Keith Yamashita is the Founder of SYPartners and a creative force who has guided countless teams and organizations through positive transformations. He started his career by working for Steve Jobs — in a humbling, revelatory experience that helped him understand the power of creativity. In his two-and-a-half decade career at SYPartners, he has worked with His Holiness the Dalai Lama, Oprah Winfrey, Starbucks, and IBM.
We spoke with Keith about how his relationship to time has changed since his stroke, the real power of collaboration, and why it’s important to just be.
Keith, you’re a dad, an entrepreneur, a storyteller, a husband, a designer, and a human of many other gifts. How do you think about time?
The world is one huge mystery and one way humankind has dealt with the ambiguity of that mystery is to make up this concept of time. It’s a fabricated concept. And what I’m increasingly understanding is how we’re all tortured by this made-up concept — humankind invents it, and yet, so few of us have a friendship with it.
I had a stroke about a year and a half ago. I would say that, pre-stroke, time was my enemy — and I tried to live life by constantly compressing multiple things into any given moment for efficiency, but perhaps also for a sense of competence. I had fallen in love with a self-image of me being busy. After my stroke, I’m making a new deal with time — we’re forging a new friendship.
I’m simultaneously able to think long-term while not squandering the present moment. And trying to understand the difference between tasks and what makes a difference.
You’ve written before that: “Birth is certain. Death is certain. The time between is a series of choices in how we spend our days.” How has your understanding of this “time between” evolved in your lifetime?
How we spend our time is how we spend our days. How we spend our days is how our life goes. How our life goes determines whether we thought it was worth living.
We often do not figure this out until the end. I didn’t really get it until age 51 — on the day I thought my life was ending. Of course, no amount of me talking about it here will convince your mind that this is true. Only you can discover it.
“How we spend our time is how we spend our days. How we spend our days is how our life goes.
How our life goes determines whether we thought it was worth living.”
How has being a parent changed how you prioritize the hours in your day and, on a broader level, your life?
My husband and I have a daughter and a son. She’s my biological child. He’s my husband’s biological child. They’re of the same birth mom, and they’re related to each other through her genetics. The adage that the love for one’s child is unlike any other love you’ve experienced in your life rings true for me. And it’s also profoundly true in my mind that I haven’t been a very good father — work, initiatives, moonshots, and big projects have all been things I felt competent at. Those first early days with my kids—the ones I call the “pooping-machine” phase — were just plain awkward for me. I never felt accomplished.
I’m actively working on being a better father, and this is teaching me that time with my children isn’t planned and cannot be planned. You must allow for simply being — taking the smile, the story, the good cry, the emotional fit, the magical moments when and how they come. And to value these moments above the others — the email, the board meeting, the conference call can all wait, it turns out. You’d be surprised.
“You must allow for simply being — taking the smile, the story, the good cry, the emotional fit, the magical moments when and how they come.”
You’ve recently shared so beautifully about your experience of suffering and surviving a stroke, and the significant transformation that ensued. What impact has this health event had on you in relation to your understanding of time?
If time = t and “t” is swiftly approaching zero, you feel all sorts of things. My first thought was: “This is a really bad day to be an atheist.” The second thought that instantly followed was that I wasn’t going to see my kids before I died. And then, of course, I cried. I remember being flat on my back on a gurney, tears flowing from my eyes, down my temples, and pooling in my ears. The tears were for all the days I was not going to be able to have with my kids in the future.
But I didn’t die. So what can I make of this day?
As one of the founders of SYPartners, your work has been centered around transformation. How does your understanding and experience of change intersect with time?
At our core, SYPartners helps humans transform themselves so that their organizations can transform. Largely, we believe it’s about the process of “true-ing” — trueing to our best selves and trueing to the deeper purpose of our organization. That work requires relishing time more — making time to drink from a deeper well (poetry, literature, film, art, etc.), taking time for imagining and listening to others and ourselves, noticing what is actually going on. And it requires momentum — using it to your favor and being swept up by it — that’s when positive change happens faster than everyone’s expectations.
To make a significant change, you have to be willing to think in “long time” — time that goes beyond each of us in our present role, or even the company’s current configuration. To me, it’s about mastering time in all its forms, as an ally — not an enemy.
