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Transitioning to a New Life at 65 MPH: Lessons from a 5-Day Cross-Country Drive With My Daughter



There is a distinct mechanical rhythm to a 1993 Chevrolet half-ton on the open highway. It doesn’t glide over the pavement like modern vehicles; it communicates every mile back to the driver through the steering column and the frame.


When my daughter, Reeve, and I packed up her truck and pointed the hood south toward McPherson, Kansas, we weren’t just transporting her into another country and across state lines for her first year at McPherson College. We were embarking on a five-day journey across the heartland—a deliberate transition between one chapter of life closing and another opening.


In the evolution of the Water Your Lawn writings, I emphasize the necessity of maintaining the soil long before you expect a yield. Raising children follows the same natural laws. You build the structure, reinforce the boundaries, and cultivate resilience during the early years so that when the time comes for them to step into their own autonomy, the roots run deep enough to hold.


Modern life encourages us to rush through transitions. We buy a ticket, board a flight, and land in a new reality many hours later, without giving our minds the time they need to recalibrate.


Driving a 33-year-old machine across 1,000+ miles forced a different pace. It required constant awareness, active management, and respect for the journey itself. Watching my daughter take the wheel—navigating the long, vast stretches of highway, keeping an eye on the gauges, and making real-time decisions—was a powerful visual of generational transition.


The “transition experience” isn't handed off in a single formal moment; it’s passed mile by mile and turn by turn. Over these vast expanses, I observed closely as confidence replaced uncertainty.


Over the course of five days, we purposely took the long way. I charted the route meticulously over many weeks before leaving, deliberately choosing roads less travelled for maximum impact; this included many secondary highways, which, during the trip, caused us to rethink my decisions, which was exactly the point.


We stopped in Billings, Montana, and wound our way through Medora, North Dakota. We spent hours exploring the Theodore Roosevelt Presidential Library—a quiet reminder of rugged stewardship, endurance, and historical perspective. Then, as a final interest, we stopped at Mount Rushmore.


We stayed in hotels and motels. I can’t recall the last time I stayed in a motel, but I purposely booked one so we could experience that uniqueness together. The motel we stayed at in Medora (aptly named the Bad Lands Motel) was a flashback to the sixties, complete with an outdoor pool.


There were challenges along the way—each minor. But any important journey will always have challenges. That is the first rule of life. Our first challenge came as we crossed the border between Canada and the States at Coutts, Montana.


Without going into the details, this particular challenge was a reminder to bring all paperwork for the University your child will attend—failure to do so results in a very long delay and possible non-entry. Thankfully, my daughter, who was in charge of it, had “mostly” provided what was needed. I say "mostly" because it was a great lesson for her in understanding that even the slightest overlooked detail can create a challenge.


After an hour-or-so delay, we crossed the border and proceeded to our first overnight stop, Billings. Billings is a nice city of over 100,00 thousand residents tucked into a wooded, “semi-lush” area of Montana. Montana is a very beautiful state; however, travelling west to east, then south into the Dakotas as we did, we found that vast areas along the southeastern edge are quite uninhabitable. It is a remarkable contrast to the beauty of the western side.  


After heading out from Billings, our next adventure awaited. This stop for me, in particular, was much anticipated. I had read an article some months earlier that informed me that, after more than a century, the Theodore Roosevelt Library had finally been completed and had recently opened. Surprisingly, at least to me, the library is built in a very remote area of North Dakota. Why there? Read on.


I have a fascination with President Roosevelt and consider him to be one of the most important presidents in US history. So I was thrilled to learn that this library was open and that, with only a slight detour for father and daughter, we could actually stop in and experience it firsthand.


Let me state this about the library: IT IS FANTASTIC! Even Reeve was genuinely intrigued. The experience begins almost immediately upon entering the parking area via the curved, narrow roadway. The exterior of the building is visually stunning. The architecture seems to blend directly into the sparse, desert-like badlands surroundings. The curved roofline and natural materials used in building the complex are native to the area, creating an effortless visual flow from landscape to building.



I did not know this until visiting the library, but Roosevelt lived as a cowboy and ranch hand for two years in the unforgiving landscape. He came here to escape unimaginable tragedy in his family. Remarkably, on the very same day, February 14th 1884, his mother and wife died at the Roosevelt family home in New York. His wife died only two days after giving birth to their first child. As we would read in the pages of his diary, samples of which are kept in the library, he would write, “The light has  gone out of my life.”

