Recently, I was given the opportunity to lead a weekend of programming for a family enterprise’s retreat in Hawaii. This family, made up of fifty plus members spanning four generations, meets annually to maintain cohesion and to stay engaged, educated, and invested in their family business. It’s the kind of project that sits at the intersection of many of my interests: working with families, leadership, psychology, finance, and sport. Ten plus years in an Olympic team locker room, a master’s in psychology, and now helping families navigate generational wealth. A perfect blend of my passions.
So why then was my immediate reaction doubt? Locally, I work with multigenerational family businesses, some in the same industry as theirs, but they are usually smaller, closer to home, and ones that I already know well. This family, bigger, older, spread across the world, and unfamiliar to me would be different. (Plus, I am not a professional public speaker!) Would my background, experience, and approach hold up at that scale? The short answer is yes! But I didn’t know it yet. I knew I was passionate about the topics of conversation, I knew I would put the time and work into learning about the family, and I knew I’d learn something along the way. That was enough for me to ignore the imposter syndrome within and dive in headfirst.
The keynote speech, titled “Championship Family Culture: Built on Hawaiian Values,” touched upon aloha, ohana, and kuleana and explained how these values hold an Olympic locker room and family together. What ties aloha, ohana, and kuleana isn’t complicated: it’s a connection to the land you come from, a willingness to give more than you take, and a pursuit of excellence measured by what it does for the people around you, not just yourself.
Today, look around — this is your locker room: different ages, different roles, from all over the country, thrown together under one name. Not much different than an Olympic team. How are we going to become a true high-functioning team, instead of just a roster of names? That’s the question that we will look to answer today.
I opened the talk with a short breathing exercise we used to do before each Team USA practice and match to get present, relaxed, and focused. To my surprise, family members came up to me days later telling me how they had begun to incorporate the exercise into their various personal routines. I also led another activity that asked the room to randomly divide into groups of five and draw their own taro plants, adding individual shoots to the plants and labeling them with name and current hometown. Then each group had to find two themes that connect all of them, separate from last name and family business. Some answers included love of traveling, reading, education, and pets! It was a Hawaiian twist on building out their family tree. I allotted ten minutes for the activity. By the end of ten, they requested twenty.
So Ohana doesn’t just mean family. It means a group that grows outward from one shared root, and stays nourished by that root even after being physically separated and replanted somewhere else completely.
The two financial literacy sessions I ran for their youngest generation were simpler but favorites of mine. We taped marks across the hallway and physically tracked how an investment compounds over time with various rates and timelines. We discussed how to choose an advisor, the emotional component of buying a house vs. the rationality of renting, and the differences between public and private investments. More than anything, they appreciated how simple and easygoing the conversations were – no jargon, no lectures, just open conversations about real life decisions.
One evening, we traded the conference room for beach volleyball courts. Members of all generations learned to play, with the more serious of the bunch splitting off into teams for some competitive action. There were a few aces, shanks, kills, and a lot of laughter. Suddenly there was a group of people becoming a team. Funny how sports work!
I came away from the weekend thinking about money a little differently. It doesn’t automatically keep the family close. In fact, without real effort, it can push people apart. Arguments over inheritance, who’s in charge, who’s contributing and who isn’t, these happen in every family. Money just raises the stakes. Talking about it openly, across generations, doesn’t happen enough, but it’s one of the best ways to keep small tensions from turning into permanent ones. That’s why this family gathers every year, on purpose. Not because having money makes staying close easier, but because without effort and the willingness to talk about it, money can just as easily tear a family apart. It was neat to observe a family that does that work and to play a small part in it. Fifty plus people, while not perfect, a true high functioning team.
As the weekend went along, the doubt I carried into it slowly faded one conversation (and one beach volleyball game) at a time. Family members, young and old, told me that the speech and workshops were valuable. I think that value partly came from what I said, but more of it came from how openly they engaged with it. There was good energy to the entire weekend, easy, unforced, and genuine. But what I felt most, before our time together was even up, was their aloha, a welcome to someone who’d started the weekend as a stranger – the very aloha I defined for them days earlier, now returned to me. In the end, I think I learned as much from them as they did from me.
About the Author
Kawika Shoji is an investment advisor and portfolio manager at Regency Capital Management. He advises individuals, families, retirement plans, and institutions to assess, develop, and implement their investment and financial goals.
