“I’d use a 3 or a 4-iron,” I said to Mr. Bernstein, the member I was caddying for at L.A. Country Club.
“Gimme the 4,” he responded.
(thwack) His ball bounced just before the green and rolled to 10 feet from the pin.
I handed him his putter for our long walk to the green.
“What sort of work you looking for?” He asked, knowing that I had an MBA and caddying likely wasn’t my dream job.
“I’m not sure yet. I’m trying to find a way to shift our culture, so I think it’s in media production, because that is a big part of what shapes us. But I really can’t be sure.”
“Why not just get a job in finance or marketing at a studio and start there? Should be easy for someone with your credentials.”
“Yeah, you’re probably right. And I would put a bullet in my head if I was responsible for the next Fast and Furious. It’s gotta make a difference.”
It was the Summer of 2004. I had just completed my MBA at Columbia and was making $15 an hour reviewing scripts and answering phones for a talent agent in an effort to learn the production side of the media business. To make ends meet, I caddied on the weekends. I lived in a 2-bedroom apartment with two other 20-somethings and their 5 cats. My “room” was the living room, where I had a mattress on the floor and my clothes in banker’s boxes, which turned out to be perfect places for the cats to leave turds.
So why would a former country club member, with a background in investment banking and tech startups, an Ivy League MBA and $150k in student loans make these choices?
At Columbia, I had taken a powerful self-awareness program that oriented me towards having a career of purpose and impact and leaving a legacy. For me, there was no looking back. Through the exercises, readings and close friendships I developed in that program, I came to the view that my life couldn’t just be about success, prestige, pleasure or acceptance, but self-expression and service. I needed to pay forward the tremendous privileges I had received and the talents I had developed. Unfortunately, I didn’t yet know how to do that. All I knew was that if I followed the money and went back to Wall Street or Silicon Valley, I wouldn’t find out.
I knew there was something inside, that I had a great work within me, but without any wizened elders at my side, I was on my own to sort it out. I needed to find my way to what Dr. King called a "complete life", a legacy that had length, width and height:
Over the next several years, I hired therapists and coaches and sat in men’s circles. I participated in numerous spiritual, personal and leadership development programs, read hundreds of books, made trips to India and Latin America, went on meditation retreats, worked with plant medicines and wandered through Burning Man camps.
It wasn’t until 2011, that I had the good fortune to experience purpose discovery work first hand, and find actual clarity about my purpose, the “why” I would give my life to.
Those 7 years between 2004 and 2011 weren’t easy. There were gurus and charlatans. There was heartbreak, failure, rejection, loneliness and shame. There were false starts in media, renewable energy, education and non-profits. But something within me kept going. I knew I had a reason to live that was bigger than myself or my family. I knew that my life had to be for something, and that if I relented, if I gave up, I couldn’t live with myself. So I kept putting one foot in front of the next, hoping the next job, course, book, guru or ceremony would crack me open to the path to wholeness, to a complete life with length, width and height.
Since February, 2012, when my purpose revealed itself, I’ve devoted myself to making this journey easier, more accessible, connected and scalable, so that no one will ever need to wander alone again. That’s at the heart of my writing, teaching, community and work in the world. But this isn’t about me.
It’s about you, the reason you’re here, the very thing you will give the remainder of your life to - your legacy. Your legacy is your gift to your people. It's the sum total of your existence poured into works.
You will need access to it in order to change your own leadership behaviors. It's the foundation of believability. It is what inspires others to join you. Folks need to get the sense that it not only matters to you, but that you are the person to do because it is a source of personal salvation, redemption and service to the greater good. They need to get that you're willing to lose it all in service. Without this connection, the “empathy, community, and shared purpose“ (McKinsey & Co., 2015) required to innovate and transform, nothing will change in your organization.
People want to see a brighter future, feel a sense of solidarity, and know they are guided by someone who really cares for them, the company culture and their impacts on society and the planet. Without a connection to their legacy, a person is at best a manager. With an awareness of their legacy and the clear connection between it and the company’s mission (who the company is for its customers, employees, community and planet), they have earned the right to lead. It's important to note, that your legacy is not the same thing as your company's mission. It's both more personal and bigger than that.
So what is your legacy? And how do you encounter it? There are several well known instances when a legacy appeared and the real story of a life and an enterprise are revealed, such as Patagonia founder, Yvon Chouinard’s awakening to his - to empower people to make contact with their true selves through nature, or Interface Carpet CEO, Ray Anderson’s awakening to creating planet positive flooring. Volumes have been written on these encounters (and many more) and their resulting organizational transformations, including: The Soul of a Business (1993), Good to Great (2001), Firms of Endearment (2003), Let My People Go Surfing (2005), Reinventing Organizations (2014), An Everyone Culture (2016).
Notice I use the words “encounter”, “appeared”, “revealed” and “awakening”. A legacy is not decided upon, nor can it be outsourced to marketing, nor guessed at by an expensive consulting firm. It is an encounter with your soul. Although this encounter can be facilitated with outside help, by people who ask good questions and hold space for revelation, it comes from within a leader's heart and soul. It can appear mid-sentence in a meeting. It can just as easily erupt in the shower, on a walk, or over breakfast with your kids.
