Ambition Shifts
Good morning, and greetings from New York City! Our newborn, Flo, just turned two weeks old and we’re still getting used to our new life with two kids. Most importantly, she and mama are healthy, and everything has gone as well as we could have hoped. We’re so grateful and in love right now.
I’m two weeks into paternity leave and finally getting settled. It has been a heart-warming and rewarding experience to be with my family undistracted, and support Eliza as she recovers from labor and nurses the baby. I’m spending my days juggling myriad chores, hanging with my eldest daughter, changing diapers, and of course snuggling with the baby. Taking a proper leave and putting my coaching practice on hold for a month has been one of the best decisions and investments I’ve made in my life. In fact, I’m surprised more men who can don’t take advantage of it given all of the benefits. Even in just two weeks I feel much closer to Eliza and my family. This time has been priceless.
Since newborns sleep 14-18 hours a day, I’ve had plenty of time to think about the future, not just what comes next for me personally and professionally, but also what kind of life my girls are going to have. As I hold my daughters in my arms, I’m left wondering what I really want for them and how my ambition ties into that. I also wonder what ambition I have left despite being in the prime of my career. In just a few years, my ambition shifted from being a world-class investor in pursuit of money and influence to a present and committed dad, coach and writer in pursuit of balance. In many ways, this new pursuit is bigger and more meaningful than my previous one.
As I see my ambition in a new light, I’m reminded of something my friend Jonathan Basker said to me as we were sitting in Madison Square Park on a picturesque evening last fall:
“For a long time I thought I wasn’t ambitious, until I realized my ambition is to live a good life.”
Amen! This was an entirely new perspective that literally stopped me in my tracks. In fact, immediately I took out my phone, asked Jonathan to repeat what he said, and wrote it down because it resonated so deeply. I had never in my life considered anything like it. So many of us, especially in tech, believe we need to set the world on fire, leave a dent in the universe and work at least sixty hours a week, and if we don’t then we’re lazy, bad or a waste of life. I’m no longer convinced it’s so black and white.
Just because I crave balance and want to embrace multiple roles doesn’t mean I can’t strive for long-term excellence in those areas. For two decades, my ambition was fueled by the businessman and investor in me, but now I’m realizing that I can be ambitious in all of the roles I play, like, the role of being a father. Is there a more audacious and noble pursuit? I honestly can’t think of one. High achievers might only associate success at work with being ambitious, however I believe you can also be ambitious about other things like health, goodness, service and fun.
But let me be clear: I absolutely want to be great at what I do and live a healthy, balanced and good life. They are not mutually exclusive.
And in this next chapter, I want to embrace both ambition and balance, which for me means patience, intentionality, focus, celebrating small victories, and taking the long road. I'm now beginning to redefine ambition and balance based on what I value rather than what I think society and others expect of me. This isn’t easy, but it’s possible—and essential!
As you can tell, I’ve been thinking deeply about this topic given the impact it will have on my path forward and my family, but I think these questions are important for all of us. I’d like to explore in my next essay how we might be able to expand our definition of ambition and align it with where we are in life and what we value.
So I’m turning to you! What’s your perspective on ambition?
How do you define ambition?
Where did your definition come from?
What’s your ambition in life?
What’s your current relationship with ambition?
How has your ambition changed over the years?
How do you balance ambition with the good life, if at all?
I wonder what comes up for you in this exploration. Any notable revelations, themes, insights or emotions? Hit reply and let me know what surfaces. I’d love to begin a dialogue, explore this topic together, and see what emerges in that space, and respond to what you share with me in my next piece.
I’ve always appreciated Oscar Wilde's definition of ambition:
“Our ambition should be to rule ourselves, the true kingdom for each one of us; and true progress is to know more, and be more, and to do more.”
What’s yours?
🌱 Seeds of Change
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Here are five things I’ve been pondering and exploring over the past few weeks. If any resonate, please feel free to forward along to friends.
🥁 Foo Fighters ft. Shane Hawkins Perform "My Hero"
This rendition of “My Hero” from the Taylor Hawkins Tribute Concert made the rounds last weekend amassing more than 7M views. It features the legendary and late drummer’s 15 year-old son, Shane, playing alongside his dad’s band with courage, gusto, and command. Death of a loved one is an inevitable change and challenge that we all experience at some point in life. Watching Shane take the stage and own the moment not only gave me chills and hope for the future, but helped me appreciate how music has the power to heal us. MTV (6 minutes)
🛑 When Will We Stop Beating Ourselves Up
We are often our own worst enemies, especially those of us who identify as high achievers. Nothing is ever good enough, including ourselves. Many of my clients have a powerful inner critic who never leaves their side and relentlessly attacks them day and night. I know I have one. Russ Hudson, the Founder of The Enneagram Institute, aptly said, “If anyone else spoke to you the way you speak to yourself, you’d punch that person in the face.” Here’s a simple and effective seven-step process for being with your inner critic and cultivating more self-compassion. Hari Prasada Das, Upbuild (10 minutes)
📈 In Defense of Radical Self-Betterment
This comprehensive essay by Dr. Gina Gorlin, a Clinical Associate Professor of Psychology at the University of Texas at Austin, is one of the best on self-transformation I’ve read in a while. As someone who has radically transformed their life, I know it’s possible for all of us but I also know it can be challenging and intimidating, especially when we don’t know where to start. If you want to embark on a journey of “raising the bar on your psychological ambitiousness,” here’s a step-by-step guide I recommend checking out. Every (20 minutes)
🏔️What Comes After Ambition
Last week, I received a text from my wife along with a link and the words, “you must read this.” I’m glad I did. As I think through my own relationship with ambition, this essay about women’s progress and ambition by Ann Friedman inspired me and has been sitting in the back of my mind. While I don’t identify as a woman and I haven’t experienced a fraction of what women endure at work, it helped me realize that I’m not alone in reconsidering my ambitions. “Women are in the midst of a revolutionary reckoning with our ambitions. We’re not resigning en masse—because who can afford to quit her job in this economy?!—but we are trying to figure out a new set of goals and guidance for our professional lives. Thanks to long-simmering inequality and stubborn sexism, clarified by the pain of the pandemic, our definitions of success increasingly lie outside the realm of work. We are waking up to the fact that our jobs are never going to love us back. And we are trying to adjust accordingly.” Elle (12 minutes)
💚 David Brooks: The Quest for a Moral Life
Earlier this year, I read The Second Mountain by NY Times Columnist David Brooks, and I walked away inspired to ditch the “first mountain life,” which is self-centered, for a “second mountain life” which is other-centered. In the book, Brooks explores the four commitments that define a life of joy, meaning and purpose: to a spouse and family, to a vocation, to a philosophy or faith, and to a community. To say it had a big impact on me would be an understatement. That’s why I was excited to stumble upon this enjoyable Super Soul Conversation between Brooks and Oprah. Here’s a solid primer, if you haven’t read the book and would like to learn more about living a “second mountain life.” Oprah’s Super Soul (1 hour, 12 minutes)