The 'Wrong Wall' Trap: Why Ambitious Leaders Fail to Find True Success | Mark J. Silverman

Summary

Podcast Summary: Right About Now – Legendary Business Advice

Episode: The 'Wrong Wall' Trap: Why Ambitious Leaders Fail to Find True Success | Mark J. Silverman
Host: Ryan Alford
Guest: Mark J. Silverman (Author of Only Tens, The Rising Leader Handbook, Executive Coach)
Date: October 10, 2025

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Episode Overview

This episode of Right About Now features a frank, insightful conversation between host Ryan Alford and executive leadership coach Mark J. Silverman. The core theme centers on why driven, successful leaders often still feel unfulfilled—what Mark calls "climbing the ladder on the wrong wall"—and how authentic leadership and self-awareness are critical for real, sustainable success. The discussion dives into the pitfalls of unchecked ambition, the realities of modern team dynamics, and practical steps to becoming the kind of leader others want to follow.

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Key Discussion Points & Insights

1. The Modern Leadership Dilemma

Timestamps: [00:26], [01:46], [02:35]

• Leadership demands more “people time” than most anticipate.

  “If you think it takes a lot of people time, it takes even more of that. And it takes your patience, it takes your presence in order to guide people.”
  — Mark J. Silverman [00:26]

• Rising through the ranks for being ambitious doesn’t prepare you for emotional intelligence or people management.
  Both Ryan and Mark reflect on personal leadership missteps early in their careers.

• Nervous system and emotional regulation are underrated skills:
  “When life throws speed bumps at you…when your ducks are running around like crazy and your people are just not being what looks like sane. Staying on track is really hard.”
  — Mark J. Silverman [01:46]

2. Defining and Pursuing Real Success

Timestamps: [03:20], [03:28]

• Success means knowing yourself first:
  “The most important thing is knowing who you are and then knowing what you want. What is the outcome you want? ... How you want to feel, who you want to be with when you get there is probably the most important thing.”
  — Mark J. Silverman [03:28]

• Not everyone operates with rigid goal orientation:
  Mark admits he’s “not very goal oriented,” but he’s clear on the person he wants to be, how he wants to feel, and who he wants to impact along the way. [04:13]

3. The Rising Leader Handbook Principles

Timestamps: [04:33], [04:38]

• Four levels of leadership:

  • Leading up (becoming a trusted advisor to those above you)
  • Leading across (collaborating with peer leaders)
  • Leading the team (direct reports)
  • Leading yourself (self-awareness, discipline, fulfillment)

• Self-leadership as the foundation: “That's the most important thing. How are you navigating family, success, work, money, pressure, all of those things?”
  — Mark J. Silverman [04:38]

4. The Inward Journey: Why Self-Work Matters

Timestamps: [05:30], [05:53]

• Building outward leadership must start inward:
  Ryan draws the analogy of the airplane oxygen mask — take care of yourself first so you can help others.

• True fulfillment and sustainability:
  “I've watched too many of my contemporaries crash and burn.... The best self help, best spiritual program in the world is to become an entrepreneur. ... And it always comes full circle to who are you? What makes you tick, what makes you worthwhile and happy and what is going to be sustainable.”
  — Mark J. Silverman [05:53]

5. Leading Across: The Hidden Challenge

Timestamps: [06:31], [06:48]

• Ego-check is essential:
  Mark shares his own struggle—either taking over or stepping back, but rarely collaborating as a true peer.

• “Coopetition” over competition:
  “You want it to be coopetition, you want to shine, you want to get promoted, but ... making sure all boats rise.”
  — Mark J. Silverman [06:48]

• Building authentic relationships helps sustain success in a cutthroat world:
  “[Even] in the face of people who are cutthroat, dishonest … if you can take the high road and you can really make your own way, it always, always, always brings you where you need to be.”

6. Coaching the “Alpha”: Tame the Dominant Doer

Timestamps: [07:48], [08:32]

• Why care about others?
  “Mark, why do I have to care about other people? Why can't we just get shit done?"
  — Mark J. Silverman recalls common client resistance [08:32]

• Mark reframes the question: what kind of work environment, legacy, relationships do you want?

• Michael Jordan metaphor: Jordan learned to win only after embracing teamwork instead of solo domination.

