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Index/Leadership/The Rising Leader
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Leadership is a Very Personal Journey

The Rising Leader · 2025-10-29 · 10 min

0:00--:--

Key moments - from our scoring

Substance score

14 / 100

Five dimensions, 20 points each

Insight Density3 / 20
Originality4 / 20
Guest Caliber2 / 20
Specificity & Evidence3 / 20
Conversational Craft2 / 20

After 800 episodes spanning the Rising Leader, Mastering Overwhelm, and Mastering Midlife podcasts, the host is taking a break when the work no longer feels like a 10 - his framework for pursuing only activities that excite him. Rather than continue with diminishing enthusiasm, he uses this moment to distill his biggest learning: leadership isn't about following bullet-point frameworks or generic best practices, but about the deeply personal work of deciding who you want to be as a leader and consciously evolving toward that vision. Drawing on conversations with leaders like one of his clients who grew from terrified junior leader to CEO, he explores how growth requires not just new skills but new ways of being. He references Michael Bungay Stanier's 10th anniversary edition of The Coaching Habit, which shifts focus from what to do and say to who you must become to ask questions authentically. The host's own journey illustrates this: as a naturally introverted peacemaker, he had to consciously become bold and outspoken, learning to speak hard truths with kindness rather than defaulting to over-niceness that undermined accountability. His message to rising leaders: clarify the life and relationships you want to create, then show up intentionally, because how you show up shapes how others show up around you.

Key takeaways

  • →Leadership is a personal choose-your-own-adventure about deciding who you want to be, not following generic frameworks - identify your starting point and desired end state across dimensions like compassion, accountability, and influence.
  • →Each rung up the leadership ladder requires new skills and new ways of being; growth is iterative and messy, involving mistakes and course corrections rather than perfect execution.
  • →How you show up as a leader directly shapes how your people show up, creating the relational environment (the water you swim in) for your entire life and career.
  • →The most effective way to stay motivated in leadership is to only pursue activities that feel like a 10 to you; procrastination and resentment signal misalignment with your core values.
  • →Leaders must often overcorrect their natural tendencies - the host had to swing from over-kindness to occasional harshness before finding the balance of speaking hard truths with love and accountability.

Topics in this episode

Leadership developmentAuthenticity in leadershipThe Coaching Habit by Michael Bungay-StanierPersonal leadership philosophyOnly 10s frameworkCEO advancement and career growthAccountability and autonomyIntroverted leadershipRising Leader HandbookMastering Overwhelm podcast

Questions this episode answers

What made the host decide to take a break from podcasting after 800 episodes?

The host realized that podcasting no longer felt like a 10 to him - it had dropped to a 6 or 7. When excitement is gone, procrastination and resistance take over, making it feel like work rather than passion, which he felt was unfair to listeners, guests, and his own growth.

What is the core insight the host drew from 400+ leadership conversations?

Leadership is a very personal journey about deciding who you want to be as a leader, not just following bullet-point rules about what to do. It requires consciously evolving your ways of being - how you show up - in addition to acquiring new skills at each level.

How does the host's own leadership growth illustrate the concept of becoming a different person?

As a naturally introverted, conflict-avoidant peacemaker, the host had to consciously become bold and outspoken, learning to speak truth even when uncomfortable. He initially overcorrected into harshness, but eventually learned to deliver hard truths with kindness and accountability.

Why does Michael Bungay Stanier add 'who you have to be' chapters to The Coaching Habit's 10th anniversary edition?

After 10 years of living with the framework that teaches what to do and say, Bungay Stanier recognized that authentic questions require authentic ways of being - you must first develop the presence and integrity to ask and receive honest answers.

What framework does the host use to decide what to pursue?

The host only does things that are a 10 to him - activities that excite him enough that he doesn't procrastinate and they don't feel like work. He applies this to podcasting, newsletter writing, and video content.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

3 / 20

The episode is almost entirely an emotional announcement that the host is pausing the podcast, with a thin, generic reflection on leadership being 'a personal journey.' The handful of substantive claims - like needing new 'ways of being' at each leadership level - are stated but never developed or evidenced, leaving listeners with almost nothing actionable.

leadership is a very personal journey
Every time you climb a rung on the ladder, you have to bring skills that work at that level, but then you have to acquire new skills and especially new ways of being

Originality

4 / 20

The 'only do tens' heuristic is a mildly interesting self-management concept but is never rigorously explained. Every other idea - leadership requires growth, be authentic, swing the pendulum when changing behavior - is thoroughly recycled motivational content with no contrarian or first-principles angle.

My newsletter will continue to go out. My videos, the media mark, as John calls it, will be still all over social media
I only do tens. When I have tens, I don't procrastinate. And it's not work

Guest Caliber

2 / 20

There is no guest in this episode whatsoever; it is a solo monologue by the host, a coach and podcast creator. The only external practitioner referenced is Michael Bungay Stanier, and only in passing without substantive content from him.

