
Two roads diverged in the woods, and I took the one less traveled.- Robert Frost
Architect Frank Lloyd Wright once told of an incident that may have seemed insignificant at the time, but had a profound influence on the rest of his life. The winter he was 9, he walked across a snow-covered field with his reserved, no-nonsense uncle. As the two of them reached the far end of the field, his uncle stopped him.
He pointed out his own tracks in the snow, straight and true as an arrow’s flight, and then young Frank’s tracks meandering all over the field. “Notice how your tracks wander from the fence to the cattle, to the woods, and back again,” his uncle said. “And see how my tracks aim directly to my goal. There is an important lesson in that.”
Years later, the world-famous architect liked to tell how this experience had significantly shaped his philosophy of life. “I determined right then not to miss most things in life, as my uncle had.”
Since I can remember, I’ve always had a knack for coloring outside the margins, and whenever possible, taking the backroads. As an avid photographer, my camera bag has been a constant companion along the crooked paths to see things most never do.
In leadership, your path to personal growth and success is rarely a straight arrow trajectory. It’s more like a squigly path of many twists and turns that leads you to where you go.
I can look back on my leadership journey, as I am sure you can too, and reflect on all of the different twists and turns it has taken over time.
But it is in the meandering and unexpected turns that you develop your sense of purpose. Meandering doesn’t reflect wasted time; it’s merely time invested in gaining a larger perspective on the journey. Crooked paths build character.
So what should your approach be to the crooked paths and meandering spirit? Allow this fellow journeyman to share a few thoughts with you.
Crooked paths give you greater insight
A natural tendency in leadership is to seek direct paths to desired destinations, thinking that this approach is the most efficient. And in some situations, that thinking holds.
But what if in your destination for your business or you personally, was filled with crooked paths, and that maybe these paths give you a greater appreciation for the destination because of the lessons you learned along the way? The insights you gain on crooked paths today will better equip you for future paths.
Crooked paths build resilience
One of the most crucial skill sets you will develop over time as a leader is resilience. It’s the one skill that will empower you to keep going when you feel like giving up. The crooked path is the secret sauce to building resilience.
Over the years, here’s what I’ve come to learn. My crooked paths at times were chosen and intentional. At other times, they were detours, and sometimes they were the result of me somehow losing my way. Regardless of how you come to find yourself on the crooked path, embrace it as your opportunity to learn, grow, explore, and not let it go to waste. On every crooked road is a lesson to learn.
So let me ask, what path are you on in your leadership journey? Don’t make the mistake of thinking that because you are on a crooked road and you feel like you are meandering, that you have somehow lost your way. It very well may be the right road, at the right time, to prepare you for the next season in your life. This is not wasted time; it’s preparation. Embrace the blessing on the crooked road.
©2025 Doug Dickerson








