In this episode, I'm tackling a question that is rattling around the corridors of the minds of us highest achievers: "When will it ever be enough?" It's a relentless echo that reverberates in the silence left by our latest triumphs, a whisper that lingers even as we scale the peaks of what I’m calling “Money Mountain” with the weight of the world on our shoulders.
For those who've pushed themselves to the brink, who've crafted empires with their bare hands and sheer will, this episode is a soul-stirring examination of the unsustainable pace of success and the personal toll it exacts. We're pulling back the veil on the harsh truths behind burnout, the undercurrents of systemic pressures, and the personalization of collective dysfunctions that lead us to question our worth, our work, and our way forward.
Join me as we explore the deeper questions that should be guiding our pursuit of fulfillment. We'll navigate through the false narratives of entrepreneurship, the courage to be beginners in the public eye, and the vulnerability required to ask for what we truly want. Tune in and transform the way you approach your goals and your life.
MENTIONED
13 | Re-Mothering Ourselves
03 | What Are You Playing For? (CEO Series)
GEMS DROPPED
“In this quest to say, ’Am I doing enough? Is it enough? Have I ascertained enough? Have I done enough? Have I created enough?’ We're really searching for, ’Will I ever be enough?’ That's the real question that runs beneath all of this, is, will I ever be enough?”
“We're asking ourselves at the end of the day, why am I not enough? Why am I not rising to the occasion? Why is this wearing me out? Why am I having these emotional reactions and responses? Why am I being a fucking human being? We're punishing ourselves for our basic needs, and it's wrong. It is wrong. It is misguided. It is misdirected. So I want you to turn that energy into some better questions. I think a better question is ’Am I fulfilled, well, and whole?’“
“That moment where the decision is available to you, it can feel like you don't have a choice. And we always have a choice. We always have a choice.”
“At a certain point, money no longer delivers. There's no return on that investment emotionally. Once you get past a certain level it caps out and you're not going to get any more enjoyment, fulfillment, happiness, even delight. All of that just falls flat. And so, well, what are you even playing for? “
“There really is no enoughness that's going to truly satisfy you…the feeling that you're actually seeking to meet, which is fulfillment. If fulfillment is what's lacking, none of this other stuff even matters. And I think that that's what we end up getting ourselves to when we first start asking this question. What's enough? You're enough. What do you want? Who do you want to be? Who you desire to be? Start there.”
STAY IN TOUCH
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