For When you Feel Unfulfilled even Though You Seem to Be At The Peak of Success

For When you Feel Unfulfilled even Though You Seem to Be At The Peak of Success

by | Nov 14, 2024 | Identity Shifts, Innovation, Inspiration, Practice Leadership

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.

You can sign up here.

Title Banner - The Significance Dilemma

When Success Feels Hollow: A Common Challenge for Leaders

If you’re feeling bored, uninspired, or disconnected, you’re not alone. Despite their accomplishments, many high-level, highly knowledgeable leaders grapple with overwhelm, exhaustion, and an undercurrent of dissatisfaction – the very opposite of the life of significance they’re craving. If this is you, you might notice you’re avoiding new ideas, resisting collaboration, or feeling disconnected from the work and people that once sparked joy.

It’s going to sound paradoxical or maybe even counterintuitive, because everything in our culture of success trains us to reach for certainty so we can make smart and impactful decisions, but your certainty about what you know is actually the reason you’re not satisfied with anything right now.

Here’s what happens when you’re rock-solid certain about something (or, worse, when you’re certain about almost everything): you stop listening. You stop engaging. You stop taking in new information and you stop picking up the signals.

And without new information, epiphany, the thrill of learning, and just plain novelty, life gets very gray, very fast.

That’s why when my highly-accomplished leaders tell me they’re bored, restless and not feeling fulfilled in their lives, I know certainty is in the room.

The need for certainty can become a mental cage, one that limits engagement, kills collaboration, and squashes curiosity. When we’re locked in certainty, people around us may feel they can’t reach us or that we’re unreceptive (because we are!), which can ultimately lead to a breakdown in relationships—the one thing we truly desire to keep strong and fully feel our lives.

No connection, no spark. At work or at home.

Here are a few examples of how certainty might be showing up and holding you back:

The Leader Who Won’t Delegate

You’re overwhelmed with every detail, utterly certain about how it should be done and convinced that no one else can do it right. This mindset keeps you overworking (may as well do it yourself…); your team underperforming; and all you locked in a vicious spin cycle that prevents both your own and your team’s growth.

The Visionary Who Theoretically Values Collaboration but Avoids It Like the Plague

In your head, you’re dreaming of the dream team and the creative exhilaration that comes from collaborating with people at the top of their games. But in reality, you default to working solo so that you get to do everything your way (because again, you’re certain about how it needs to be done); don’t have to moderate your plans or process to accommodate anyone else’s perspective; and honestly, you need to feel like you’re the certain center of everything at work (feeling feeling sidelined or irrelevant is your personal kryptonite). As a result, you never get to that impactful place where everyone’s working in synergy and magic happens. Instead of experiencing the exhilaration of collaborative creation, you end up resenting everyone around you and fail to cultivate the empowered, collaborative team of your professional dreams.

The Partner Craving Connection but Stuck in Habit

You want to connect more deeply with loved ones, so you invite them to do things you’re certain will create that feeling…even if they would rather do anything but that activity. An example: you love hiking and feel deeply connected to nature, so you’re certain that if your partner went hiking with you, the two of you would have a transformative experience that would bring you closer together. You suggest it to them, but they hate hiking and resist, but you’re so certain it’s the thing that will make a difference in your relationship that you relentlessly persist. And now you’re in a fight and feeling further apart than ever. Your certainty is actually blocking the opportunities to connect and intimacy you crave.

Your  Indicator Light – How Certainty Feels

Lots of colds, maybe even a few injuries (how’s that knee doing?). A bit more bossy or a bit more distant with your team. A little shorter with your kids. Avoiding meetings. Taking way too many meetings. Taking offense. Ruminating when you should be sleeping. Putting your head down and just doing the job. Being so preoccupied with everything else that your job feels impossible or insignificant. Demanding the impossible from your spouse, right now.