7. Practical Leadership Takeaways

Timestamps: [09:20], [09:34]

• Two key practices:

  1. Health Baseline:
     “Take care of your sleep, your exercise, your food and your well being. If you're tired and you're grumpy and you're on edge, you're in fight or flight. ... You're just at a deficit from the get go.”
     — Mark J. Silverman [09:34]

  2. Contemplation Practice:
     “Sit and drink coffee without your phone. ... So you can sit with other people's feelings and thoughts and craziness and stay centered and grounded.”

• Self-care and grounded presence are foundational for all leadership effectiveness.

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Notable Quotes

• “If you think [leadership] takes a lot of people time, it takes even more of that.”
  — Mark J. Silverman [00:26]

• “The most important thing is knowing who you are and then knowing what you want.”
  — Mark J. Silverman [03:28]

• “You start working on all these outer goals...and it always comes full circle to who are you? What makes you tick, what makes you worthwhile and happy and what ... is going to be sustainable.”
  — Mark J. Silverman [05:53]

• “You want to be seen, you want to get promoted, but you want to do that in the context of making sure all boats rise and that's the way to do it.”
  — Mark J. Silverman [06:48]

• “If you're in fight or flight, you can't be creative, you can't create relationship, you can't think.”
  — Mark J. Silverman [09:34]

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Key Segments & Timestamps

• Introduction & Problem Framing: [00:00–02:35]
• Success, Fulfillment, and the “Wrong Wall” Trap: [03:20–04:33]
• Leadership Principles from The Rising Leader Handbook: [04:38–05:53]
• Inward Leadership & Entrepreneurial Wisdom: [05:30–06:31]
• Leading Peers and “Alpha” Leadership Challenges: [06:31–08:32]
• Immediate Takeaways for Developing Leaders: [09:20–10:14]
• Resource Plugs & Wrap-Up: [10:14–10:57]

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Resources Mentioned

• Mark J. Silverman’s Website: markjsilverman.com
• Free copy of Only Tens available on his website
• Books: Only Tens, The Rising Leader Handbook
• Podcast: The Rising Leader Podcast

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Closing Tone

Both host and guest maintain an energetic, no-nonsense, practical tone throughout, peppered with relatable anecdotes and candid personal reflections. The message for listeners: success in business and leadership isn’t about following a pre-built map—it's about defining your own goals, developing a genuine awareness of self and others, and weaving personal well-being with ambition for a more sustainable journey at the top.

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For further details and the full episode, visit RyanIsRight.com, where you can also find highlight clips and resources mentioned above.

Transcript

[A]

On today's episode of right About Now, I talk with Mark J. Silverman. He is the author of Only ten's Executive Coach. We break down what it takes to be a leader today. Some of the roadblocks that some of the early leaders. Hey, you've been an alpha your whole career. Now you're leading other people. How do you get others involved? How do you make impact across your teams as a leader in today's business world? All that and more right about now.

[B]

The biggest conversation I have with leaders is that leadership takes so much more people time than anybody ever expected. If you think it takes a lot of people time, it takes even more of that. And it takes your patience, it takes your presence in order to guide people.

[C]

This is Right about now with Ryan Alford, a Radcast Network production. We are the number one business show on the planet with over 1 million downloads a month. Taking the BS out of business for over 6 years and over 400 episodes. You ready to start snapping necks and cash and checks? Well, it starts right about now.

[A]

What's up, guys? Welcome to right about now. We're always bringing you today's best and brightest guests. We're trying to bring you value. Not about yesterday, not about next year, about today. Now. Right about now. That's what we've got. Author of the Rising leader Handbook, Mark Silverman. What's up, Mark?

[B]

Hi. Good to see you.

[A]

Good to see you. Appreciate you for coming on. Passing the fortress of armor that is our team. That said, you need to talk to Mark. Highest compliment I can give you is you pass that.

[B]

You know, I needed that self esteem boost.

[A]

You're a smart guy, doing smart things, helping smart people. So that's value. That's what we're here to do. I know we're working with leaders. We're teaching them how to have and utilize and keep emotional intelligence. Challenges you see or the problems that.