“To make a significant change, you have to be willing to think in “long time” — time that goes beyond each of us in our present role, or even the company’s current configuration. To me, it’s about mastering time in all its forms, as an ally — not an enemy.”
What’s the secret to spending time wisely in collaborative settings?
In many ways, my job is to manage the flow of energy in a team. To be a source of light in an otherwise dark room, an optimist for what is possible. In this role, I try to get a few foundational things right: Getting the right, diverse group of individuals to the table. To have each bring something that inspires them into the room. That inspiration doesn’t have to be joyful; it can come from dissatisfaction about something, anger about the status quo, feelings about something that can be improved. To ensure every person feels invited and seen. And then to frame the work with a beautiful question.
Too often, we convene intending to get to a “yes” or “no” — a decision. The real work of teams is to invent something no one could on their own. A beautiful question is one that, in its first act, seems very innocent. In its second act, it draws you into complexity, and then, in its third act, opens you up to a realm of possibility that goes far beyond where you have tread before.
“The real work of teams is to invent something no one could on their own.”
What time management techniques have you found effective for efficiently managing a project? What’s your advice to others who are looking to improve in this regard?
Since I was 28, I have been a fan of Getting Things Done. David Allen taught me how to create a leak-proof system so that you are no longer worried about all you are doing. His phrase, “Mind like water,” stuck with me.
How do we create systems, so our brains are not constantly plagued by this gnawing feeling we are behind, or missing something, or late? Put the angst into the system so that you can have a mind like water — a disruptor can be cast into the water, then naturally absorbed, with ripples that dissipate effortlessly.
What strategies have worked for you in determining when to say “no” and when to say “yes?”
My stroke represented a declarative period on the long sentence that had been my life up to this point. The sentence that came before was: “I want to change the world, and to show my loyalty to the mission; I’ll exhaust myself.” The sentence that I am trying to write now, after my stroke is: “I want to nourish myself so that I can nourish the world.” Changing my foundational mission, just in degrees, is making a very big difference in what gets elevated to a “yes” in my life.
The first question in my decision tree is: “How will this nourish me?” I used to think a question like that was selfish. I’ve come to see that without a strong “yes” to this question, none of the following acts will ever achieve what I hope they might because I will get eaten up in the process.
“The first question in my decision tree: ‘How will this nourish me?’”
What’s one non-negotiable thing you always make space for in your life? What’s something you’d like to do less of?
I was always the last kid picked for sports. I have never considered myself an athlete. As part of my recovery, I have had to get fit and lose 40 pounds. Before my stroke, if I had any time for working out, it was only after I had exhausted myself in pursuit of my to-do list. And for that reason, it almost never occurred. Now, I put working-out times as the rocks in my schedule and everything else is water that flows around them.
Did you have any rituals growing up that you’ve cherished and carried with you?
At age 11, my dad gave me a Polaroid SX-70 camera. It changed my life. It sanctioned looking at the world — to freeze it in a photograph — as a legitimate act. To this day, I am happiest when I have a camera in my hand, and I’m taking notice, taking time, being awake to the miracle of what is around me.
What makes you feel like you’ve spent your time well?
Did I pursue a beautiful question? Did I get time with my kids? Did I see the world through the eyes of inspiration? Did I not pass out at Soul Cycle?
Sometimes we think that time well spent is only about being in our highest sense of success and happiness. I remind each of us that nourishment comes in many forms — not just accomplishment, bliss, and joy. Time well spent can be sitting in the darkness of our days, our suffering, and the things that make us avert our eyes. That’s where the light gets in. You don’t realize that unless you’re willing to spend some time in the dark parts of your life.
“Time well spent can be sitting in the darkness of our days, our suffering, and the things that make us avert our eyes. That’s where the light gets in.”
Imagine you’re reflecting at the end of a day or other period of time where you felt that your time was well spent. What did you do? How did it feel? How much time did you spend doing it?
I’m starting to realize, for me, that all the details of the day don’t matter. What matters to me is whether I have sought joy in as many places as possible. Yet not shying away from suffering and sadness. Richness comes in the polarity.
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