Grief-stricken and filled with sorrow, he would eventually travel to these western badlands to immerse himself in the cowboy culture and to find a renewed purpose for life. The two years he spent in this place forged the iron will and tenacity that would define his presidency and the remainder of his life.



On the days we were here, the temperature reached 41 degrees Celsius. The wind was so hot it felt as though your skin was burning. This is the daily life he inhabited in 1884, from a life of privilege in New York to fighting for your life every day in these badlands.  

After spending many hours immersed in the library, we stayed overnight in the quaint town of Medora, thoroughly enjoying the hospitality of a town that, in the off-season, has only 300+ full-time residents. As the evening came to a close, we sat on Main Street with dozens of other visitors having an ice cream cone and chatting amongst ourselves like we were all old friends who arrived accidentally at the same place. Two Canadians enjoying the friendship of our closest country neighbours. No politics, no animosity, just humans respecting humans.


The visit to the Roosevelt library and the little town of Medora will stay with me always. The interactive nature of that library really draws the visitor into Roosevelt's life. We booked tickets well in advance, and I am glad we did. It was very busy. As you enter, you are issued a wrist tag that lets you build a digital diary of the stops you made in the library, which is later emailed to you. It is so cool. If you view the photos below, you will clearly understand how it works.


My favourite parts were the political section, learning about the bravery of TR, and sitting in the curved room to listen to the words of Roosevelt'ss famousspeechh," The Man In The Arena". This experience was further enhanced by the visuals they created. It was spectacular. Reeve and I were mesmerized, and I ended up video recording it three times, each with a different speaker's voice.


We thoroughly enjoyed Medora but knew we had many more miles to travel, so after a proper western-style breakfast, Reeve took the wheel, and the next leg of our journey began.


On this day, we headed to Mount Rushmore. Along the way, we researched who each of the presidents carved there is. For your knowledge, they are Washington, Jefferson, Roosevelt and Lincoln.


As we neared Mount Rushmore, and this is by complete coincidence, we watched thousands of motorcycles rumble into Sturgis, South Dakota, for their annual event.  I knew that the bikers took over this town for a specific time in the summer, but I had no idea it would be the week we were driving through. It is quite a sight and sound.


As we drove these final miles surrounded by motorbikes of all makes and models, we meandered into the Black Hills and stood beneath the carved granite of Mount Rushmore. Fun fact: the black hills are named for the black bark of the ponderosa pine trees that cover the mountains. These trees have a heavy black bark that slowly turns to a rustic colour as they age.


My daughter is an accomplished artist, so her interest was focused on who actually came up with the idea to carve the presidents and, more importantly to her, how they went about carving the faces. That story in itself is fascinating, so I encourage you to look it up.  


Along this amazing trip, right up until we arrived at McPherson and moved Reeve into her dorm, was everything a father could have hoped for. I had an opportunity to spend precious time with a child I dearly love and find fascinating. These are moments I will treasure forever, as I hope Reeve will, upon reflection. I write about moments a lot in my books. Moments form the chapters of our lives that become memories. These memories become our lived experiences, which ultimately inform our book of life. Make yours count.


Every stop along this journey, every conversation with Reeve, every new turn created powerful moments for us to lock into. The landscape visuals sparked curiosity, leading to conversations on a range of topics.


I tried deeply to listen intently and used each new conversation to learn more about my daughter's state of mind, her ambitions, her curiosity about the world, even her anxiety and excitement about starting this chapter of her life. These long, deep, and oftentimes humorous conversations were a reminder that understanding as much as possible about your child, no matter their age, is immensely important for understanding their state of mind and mental health.


These are also teaching moments. Impactful moments allow us to gauge how our children are doing subtly. Equally important is the understanding that all journeys, no matter how long, require intentional structure to maintain our mind health and physical resilience.


You don't abandon your habits just because you're outside your normal environment; you adapt the environment to match your standards. Most of us know this instinctively. We have lived long lives and have learned that the result is less about the destination and more about the journey.


Now, with the '93 Chev safely parked on the campus at McPherson, the real work begins for Reeve. But the foundation is built.


To every parent, leader, or founder navigating a major transition: cultivate the ground, trust the system you’ve built together, and when the time comes—let them drive.

 
 
 

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