The Honest Cost of Leadership | Mayor Derek Kawakami
Mayor Derek Kawakami has spent eight years leading the island of Kauaʻi through a global pandemic, personal loss, and the everyday grind of public service. On this episode of Greater Good Radio, he sat down with Evan Leong to talk about what leadership actually costs — not the version people see in press conferences, but the quieter version that plays out at home, in the middle of the night, and in the moments no one is watching.
A Local Boy Who Never Set Out to Lead
Derek didn't grow up dreaming of public office. He describes a Kauaʻi childhood straight out of Stand By Me — riding bikes to Kipu Falls, sneaking into hotel pools, and running free on cane haul roads with almost no supervision. That upbringing shaped who he became: a self-described "average" guy who isn't excellent at any one thing but is good at figuring things out and bringing people together. It's a humility he's carried into the mayor's office, and it's part of why, when he finally stepped into elected life, the weight of it caught him off guard.
The Loneliness Nobody Warns You About
Derek is candid that the hardest part of leadership isn't policy — it's internal. He talks about moments during COVID-19 when he was making decisions that put Kauaʻi at odds with the state, "calling our own audibles" while the rest of Hawaiʻi went a different direction. Even surrounded by a team he trusts completely, he admits there were moments that felt genuinely lonely — the kind of isolation that comes from knowing a decision is yours alone to make, with only 70% of the information you wish you had.
Choosing His Family, Out Loud
One of the clearest costs of the job, Derek says, is time — and he's learned to protect it fiercely. He talks about turning down galas and events to be with his daughter, and being honest with people about why. Becoming mayor, he says, clarified his priorities in a way nothing else had: he's a dad first, a husband second, and a public servant third. Holding that boundary isn't hard for him anymore — he calls it liberating — but he's clear that it came from consciously deciding not to be everyone's cup of tea.
Knowing His Own Kryptonite
Part of leading well, for Derek, meant confronting his own weaknesses head-on. He shares that he quit drinking entirely once he became mayor, recognizing it as the one thing that could undo everything else he'd built. It wasn't an overnight decision — it took a few false starts before it stuck — but he speaks about it as an act of self-awareness rather than shame, one more example of a leader deciding in advance what he wasn't willing to risk.
Grief, In Public View
Perhaps the most searing cost Derek discusses is personal loss. Within an 18-month span, he lost his mother, his father, and his older brother — the last to suicide. Rather than keep that private, Derek talks about it openly, pushing back against a culture he sees in Hawaiʻi that discourages people, especially men, from showing vulnerability. He believes that silence is part of what's costing young men their lives, and that leadership sometimes means going first — being the one willing to say the hard thing so others feel permission to do the same.
What Makes It Worth It
Despite everything it's taken from him, Derek doesn't describe his time as mayor with regret. He points to small, human moments — like coming home during COVID, exhausted, to his wife and daughter waiting to film another silly video for their Stay Home Kauaʻi series — as the memories he'd hold onto above all else. It's not the achievements he treasures most; it's the feeling of being wanted, and of a team and family who never let him carry the weight completely alone.
The Real Cost, and the Real Reward
Derek Kawakami's story is a reminder that leadership always asks for something — sleep, certainty, private grief, a drink at the end of a hard day. What he offers instead is a model for paying that cost honestly: naming it, protecting what matters most, and leaning on the people who show up for you when it counts. As he moves into a statewide campaign for Lieutenant Governor, that honesty may be his most valuable asset yet.
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