Stories from the Road: What Biking 4,100 Miles across the U.S. Taught Me about Life and Business

Agency Culture, Industry Experts, Leadership, Personal Lines, Small Commercial Lines

Dale Steinke recently embarked on a once-in-a-lifetime adventure, biking solo from Seattle to Boston in 56 days. As of this writing, he has raised more than $13,000 for cancer research.

Barren sunbaked hills and dry gullies stretched to the central Montana horizon. The forecast called for headwinds and a “dangerously hot” day.

“Rough narrow road next 40 miles” read the sign, summing up what lay ahead as sweat stung my eyes.

Stories from the Road: What Biking 4,100 Miles across the U.S. Taught Me about Life and Business

The conditions promised plenty of obstacles, but I was in the midst of bicycling solo from Seattle to Boston and I hoped I’d adequately planned for this challenging stretch.

In many ways, my adventure was a vacation – a time to set work aside and achieve something I’ve dreamed of doing most of my life. But the long days riding alone gave me plenty of time to think about life and business, and how we can personally and professionally achieve big, meaningful things.

As I’ve reflected on the eight-week journey, one particularly grueling day in central Montana epitomized the many lessons from the 4,100 miles. Here are some of my greatest takeaways:

Having a solid plan instilled confidence and greater certainty I could reach my goal

I didn’t just decide to hop on a bike one day and pedal in the general direction of the East Coast. It required a detailed plan that included conditioning my body for the long days of riding, sketching out a budget and collecting the right gear.

It also meant obsessively mapping my route and breaking it down into achievable increments that ensured I’d have access to food and somewhere to sleep at the end of each day. Because of that, I had a good picture of what to expect on the road ahead and how to overcome likely obstacles, such as the lack of fresh water and shade on this particularly oppressive day.

Stories from the Road: What Biking 4,100 Miles across the U.S. Taught Me about Life and Business 4

To stay upbeat, I mentally broke up the ride into smaller pieces rather than focusing solely on the overall 70 miles. At 7 miles, I did a water bottle toast for being 10 percent done. At 23.3 miles, I was a third of the way and enjoying an energy bar. And at the halfway point, I took time to stretch.

In riding, as in work, I find I do much better tackling big objectives when I create an overall vision for where I want to end up, then break that down into a multi-step plan with bite-sized increments.

Having a plan is great, but you have to be flexible when the situation changes

I’ve been thinking about doing this trip for years, but it was nothing more than wishful thinking until I started developing a plan in 2017, then determined when I’d put it into action: In 2020.

So much for that.

When the pandemic upended the world, I couldn’t just bull my way forward – I had to put everything on hold. Instead, I focused on keeping myself and my family healthy while waiting for another opportunity.

Stories from the Road: What Biking 4,100 Miles across the U.S. Taught Me about Life and Business 3

Answering some emails from one of my campsites

With some adjustments to my plan, I knew I could use it in 2021 once I was able to get vaccinated and ensure that places to buy food and sleep would be open. On the road, I had to make further tweaks, adjusting routes to deal with detours and dangerous weather.

To beat the heat and the wind that would build up to 30 mph later this day, it meant quickly eating something convenient and leaving well before the sun rose above the Montana horizon.

It brought home for me that having a plan doesn’t mean you have to obsessively follow it when you get new information, or the rules change. The ability to quickly adapt and change course is just as important as the original plan you put in place.

Be willing to ask for – and accept – the kindness of strangers and friends alike

I took this journey not only to challenge myself, but to rebuild my optimism for our great country by experiencing it up close, and to champion a cause supporting research to find cancer cures. To be successful at that, I had to step out of my comfort zone, overcoming my introverted nature and reluctance to ask others for support.

Every day I took a deep breath, put a smile on my face and introduced myself to people who were just as much strangers to me as I was to them.

And just like that we were strangers no more, but people partaking in a shared adventure.

One thing that struck me was that almost everyone asked if I was supporting a cause. This is where I’d get uncomfortable because I felt like they would think I was asking them for money when I said yes.

Instead, I’d tell them about my friend and riding partner who had hoped to share some miles with me, but lost his battle with cancer just weeks before I began my ride.

Many surprised me by making donations. Many offered other greatly appreciated support.

Stories from the Road: What Biking 4,100 Miles across the U.S. Taught Me about Life and Business 2

Dipping my rear wheel in the Pacific at the start of the journey.

During my time in Montana, Tom from Lewistown reminded me to fill up my water bottles – then topped them off for me at his house when we discovered the spigot in the nearby park wasn’t working. He saved me from a very thirsty 50-mile stretch across a mountain range and arid ranchland.

Neighboring campers – including ranchers and farmers – invited me to join their farm-to-table dinners, filling not only my body, but my soul with cherished memories and a deeper understanding of where our food comes from. A motel manager in Pepin, Wisconsin, even gave me $11 from his pocket to donate to my cause.

People felt my trip was making a difference and that by supporting me in whatever way they did, they were helping further the cause too.

Getting past that reluctance to open up to others did make me feel more optimistic and made my journey easier. Being open to accepting help from others with our plans and the adjustments we need to make when our world keeps changing makes us all stronger.

As I look forward, these lessons will stay with me for a lifetime – in work and life. What is the greatest adventure you’ve been on and what lessons did you learn?

Stories from the Road: What Biking 4,100 Miles across the U.S. Taught Me about Life and Business 5

With my wife, Doree, and son, Alex, at the finish line at the Atlantic in Boston

Dale Steinke

Director, Independent Agency Digital Marketing

Dale Steinke leads a team of experienced marketers who help personal and commercial independent insurance agencies grow their overall business through more effective marketing. With 20 years of experience in online and digital technology roles, his primary focus is to deliver digital marketing tools, tactics and services through the industry-leading Bricks & Clicks program.

Outside of work, you’ll probably find Dale on a bicycle or in the kitchen cooking for his family and friends in Seattle.

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