Ep234 Machen MacDonald—When Success Feels Hollow: How to Move from Achievement to True Fulfillment


In this transformative conversation, executive coach Machen MacDonald reveals why so many successful leaders feel stuck at their peak—and what actually moves the needle when winning isn't enough anymore. Host Mike O'Neill guides Machen through a vulnerable exploration of the gap between achievement and fulfillment, uncovering why leaders calibrate instead of celebrate their wins.
Listeners will learn how to recognize the three journeys every leader takes (the one they plan, the one they're on, and the one they wish they went on)... how to stop operating from doubt, fear, and anxiety and start leading from wisdom and love... and why "letting go" is actually the most powerful move a control-oriented leader can make.
Machen shares raw insights from nearly 25 years of coaching, including how his marriage nearly ended when his business was thriving, what it means to "provoke brilliance" in yourself and others, and why joy won't enter a home where all emotions aren't welcome. Mike expertly draws out practical frameworks like the "Guide Your Mind" principle and helps Machen illustrate how celebrating success actually impacts physical health, relationships, and leadership capacity.
Whether you're a CEO feeling the weight of decisions, a Vistage chair facilitating breakthrough conversations, or an executive who's checked every box but still feels empty, this episode offers a roadmap from success to significance—and permission to finally take in the view from your summit.
Find all the show notes and links here: https://www.unstuck.show/234
Machen MacDonald 0:00
Three journeys people go on, the one they plan, the one they're on, and the one they wish they went on. Comparison, this contrast that goes on, and that's where people get stuck, is, rather than accepting what is and really experiencing, soaking up the view and the accomplishment, they're already back at the maps trying to figure out which mountaintop to get to next.
Mike O'Neill 0:25
Welcome to get unstuck and on target. The weekly podcast that offers senior leaders insights and strategies to not only lead with confidence and vision, but also to achieve groundbreaking results. I'm your host. Mike O'Neill, I coach top level executives on the power of ethical leadership to forge teams to be as united as they are effective in each episode, join me for insightful conversations with leaders just like you, providing practical advice to help you get unstuck and propel you and your company forward. Let's get started. Matron just shared something I can't stop thinking about. He said that most leaders operate from doubt, fear or anxiety, rather than from wisdom and love, and that imposter syndrome is just you nibbling at the edge of who you think you are. We're digging into why successful leaders struggle to celebrate their wins, and what it's actually costing them, not just professionally, but physically and relationally. Machen gets vulnerable here he shares why his marriage almost ended when his business was thriving, how his need to control everything was trying to mold smoke. He also breaks down the three journeys every leader takes, the one they plan, the one they're on, and the one they wish they went on. Sound familiar? If you've been racing from summit to summit without taking end of view, what comes next might shift your perspective. Let's continue. You know that moment when you realize you've won the game, but the victory feels hollow. My guest today, Maisha McDonald, has spent nearly 25 years helping successful leaders navigate that exact moment when hitting every metric isn't hitting the mark anymore. Mason's not your typical coach. He's been in the arena. He's built five companies. He's climbed from financial advisor to executive leadership. He knows what it's like when Sunday night dread creeps in despite Monday's success. What's caught my attention about Mason is that he doesn't believe that you need more strategies or frameworks or five year plans. He believes that your next breakthrough is already inside you. It's just needing some provoking. He actually calls it provoking brilliance, turning your hidden insights into your next breakthrough. And after 25 years of helping leaders transform success into significance, he's got it down to a science. Today we're digging into why so many accomplished executives feel stuck at their peak and actually what moves the needle when winning isn't enough anymore. Welcome Nation. Wow.
Machen MacDonald 3:29
Thanks, Mike. Great to be here. Well, we have had
Mike O'Neill 3:32
opportunity to speak on more than one occasion before we hit the record button. But what strikes me is if the working title of this episode is from success to significant, when winning isn't enough, you've worked with leaders who, by every external measure, they've made it yet they've come to say they're feeling Stuck. What's really happening in that gap between that achievement and a film and the sense of fulfillment.
Machen MacDonald 4:07
Great question. What's happening in that gap is a judgment that is in alignment with the current self belief of somehow, not enough.
Mike O'Neill 4:26
That being said, Do you see a pattern when that belief tends to take hold with these people?