When certainty takes over, it doesn’t just affect your actions; it seeps into your emotions, thoughts, body and behaviors. So when you’re seeing these patterns, they’re warning lights that you’re locked in certainty and locking yourself out of the personal and professional vibrancy you’re craving.

Curiosity-The Antidote to Certainty

To break free from certainty, you must cultivate the skill of curiosity—your willingness to see things differently, to embrace possibilities, and to listen to perspectives you might not expect. Curiosity invites you to step out of the confines of “knowing” and into the boundless world of “exploring.”

Leaning into curiosity requires that you learn how to pattern-interrupt, and this is where a bit of inspiration from Mr. Rogers can help.

The Mr. Rogers Exercise

If you remember Mr. Rogers’ Neighborhood, you’ll recall that Mr. Rogers would start each episode by coming into our homes, changing his shoes, and putting on his cardigan, signaling a shift from the everyday world to the Land of Make-Believe. Here, he’d interact with a world of curiosity, imagination, and possibility.

As a leader, you can create your own rituals to signal a similar shift, stepping out of certainty and into a mindset of openness and discovery:

  1. Change Your Environment: Whether it’s putting on a different sweater, going to a new space, or simply adjusting your workspace, choose a physical act that symbolizes stepping into a fresh mental space.
  2. Embrace the Land of Make-Believe: Imagine you’re entering a world where anything is possible. Visualize challenges as opportunities, and let go of the need to control the outcome. Ask yourself, What might be possible here if I approach it with curiosity?
  3. Invite Others Into This Space: Once you’re in this open mindset, reach out to someone who sees things differently. Start a conversation that’s focused on exploring new ideas, asking big questions, and creating fresh possibilities.
  4. Ask Questions and Co-Design: Having all the answers is the death of curiosity, so you have to be willing to not have all the answers, all the time, and that means asking questions. In our earlier example, you heard about the hiker who wants to connect with their partner, who wants NOT to hike but probably also wants to connect. If our hiker had voiced that desire and leaned into curiosity, they would have asked their partner how they could make more connection and intimacy happen, and they probably would have been snuggling on the sofa or drinking wine by the beach right now. When you ask questions, you start co-designed experiences and that is what lands you in the joy that makes life a delight.

Using these specific practices to lean into curiosity helps you escape the death-grip of certainty that dulls your life and makes you restless. Curiosity rather than certainty is what reawakens the innovative, collaborative spirit that fosters meaning, drives true impact, and fuels your life of significance.

Curious on diving deeper? Join The Significance Project!

Jen Karofsky | Thought Partner & Coach for Visionary Leaders & Significance Seekers

 Jen Karofsky collaborates with leaders who are ready to disrupt the status quo and craft a life of legacy, deep connection, and purposeful impact. Through intentional coaching and bold thought partnership, Jen Karofsky helps you align your work, your values, and your vision to create transformational change in your world.

Join The Significance Project to redefine success and step into your power.

Join

The Significance Project

My monthly(ish) newsletter for the tools, tips and provocations you need to live your life of significance.

More on the BLG:

When the Metrics Don’t Fit

by |

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.. You can sign up here.Why ambitious visionary leaders need a different kind of measurement at this stage of growth.There’s a rhythm many...

read more

The Collaboration

by | ,

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.. You can sign up here.When Success and Significance build something real—together. Part 5: There comes a point in a high-achieving life...

read more

Leadership with Substance: Why Being “Wishy-Washy” Won’t Work

Leadership with Substance: Why Being “Wishy-Washy” Won’t Work

by | Oct 16, 2024 | Innovation, Inspiration, Practice Leadership

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.

You can sign up here.

Title Banner - The Significance Dilemma

In today’s world, leadership of substance is more crucial than ever. But what we are seeing in businesses, universities, religious institutions, and government bodies is alarming: leadership that caves to the loudest voice rather than standing firm on a robust belief system. Leaders are bending to every gust of public opinion, and frankly, I’m thinking, What the f*ck are you doing?

