I met Lenn at Meta (then Facebook) when I joined the mobile partnership team in 2013. For me, it was a golden opportunity to join Facebook after working at Apple and Microsoft.
Facebook was growing fast yet their main growth came from desktop users (I mind you, it was 2013). The growth rate of mobile users was exploding and they desperately needed to grow users on iOS, Android, and other mobile platforms. Like everything is about AI now, it was mobile then.
A cool job at a fast growing company, traveling around the world working on the growth of mobile users of FB with smart and passionate coworkers—everything looked perfect for my career and life. Yet I started noticing growing uneasiness inside me. I couldn’t name what it was though.
About four years passed. My career was going well but that internal uneasiness kept growing like a cancer. Empty, incongruent, feeling lost, meaningless - these were adjectives I’d use to describe how I felt but I could never talk about it.
“Come on, it’s a cool job at a respected company! Look at your resume - Apple, Microsoft, and now Meta! You dreamed of this! Don’t blow it. Just be grateful for it and keep going. You are on track!” This voice held me back, until the moment of truth came, urging me to do something about the deep incongruence I felt about my career and my life.
Career of Alignment over Achievement
Now I know clearly what that empty hollow was about. It was misalignment, quoting Lenn‘s words from his first book, Breaking Asphalt. Reading his book, I felt a sense of camaraderie that I wasn’t alone in suffering from misalignment. We didn’t talk about it then, but he also suffered from it. And he didn’t stop there. He realized he was trapped in the grand illusion of safety. He writes,
“Comfort feels pleasant momentarily but often disguises itself as safety, creating a false sense of security that discourages exploration.”
This discernment of comfort and security propelled him to get off the “clear path to lesser goals” and instead chose to step into the journey of uncertainty, searching for alignment in his work. In this process, he discovered a simple truth: alignment matters more than achievement for us to claim that we lived a good life.
This journey isn’t easy or straightforward. It’s a big Placeholder phase in your career and life; there are no maps or guideposts. It seems super chaotic and at times scary, making us hesitate to enter it. The paths you end up walking through this phase might be much steeper and harder than the one you walked so far, like seedlings peeking out through hard asphalt. Yet it will reward you with the sense of alignment between yourself and your work, which will add momentum beyond just movement to your life.
This book is not a memoir but an impressive culmination of his own growth and transformation through alignment. He shares not only his own stories but also other examples of lives well-lived with alignment. Through his original SEPARATE framework, he also walks you through how to make this possible for yourself.
Reading this book, you will feel as if you are taking a long walk with Lenn in dialogue of stories and reflections to contemplate the alignment in life. Finishing the book, you will feel empowered to work on defining your own alignment.
“What holds you back from your greatest potential isn’t insurmountable challenges but the comfortable allure of clearer paths toward lesser goals. True success doesn’t lie in external validation; it lies in living in alignment with your unique gifts, deepest values, and authentic passions. When you break through the asphalt of external validations and societal norms, you create a life of overflowing with meaning, joy, and creativity.” - <Breaking Asphalt>, Lenn Pryor
Two Authors, Two Journeys, and One Question
When I reconnected with Lenn many years later, we found each other in a similar situation. We both left our decades-long careers in tech and went on different journeys to reclaim the authorship of our stories of career and life. Although our journeys looked different, it was about the same question: How do we rethink work so it actually works for us?
This synchronicity, which is so marvelous in itself, also led us to write each of our books: The Placeholder and Breaking Asphalt. While The Placeholder goes deeper in the beginning phase of finding alignment, Breaking Asphalt guides you how to walk on the steeper path beyond the beginning toward alignment.
Do you feel anxious and threatened with your career because of the surge of AI? Do you ever feel that you are at an important junction in your career? Have you been feeling that you are “missing” something, although your career looks good on paper? Are you rethinking what success means to you and ready to explore deeper questions about work and life?
If so, Lenn and I are here for you. Let’s walk together from The Placeholder to Breaking Asphalt.