Next season, next mountain
In 2014, I hiked to Mount Everest Base Camp, and in 2023, I climbed Mount Kilimanjaro. These experiences gave me new clarity to reflect on my life and future. Standing at the summit of Kilimanjaro, I had an epiphany: the mountains we climb aren’t just physical; they symbolize the challenges we undertake and the growth each journey creates.
This metaphor has since become a guiding principle: there’s always a mountain behind the one in front of you. Reaching a summit isn’t the end—it’s a chance to look around, breathe deeply, and choose the next ascent.
My timing, not theirs
After 32 years at ExxonMobil, I chose to step away from my corporate career well before I had to. With nearly a decade left before mandatory retirement, many people assumed I’d stay on the familiar path. But deep down, I knew I was ready for something different. My career had been extraordinary—global roles, incredible people, and transformative projects—but it had also become familiar. I realized I could either keep repeating a pattern or reinvest everything I’d learned toward a new legacy.
The foothills of a new adventure
Leaving was both liberating and unsettling. For the first time since my 20s, my alarm clock wasn’t going off at 5 a.m. each morning. I no longer had a steady paycheck arriving in my bank account. But I pushed through and gave myself six months to reset, something I now realize was essential. Those months were the best of my life: quiet mornings with my wife, time with my kids, and unhurried conversations with friends. But it was also a surprisingly hard pause. After decades of constant motion, I had to relearn how to simply be, and to trust that a new purpose would emerge.
Finding purpose at All Sober
While still at ExxonMobil, I’d been donating my time to help a small start-up called All Sober, which utilizes technology, data integration, and AI to transform addiction recovery. Addiction has touched my own extended family, which cemented my belief that the world needs a better, more connected approach to lifelong recovery.
Near the end of my six-month pause, All Sober asked me to step in as CEO, and it felt like the right opportunity at the right time. I now lead a team building tools that connect every part of the recovery journey, so no one has to navigate the hardest chapter of their life alone. The work is challenging and intense, but it’s deeply fulfilling. I’m busier now than I ever was at ExxonMobil, but it’s good busy. It’s energizing, purposeful, and filled with possibilities.
Lessons in vulnerability and legacy
My journey has been shaped not only by action, but by reflection. While taking a leadership course at the University of Michigan, a professor encouraged me to share my personal story with his class, which he later turned into a business school case study titled “What Is a Life Worth Living?” It forced me to step outside my comfort zone, reveal my deepest thoughts, and explore what really matters: purpose, family, and connection.
As part of my story, I shared one of the most powerful lessons I’ve learned, which came from watching my father’s final days. As my family gathered to say our goodbyes in the ICU, I shared with his medical team the wonderful things he had done in his life. The doctor told me he already knew my father was a special person because, after seeing a lot of people pass away, “the jerks die alone.” That rather blunt statement reminded me that leadership isn’t about titles or achievements—it’s about the relationships we nurture and the lives we touch. At the end of the climb, what matters most is who is standing beside you.
The mountain ahead
My ExxonMobil career was one amazing mountain to climb. When I finished, that was not the end, just the beginning of the next climb. Today, I’m climbing a new mountain with All Sober, and I have the opportunity to help millions of good people in their recovery journey. Next year, I’ll attempt Mount Aconcagua, the tallest mountain in the western hemisphere—a personal challenge that mirrors what’s still ahead of me in life.
When the next summit comes, I’ll turn and face it with gratitude and anticipation. For me, retirement isn’t about slowing down. It’s about choosing your mountains—challenges that stretch you, inspire you, and allow you to leave the world better than you found it.
Click to watch Habib’s “A Life Worth Living” Interview: Part 1 | Part 2.