The Risks and Rewards of Standing Firm

Too often, these leaders buckle under pressure from the noisiest group, making disastrous decisions that impact people’s lives in intimate ways. I see leaders walking back their choices, attempting to please both sides of an argument, thinking they can maintain power by keeping everyone happy. They chase after the status of leadership rather than living its substance. This is morally weak leadership. When you are obsessed with the position, but not the values that should anchor that role, your leadership becomes diluted, irrelevant.

There are leaders today who are not rooted in any meaningful belief system, which makes them dangerously susceptible to the whims of popularity. Wishy-washy leadership is dangerous—whether in the public eye, in your relationships, or in your business. It lacks conviction. We are witnessing this all around us, and it’s eroding not only our institutions but our trust in leadership itself. 

There is  a saying: “You can always tell a leader by the arrows in his back.” These arrows are the scars of standing firm in one’s beliefs, even when facing resistance. True leadership isn’t defined by popularity or approval—it’s marked by the willingness to face adversity, criticism, and even hostility in the pursuit of what’s right. Leaders who stand for something substantial inevitably become targets, but that’s exactly what distinguishes them from the rest.

Here’s the thing: When leaders focus solely on securing their position and maintaining their power, they are no longer impressive. Real leadership is about something deeper, something morally-founded. Something significant.

I’ve observed this deterioration for some time, and it fuels my dedication to the work I do. What drives me is the opportunity to collaborate with people who have a strong moral compass and a genuine desire to lead in a way that makes a meaningful impact—both personally and professionally. We need this kind of leadership now more than ever, not for recognition, but to create lasting, positive change in the world.

This is not a challenge for the faint of heart. And it isn’t just for those in formal leadership roles. This is a call to leaders who want to be a force for good and create significant, positive change in the world. The world doesn’t need more figureheads, more “leaders” obsessed with looking the part. The world needs principled individuals who desire to lead more than they desire the title.

Any leader learns along the way how to manage conflicting personalities and competing priorities. It’s part of the game. The trick is to make sure the game isn’t playing you. A diplomatic stance can be essential and it will serve you well; but only if it doesn’t take priority over your moral compass and is, in fact, guided by your moral stance. If you feel the burning inside you or a sense of dissatisfaction, or frustration because you’re not saying what needs to be said, it might be time to re-anchor into what matters to you and your vision. Stop biting your tongue and watering down your decisions. Choose to be a leader of substance, instead.

The Hero’s Journey: A Path of Moral Integrity

There’s a moment on the Hero’s Journey when the hero must make a choice—do they stay true to their calling, even if it means walking a lonely path, or do they let the glittering promises of success seduce them off-course? The dragons and villains in our world are pulling leaders off their moral foundation with the allure of status and recognition. When this happens, purpose grows distant. You no longer make the impact you were meant to make because you’ve traded your values for a seat at the table. You abandon yourself and your vision.

But here’s the truth: real significance in leadership isn’t about being liked or about checking boxes. It’s about conviction. Dr. Martin Luther King Jr wasn’t popular with most of America and even other church leaders in his time, but he was steadfast. He wasn’t wishy-washy. He wasn’t a people-pleaser. He stood firm, even when it was lonely, and that is why he was able to move mountains and create a legacy. 

Many leaders today confuse “aloneness” with loneliness. Standing firm in your beliefs might make you feel isolated, but that’s different from loneliness. It’s the solitude of significance, the place where only a few can stand because they have chosen the morally right, rather than the popular, path. I know it is risky to take a stance – Dr. King certainly paid the ultimate price for it – but most of us aren’t risking life and death when we take an unpopular but necessary stance. The stakes might be high, but they’re not that high (even when it feels like it.)

I’ve had to make hard choices myself, to disrupt relationships and my work in order to stay true to my moral foundation. I had to break the patterns that kept me playing small, because I realized I didn’t want to live in a beige, bland reality. Yes, it seemed easier to live that way, but, for me, it felt meaningless.

