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Dream big
I have always found that plans are useless, but planning is indispensable.
—Dwight D. Eisenhower
Without leaps of imagination, or dreaming, we lose the excitement of possibilities. Dreaming, after all, is a form of planning.
—Gloria Steinem
Don’t ever let somebody tell you you can’t do something, not even me . . . If you want something, go get it. Period.
—Chris Gardner (played by Will Smith) in The Pursuit of Happyness
Dream big because the world is overflowing with opportunity. Dream big because society has real problems that need fixing. Dream big because there’s nothing to strive for without a dream.
Refuse to think small. Don’t let long odds hold you back. Don’t ask whether something is possible, figure out how you will get it done.
Big dreams generate the energy you need to succeed at anything. They stir passion, create meaning, and spur creative thinking. They call on people to do something everyone secretly yearns for: to take on an “impossible” challenge and prove everyone wrong.
Big dreams inspire others to join together in common cause. When the stakes are high and we’re quenching that deep human desire to pursue something larger than ourselves, collaboration flourishes and petty conflicts recede. When you believe that anything is possible, everything becomes possible.
Entrepreneurship is inherently risky, and if the reward isn’t big enough, the risk won’t be worth it. But a clear and compelling vision for the future will give everyone the courage they need to leave comfort behind and leap into the unknown.
Dream big—because your ambition is the cap to your potential. The more you can dream, the more you can achieve.
Live your life like it’s a movie
Every protagonist struggles at first—and ultimately triumphs
I love movies. I’ve learned at least as much from great movie speeches as I did from going to Columbia. Al Pacino’s incredible “game of inches” speech in Any Given Sunday. Will Smith’s character talking to his son about protecting his dreams in The Pursuit of Happyness. Every minute of Rocky.
I even try to live my own life like it’s a movie. I’ll tell you what I mean.
Think about a montage sequence. Filmmakers condense days or weeks or years of tedious work and preparation into a single two-minute scene with uplifting music that propels you forward.
When I was living through periods of struggle, I actually thought of those repetitive and difficult moments as part of the montage sequence of my life.
That helped me enjoy commuting two hours each way to high school in San Francisco, regularly working until 1 a.m. through the week and at least one weekend night at a New York investment bank in my twenties, and running ten miles before work to keep in shape so I could complete a marathon in each of the fifty US states. The minutes go by faster if you allow yourself to hear that inspirational music in the background the whole time.
In a sense, I was filming the movie of my life day after day after day.
Just like any good movie, there were moments of joy, doubt, love, fear, loneliness, heartbreak, struggle, hope, betrayal, redemption, and triumph. I learned to enjoy each moment because I knew that every story had to have those ups and downs to be worth watching. And as every movie I’ve ever seen has taught me, when things seem most hopeless and impossible, it means that something truly great is likely around the corner.
Almost any experience can be filled with a heightened sense of significance when seen through the eyes of a film buff.
Picture me on a bus at 6:45 a.m. carrying a Rasta bag, a boom box, and licorice root to sell at my elite, predominantly White private high school.
Cut to me sitting alone in an office on the sixty-third floor of 30 Rockefeller Center in Manhattan, my suit rumpled after a long day, my desk illuminated by one of those old-school banker lamps with the green shade.
See the wide shot of me running along a shoreline path with the New York skyline towering above me as I prepare to raise $1 million for nonprofits by running marathons.
When I took the BART train and two buses from my home in Berkeley to my school in San Francisco each morning, I chose to see that as the opening scene of an epic journey: sunlight peeking over the tops of buildings while suit-wearing professionals filled with intense purpose traveled to do what I imagined was exciting work in one of the coolest cities in the world.
There are, of course, other ways to view that same scene. Haggard commuters dragging themselves into work in some lifeless office very early in the morning could have been a signal of the drudgery ahead in adult life. But adding substance, meaning, and glory to the scene, seeing the light rather than imagining the darkness, viewing it as a journey rather than a commute—all of that helped me start each day filled with dreams and possibility.
Living my life through this cinematic lens inspired me to advance the plot of my life. Something exciting always happens in movies, so if my life is a movie, something had to happen for me, too. And as the protagonist in my own story, I knew it was up to me to make something happen.
What’s more, I had to move fast because I didn’t have much time. A great film can tell an epic story that spans a lifetime in just ninety minutes. A movie trailer boils that down into just three fast-paced, high-energy minutes.
Meanwhile, the rest of us live each day of our lives minute by minute and hour by hour. In three minutes, we manage to live . . . three minutes.
Human memory functions more like the movies than our daily experiences. When we’re looking backward, we remember only the biggest triumphs, the most meaningful interactions, the most difficult struggles—and let everything else fade away.
I try to do that in real time. To look at myself through a new lens. To put the mundanity and struggle into context. To add a larger, bolder arc to my own narrative even as I’m living it.