But it cannot be decided upon. It must arrive as a revelation, as an incandescent truth that was always there right in front of you. When it is revealed, two things happen. The first is that feels a little obvious, like a coherent pattern that emerged from the data you've been staring at for years - “of course, that’s what I’ve been doing this whole time.” The second is a religious conversion, of feeling something sacred erupt inside you as new energy to incarnate your legacy, let it guide your leadership. It shapes how you do business, communicate, develop people, shepherd culture, deliver for your customers, capitalize your company and serve the community and earth’s ecology.
This is why every conversation about culture change begins with someone on fire. My hope is that seeing yourself as a steward of your people’s flourishing and our nation’s purpose, and making an impact you can be proud of is part of your legacy. My greatest hope for you is that you die a good death…
With gratitude, tenderness, fulfillment and a sense of legacy completed…
With the bone deep knowledge that you did what you came here to do...
Surrounded by those you love, and...
Able to look your grandkids in the eyes and honestly tell them “I did everything I could to make this world better for you”.
Your access to your legacy and a noble death is to bring forth what is inside of you and your enterprise, and take it out into the world as an act of service. Numerous traditions have provided us similar guidance, e.g.,
“If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you.” - Jesus Christ, Gospel of Thomas
“It is better to strive in one’s own dharma [fate, purpose, legacy] than to succeed in the dharma of another. Nothing is ever lost in following one’s own dharma… The ignorant work for their own profit... the wise work for the welfare of the world, without thought for themselves... Perform all work carefully, guided by compassion.” - Krishna, Bhagavad Gita
"To be nobody but yourself in a world which is doing its best, night and day, to make you everybody else means to fight the hardest battle which any human being can fight; and never stop fighting." - e.e. cummings
Before you can be clear on your legacy, we need to know what legacy actually means. Even among trained purpose practitioners, answers somewhat vary. Below is how I hold it.
Now legacy is much more than this, as I’ve explored in my previous book, Planet on Purpose, e.g., its also fun and spacious, creative and sensual, etc., but this is the part that matters right now, because without it, you cannot lead your organization into a purposeful future, nor steward the sacred purpose of our nation. So what is it?
We're looking for what is yours to give your life to and die for. As Malcolm X said, “If you’re not ready to die for it, put freedom out of your vocabulary.” Same with your legacy. It has to bleed. It's not your kids, their college funds or your reputation. It's not a hobby. It's found in your suffering.
Your access to fulfilling this destiny is through the transformation of your suffering into wisdom, creativity, care and service. You are on the path of “follow your blisters”, as Michael Meade declared, and that means leading from a place sourced in your heartbreak, in your weakness, pain and loss.
This means standing naked before the largest entity you hold dear, e.g., God, Source, the Universe, Life, etc., with your deepest heartbreak in your left hand and all your gifts, virtues, experiences, capital, and relationships in your right. It’s you saying, “Take me. Use me. Let’s do this. I’m tired of half-measures and simple pleasures. I’m ready. I’m here to fulfill my legacy or die trying.”
It’s likely you already know or could generate a quick inventory about what’s in your right hand. But can you tell me what’s in your left? Before you move any further into this book / your journey as a leader, there has to be something at stake, something you’re willing to change everything for. So what is it?
For me, it’s sourced in not ever being good enough for my dad. I never felt seen, like my gifts and talents mattered. I received affection and praise only insomuch as I mirrored my father’s values and aspirations. I was denied affection and shamed when I shared the contents of my soul - my creativity, my femininity, my values and aspirations. Well-intentioned as he was, this left me a fraud, a prostitute, a machine who performed for his praise. Behind the facade of good manners and athletic, social and academic achievement, I was deeply unhappy.
I know the pain of spending a quarter century trying to be someone I’m not. I know the pain of getting good at lying to myself and others. I know the pain of being dead inside. So I’m willing to die for soul, for purpose, for the right for everyone to be blessed - to have their gifts seen, accepted, developed and stood for by others. I want every person to be liberated by the dignity of their soul and fulfilled by their purpose, to know that they matter, are wanted and are blessed.
Of course there are many ways this shows up. Blessing is a thread woven throughout my life. It’s not just in writing books and culture change work. It’s in my marriage, my friendships, my mentees, my racial justice work, my men’s circle, my self-care, the way I relate to children and connect with my neighbors.
In this sense, legacy is the one and many, the parts and the whole, a guiding light that is equally useful in a marriage, a boardroom, and a shipwreck.
For the rest of this book to be of most use to you, you need to agree that you do have a legacy, even if you’re not crystal clear on what it is right now.
If you feel like you're close and would like some more clarity, I invite you to journal a few sentences for each of these prompts. Please be warned, answers to these questions will bring up painful memories and might re-traumatize you, so check-in with yourself to see if you have the energy and psychic stability to dive in. If you don’t feel ready for it or have no clue what it might be, I invite you to work 1:1 with a trained purpose practitioner (see Appendix A: Purpose Activation Resources). As a reminder, this is about you, not your organization, career or role.
Now review what you’ve written and circle the powerful and evocative phrases. What themes do you see? Any new information about your legacy? Now, you don’t need absolute clarity right now, nor understand all its implications for your career, relationships and organization. All you need right now is the awareness that something is there inside of you, some kernel of passion, aliveness and heartbreak that will transform your life and the world if you give attention to it.
The next chapter, “Culture Change is a Matter of Life and Death”, we explore what is at stake in this next phase of your leadership, you might discover some new information about your legacy.
Chapter 3 Summary:
Chapter 3 Reflection Questions:
Chapters will be published each week. Subscribe below to receive an email notification of newly available chapters.