Lead with the best version of yourself.

When You Lose Your “Why”

by Mark D. Jacobsen

In earlier episodes of the From the Green Notebook podcast, hosts Joe Byerly and Jacob Gawronski concluded each interview by asking their guests a question made famous by Simon Sinek: “What’s your why?

It’s a great question because it reveals so much about an individual’s character, values, and motivations. If Sinek is correct, why is the most important question a leader can ask, because everything else builds on that foundation. A clear why motivates strong leaders, creates and sustains powerful visions, inspires teams, and compels followers. We often spin our wheels trying to answer what or how questions, but why takes us a level deeper, to the source from which all other questions flow.

I love the prominent use of this question in the podcast, and I love hearing the range of answers. However, the question can also be disconcerting.

Recently, after catching up on the podcast—on a solitary drive through rural Alabama after a glorious day reconnecting with nature—I switched off the stereo and contemplated how I would answer the question. After some consideration, I had to admit an uncomfortable truth: I don’t know my why. Not right now, anyway.

I suspect I’m not the only one, so I’d like to share a few thoughts on how I got here—and how we navigate these seasons when our why is no longer clear.

An Uncomfortable Admission

It’s embarrassing to admit that I don’t know my why. It feels like a transgression.

Our modern world expects us to present a carefully curated and polished brand to the world. We should distill the essence of our complex, messy humanity into a one-line pitch that will inspire peers, subordinates, and future employers when they scan our LinkedIn or Twitter pages.

Our brand should be upbeat, collaborative, inquisitive, and clever. If we have entrepreneurial ambitions, it should leave us open to a side hustle, ideally with multiple options for future revenue streams. If we are leaders, it should reflect our core values. More than anything, it should be authentic—or at least, appear authentic, because the truth is that we craft this brand over months or years, with constant tinkering in response to market feedback or anticipated social responses.

Asking why should take us deeper than that, but there is a danger that this question simply becomes another demand to package our lives into a tidy story.

Here’s the truth: no plan survives first contact with the enemy, not even a life plan. Life is complex, multifaceted, and ambiguous. We juggle myriad responsibilities even in the best of times, and life frequently throws curveballs. We often achieve goals in pursuit of our why, only to experience a sense of restless dissatisfaction. Sometimes we discover that our why no longer rings true; we have been living out somebody else’s script, conditioned by our upbringing and a lifetime of social expectations. In other cases the way forward seems blocked, and we have to reinvent ourselves. Most people weather several of these storms over the course of their lives.

In other words, we all find ourselves in wilderness seasons when our why becomes unclear or needs to change.

My Story

My life has evolved through a series of whys. As a cadet at the Air Force Academy, I dreamed of being an astronaut because I loved to fly and yearned to explore space. I earned an Astronautical Engineering degree, studied Russian, and became a pilot.

My collision with the Afghanistan and Iraq wars changed everything. My previous dreams rang hollow; my new why was to understand how our country failed so disastrously in order to help create better Middle East policy in the future. I earned an Olmsted scholarship, learned Arabic, and spent two years earning a Master’s Degree in Conflict Resolution in Jordan.

I thought I’d found my why, but after my return to the U.S. and reentry into a C-17 Squadron, I felt lost. I realized the Air Force would only ever view me as a C-17 pilot, and felt blocked in my efforts to continue pursuing my policy-focused why.

I drifted until I landed an opportunity to return to academia while still on Active Duty. I developed a deep passion for a research topic: using complexity theory to conceptualize the ambiguous multi-sided wars our country kept facing, which I believed could lead to more effective strategy. When I began an Air-Force sponsored PhD, I struggled to find support for my research agenda. I pivoted to better align with my department’s expectations, but along the way, my passion flamed out and I lost sight of my why once again.