Machen MacDonald 4:34
Yeah, especially at at the summit, right when they've achieved that mark, whatever that might be, is there's this conditioning that happens for most people, of not celebrating right, and not taking in the view from the summit. It's kind of. So I'll say it this way. There's three, three journeys people go on, the one they plan, the one they're on, and the one they wish they went on. And so oftentimes there's this comparison, this contrast, that goes on, and that's where people get stuck, is rather than accepting what is and really experiencing, soaking up the view and the accomplishment. They're already back at the maps trying to figure out which mountaintop to get to next.
Mike O'Neill 5:34
It's a great visual that you just shared.
Machen MacDonald 5:39
Why did, why do we do
Mike O'Neill 5:42
that? In your opinion,
Machen MacDonald 5:46
in my opinion, I think it's primal. It's it's an awareness and alertness of survival. And we're all. We all have that base wiring, however we interpret it and we condition it differently, given our environments and challenges and opportunities and even traumas through our life and what we need to do to stay within the tribe, ie stay alive.
Mike O'Neill 6:17
So you describe as both primal and life experiences. What is it about successful people that choose not to truly celebrate successes?
Machen MacDonald 6:34
It's not that they don't celebrate it. It's they don't they don't allow themselves to really soak it in, right? They'll have an event. They'll have, you know, they'll recognize other people. They don't allow their nervous system to experience the goodness, maybe for a fleeting moment, then it's okay. Where's the threats? Where the opportunities, rather than celebrate, they calibrate.
Mike O'Neill 7:06
I think that's a much better choice of words. They calibrate. It seems to me that one of the things you're doing is you're helping your clients move from calibrate to something more. Is that particularly challenging for successful people to develop these new behaviors?
Machen MacDonald 7:30
Not when they experience it. It's a feeling, it's an emotion, it's a it's a total biochemistry change for people, a lot of times, when I've worked with with team leaders and executives and even athletes, and when they really allow themselves to feel almost that euphoric feeling of accomplishment, actually, health issues Become better challenges that they've experienced, ailments, pains dissipate. Relationships get better. It's really unblocking the flow, right? The flow is well being. We're part of that flow, and if we don't allow ourselves to feel that flow, it blocks off energy, ie, relationships get challenged. Physical issues become a challenge. And so it's really opening up the flow on so many levels.
Mike O'Neill 8:30
You know, you've kind of touched on this a little bit, but let me go back to this just kind of for a moment. And I've read in some of your posts that the decisions for folks sometimes feel heavier as leaders advance. Can you kind of walk us through? Maybe paint that picture that you're good at doing it. What does it look like? How does decision making change when they're able to shift from building success to building significance?
Machen MacDonald 9:03
Good question. It's it's about appreciation. It's acceptance. It's moving more towards appreciation and acceptance and away from from judgment. And what I mean by that is as things come about and unfold, if we whatever happens, right? It's perfect the way that it is. If it was meant to be another way, it would be the other way. And so as as leaders ascend that mountaintop or move up into leadership, they're getting really, really, really close to their edges. And a lot of people call it imposter syndrome, right? All it is, in my opinion, in my judgment, is you're just nibbling right at the edge of who you think you are as well as who you think you're not. And we have to cross that. Line, and that's uncomfortable as hell. It can feel messy and awkward, and that's a threat. So a lot of leaders that don't have that that resource, they'll pull back rather than stepping and leaning into it, and as we lean into it, that edge increases all the way around us, relationships, health, career, opportunity, income, worth and confidence, right? A lot of people come to me, and I'm sure they come to you when they need a little more confidence. And it's not confidence that they need, it's courage.
Mike O'Neill 10:45
You know, when you mentioned going right up to the edge and the tendency just kind of pull back, I introduce your term provoking brilliance. It strikes me as being maybe a kind of a slight push a little bit. Maybe that's bad choice of words, but when you use that phrase, provoking brilliance, what does that mean?
Machen MacDonald 11:06
Please. Yeah, thanks for asking that. So brilliance is representation of our wisdom, our heart, our genius, and when we're in alignment with our head and our heart and following what our soul is wanting us to follow. I call that coming from love, pure and simple. Okay. Ego tends to show up in the form of doubt, fear or anxiety, and it makes a story up that feels really real, that if we do this, we're going to get annihilated. And so we, oftentimes, leaders, will operate out of doubt, fear, anxiety, rather than that alignment of wisdom, genius, love, power, and that's where provoking brilliance is really calling them out and saying, This is the place you want to operate from. This is where the solutions are not here, not here, but here.