As Lin-Manuel Miranda sings in Hamilton: “If you stand for nothing, Burr, what will you fall for?” We have become a society of leaders who fall for everything because they stand for nothing. Leadership today feels like a popularity contest, with leaders more concerned about social media standings than moral standing. But true leadership requires the courage to follow your moral compass, to not be wooed by the fleeting temptations of status and recognition.

 

Finding the Courage to Lead with Integrity

To lead from a place of moral integrity is to know that you will never satisfy everyone. Real integrity is not about being the whole thing for everyone; it’s about being that sharp slice of truth that people can rely on. When you abandon yourself, your leadership is hollow, and when you get to the end of your life, it won’t feel the way you wanted it to.

We are in a time where leadership has become a popularity contest. It’s about shiny things and status and social media standings. But true leadership requires the courage to stand firm in your beliefs, to not be wooed away from your moral compass by the temptations of success.

You can’t stand for your work, your family, or your community if you don’t first stand for yourself. Leadership is about more than popularity—it’s about principles, moral courage, and a True North that guides every decision. Leadership of significance is bold, truthful, and colorful—it’s not watered down to suit everyone’s tastes.

So I’m asking you: Will you stand for your values? Or will you, like so many others, fall for the allure of fleeting success? Because if you don’t stand for something, the world will pull you off course, and in the end, you’ll have nothing of substance to offer.

The world is on fire right now, and it needs you—leaders with integrity, conviction, and a robust belief system. We don’t need more leaders seeking status. We need leaders of substance, leaders who will leave a legacy that actually matters.

“No leader escapes their career unscathed, or perpetually beloved.” But in the end, it’s the leaders with the arrows in their backs who are the ones remembered for making a true difference.

Will you be one of them?

 Reach out if you are ready to lead with substance.

Jen Karofsky | Thought Partner & Coach for Visionary Leaders & Significance Seekers

 Jen Karofsky collaborates with leaders who are ready to disrupt the status quo and craft a life of legacy, deep connection, and purposeful impact. Through intentional coaching and bold thought partnership, Jen Karofsky helps you align your work, your values, and your vision to create transformational change in your world.

Join The Significance Project to redefine success and step into your power.

Join

The Significance Project

My monthly(ish) newsletter for the tools, tips and provocations you need to live your life of significance.

More on the BLG:

When the Metrics Don’t Fit

by |

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.. You can sign up here.Why ambitious visionary leaders need a different kind of measurement at this stage of growth.There’s a rhythm many...

read more

The Collaboration

by | ,

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.. You can sign up here.When Success and Significance build something real—together. Part 5: There comes a point in a high-achieving life...

read more
The Brutal Truth About Success and Fulfillment

The Brutal Truth About Success and Fulfillment

by | Sep 19, 2024 | Innovation, Inspiration

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.

You can sign up here.

Title Banner - The Significance Dilemma

 Welcome to a profound exploration of success and fulfillment. In a world where achievement is often measured by material gains and social accolades, we are driven to climb higher, earn more, and seek external validation. Yet, this pursuit can lead us into a trap—a seductive illusion that promises significance but often leaves us feeling empty and unfulfilled.

 

The Brutal Truth About Success and Fulfillment

We’ve been fed a lie—a lie that tells us climbing higher, earning more, and achieving external recognition will lead to the impact and significance we’re craving, not to mention lasting fulfillment. It’s a seductive trap, but a trap nonetheless. Decades of research, including the Harvard Study of Adult Development, show that the things we’ve been taught to chase—money, status, and success—pale in comparison to what truly brings deep satisfaction (and happiness). 

So why do we keep letting the world convince us to play the small status quo game instead of doing what it takes to make a big impact and make our visions for our lives and our work real?