I also spent years investing in defense innovation. I founded and led a moonshot effort to use swarms of small drones to break starvation sieges in Syria, which gave me the clearest why of my life. When that effort failed, it left me reeling. Later, I founded and led a UAS-focused software development team at the Defense Innovation Unit, which was uniquely poised to help DoD adapt to urgent sUAS threats. It was the most successful thing I ever led—and gave me a passionate why once again—but everything came apart due to DoD talent management challenges and then a damaging merger.

I now serve in a military professor role. I love my job and find great fulfillment in teaching and writing, but I am still piecing together my overarching why. I am in a season of exploration and waiting. I live each day as it comes.

My setbacks over the past few years were so brutal and unexpected that I felt compelled to write a book to help others grow through their hardship experiences, titled Eating Glass: The Inner Journey Through Failure and Renewal. A key theme in the book is the loss of purpose and the process of rediscovering it.

The book led to many conversations with readers who faced similar experiences. My story is hardly unique. We all grow and change. We all have seasons in which we burn with clear purpose, as well as seasons when we feel adrift and uncertain.

Thriving in the Wilderness

Losing touch with our why can feel devastating, but there is good news. These seasons in the wilderness are a normal part of the human experience. Everybody faces them, and they are seasons in which some of our deepest personal growth can occur.

When you feel this sense of dislocation, recognize that your deepest unconscious self is sending you a message: it is time to grow into a truer version of yourself. If you truly embrace that call, and do the inner work to navigate this season, you will emerge a more authentic, centered leader with greater reserves of resilience, empathy, and wisdom.

Here are a few lessons I have learned from my own seasons in the wilderness.

  • Recognize that the pursuit of why is a continual journey. Life is always in motion. You are a work in progress, continually growing through new aspirations, experiences, relationships, setbacks, and successes. Your purpose at any given time—your why—might ultimately be less important than your continual pursuit of purpose. It is this ongoing, thoughtful process of reflection that keeps you alert, fresh, and engaged with your life.
  • Focus on your values. Through all my ups and downs, my values have endured. Strong values are trustworthy lights to navigate by. When you feel adrift, you can never go wrong by living out timeless foundational values like respect, compassion, kindness, generosity, selflessness, justice, curiosity, and imagination. They will get you through the day, and a lifetime of such days amounts to a life well-lived.
  • Cherish your relationships. A satisfying life is ultimately about rich human connection. Our most noble whys ultimately serve this end. Somehow, even if indirectly, we want our lives to advance human flourishing. Even when we lose the thread on a unifying purpose, we can continue living for the people around us—our families, friends, peers, subordinates, or communities at large.
  • Embrace exploration and discovery. A key theme in innovation literature is that innovation moves through phases. In divergent phases, a team relaxes assumptions, abandons preconceived notions, and explores widely. In convergent phases, a team hones in on a path forward and relentlessly executes. Life moves the same way. We have convergent seasons when our lives seem aligned behind a single purpose and we focus on execution. But we also have divergent seasons when we lean back, take stock, and let ourselves explore new possibilities within ourselves and our world. Embrace the freedom and possibility that those seasons bring.
  • Learn the deep lessons. Wilderness seasons can be tough. Feeling disconnected from purpose can feel deeply disorienting and trigger anxiety and depression. However, this very experience of lostness can teach us deeper lessons, if we are willing to learn. The wilderness can teach humility and empathy, which ultimately makes us better leaders. It forces us to reckon with our priorities and ensure we are authentically living the lives we say we want. The wilderness can teach us to relax control, lean on others, and look deeper within ourselves for resources we never knew we had.
  • Trust the inner journey. When you lose the thread of why, it might feel like you’ll never regain it again. Trust that you will. Life carries you onward like a river, and sooner or later, it will float you out of this wilderness back into the sunlight. You will reconnect with why, and enter another convergent season. In the meantime, trust the journey. Enjoy the process as best you can, and keep showing up. You’ll get there.

Mark D. Jacobsen is an Air Force officer, professor, and writer. He writes about whole-hearted leadership at markdjacobsen.com. He is the author of Eating Glass: The Inner Journey Through Failure and Renewal.

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