Paths, Puzzles, and Purpose

“Go down roads that don’t lead anywhere, immediately.” 

– Malcolm Gladwell

On a perfect fall day with blue skies, ambient temperatures, and vibrant fall foliage, my husband Reed, our golden doodle, Chessie, and I hiked the challenging 5.2-mile Boone Fork Trail. Today was different; it was overcast, in the 40s, with wind and drizzling rain. Undeterred, my daughter Joye and I began the trek, but this time, I decided we should tackle the orange-marked trail by doing it in reverse. The numerous majestic waterfalls were at the one-mile mark when approached from this direction. Shortly after that, we would scale the most rigorous elements of the hike – climbing boulders on rickety old ladders and rotted wooden steps. Facing the most challenging obstacles was best when we had the most energy. It was a good plan until it wasn’t.

We parked the SUV at the Julian Price Memorial Park. We donned hats and gloves, pulled up the hoods of our rain gear, bent into the wind, making our way to the trail. Given the dismal weather, the path was understandably barren with few other hikers. We embraced the peace and tranquility of being out in nature. In time, the blustery weather died down, although the sky remained overcast. We reached each magnificent waterfall scaling one boulder or ladder after another. In time the trail took us deep into the woods, where we traversed several rapids stepping on stones and climbing one by rope.

As we approached the four-mile mark, I knew we were getting close to the end. We entered a campsite. Weeks earlier, several small tents were erected. Today, the place was desolate; try as we might, we were still looking for the connecting path. Walking through the campsite and eventually circling its entirety, there was no sign directing us to the trail. I remembered passing a camp host home and bathroom building near a major road on my previous trip. A half-hour later, we discovered a barely discernible leaf-covered path which we followed and eventually spied orange markers on a tree.

Further in, we spotted the host cabin, and to encourage Joye, I said, “We must be on the right path now!” Shortly after that, the trail took us into dense woods. We walked for nearly a half mile, and I didn’t see anything familiar. I became convinced we were headed back to where we had begun. I feared we would repeat the entire 5-mile trek if we kept going. Sunset was fast approaching, and I knew we shouldn’t be out in the woods after dark. We were hungry and tired and now second-guessing each decision.

Joye recalled that our current path had divided at one point, so reluctantly, we reversed course. We found where the trail forked and took the other option, and after walking some distance, I knew nothing looked familiar. Footsore, exhausted and lost, I suggested we find our known landmark, the host cabin, and make our way by the nearby road, where we might see a sign for the park. Once on the highway, we had another decision: do we go right or left? With some deliberation, we took a left. As it turned out, that was a good move, as we were just about a mile from where we parked. When we finally spotted the park entrance, our weary hearts lifted. When we reached my SUV, I checked my apple watch; with all the reversals and repeated paths, we had hiked 7.6 miles, 2.4 miles more than our plan.

I relate this story to suggest that as we begin 2023, many of us will set new personal goals and create detailed plans to achieve those objectives. Goal setting is necessary to grow as a leader. However, even with the best-laid plans, most of us will get off track and derailed at some point. Just as Joye and I did on that trail, we had a goal and a plan yet got disoriented and lost. Numerous books and articles describe how to get back on course, reset and revise timetables, and keep moving forward. In this post, I want to address those times when we get off course or face a predicament by answering two questions:

  • Could frustrating diversions and problems be worth acknowledging and examining?
  • Could dilemmas hold more value than the glories we attribute to success?

Let’s consider three examples of the puzzling paths and see what we might garner from these actual events.

Stagnant Paths

I know a gifted aviator. After serving as a Navy Pilot, he joined a major airline and initially advanced quickly. At one point, his boss told him to expect a promotion, only to have the new role rescinded without explanation a few days later. Through no fault of his own, he plateaued as an Assistant Chief Pilot. Colleagues with far less leadership and technical ability advanced while he remained at the same level. Regardless of his title, he continued to do his work with excellence. Through his exceptional people skills, he tackled projects and programs where others had failed in the past. To this day, he consistently earns superior performance ratings and maintains a stellar reputation. As he approaches retirement, it remains a quandary as to why he stayed a supervisor.

Disappointing Paths

She lost her well-paying job to downsizing. It was difficult as she was a single mother of three and still completing her Masters. Initially, she joined a consulting firm with fellow downsized colleagues. Through her contacts, they approached several entities to secure long-term contracts. However, her partners abandoned her when they secured a project that arbitrarily excluded her participation. Needing income, she pursued consulting work with a previous client. The partners resented her for this action, although she reminded them that they agreed to a gig to which she could not contribute. Bruised and confused, she realized she was on the wrong path with the wrong people. Four months later, she secured employment with a company and left the consulting firm. The experience with the fiasco firm is a piece of her story that still baffles her.