Mike O'Neill 12:19
I love that. I understand you're a Vistage chair. And for those familiar with visage, they might kind of go, Hmm, that's an interesting choice. Maisha, what makes you a great Vistage chair?
Machen MacDonald 12:37
Oh, man, I what my members would probably tell you is that I allow space for their answers and their ability to line up come together. I don't offer answers. I just stay curious and ask questions. Oftentimes, newer members don't necessarily know the questions to ask to help another member. They want to, they want to provide solutions. Yeah, and so being a good chair is is being able to facilitate that wisdom that the other members have and and give it some space so that the member that's having a situation processed has the space to tap into their own wisdom and get the other members to recognize that, and then ask the questions that will lean that member in towards their wisdom. And so sometimes I might ask, you know, is anybody curious about how this may be impacting his relationship at home? And everybody's like, Oh yeah. How is that impacting the relationship at home, you know? And so sometimes it's just tossing a little bit of a curiosity bomb into the room, if you will. And a lot of times I will just, I'll this may sound awkward or weird, but I'll pray it into the room before I say it out loud. And oftentimes I do that, and then another member will actually ask that question. It's really magical,
Mike O'Neill 14:32
you know, I can see how you being who you are, and how you operate, particularly one on one. That my first thought was, how would that translate into vicious chair? And I guess what I'm envisioning is you're being true to you and how you're providing quote, leadership, if that's the right term. But what I'm also sensing is that you through. Your actions are actually coaching the members of your group on the do the exact same thing with themselves and perhaps within their own organization.
Machen MacDonald 15:13
Yeah, what many of the my members share with me is that there'll be stories of where they come back the following month, and they'll say, you know, I did what you did at the last meeting with my team. You know, I just I let go, and I let their wisdom find its way. And that's a big one for most leaders. There's a lot of leaders that that have a challenge loosening the grip. And you know, the quality of anyone's life is is correlated to their ability to handle uncertainty. And most leaders have to be more okay with uncertainty than the average bear, so it's really helping them learn that piece of it.
Mike O'Neill 15:59
Make sure you've built five or more companies letting go. Did that come easy to you early on? Hell? Tell me more.
Machen MacDonald 16:11
Well, being a recovering perfectionist and control freak, where I learned most of this, and I'm I'm going to go really transparent and vulnerable. Here is about 15 years ago, my wife and I were bumping up against a really hard place together, and it was when I was kind of in the throes of building a business, and the business became, quote, The Other Woman, right? All my time and energy and attention was there, and I was justifying or rationalizing with rational lies as to why that was the most important place to put my time and energy, and so she was not feeling connection, and it caused a huge rift in our relationship, we were actually separated for a short period of time. We're back together. We've been together now for 33 years, and every day is almost like a honeymoon. So we found something, but it was at during that time that I did some really deep work and recognized that my wanting to control things was like me trying to, you know, mold smoke, right? It? I had to really let go and be curious and listen for what the other people need, as well as ask clearly for what I need, because most people are tripping over themselves, you know, either attacking or going passive aggressive or the silent treatment in a tragic way of not knowing how to ask for what they need or listen for what other people need. And it's really that simple, because once we're clear on what people need, we can help tee it up. If we can do it, we do it, if we can't, we help connect them with people and resource that can
Mike O'Neill 18:04
what you were describing sounds like that might have occurred earlier in your professional life. Am I understanding that correctly?
Machen MacDonald 18:12
Yeah, yeah, yeah. I appreciate
Mike O'Neill 18:15
your openness. May I maybe follow that up with what you know to be the question, and it may be the same answer, and that is, can you maybe share a time when you perhaps felt stuck at your own Summit, when that happened? What helped Mason break through?
