The Inner Journey of Leadership with Leadership Freak, Dan Rockwell

In this episode of The Leadership Habit podcast, Jenn DeWall talks to the self-proclaimed “Leadership Freak,” Dan Rockwell, about the inner journey of leadership. Dan is the author of the highly acclaimed blog Leadership Freak. He is also the co-author of the recently published book The Vagrant: The Inner Journey of Leadership: A Parable.

Dan’s concise and practical articles are read in every country on the planet. Inc. Magazine recognized Dan as a Top 50 Leadership Expert in the English-speaking world and a Top 100 Speaker. The American Management Association lists Dan as a Top 30 Leader in Business. We hope you enjoy this episode and learn more about the inner journey of leadership!

Episode Summary

As the episode opens, Jenn introduces Dan Rockwell to The Leadership Habit Audience. Dan is from central Pennsylvania, the home of Little League. He explains he lives in the countryside outside Williamsport with his wife, who was his childhood sweetheart. From that home, he writes his blog, Leadership Freak.

How Dan Became the Leadership Freak

He began writing the blog about 12 years ago. At the time, he had an urge to find more meaning in life and committed himself to writing five days a week for a year to see if it got any traction. Before starting the blog, he had minimal writing experience, so it was an interesting choice! Now, his blog has an audience of readers from every corner of the world.

Jenn congratulates Dan on his blog and asks how he can write so consistently. He explains that he has made it a habit. He has made it a routine to start writing first thing every morning, and when he goes to bed, he is already thinking about what he wants to write the next day.

Dan shares that his topic that day was about the myth of total independence. While leaders should be self-reliant, no one can be successful without the help of others. Jenn agrees with that and tells him that her aunt once told her there is no such thing as independence, only inter-dependence. She believes that connecting with others is the key to happiness and success.

The Inspiration for The Vagrant

Next, Jenn asks about the inspiration for Dan’s new book, The Vagrant: The Inner Journey of Leadership: A Parable.

Dan explains, “So, I’ve had this story in my head for about 10 years. It’s the story of a person who basically engages in self-defeating behaviors. Who hasn’t done that? I mean, everybody does stupid things, thinking they’re smart things. You know, like too much time just by yourself, too much time saying I’m going to be my own person. We have all engaged in self-defeating behaviors.

I started thinking about my own self-defeating behaviors. And I thought of this story, and I tried to write it, but it just wasn’t my style. You know, I’m still learning how to be a writer. So, I reached out to John David Mann and told him my story. He’s written 40 fables, 40 or 50 books. I don’t know how many. But he was the best I could think of– speaking of getting people in your life. And so I reached out to John, I said, Hey, I have this story. He said, tell me your story. So, I told him the story. He said– and this was the first phone call. He said, Dan, I love it. I got chills. Let’s do it. And that was about two and a half years ago.”

The Inner Journey of Leadership

Jenn then asks Dan what he would want a new leader or a struggling leader to learn from his book. He shares that he would love to help new leaders avoid some of the common pitfalls on their journey. As a business coach, he has also helped experienced leaders who feel lost in their journey. He hopes his book can help struggling leaders engage in self-reflection to discover their own self-defeating behaviors. Through that inner work, leaders can become better at their work and happier in life.

Self-Defeating Behaviors

Later, Jenn and Dan discuss some self-defeating behaviors that can slow down any leadership journey. Dan discusses how some leaders are held back by their inner critic or accuser. Jenn agrees that a lack of self-love can hold people back.

Another self-defeating behavior is avoiding self-reflection. A lack of self-awareness can lead to problems. Dan shares a personal example, “You know, people have said to me, you’re pushy. And it’s like, but I’m a fuzzy teddy bear. Well, that’s a disconnect. People see me this way. I see myself in another way. That ends up in self-defeating behaviors. I start doing things that don’t work.

That’s where self-reflection comes in. And structured self-reflection, not just sitting under a tree and contemplating the meaning of life. And by the way, that’s not all bad. I mean, you can, you know, contemplate the meaning of life. That’s good. But this is a book for managers and leaders and people who wanna do well in work and in business. So, learning structured self-reflection helps you see how people see you. Truly understand what you’re after and think, is that getting me where I want to go?”

Practicing Self-Reflection

Then, Dan and Jenn discuss some ways leaders can practice self-reflection. Dan explains there are five practices in the book, but he can share a straightforward method to begin with. He suggests thinking about a few of your goals and then designing three to five questions to ask yourself. For example, how am I progressing towards this goal? How did I succeed in that today? How did I fail? What will I try differently? And practice writing answers to those questions daily to reflect on those things.

Avoiding Self-Deception

Dan also warns about the tendency for self-deception if we don’t invite others on our leadership journey. As leaders, we need to invite feedback from others to improve our self-awareness. Otherwise, you may not know which self-defeating behaviors are holding you back. Part of becoming an effective leader is understanding how you are perceived by others.

Jenn agrees but also cautions that as much as we need feedback, it is important not to let other people’s opinions take you off your path. Dan agrees that there must be boundaries and that feedback should be constructive.

Final Thoughts

As the episode closes, Dan shares some advice for aspiring leaders. A successful leader’s journey starts with their habits. He encourages everyone to start some sort of self-reflection practice. He suggests keeping it simple and short until it becomes a long-term habit. Building self-awareness is the first step to leadership effectiveness.

He also asks the audience to consider supporting their local bookstores to get a copy of his new book! Either way, The Vagrant will be available on September 19th, wherever books are sold!