Let’s get one thing straight: I’m not telling you to sell all your belongings and live off-grid in a yurt. I’m saying that the status quo version of success isn’t big enough for you. It’s not truly success; it’s the illusion of success. Getting off that hamster-wheel and into the game only you can play is how you create a far greater impact while also savouring your rich life. That’s the path to cultivating significance in every area of your life, from your work, to your impact, to your relationships, to the way you experience joy at home.

We hear it all the time—“money doesn’t buy happiness”—but where’s the guidance on what will create deep satisfaction?

Where are the strategies for building a life of high impact and high significance, one that doesn’t just sound good on paper but truly satisfies your soul?

Here’s the truth: Most of us have sacrificed moments of joy, connection, and meaning for achievements that we secretly knew wouldn’t fulfill us. How many times have you let significance slip through your fingers because you were too busy grinding for the next thing? Too busy proving to the world (and maybe yourself) that you’re successful?

Let’s Talk About Pleasure—Real Pleasure

Pleasure has been framed as indulgent, something we should save for “after the work is done.” But what if we’ve had it wrong all along? Pleasure isn’t a luxury—it’s essential. Savoring a meal, laughing with someone you love, feeling the sun on your skin—these aren’t distractions from your goals; they’re the foundation of a life well-lived. They’re also – and this is less well-known – a secret northstar for knowing your next brave move, professionally or personally, to make that big impact you’re envisioning. Joy and pleasure can also be an endlessly renewable source of fuel that propels you forward (they work way better to get you going than stress!). 

Those moments you brush aside because “there’s more work to do” or “it’s not productive enough”—those are the moments that contain information you need to plot your path forward to professional significance and make life rich (personal significance!). And I’m not talking about the fleeting dopamine hit from buying a new car or landing a promotion. I’m talking about the lasting texture, depth, and meaning that come from embracing life’s pleasures.

So Why Do We Keep Making Life So Damn Complicated?

With all the knowledge at our fingertips, why do we keep chasing what society tells us to? Why do we pursue more money, a higher status, and some arbitrary checklist of success when deep down, we know it won’t bring us what we’re truly seeking?

True success isn’t measured by how much you accumulate; it’s about how aligned your life feels with who you truly are. It’s about the impact you make. It’s about the visions you realize. It’s about the depth & intimacy of the relationships you grow. It’s about waking up every day feeling that your life is rich—not because of what’s in your bank account, but because of what’s in your heart.

So here’s the real question: Are you brave enough to cultivate true significance and genuine impact, rather than settling for the status-quo version of success? Are you willing to face judgment, to disrupt your own narrative, and to reclaim what makes you feel truly alive?

What About You?

As you move through this month, I invite you to ask yourself some uncomfortable questions. 

  • What pleasures are you sacrificing in the name of success? 
  • Does success really require less joy and meaning…or could more joy and meaning be fuel for the kind of significant success you’re envisioning?
  • Who or what have you sidelined in your pursuit of more? 
  • And most importantly, are you ready to disrupt the story you’ve been living and discover what will truly make ALL AREAS of your life significant?

This is your opportunity to stop chasing and start cultivating significance, joy, and meaning.

Ready to Step Into the Arena?

This is the work I do in my 1:1 high-proximity coaching where you’ll stop chasing the illusion of success and start creating true significance. These are also the lessons I share in my newsletter, The Significance Project. You can subscribe here or schedule your first call…

…so you can start your journey towards a life of profound impact, rich relationships and deep fulfillment. You know, significance.

Jen Karofsky | Thought Partner & Coach for Visionary Leaders & Significance Seekers

 Jen Karofsky collaborates with leaders who are ready to disrupt the status quo and craft a life of legacy, deep connection, and purposeful impact. Through intentional coaching and bold thought partnership, Jen Karofsky helps you align your work, your values, and your vision to create transformational change in your world.

Join The Significance Project to redefine success and step into your power.

Join

The Significance Project

My monthly(ish) newsletter for the tools, tips and provocations you need to live your life of significance.