Repeated Paths

A West Point graduate and Army Ranger had a successful military career before leaping into corporate America. His transition into a civilian role was chaotic, involving seven different employers and relocating his young family six times in 8 years. He left his first employer when they kept working him at night, he joined another company, and after extensive sales training, they decided not to place him in the role. Undeterred, he kept applying. His third job went well until the company downsized a year later. In the following position, the Ranger was let go after 18 months when the company shifted territories. Next, he became a manager in a paper plant. His boss, known as “Tiger,” became intimidated by this ever-confidant young man. His boss began to look for ways to undermine the West Pointer’s improvements with their production process. Eventually, Tiger gave him an ultimatum: sign a resignation letter and get a severance or, leave with nothing. He took the severance, and in time, the Veteran took a new role with a more secure future. It is a paradox that he spent eight years in a perpetual churn.

In each of these stories, the people were talented, driven individuals with goals and plans. For each of them, there appears to be no purpose behind the diversions and conundrums they faced. Each of us will continually face road bumps and paradoxical paths as part of the human experience. Perplexing scenarios can take many forms, from career challenges to painful relationships to protracted health issues. We will each face uncertainty and confusion. Can anything be gained from the puzzles of life?

Malcolm Gladwell’s Master Class

Not long ago, I was intrigued by a Master class featuring the brilliant and accomplished author Malcolm Gladwell. He explained that when structuring a narrative, he often employs open-ended puzzles. Questions that don’t have easy answers. The perfect argument is too apparent, Malcolm emphasized. In one sense, textbook reasoning insults the readers. Life is complex. The story isn’t as engaging when it fits together like a Hallmark movie. In going back to the history of the perpetual pilot supervisor. Would we remember his tale if all had gone as planned? Would his story intrigue or bore us if he had made it to the top of the airline? Or the young single mother and the consulting firm fiasco. Would her disappointing path be memorable if she hadn’t lost her job and experienced a failed partnership?

How about the exasperating story of the West Pointer who went through more jobs than most people do in 20 years? Would we remember his tale if his first job was successful, and he stayed 20 years and retired as a Vice President? The answers are obvious, no, we wouldn’t remember or be intrigued by these stories if everything always worked out. To make us better writers, Gladwell encourages his students to “Go down roads that don’t lead anywhere, immediately.” And the same can be said when traversing life.

Divergent Paths and Moving Through

If we expect to be derailed and have our plans disrupted, aren’t we better prepared to discover something new? As we begin working on our 2023 goals, we can normalize getting off track, becoming disoriented, and maybe even bruised.

A person living in a frustrating scenario may object and ask, “Is there a purpose behind this predicament?” We can find the answers to that question outside that episode. A perplexing situation is overwhelming. When Joye and I were lost in the woods, nothing seemed familiar. We were tired and confused. We could panic, make poor decisions, or give up. Or we could choose to keep moving. And with more life experience, we gain perspective and begin understanding even in the most confusing and disheartening situations. Returning to the three divergent paths, here is what they discovered from their dilemma:

Overlooked for promotions, the Pilot did get discouraged. However, he kept focusing on doing his current role well and treating people with respect regardless of their status. He built bridges between union pilots and management. As a result, Senior leaders seek him out for advice on critical issues. Without a high position, he is still a valued change agent. Could it be that he earned his reputation and influence by spending years working with and through people who outranked him? Is having an impact without authority a more valuable skill set in life than merely having authority?

The single mother learned to make better choices with business partners. A few years later, she joined forces with a company but continued to lead her firm. She took what she learned from responding to several RFPs with the fiasco firm to go after and win a large contract that lasted five years. Can learning occur even in confusion? Do lessons last longer when we experience disappointment rather than success?

The frequent job losses and cross-country moves humbled the West Pointer, forcing him to explore other ways to obtain a job. He hired a career coach who taught him to find a career based on his natural skills and passions rather than applying for jobs and hoping everything would work out. The Ranger learned how to network and find untapped sources for job leads and secured a better fit in his next role. Did the frequent disruption force him to ask questions and seek better answers? Did he then acquire skills that would prepare him better for his future?

“Not all who wander are lost.” – J.R.R. Tolkien.

This quote is from Tolkien’s masterpiece trilogy, The Lord of the Rings, and refers to the character Aragorn (a.k.a. Strider, The North Ranger), who grows up without knowing he is heir to a king. As an adult, he learns of his royal status and chooses to spend a long time in the Wild. Through years of wandering, Strider intends to gain the knowledge and experience he needs to be a good king. He is never lost but rather on a quest to become a great leader. In other words, The North Ranger had a purpose that he kept sight of even as he traversed many miles, fought intense battles, and tackled numerous leadership challenges. If you have read the famous trilogy, you know Aragorn became a great king and led a prosperous kingdom during his reign.(1)

As you begin 2023, see yourself on a quest. Be clear on your purpose. If you have never done so, write a personal mission statement. In a few words, declare what you are on earth to accomplish. As you set goals and develop plans, ensure they align with your raison d’être. And then begin your quest. If you find yourself on a detour or circling the same path twice, know you are in good company. Dig deeper, revisit your purpose, ask questions, ask for help, never quit – and keep moving! In time you will see that the lessons of a divergent path or the perplexing paradox are worth examining. What you learned when you felt lost and confused may be what is needed to make you a great leader.


(1) Hawk, L. J. (2020, July 7). Not all who wander are lost: What Tolkien really meant. Sparkous. Retrieved January 6, 2023, from

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