[B]

You tackle the most, getting derailed, that's, that's probably the number one challenge. Everybody that I work with is super talented, they're super smart. They know their jobs better than I will ever know their jobs. They even know leadership. Like they've read a lot of the same books you and I have read. Been to some trainings. The problem is, you know, the nervous system regulation, emotional regulation. When life throws speed bumps at you, what do you do when you get your ducks in a row and then all of a sudden your ducks are running around like crazy and your people are just not being what looks like sane? The biggest conversation I have with leaders Is that leadership takes so much more people time than anybody ever expected. If you think it takes a lot of people time, it takes even more of that. And it takes your patience, it takes your presence in order to guide people. Because everybody is dealing and especially these days is dealing with so much. Staying on track is really hard.

[A]

They don't teach you that one. You know, like, I came up and rose through the ranks at ad agency world a long time. I mean, it's been a while, but then suddenly you're in a leadership role because you were smart and, like, ambitious and you could do certain things, but it doesn't mean you're suddenly magically ready to handle and deploy emotional intelligence at all times. And looking back, I cringe at even some of my own methods and the madness of it all. I mean, that's the one thing. Now we joke sometimes. Well, there's a coach for everything but you. Damn, I wish there had been a coach when I was coming up 20 years ago.

[B]

I remember hiring a sales coach when I was a sales guy. I paid my own money to hire a sales coach even before I knew what coach. I wasn't the coach, but I knew that there were people who could help me get from point A to point B faster with less turns in the road.

[A]

What's the key to unlocking success for leaders today? What's the big aha unlock that you can help them discover?

[B]

People's definition of success is different. And a success for an entrepreneur, a success for an executive might be something different. But I think the most important thing is knowing who you are and then knowing what you want. What is the outcome you want? How many times have you heard people say they'd climb the ladder, but it was on the wrong wall? Not knowing exactly what you want, the outcome you want, how you want to feel, who you want to be with when you get there is probably the most important thing.

[A]

It seems so simple, Mark, but it's very true, because you will sometimes. What do they say? You can't follow the map. But if you don't know where you're going or don't really know what you want to happen, and I think that's the challenge is sometimes they're like, I just don't want this chaos. Well, clearly. But what are the outcomes that we're trying to get to?

[B]

And it's interesting because I'm not very goal oriented. I've accomplished a million things in my life. I don't have a vision of I want to be here and have this, but I do Have a vision of, I want to be this person, I want to feel this way and I want to be around these people. I want to have this impact. And then I like to see where life takes me with those things.

[A]

What are the tenets, principles of the Rising Leader Handbook?

[B]

It's basically the codification of what I do in my coaching. So it's leading up, becoming a trusted advisor. Nine times out of ten, I'm working with super talented, super aggressive, super ambitious folks who are really good at what they do, but they don't know how to handle a CEO. They don't know how to be a trusted advisor to someone else and kind of take their ego, set it aside and work for the greater good. So it's leading up and it's leading across. How do you be a leader on a team full of other ambitious, energetic leaders? Right. Because again, you can be a bull in a china co closet, you can make enemies or you can build a coalition. You can build people who are going to support you when you get promoted. And they're like, yes, that person. I will follow that person. Then there's leading the team. And then the most important thing, which is I use all those other things for leading yourself because that's the most important thing. How are you navigating family, success, work, money, pressure, all of those things?

[A]

Yeah, I mean, that's a big one. I think sometimes we're so focused outward, a lot of it starts inward, working on ourselves and how we're leading ourselves and taking a look in the mirror. A lot of times, times I think is more important. I think it's easy to go, well, how do I do these things to help these people and all that. But it's like, okay, it's kind of like that old, what they say, the oxygen mask. Like when the plane's going down, you got to give yourself oxygen first before you can help others.

[B]

It's all going to end there anyway. One of the reasons I'm a coach is because I've just watched too many of my contemporaries crash and burn. I've watched friends die after they've made millions. I've watched marriages come apart. You know, the best self help, best spiritual program in the world is to become an entrepreneur. What happens is you start working on all these outer goals, you start working on, on creating this thing. And it always comes full circle to who are you? What makes you tick, what makes you worthwhile and happy and what, and fulfilled and what is going to be sustainable. It always comes back around that way. Whether you do it by slamming into a wall or doing it proactively is your choice.

[A]

I'm going to focus on one thing here because I think it's important. I think leading across is difficult. I struggled with that a lot. And I think a lot of people in that target range that you said that you help, that's probably something they struggle with. Talk to me about maybe specifics of how they can help lead across.