Make decisions you’ll be proud of when you’re old
An important goal of life is to be content in your rocking chair
When you’re in the middle of a complicated situation—deep in the details and the trade-offs—it can sometimes be hard to see the right path forward.
I’ve found it helpful in those moments to imagine myself looking back at the decision from the future. From that distant vantage point, what would I feel about the decision I’m making today?
It’s remarkably clarifying. And it works better the more vividly you imagine your future self and the more seriously you take it.
I’ve developed a very clear picture of myself in, say, the year 2050: Benís and I are living in the beautiful city of San Diego and enjoying its perfect weather and gorgeous ocean views. I’m seventy-one years old, sitting in a rocking chair on our porch, looking out at the water and reminiscing. I might be drinking some lemonade. Most important, I have no regrets.
This exercise—which I call the “rocking chair test”—has led me to a few realizations.
The most important factor in my happiness is my family. When I imagine a future where I’ve accomplished more than I ever dreamed—but ended up divorced from my wife and estranged from my children—it’s a million times worse than when I imagine accomplishing absolutely nothing except nurturing my closest relationships and earning my family’s love.
Decades from now, I won’t even remember most of the decisions I’m making right now. I make multiple tough calls every single day, but when I think back, I can recall only a handful of decisions that I made last year. It’s liberating to realize just how much our brains inflate the importance of the things right in front of us when most “big deals” aren’t very big at all.
The decisions I’ll remember most are the ones I’m either proud of or regret. If no answer seems totally right in the present, I tend to choose the one I know I’m least likely to regret. And if I can tell that one of the paths is the right thing to do even if it’s going to make some people angry, I work hard to find the courage to do it. Because I know that the more moments of pride I create in my life, the more content I’ll be in that rocking chair.
Over the last few years, the choices that have been toughest have generally been around difficult HR decisions—letting someone go who I like personally but know isn’t right for the role—or moments when our country feels like it’s faced with a moral reckoning and I feel moved to speak out.
It can be hard since, as a business leader, I represent people with very different views. I cherish our country’s history of open debate and I don’t want to make anyone who works at Compass feel like they don’t belong. But in cases like President Trump’s executive order in early 2017 barring entry into the United States by people from certain countries with Muslim-majority populations, often called the “Muslim ban,” the White supremacist and neo-Nazi rally that took place in Charlottesville, Virginia, in August 2017, the separation of immigrant children from their families at the border, and the murder of George Floyd by Minneapolis police in 2020, I chose to share my personal views with the entire Compass community and the public.
When I’m in that rocking chair in thirty years, I’m pretty sure I’ll be proud of those decisions to speak up.
Twenty-two items from the bucket list I wrote at age twenty-two
When I was having a hard time getting over the breakup with my college sweetheart, I decided to dream my way out of the pain by envisioning a positive future. So I wrote down my Top One Hundred Lifelong Ambitions and Experiences. Under the heading Objective of List, I wrote: “To be used as a reminder of who I am at the core when life gets too hectic and the world is too overwhelming.”
Here are my top ten life goals from that list.
Marry an intelligent, honest, imaginative, creative, driven, hopelessly romantic, curious, selfless, joyful, patient, demanding, loyal, supportive, funny, charismatic, affectionate, thoughtful, spontaneous, adaptable, attentive, supportive, centered, reliable, dependable, emotionally stable, kind, challenging, magical, confident woman who will run with me, treats everyone the same, is my best friend, has a deep desire to be an amazing mother, can talk about her emotions, is comfortable in every environment and at peace with her place in the world yet still ambitious, is a true partner in every way, cuddles with me, camps with me, loves me for who I am at the core, and who makes me want to be a better man
Earn the love and respect of my children
Grow to be completely comfortable in my own skin
Find a profession that represents the best and highest use of myself
Learn to make bad events/conflict/competition make me better and not bitter
Be the best husband, father, and friend that I can be
Have a cartoon that I watch with my kids religiously every Saturday
Play with my grandchildren and tell them my life story while they get bored listening to it for the tenth time
Raise my kids to be confident, curious, centered, and content (the rest will follow)
Talk to my mother, children, and wife every day
And here are some entries from the rest of the list (which ended up being 105 items long).
21. Motorcycle across Latin America (north to south)
24. Open for a reggae/rock concert saying, “Are you ready” . . . and the audience says “YEEAAHH”
39. Write an autobiography called Search for the Sparkle, and a book of advice to pass along to the next generation
44. Become the CEO of a Fortune 500 company
62. Save someone’s life
64. Take my kids to the soup kitchen every holiday season to show them the diversity of the world they live in
68. Study the Seven Wonders of the Ancient World and visit the Seven Wonders of the Modern World
73. Get to a point in my life, emotionally or financially, where I don’t care about money
81. Call the president of the United States to advocate for somet...