Machen MacDonald 18:37
Yeah, so the first one that really comes to mind is with the first book that I wrote, provoking it brilliance is the name of the book. And I wrote the book fairly quickly. I wrote it in about six months, but it took me another year and a half to get it out into the world, because, you know, that's my baby, and I didn't want the world to tell me my baby was ugly, right? And I was very creative in all of the ways that it wasn't ready yet, right? It's not the right time. And I was actually working with a coach at the time, and he helped me understand that it was again. It was that doubt and that fear and that angst, right, the ego, if you will, that was striving for perfection, that that's what was tripping everything up. And when he helped me understand, get myself out of the way, it's not about me. The messages in the book are for other people, and by me holding back on it. People are going without maybe it's only one person that reads one chapter that gets the hit that that one person needed it. It really got that. It wasn't about me. It's about really serving other people. It got me to get off the dime and then do the things I had to do to get. Published. And then from there, I've gone on. And I, you know, when I write a book, it takes me 90 days from concept start to publish, because how many books have you written? Seven? My goodness,
Mike O'Neill 20:14
has book writing gotten easier for you?
Machen MacDonald 20:21
Yes. And I'm now, I'm actually finishing another book, but it's, it's, it's a story, it's, it's fiction. All my other books have been more just subject matter, how to what to do, kind of things. This one is a story of a leader in corporate America, has a fall from grace, finds redemption, hero's journey, but it helps four key lessons core, four key leadership lessons embedded within it, and being able to write in that style that's that's been a Challenge.
Mike O'Neill 21:00
I know people who write a book and stop you've wrote a book and you've kept on going. How has writing a book made you a better coach, a better husband, perhaps parent, and what ways have has that opened up things for you.
Machen MacDonald 21:23
For me, it helps me refine the message like you. I'm sure Mike, as you're coaching, you know, with every coaching call that you have, you're you're learning what's going on for other people, and getting ideas and solutions, and hearing their ideas and solutions, and it it becomes more and more rich, and how you lead them, how you might share something with them. And so writing books has done the same thing, because a lot of the content I'm pulling from real life experience, and it's like, okay, you know, it could take me 10 pages to write a concept, but now I can get that concept down to maybe one or two paragraphs, so that it's really rich and meaningful and impactful.
Mike O'Neill 22:20
You know, I'm trying to envision, if you and I are working together, let me make a stab at it. The process of writing that goes into a book requires careful thought, but after that thought is taken care of you, you're able to perhaps, express your ideas, maybe better, perhaps even more succinctly. But what I'm already seeing in you, and those people who are listening or watching can see this plainly, is you are very thoughtful, and my sense is that the questions you ask your clients are very purposeful. How has writing a book made you better at asking those questions?
Machen MacDonald 23:20
Writing the book. I'm trying to think how to put this into words as I write I'm, it's really almost a download for me. And then it's a matter of, you know, getting it the words right, and it's as I'm as I'm going through that process. I'm getting visual hits, auditory hits of past meetings with clients, or being aware and holding space for particular client that I know I'm going to be talking with maybe later today or next week. It's like, oh, you know, how is their situation in alignment with this, and it'll give me kind of this permission to kind of tweak and twist and flip the knobs and turn the levers and and then bring that experience or that process to the client meeting.
Mike O'Neill 24:20
I'm so pleased you said what you said. And that is, I think some people might have the impression that coaching is spontaneous, and that, you know, you wrap up your coaching session and no more thought is given by the coach. And what you're just describing is you're always thinking about your clients you may be anticipating an upcoming client session, and you're already beginning to formulate, how might I approach this issue, and I think that is the biggest differentiator from the average coach, and that is, it's very. Separate it sounds based on your description. Though you're a prolific writer, your speaking style is very measured, if you would. And does that make sense what I'm saying? Yeah. But when you say things, the words you use are rich, and you're able to help you use senses in the words that you choose. You see that in yourself, correct?
Machen MacDonald 25:32
I get what you're saying, Yeah, okay.
Mike O'Neill 25:36
Have you been able to now that you've been doing what you're doing as long as you have. Do you feel that you are now using all of these talents that you were given, all these experiences, has it kind of coalesced in a way that you're pleased with
Machen MacDonald 25:56
here? Here we are at the summit and not celebrating? I reading, I feel really, really blessed and on purpose knowing that I'm in the right place, doing the right thing in the right way, at the right time with the right people, and I know there's so much more to experience. So I'm just, I'm a real curious bird, you know, I'm always enrolled in some kind of a course. I do a lot of deep personal work as well. I'm involved in lead men's groups, you know, I just, I'm, I'm, I'll say it this way, I'm on this journey to really experience God, if you will. And it's just there's so many possibilities, so infinite realities, if you will. And it's like I get the opportunity every day to go play in that and then I get these distinctions as, like, Ooh, I like that, you know. And I'll bring that into myself and my abilities. And I also get some feedback time at times where that's, you know, maybe not such a favorable way, or trade like, Okay, that one I'm going to move out of the container. It will. So it's, it's, I get it that a lot of it's coalesced, like you said, and it's still coalescing.
