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Day One: Committing to a broader definition of leadership

Leadership is too exclusive and narrow. We need to do the hard work of opening its possibilities beyond just the privileged, Drew Dudley says.

10 min read


Drew Dudley

Drew Dudley

There are two big problems with how leadership is discussed and rewarded.

The first is that leadership is equated with status, so that people in management positions or authority roles are automatically thought of as leaders (and, by default, effective leaders). The second is that leadership takes many forms but is usually only discussed in terms of heroic, vocal or aggressive leadership.

So we wind up with people only knowing and seeing superhero leadership conducted by famous or powerful people. Even humbler versions of leadership theory can wind up focusing on traditional leadership archetypes and not everyday people in everyday life.

That’s an incomplete picture of the world, and it also gives an incomplete insight into how people can become leaders, how long it takes and the quiet, hard work involved. Many people can’t envision themselves as those outsized leaders, whether because of personality or circumstance or because they look nothing like them. And if you can’t see yourself as a leader, how can you believe you can become one?

I’m not immune to overly highlighting big names, but I try to think of workplace leadership (and communication, and other skills) as being things we develop over time, and an ongoing basis.

We must build habits, and this isn’t easy. There are setbacks. Our skills can decay if not exercised. I try to share with my readers the importance of examples to illustrate, tactics for us to apply and stories to motivate us.

So, I was intrigued by the book “This is Day One: A Practical Guide to Leadership That Matters,” (August 2018, Hachette Books) by Drew Dudley, and its promise that “This book examines what a leader should do on Day One. That’s its only focus. It doesn’t really get to day two.”

The other promise of the book is that it will show “How you can embrace the idea that there is a form of leadership to which we all can and should aspire. A form of leadership you’re already living without giving yourself credit for it.”

I spoke last week with Dudley, a day before the book published. We talked about a range of topics, but I specifically asked him about the thinking behind the book’s thesis and the challenges of writing about leadership in a way that is truly inclusive and diverse.

Why we need to recommit to being better without being addicted to our failures — and the personal reason Dudley knows this

Even before digging into the book, I had a question about the Day One approach. Starting each day anew sounds good, but what about people who tend to revisit their mistakes and live them over and over? This approach could instead turn into a daily recrimination.

“I think one of the key pieces is to not try to convince ourselves that it can be avoided,” Dudley says. “If we think that we can avoid it, not doing so is just yet another failure.”

Dudley once asked a daredevil friend how he lived without fear. That friend’s response: “Oh, I don’t live life without fear. I just have a really healthy relationship with fear.”

This friend, Dudley says, had to accept that people spend a lot of their lives trying to avoid things rather than learning to deal with them — “pain, and jealousy and failure” being just three of them.

So, instead of trying to avoid these feelings, examine them, try to discover the source and then train yourself on how to deal with these things weighing your mind down. This is where Dudley’s “Day One” mindset comes from.

“I know that a shift in mindset doesn’t sound like it’s powerful. … But this particular shift in mindset is one that has proven to help not just me but a lot of people. In many ways, I’ve adopted a philosophy that came from my battle with alcoholism, and how I have remained committed to my sobriety.

“We are addicted to focusing on our failures.”

Addictions are habits, and habits are hard to break and hard to build. Not only that, but there is a lot of pressure on people when they are trying to break or develop habits. Similar to rehashing old mistakes, a slip-up in building a habit can send people into a tailspin.

I think of habits a lot in the context of William James, who wrote a treatise on the subject, but even he may have placed undue mental strain upon people in this advice:

“Never suffer an exception to occur till the new habit is securely rooted in your life. Each lapse is like the letting fall of a ball of string which one is carefully winding up; a single slip undoes more than a great many turns will wind again.”

Dudley suggests another way, one that might feel familiar to some readers.

“If you don’t want to have a drink for the rest of your life, you choose not to have a drink today. And then you have to treat every day of the rest of your life like you did Day One of your recovery. And a big focus of the book is the idea that Day One has an inherent commitment, humility and forgiveness to it. Meaning that if you screw up on Day One, you can forgive yourself and recommit, but if you manage to do something successful for 25 years in a row, it doesn’t matter — you still have to recommit to those behaviors.”

Dudley is such a proponent, in part, because he was a sort of test run for the ideas in the book.