[B]

It's really important to check your ego. So for me I was really good at either taking over or stepping back. I can lead and I could get everybody across the finish line or I could be a helper. I wasn't really good at keeping my power along with other people because all of my self doubts, all of my insecurities would show up. And when that happens, you start to have kind of weird relationships. So shoring up your own self worth and having people to talk to is so important. Having a coach, having friends, having mentors so you know who you are, you know your worth. When you know who you are and you can trust that, then you can look to see how you can help the other team members win. What you want is you want everybody to win, you want it to be coopetition, you want to shine, you want to be seen, you want to get promoted, but you want to do that in the context of making sure all boats rise and that's the way to do it. You're going to run into people who are cutthroat, you're going to run into people who are dishonest. And if you can take the high road and you can really make your own way, it always, always, always brings you where you need to be.

[A]

That's great advice, Mark. And I think as I heard you say that I'm thinking to myself again like I put myself in this position Both now and 20 years ago, like going I needed coaching in that way. Whether by self doubt or just not exactly knowing how to make others, elevating others, not because I was trying to like necessarily be the shining star, but because I just was a dominant doer. And I think that's the challenge is like I'm just bull in China shop getting shit done versus how do I leverage all these other talented people and make them feel part of the group Because I do need them and I think, you know, starts with a lot of those things. But how do you think those people that are kind of that alpha, how do they tame that to a degree to work well with others?

[B]

The first conversation I usually have is why do I need to do that. I can't tell you how many times I've had a conversation of Mark, why do I have to care about other people? Why can't we just get shit done? And I have to have those conversations about what kind of work environment do you want to show up in? What? Who do you want at your funeral? Who do you want at your retirement party? What kind of world you want to create around yourself. Once we get established a reason for doing this, I point them towards Michael Jordan and the Bulls. When Michael Jordan was Air Jordan on his own, they weren't winning championships. You know, he goes off to the Olympics, he learns about teamwork, he comes back, he brings that to the Bulls and all of a sudden they're unstoppable. He knows who's talented in what area. The sum is, is greater than the parts. It's the same thing for any team. You can do more with, with everybody else's talent.

[A]

There you go. As we close out Mark, what's a good maybe something up your sleeve for those potential future leaders, current leaders and exercise. Something that Mike could be that our audience could take away in their leadership journey.

[B]

I'm going to give you two. One is take care of your sleep, your exercise, your food and your well being. If you're tired and you're grumpy and you're on edge, you're in fight or flight. If you're in fight or flight, you can't be creative, you can't create relationship, you can't think. Fight or flight just narrows it all down and you're screwed. You're just at a deficit from the get go. So those people who are running on fumes are not anywhere close to even adequate, let alone their best. The second is a contemplation practice. You've got to go for walks without your phone. You've got to sit and drink coffee without your phone. You've got to be able to sit with yourself, your own feelings, your own thoughts so that you can sit with other people's feelings and thoughts and craziness and stay centered and grounded.

[A]

Very practical, but very true. You're awesome man. I appreciate you. Talk to me about where we can find more on your books, how to work with you, et cetera.

[B]

Sure. So my, my website is Mark J. Silverman.com Mark the letter J Silverman.com My first book, Only Tens, which is yesterday was its 10 year anniversary is free on my website. So you can go there and just grab a book and that's, that's my becoming an entrepreneur. With ADHD and how I work with that. The Rising Leader handbook is available. I have the Rising Leader podcast. I'm all over social media. They call that media. Mark with the video camera in my face all the time.

[A]

Mark is out there. Go check out his stuff. Super knowledgeable and doing a lot of great things in the leadership space and just in preparing leadership for the modern world. Thank you, Mark. Really appreciate you coming on.

[B]

This was fun. Thank you so much.

[A]

Hey, guys, you know where to find us. Ryanisright.com, we'll find highlight clips, the full edited video and audio, and of course, links to all of Mark's stuff, including a free book. Dude, go get that thing. Mark's got a lot of value to share. Go. Go get some of it. We'll see you next time.

[C]

Right about now, this has been Right about now with Ryan Alford, a Radcast network production. Visit ryanisright.com for full audio and video versions of the show or to inquire about sponsorship opportunities. Thanks for listening.