Mike O'Neill 27:32
But the way you describe it, it's acknowledgement that if you're really going to be good at what you do, you have to be willing to do your own heavy lifting, your own deep introspection, and that's exactly what you just kind of shared that you're you're hungry to learn more and more, but what you're finding is it's opening up that many more things that are energizing you, personally and likely professionally.
Machen MacDonald 28:03
Yes, exactly. The horizon is always changing, right? The more we know, the more we know we don't know. And it's like, every time that that window reveals itself, it's like, oh my gosh, you know, it's like, let's go play, and I get to do it with my clients and friends and colleagues. And it's, it's rich,
Mike O'Neill 28:27
Mason, we've had a conversation totally unscripted, as you know, as our listeners know, but there may have been something you said, Gosh, I sure hope Mike asked me a question about x. Is there anything that you would like to share that maybe has not come up that you think would be helpful to kind of round out this conversation.
Machen MacDonald 28:46
Yeah, what I what I'd love your listeners to to get an experience, is that no matter where you find yourself, right, we can't necessarily control the situations or circumstances that we find ourselves in. However, we can always choose the healthiest perspective from which to operate and create a new reality, moment to moment to moment. I call it going to the gym. Gym, meaning guide your mind in every moment and let your emotions be the gage on your dashboard when you're feeling good, good indication you're doing things well when you're not feeling so good, it's an indication to adjust. With that being said, the tricky part is judging ourselves when we're not feeling good or joyful or productive, but I heard this the other day, and I thought it was brilliant, and that is, Joy is the matriarch of all emotion, and she will not enter a home where all of her children are not welcome. Wow. Yeah. So. Allow and accept and appreciate whatever you are feeling and be open and aware and curious to the message to the why? What's the emotion wanting you to know so that you can serve yourself and serve others better?
Mike O'Neill 30:23
Nation, you have served our listeners well by this conversation. If folks want to reach out and connect with you and learn a little more about what you do and how you do, what's the best way for them to do so,
Machen MacDonald 30:39
you know the best way is really through LinkedIn. I'm fairly active on LinkedIn with posts and interactions and so forth. The other option is they can hit our website, which is pro brilliance.com, and I will, I will warn the listeners, it's a little outdated website, but at least it gives you a little idea, it'll taste well,
Mike O'Neill 31:02
obviously, we'll put the link to the website in the show notes. We'll also put your LinkedIn profile link. But for those listening, spell your name for the folks so they know how to how to spell your first name, particularly
Machen MacDonald 31:18
sure it's machen, M, A, C, H, E N. Last name is MacDonald, and that's m, A, C, D, o n, a, l, D,
Mike O'Neill 31:29
well, you just corrected. I was slightly mispronouncing your first name because it's machen, not machen. And so thank you for for kind of clarifying machen. Thank you so much for spending time today and just being who you are on this podcast. Thank you.
Machen MacDonald 31:47
Thank you, Mike. This has been great.
Mike O'Neill 31:50
So if Mason's message, if that resonated with you and you're feeling that tension between where you are and where you could be, let me encourage you connect with him through the links that he just mentioned that will be found in the show notes. And if you would like to explore maybe the organizational side of getting unstuck, maybe building teams or developing leaders or creating sustainable growth, I offer complimentary two hour game plan sessions that's two full hours of actual coaching, not a sales pitch, but this is by invitation only, because I only can do a few of these each month. If that would be something that would be beneficial, you'll find a link in the show notes as well. So to everyone listening, thank you for having the courage to question what's next, and even when now looks perfect on paper. I hope this episode has helped you get unstuck and on target. Thank you for joining us for this episode of get unstuck and on target. I hope you've gained insights to help you lead with confidence and drive your organization forward. Remember, at bench builders, we're committed to your success, your leadership excellence and your strategic growth. If you've enjoyed our conversation today, please leave a review, rate and subscribe to keep up with our latest episodes. This show really grows when listeners like you, share it with others. Who do you know, who needs to hear what we talked about today? Until next time, I encourage you to stay focused on the target and continue to break new ground on your leadership path. You
Speaker 1 33:44
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