Strong Poems, Strong Women, Strong Inspiration
"The best way out is always through." — Robert Frost
Walking the Road Through: Lessons from Frost for My Daughters
Robert Frost’s words have resonated with me at different stages of my life. I first encountered Frost in my early 20s—a time when I was just beginning to navigate the world. Gifted to me by my godmother, the lines of The Road Not Taken became a beacon as I prepared for a new leap (and more new leaps to come) that would reshape my life and career over and over. Recently, as my eldest daughter chose Middlebury College—a place deeply connected to Frost’s legacy, I have reconnected with his poems and they have taken on renewed significance.
The poetic reconnection caused me to reflect on my journey from a college student, to a secure W2-salaried role to the unpredictable world of entrepreneurship. While Servant of Servants speaks to a different kind of struggle, its core lesson—‘The best way out is always through’—has come to symbolize resilience and perseverance in my own life. The original intent remains powerful, especially for my daughters. Frost’s wisdom reminded me that the way to a better life isn’t to sidestep challenges—it’s to walk right through them. And that realization guides not only my personal and professional growth but also the lessons I want to pass on to my daughters.
A more modern take, one closer to home for my daughters, is Daya’s Sit Still Look Pretty—a song that filled our kitchen as we played games and grew up together. Both powerful, I tend to think of Servant of Servants as more my mother-in-law's perspective of being trapped and duty to the life chosen for women. Daughters, know thy past. But I would suggest the evolution of thought promoted by Daya where she more rebels against the hopelessness of the speaker of Frost’s poem whose mindset has been conditioned to accept life for what it is.
The Women Who Inspire Me
I always wanted daughters. And I was blessed with two. Before the inspiration my daughters brought for me, the desire to continually want to become a better man and father, my life was enriched by strong, hardworking women who have shaped me. My wife, a constant force of dedication and resilience, has stood by me through every risk and every road less traveled. My mother, an educator, instilled in me a love for learning and the importance of relationships, both invaluable for pushing through the inevitable challenges. And my late mother-in-law, whose continual worry for the future of women, inspired me to promise to create a world full of opportunities for her granddaughters. Every day, I work to honor that promise—not just by setting an example, but by ensuring my daughters know they can achieve anything (but they have to work hard, dream big, take risks, and get back up when knocked down and say “I’m ok!”).
Rethinking Security: From Privilege to Ownership
Growing up, I had opportunities that I didn’t fully appreciate at the time—access to education, encouragement to pursue financial security, and the assumption that I could build a stable career. But with those opportunities also came expectations: work hard, get a job, and stay secure in someone else’s system. I followed that script until I realized that security isn’t always found in a steady paycheck (nor in any status quo). For me, it lies in ownership—creating something meaningful that aligns with my values and gives me the freedom to live authentically.
Embracing the Leap to Entrepreneurship
Choosing to leave a salaried job midcareer and start my own business forced me to confront my fears and embrace uncertainty. It made me reflect on the weight of expectations—those placed on me and those placed on others. While I had the privilege to take this risk, I recognize that not everyone has that opportunity. This awareness has shaped my approach to leadership and decision-making, reminding me that meaningful change often comes from stepping outside what feels safe and familiar—while never taking that privilege for granted.
The transition wasn’t easy. The corporate world offered a clear structure, stability, and a definition of success that was widely accepted. Walking away from that meant redefining my own version of success—one built on autonomy, purpose, and a willingness to navigate discomfort.
Building a Legacy for the Next Generation
Watching my daughters grow, I see the world opening up for them in ways that my late mother-in-law could barely dream of. My eldest now embarks on her own “road less traveled” at Middlebury and my youngest travels yet an even less trodden path (honey fight for your right, never feel trapped, and I am always here to grow with you). My journey isn’t just about stepping away from the corporate world—it’s about reimagining security, redefining success, and inspiring the next generation to embrace their own paths, wherever they may lead. In my line of work, legacy is often about money. But for me, I hope my legacy for my daughters is to go through the challenges and take the path that is right for them.
So, I ask you: What challenge have you been avoiding? What leap are you ready to take? Remember, the road through may be difficult, but it’s the only path that leads to something greater.
Let’s walk this road together.