“I look at it this way: Eight years ago this week, I was a 310-pound alcoholic, with untreated bipolar disorder, and I was in a toxic relationship at work. And anybody in that position has a ton of old mistakes and lost opportunities to dwell on.”

What Dudley’s book tries to do, as he had to, is look at what is happening today — what behaviors are aligned with who you want to be, and which aren’t. This process “did not deny the fact that I had mistakes, it just made a healthier relationship with them. It said, ‘yeah, that’s a part of my life, but it shouldn’t impact how I act today.’”

This is a seemingly simple mindset shift, but it is intended to lead to powerful behaviors, Dudley says — namely, identifying your personal values and committing to living them each day

There are more leaders than we acknowledge

Dudley’s book and his idea of leadership is clearly meant to be broader and more inclusive than “man in powerful role,” and it’s also meant to give a sense of some control back to people — commiting on Day One is a personal act. But how possible is this?

I specifically asked him how the book and its lessons would be applied and followed by, say, women, people of color, people with disadvantages of opportunity or anyone who doesn’t fit the stereotypes of leadership qualities, and so on.

This was a concern for Dudley as he wrote the book. He knows he has it, relatively speaking, pretty well. “If you’re going to talk about leadership, you have address the fact there are systemic barriers to leadership. People who don’t have the privilege, like I do, like we do, of being a straight white guy, right?

“Women and minorities are underrepresented in the leadership examples that we give to children, when they’re explicitly taught about leadership, and they’re underrepresented in the popular culture. And that causes a wall to be built between most people’s concepts of themselves and the concepts of leadership, for anyone who’s not a straight white guy. Now, look, that problem exists for everyone, but less so for straight white men.”

People shut out of leadership can’t bear the burden of rectifying that wrong

Dudley is about helping people make choices within their own lives, but he’s also well-aware that the universe of choices is bigger for some people than for others.

“I hope that rephrasing leadership as a daily choice that is available to everybody, and providing a clear process on how to make that choice, that’s gonna help many people start to break down that wall between their identity and leadership,” he told me. “But, what I really want to make clear, the responsibility for breaking down those walls, I don’t think it just falls to the people who have been hemmed in by them. It doesn’t just fall to women and minorities.”

He expanded on this later in our interview: “We can’t ask people who have systematically had their identity separated from the concept of leadership to just unlearn that. All of us, I think, have to commit to broadening our definition of leadership.”

People in privilege have to be part of the solution, not the problem

Dudley talked about the three prisms in which we view leadership: people with power, wealth and/or influence.

“When we start recognizing that leadership comes from different places other than these positions of power, we are actually starting to recognize that those positions are not positions that most people who don’t look like me have had access to, but they’re still out there creating moments of leadership … those of us with privilege need to better recognize that this leadership is out there being demonstrated.”

Dudley was quick to name some of the hard realities of his book and the topics it addresses. For instance, his book is a guide to helping people help themselves, but that doesn’t eliminate the fact that many obstacles are not of our doing, especially for marginalized people.

Two, he acknowledges his own privileged worldview in being the author and in some of the examples he used in the book. In short, “some of the problems I aim to solve in the book are problems that many people would consider themselves fortunate to have.”

Moreover, these narrow examples of leadership start long before adulthood, as he told me. Fixing these problems also includes “being more conscious in the examples of leadership given to kids, that means continuing to point out when women and minorities are underrepresented in television and movies and pop culture.”

The third, and most severe, issue is the role of privilege in resisting any change that opens up opportunity or access.

“We have to do it together because women and minorities are used to having white men push back when they try to broaden accessibility of anything,” Dudley told me.

For privileged people, he added, “we also have to start recognizing this form of leadership — even though it means it opens the concept up to more people. Because, traditionally, people in power do not like it when more access is given to anyone because it makes us feel like we’re less special.”

But Dudley is also hopeful.

“I really hope that a whole bunch of people — anyone who feels like the idea of leadership has been systematically pushed away from them — I want them to benefit from this.”


James daSilva is the longtime editor of SmartBrief’s leadership newsletter and blog content, as well as newsletters for distributors, manufacturers and other professions. Before SmartBrief, he was a copy desk chief at a small daily New York newspaper. Contact him @James_daSilva or by email.