More on the BLG:

When the Metrics Don’t Fit

by |

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.. You can sign up here.Why ambitious visionary leaders need a different kind of measurement at this stage of growth.There’s a rhythm many...

read more

The Collaboration

by | ,

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.. You can sign up here.When Success and Significance build something real—together. Part 5: There comes a point in a high-achieving life...

read more

The Significance Dilemma: Embracing Thought Leadership in Pursuit of a Meaningful Life

The Significance Dilemma: Embracing Thought Leadership in Pursuit of a Meaningful Life

by | Aug 20, 2024 | Innovation, Inspiration, Practice Leadership

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.

You can sign up here.

Title Banner - The Significance Dilemma

In the realm of thought leadership, a profound paradox emerges for those who seek to live a life of significance. The challenge lies not just in excelling within the established rules but also in daring to redefine them. This dilemma is central to what I term “Warrior work”—the pursuit of creating impactful and transformative change.

The Existing Game and Its Players

In every field, there are those who navigate the current system with ease. For many, this game is comfortable and familiar; they may not even recognize it as a game. They are content with the status quo because it serves them well. However, for thought leaders, this mere participation is not enough.

The Disruptors: 

Then there are the disruptors. These individuals play the game reluctantly. They recognize its flaws and feel confined by its constraints, yet they struggle to envision an alternative. Their dissatisfaction is palpable, but without a clear path forward, their disruption may not lead to constructive change.

Visionaries and Game-Changers: 

The most intriguing players are the visionaries. They not only understand the game but also see beyond it. These are the thought leaders who don’t just want to play the game better; they aim to create a new one entirely. They recognize the purpose of the existing system and excel within it, but they are driven by a vision for something greater.

The Dual Existence of a Significance Seeker

For those called to be significance seekers, life is a constant balance between two planes: maintaining success in the current paradigm and forging a path toward a new one. This dual existence is a hallmark of true thought leadership. These individuals see the limitations of the status quo and are drawn inexorably toward creating meaningful impact.

The Inner Conflict

Many successful people find themselves wrestling with dissatisfaction despite their achievements. This isn’t a sign of failure but an indication of their potential for thought leadership. It signals a deep-seated desire to contribute to something larger than themselves, to create a legacy that transcends traditional measures of success.

Embracing the Dilemma

The journey towards a life of significance is fraught with contradictions. It requires playing by the rules while simultaneously seeking to rewrite them. This tension is not a barrier but a necessary part of the journey. It fuels the drive to innovate and redefine what success looks like.

To those feeling the pull towards a life of greater significance, know that your time to act is coming. Thought leadership is not just about excelling in the game but about changing it for the better. As you navigate this path, remember that the challenges you face are not obstacles but opportunities to forge a meaningful existence and lead transformational change.

Ready to step into your role as a thought leader and redefine the rules? 

Join our community of changemakers and start your journey towards a Life of Significance today.

Jen Karofsky | Thought Partner & Coach for Visionary Leaders & Significance Seekers

 Jen Karofsky collaborates with leaders who are ready to disrupt the status quo and craft a life of legacy, deep connection, and purposeful impact. Through intentional coaching and bold thought partnership, Jen Karofsky helps you align your work, your values, and your vision to create transformational change in your world.

Join The Significance Project to redefine success and step into your power.

Join

The Significance Project

My monthly(ish) newsletter for the tools, tips and provocations you need to live your life of significance.

More on the BLG:

When the Metrics Don’t Fit

by |

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.. You can sign up here.Why ambitious visionary leaders need a different kind of measurement at this stage of growth.There’s a rhythm many...

read more

The Collaboration

by | ,

This post is an excerpt from The Significance Project. If this resonates with you, I’d love for you to be part of the community.. You can sign up here.When Success and Significance build something real—together. Part 5: There comes a point in a high-achieving life...

read more