Lupberger: Ownership and the Art of Recharging

by Patrick OToole

I just returned from an eight-day motorcycle trip in Alaska. We rode into the state’s gigantic interior on dual-sport motorcycles that are good for both on-road and off-road riding. I had done some off-road motorcycling when I was younger, but it had been several years since I had done any extensive riding. My brother-in-law had done a similar trip to Alaska, and he had nothing but good things to say. With his endorsement, I made my tour reservation and left for Alaska on Aug. 20. It was quite an adventure.

I had never been to Alaska and one thing I can emphasize is that Alaska is big. You can fit California, Texas, and Montana into the land mass of Alaska. Due to its size and untapped interior, it’s still a rugged frontier. The ride was called the Northern Lights Tour, and the promise was to ride into the interior and experience the vast grandeur of the place.

The Challenge

There aren’t many paved roads where we were going. It was about a 50-50 split between riding on paved highway and unpaved dirt roads. We started in Anchorage heading north. What I hadn’t anticipated was the variation in weather. Over the course of the ride, we encountered rain, fog, strong crosswinds, and even snow. That is where my inexperience started to expose itself. Because it was a scheduled eight-day ride, you don’t stop due to weather. You gear-up and ride through it.

I was part of a group of 10 riders. All had more experience than me. I learned first-hand how quickly a dirt road becomes a muddy and slick surface during a rainstorm. Experienced riders know this. My learning curve was accelerated. There was no going back. This was just one of several white-knuckle rides over the course of the trip. Job No. 1 was to keep the motorcycle upright in all weather conditions and keep going. I dumped the bike twice.

The author, right, with his son Ryan, a company owner in New York, who also took part in the Alaskan motorcycle tour.

The other riders could see my inexperience and it was humbling. With that said, I also got to see the support that came from the group I was riding with. In both cases when I dropped the motorcycle, within 10 seconds other riders where there to help me get the bike back up again. There were no judgements. They had all been there. They just wanted to make sure that I was okay.

During stretches with paved highways, the experienced riders also knew how to safely maneuver on wet concrete. They had no issue with speeds up to 75 or 80 miles an hour on wet roads. That opportunity to learn combined with the opportunity to take in some beautiful and dramatic scenery is why we were all there. I asked one of the more experience riders what was the secret to riding faster. Without hesitation, he said there was no secret. It was experience and ‘time in the saddle’. He said if I didn’t feel comfortable at some speed that I should just slow down. He told me not to rush, but rather to ride within my ability. Everyone would wait for me and enjoy the scenery and camaraderie while doing so.

The Return

I’m back home now and still vibrating from the trip. It was challenging but there was a sense of excitement and anticipation each day of the ride. After reading my experience above, you may be wondering why I chose to go on this trip. Simply, it was a breakthrough moment and experience for me.

As I am over 60, I am watching as some of my peers who have achieved financial security are becoming somewhat risk adverse. They are choosing comfort and security and I understand that. These are the same people who have labored most of their adult lives raising a family and building successful businesses. For me, a simple summary is that I don’t want to enter the next chapter of my life without the same driving purpose that has allowed me to build a successful remodeling and consulting business. I don’t plan to go quietly. I want to maintain that passion that has got me where I am. I want to fuel that passion.


After coming home, I am now thinking about another ride and where I want to go next. I’m going to dinner with my brother-in-law, a very experienced rider and we are looking at a ride next year in Europe. I want to include my wife and son in the next trip so this can be a family affair. My son also rides a motorcycle so he would be joining us in our next adventure. Before I do another ride like this, I do plan to complete a riding course so that I can approach the next trip with more experience. That is on my immediate agenda.

I have previously written some past blog postings regarding transition and exit-planning for contractors. I am in a similar place in my own life. With my consulting business, I got into transition planning because very few contractors proactively design their business transition and exit. Many will just close their doors leaving years of goodwill, loyal employees, and trade-contractor and supplier relationships to just disappear. It doesn’t need to happen like this, but a good transition plan can take years to plan and implement.

In line with this, any business transition can be a challenge. According to 3C Strategic Advisors in Scottsdale, Ariz., there are three reasons that owners regret selling their company:

  1. loss of identity,
  2. a change in lifestyle,
  3. and no clear vision for what is next.

When you have raised a company from infancy and you have nurtured that growth for 15, 20, and 25 years, what comes next? You can’t work forever. The real job of a successful business owner is to remove themselves from day-to-day operations so that the company can run without them. This takes time, but when done successfully, you can build a transferable asset creating a financial payoff for you and a solid business opportunity for the new owner who may be a past employee. And you don’t have to sell the business. You can also take on the role of a strategic advisor working 10 to 15 hours a week as the company continues to reward your experience and guidance.

Let me come full circle back to Alaska. Much to my surprise, I found a renewed passion for growth and experience on a motorcycle trip to Alaska. That passion is not construction, but in an experience that will continue to challenge me. I will continue to do my consulting work but a challenging motorcycle ride once or twice a year will keep me sharp and keep things interesting.

This was a breakthrough experience for me—a recharge. Even in this busy marketplace, I would encourage you to do the same. What have you put off due to work? What activity excites you when you think about doing it? If I can assist you with this personal evaluation, contact me at Life is short. If not now, when? QR

David Lupberger, CR, is a blogger for He is a business consultant and former remodeler whose writing focuses on ownership and management issues. Lupberger posts new columns every other Monday.

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