, “Am I being honest with myself?” you could ask, “What can I do to be more honest in my interactions with others?” Let’s use the value of empowerment as another example. “Did I help somebody succeed today?” is a broad question. It’s easy to respond “yes” without identifying any actions. So let’s make the question more specific: “How did I help somebody succeed today?”

When you answer action-oriented questions every day, you’ll start to figure out which of these questions give you the most options, fit best into your life, and get you most excited.

About the author

Drew Dudley‘s TEDx talk “Everyday Leadership” has been viewed close to five million times and praised by Time, Business Insider, and Inc. magazine. Dudley is the founder of Day One Leadership, where he works with individuals and organizations around the world to unlock their leadership potential.

Genres

Management, Leadership, Inspirational, Self Help, Personal Development, Business, Canada Cultural, Motivation

Table of Contents

Introduction xv
Part I This Is Day One 1
1 This Is Day One 3
2 The New Guy 7
Mustafa 8
3 Are You a Leader? 13
The Lollipop Moment 17
Everyday Leadership 23
4 Plan to Matter 27
Your Personal Leadership Philosophy 29
“Could You Explain What That Word Means?” 31
Values: Criteria for Decision Making 34
5 Day One Leadership 43
A Personal Culture of Leadership 43
Living Up to Your Ideals 44
Finding Leadership 48
6 Operationalizing Your Leadership Values 53
Part II Six Key Leadership Values 57
7 The Big Six 59
8 Impact 62
Just 63
Mr. Peters 64
9 Courage 71
Rejection Therapy 71
Confidence vs. Courage 74
The Magic Question 78
The List 81
Change Is Courage 88
Too Young to Settle 94
10 Empowerment 102
The Problem with Drew Dudley 102
Here’s the Part Where I Use a Buzz Term 105
Turn In Your Service 109
11 Growth 114
Empowerment vs. Growth 114
“Don’t All Books Have Stories?” 115
One Day vs. Next-Day Leadership 120
Why Are You on the Train? 124
The Edge of the Bed Question 127
12 Class 135
The Player to Be Named Later 135
Leaders Elevate 136
Elevating Email 138
13 Self-Respect 142
Treat Yourself First 142
Recognize That Happiness Must Be Cultivated 144
Recognize That Greatest Is the Enemy of Great 147
Stop Wearing Your Fake Leg 155
Plan for Failure 157
The Five Steps of Everything 161
Recognize That Things Don’t Happen for a Reason 164
Heal 166
Think Like a Landlord 168
“The Man You’re Going to Be One Day” 171
Only Hurt People Hurt Others 174
2,180 176
Part III Defining the Things You Want to Define You 181
14 Identifying Your Own Key Values 183
Now It’s All About You 183
Your Three Assignments 184
Assignment 1-The Three Key Values Hypothetical 184
Assignment 2-Your Edge of the Bed Advice 186
Creating Your Own Edge of the Bed Advice 190
Assignment 3-Your Best and Your Worst 191
Reverse-Engineering Values 192
Surfacing Values 199
Value Perception vs. Value Reality 202
15 Creating Your Own Questions 206
What Makes an Effective Question? 206
16 Practice Identifying a Good Question 211
17 Putting the Day One Process into Action 215
18 What Kind of Day Has It Been? 222

Appendix I Value List and Definitions 225
Appendix II Sample Action-Driving Questions 233
Appendix III Value Tally Sheet 247
Acknowledgments 249
Endnotes 253

Review

Drew Dudley’s “This Is Day One” is an insightful and practical guide to leadership that challenges conventional notions of leadership and encourages readers to embrace a more authentic and compassionate approach to leading. The book is structured around the concept of “Day One Leadership,” which emphasizes that every day is an opportunity to lead and make a positive impact. Dudley shares personal anecdotes and experiences to illustrate his principles and provides actionable advice for individuals at all levels of leadership.

The book begins by questioning the traditional image of leadership as an extraordinary act and suggests that it’s the small, everyday actions that truly define a leader. Dudley introduces the concept of “lollipop moments,” where seemingly minor actions can have a profound impact on others, and he argues that anyone can be a leader by recognizing and embracing these moments. He goes on to explore essential leadership traits like authenticity, self-awareness, and empathy, all of which contribute to meaningful and lasting leadership.

Dudley offers a practical framework for developing leadership skills, including self-assessment exercises and reflection questions. He also delves into the importance of resilience and emphasizes that leadership is a journey of growth, not a destination. The book concludes with a call to action, urging readers to embrace their “Day One Leadership” and make a commitment to creating positive change in their lives and the lives of others.

Drew Dudley’s “This Is Day One” is a refreshing and thought-provoking take on leadership. Dudley’s storytelling and relatable examples make the book engaging and accessible to readers from all walks of life. He challenges the traditional notion that leadership is reserved for a select few and, instead, empowers individuals to recognize the leadership opportunities in their daily lives.

The book’s strength lies in its actionable insights and practical exercises that help readers develop their leadership skills and self-awareness. It emphasizes the importance of authenticity, empathy, and resilience, qualities that are often overlooked in leadership literature. Dudley’s approach is a valuable addition to the leadership discourse, as it encourages a more inclusive and compassionate form of leadership.

In “This Is Day One,” Drew Dudley provides a compelling argument for redefining leadership and offers a roadmap for readers to become more effective, compassionate, and impactful leaders in their personal and professional lives. Whether you’re a seasoned leader or just starting your leadership journey, this book is a must-read.