Reboot Podcast Episode #94 – When Is Enough, Enough for Me? – with Steve Kane

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

Episode 94 // November 8, 2018


Steve Kane

Steve Kane

Author, entrepreneur, and investor

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Episode Description

For leaders in the modern world, dodging the constant bombardment of projected successes that others display across various media outlets can be exhausting.  Comparing ourselves to others can lead to an overwhelming sense of inadequacy, which often ripples out to thoughts of insecurity about our work, our relationships, and the way we are perceived by our peers. As Theodore Roosevelt so poignantly observed, “Comparison is the thief of joy.” By allowing our gaze to become so outwardly attuned, we create an internal roadblock against finding peace and equanimity within our own lives.

On this episode of the Reboot Podcast, Jerry is joined by longtime friend and self-described serial entrepreneur, Steve Kane. In this discussion, Steve comes to Jerry with the lingering question, “When do we begin to know when enough is enough?” Together, they explore the pivotal role Steve’s father played in molding the baseline for determining his “enough,” and how his own radical self-inquiry supported Steve in making a difficult decision during the successful exit of his third startup, Gamesville.

As they ponder the question of ‘enough,’ Jerry and Steve touch on the ways in which we, as humans, yearn for safety, love, and belonging, and how, ultimately, our ability to expand our awareness of ‘enough’ is an act of continuous practice, one which allows us to take stock of our lives at any moment and truly consider, “When is enough, enough for me?

Steve Kane on Twitter |  #30 – Who Do You Turn To? – with Yancey Strickler & Ian Hogarth | Reboot Bootcamps

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Show Highlights

Top Quotes:

“We drive ourselves a little crazy worrying about the pursuit of happiness, or are we happy enough, or what is happiness?” – Steve Kane

“One of the things that makes modern people unhappy is this relentless feeling that they don’t have enough or that they’re not living the right life, or that they’re not doing the right thing, or that they’re not owning the right possession, or doing the best job; comparing themselves to everybody they know.” – Steve Kane

“Comparison is the thief of joy.” – Theodore Roosevelt

“The mission is to buy low and sell high, not buy lowest and sell highest.” – Steve Kane

“I feel sympathy for today’s entrepreneurs, who I think climb out of the gates in a world comparing themselves to all these things that are so challenging.” – Steven Kane

“There’s something really powerful in being able to check in with one’s self and ask the question, “When is enough, enough?” But, “When is enough, enough for me?” – Jerry Colonna

“It seems so obvious now, but it did not seem at all obvious then, but the bird in the hand was enough.” – Steve Kane

“If we go too far down the path of the comparison, then enough is never enough.” – Jerry Colonna

“I hope that, in my own personal journey, that I can focus on the process, whether it’s mindfulness and meditation, or just the process of living my life and trying to enjoy every breath ’cause I know that I don’t have an infinite number of breaths.” – Steve Kane

“The relationship to understanding when is enough, enough for me, is, in fact, an ongoing and dynamic practice.” – Jerry Colonna

“It’s not a binary thing, success or failure. New beginnings aren’t all phoenixes rising from ashes. Sometimes they’re babies being born into the world.” – Steve Kane

“There’s this tremendous pressure to maintain the image, and to live unhappily.” – Steve Kane

“Enough is enough any time we need it to be, if we are choosing to begin again.” – Steve Kane

“When is enough, enough for me to feel my big three: love, safety, and belonging? When is enough? What would be enough to make me feel loved, safe, and that I belong?” – Jerry Colonna

“Radical self-inquiry is not an ends, it’s a practice.” – Steve Kane

“The good news is that we can begin again, at any moment we want.” – Steve Kane

“What is enough, for me, in this moment, in my life, as I exist right now?” – Jerry Colonna

“Maybe the pursuit of happiness is just an awareness of our vulnerability, rather than an attempt to squelch it.” – Steve Kane