I was just on a webinar with Michael Bungay-Stanier, the coaching habit gentleman who has been on our podcast three times, my personal coaching hero
I was just talking to one of my clients earlier today

Specificity & Evidence

3 / 20

Numbers cited (800 episodes, 400 conversations, 30 years experience) are credential claims, not analytical evidence. The one client story is completely anonymized and resolved with no concrete detail about what actually changed or how. No metrics, timelines, or named frameworks are substantiated.

He's crushing it. He's now CEO of his company. And that was the dream when we first started working together
insights and wisdoms from over 400 conversations I've had on the Rising Leader podcast, on the Mastering Overwhelm podcast, on the Mastering Midlife podcast

Conversational Craft

2 / 20

This is an unstructured solo monologue - there is no interviewing, no follow-up questions, and no intellectual tension of any kind. The host narrates his emotional state and offers loose reflections without any scaffolding, challenge, or craft that would benefit a listener trying to learn something.

Sat down, turned on my camera, turned on my mic, and I realized I'm super sad, and that topic isn't going to work for today
I haven't decided. So then I thought, okay, let's do a summary of what I've learned

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

leader20show12podcast11love8rising7leadership6learn6life5skills5coaching5today5tens5continue4speak4grow3place3

Episode notes

We all love following a plan. But sometimes, life and leadership require us to pause, check in, and deeply honor whatever moment we’re in. Today, I sat down prepared with a topic, an outline, and all the excitement to share. But the truth is, I’m feeling sadness and loss, and that feeling led me to reflect on my personal journey and the deeper side of leadership. I’ve decided to take an indefinite break. Maybe it’s for a week, maybe longer, maybe it’s the last episode for a while. I know this is the right time to step back and only continue when it’s a true “ten” for me, when enthusiasm and authenticity return in full force. And in this reflection, I’m inviting you to reconsider what being a rising leader really means for you, at this precise moment. Over the course of 800 episodes across three podcasts, I’ve had the privilege to interview extraordinary leaders, CEO clients, and thought leaders like Michael Bungay Stanier. My journey is marked by a relentless search for authenticity, not just the list of what leaders “should do,” but who they choose to become.

Full transcript

10 min

Transcribed and scored by The B2B Podcast Index.

What do you want your life to look like? Because again, depending on how you show up is how people show up around you and how people show up around you is the water you're going to swim in for your life. Welcome to the Rising Leader Podcast. If you're rising through the ranks of your organization so fast that your leadership skills need to grow as fast as your responsibilities, you're in the right place.

If it seems you need a special set of skills to lead on a team of talented competitive peers, you're in the right place. If you're looking to become a trusted advisor to the CEO, you are definitely in the right place. 2025 is going to be a year of rapid change with unexpected twists and challenges. To meet the moment, we're going to need to be our very best in every situation.

We will need to be even-tempered, make smart decisions, and care for our mental health if we're going to continue to excel in our roles and for our families. This means we will be taking a little detour in our conversations over the next few months. I've invited some of my favorite spiritual, mental health, and resiliency experts to explore how we can stay on top of our game no matter the turns in the road. Of course, you can continue to explore our past shows for boots-on-the-ground leadership inspiration.

This is going to be good. Thanks for listening, and enjoy the show. Before we begin the show, I'm excited to let you know that the Rising Leader Handbook is available wherever you get your books. Yes, it's been finally published.

I'm so excited to share with you the insights and wisdoms from over 400 conversations I've had on the Rising Leader podcast, on the Mastering Overwhelm podcast, on the Mastering Midlife podcast. Also interjecting my own experience over the last 30 years and the last 10 years of coaching. So please let us know what you think. I hope you enjoy.

Also remember, you can still go to my website and get a free copy of Only 10s, as well as video resources, books, suggestions, and free courses. Now, enjoy the show. Had my topic for today all thought out, planned out, outlined out, and ready to go. Sat down, turned on my camera, turned on my mic, and I realized I'm super sad, and that topic isn't going to work for today.

What I feeling is sadness and loss because I made the decision that this is going to be my last podcast episode in a while I don know if it forever I don know if it for a week I don know if it for several months or until another idea comes along And I wrote in my newsletter today that it just no longer a 10 for me I love podcasting I love interviewing people I love sharing ideas. I love growing together. I love all those things. But it's like a six or a seven for me now after 800 episodes of three different podcasts.

Just not feeling that excitement, When I don't feel that excitement, procrastination comes in. It feels like work. It just feels like going uphill. And I don't think that's fair to you for listening.

I don't think that's fair to the guests. And it's definitely not fair for whatever's next for me. So I haven't decided. So then I thought, okay, let's do a summary of what I've learned.

Over 800 episodes of speaking to amazing leaders, amazing people. People have just figured out all different kinds of things in life. and about leadership, since this is the Rising Leader podcast. And what I've come to, especially in feeling emotional in this whole thing, is that leadership is a very personal journey.

