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