Why the Road to Meaningful Work is Rarely Straight
Curving roads are enchanting when witnessed from above and yet are rarely restful to traverse. They take longer. They require you to slow down. They keep you alert, compelling you to train your focus on where you are. Because they twist and turn, it’s hard to decipher what lies ahead. As I left the academy to begin my coaching practice, I felt drawn to the novelist E.L. Doctorow’s reflections that “Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way.” It gave me a hint that building a practice would follow a path akin to writing—meandering, unpredictable, and emergent.
The transition wasn’t easy—it was a shift from a career with an established trajectory to work that was congruent yet came with no map. Doctorow’s quote stayed with me as I made my way and accompanied my clients in finding theirs. Over the years, a clear insight emerged: when it comes to aligning your work with your values, forward movement does not take place in a straight line.
Sometimes, you need switchbacks. Seeking alignment brings us into contact with things that are congruent and misaligned, asking us to make choices. This sparks an interplay of desire and fear. We touch possibilities that open us up and meet challenges that make us halt. This back and forth movement can feel like stasis if we imagine the journey as a straight path. Yet, mountainous terrains require spirally roads.
We often circumambulate the same conundrums in the process of clarification. I have come to see that understanding the twists and turns, even anticipating them, equips us with the perspectives we need to navigate.
The Arc of Transformation
I spent the past month reflecting on the journeys I have witnessed with my clients. This became an exercise in cartography—of mapping the path of finding congruence, with some predictable turns that come up. In doing this, I also traced the shape of the process I use to support people—one that emerged from hundreds of hours of coaching clients through the bends in the road.
I have distilled this process in a video to provide a vantage point to help folks anticipate what arises along the way.
🎥 Watch it below to see the arc of the path
The process I described in this video provides a way to navigate the twists and turns in the road.
The key to beginning is to create a container for discovery: a place to imagine, explore, access your buried dreams and wild ideas, and give yourself permission to move towards what you want.
Alongside this, it is crucial to identify places where you feel alienated and to discover enlivening ways of working and being. This recognition on its own is not enough. Through years of working with clients, I have found that it takes time to integrate and embody these discoveries. You can do this through daily practice—of bringing what matters to you from the backdrop of your mind to the center of you days. To avoid becoming overwhelmed as you test new possibilities, I suggest you do this by taking incremental steps to explore new avenues for work.
One of the most transformative parts of the process lies in gently shifting the protective patterns we all develop to shield ourselves from disappointment and failure—whether it is overwork or avoidance, diminishing our needs, or compromising our boundaries. By identifying and changing these patterns, you can release the barriers that have held you back.
It is a process of transformation that takes place from the inside out. It is a journey of becoming you, so you can build a life that is values-aligned and genuinely yours.