You'll go on LinkedIn or YouTube and you will see so many energetic, put-together people with their bullet lists of how you should act, how you should be, what you should do, what you should keep track of, all of those things. And they're all right. None of them are wrong. There's all these skills that you need as a leader.

There's all these things you need to do to be a good leader. There's also ways you need to be to be a good leader. And that's where it's very personal. When you step into leadership, if it's thrust upon you or you put your hat in the ring and you decide, I'm going to lead, you've made a decision to step out of your comfort zone because, and I don't care who it is, if you're leading people, it's outside that comfort zone.

You have a responsibility to, even if you're nefarious, even if you're a bad person, you still have a responsibility to keep up this momentum, to keep this energy up, and it's a lot. So the choose your own adventure is, who do you want to be as a leader? Do you want to be effective? And what does that take?

What is your personality type? What's your starting point now in effectiveness for yourself and then in fostering effectiveness in other people to where you want to be. If you want to be compassionate and loving as a leader where do you start for yourself for your family and where is the end point where you want to be in loving If you need to learn how to hold people accountable to goals and to what they say and create autonomy, where are you on that spectrum? And then where are you on that spectrum to influencing other people?

And how do you have to grow to that end point? And it's always a journey. I was just talking to one of my clients earlier today, and I reminded him and I said, He's crushing it. He's now CEO of his company.

And that was the dream when we first started working together. And I said, what do you remember of you way back when, just before you started this journey, just before you threw your hat in the ring for this? Remember how terrified I asked him? And he said, all these things were hard for me.

All these things were outside of not only my comfort zone, but outside of my skill set. And now they are part of my every day. It's how I show up. And he got to see how he grew.

Every time you climb a rung on the ladder, you have to bring skills that work at that level, but then you have to acquire new skills and especially new ways of being. I was just on a webinar with Michael Bungay-Stanier, the coaching habit gentleman who has been on our podcast three times, my personal coaching hero. And he's putting out a 10th anniversary edition of the coaching habit. and what he said when he first started his webinar was that the coaching habit tells you what to do, tells you what to say, what to ask.

And he says after 10 years of living with this, he wants to put a few more chapters in on who you have to be. How do you need to show up in order to be able to ask these questions authentically, to get authentic answers to these questions? So that's the question for you. If you're listening to the Rising Leader podcast, that means you're a leader, you're an aspiring leader.

And who do you want to be as a leader? How do you want to show up? What do you want your life to look like? Because again, depending on how you show up is how people show up around you.

And how people show up around you is the water you're going to swim in for your life. Who do you want those people to be? How do you want them to act? How do you want them to treat you?

How do you want to treat them? What do you want these relationships to be like, and then consciously creating one step at a time, one mistake at a time, stepping on a rake and then getting it right. And then growing from there and watch your people grow with you. Wouldn't you love to be the leader who, when you change jobs, everybody comes along with you.

That a cool kind of leader to be That a community that you build So for me as a leader I had to be outspoken about a lot of things And I naturally introverted I'm naturally a little bit shy. Naturally don't want to make feathers. I'm a peacemaker kind of guy. And my brand is telling the truth.

My brand is being bold. My brand is being a little unvarnished. Because that's what I've aspired to be as a leader. I learned that my niceness and my over kindness in leadership was detrimental.

And I had to learn how to speak up. I had to learn how to speak truth. I had to do it clumsily. Right.

So when you're too kind and too nice and too like that kind of leader, you're going to swing the pendulum and you're going to screw up and you're going to be rude and you're going to be mean and you're going to be ineffective sometimes. And then the pendulum swings back. And now you can speak the truth with kindness. You can hold people accountable with kindness, right?

You learn how to get there. I can say things to people now that are so harsh and so confrontational and so rough. And I can say it with love. And I can say it while I'm on the other side of the table with my arm around them, knowing that we're a team, right?

That's something that you learn as a leader. So I hope you continue to learn. My newsletter will continue to go out. My videos, the media mark, as John calls it, will be still all over social media.

And I'm not going to stop writing. And I may come back to a podcast when I'm inspired. Again, when I only do tens. If you want only tens, it's free on my website.

You can have only tens. I only do tens. When I have tens, I don't procrastinate. And it's not work.

That's what I'm going to do with the podcast. I appreciate your time and your attention and the feedback and the notes and the, oh my God, like there's 800 episodes and the people that I've had to speak with and the things that I've learned and how I've grown. I can't believe it feels like a blink of an eye, but this break should be fun. I love you a ton.

Have a great rest of the day. Thank you for joining today's conversation. If you got value, please share the episode, give us a thumbs up, write us a review. And if there's a topic you'd like us to cover or a question that you have, send them my way.

Look forward to connecting on the next episode of the Rising Leader Podcast.

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