The annual Register Great Bike Ride Across Iowa (RAGBRAI) was held last week, and it reminded me of the lessons that I learned by completing it six years ago.  We rode 407 miles in seven days, and while it was not easy, I can honestly say that I did not labor during the long days in the saddle. That wasn’t necessarily due to my physical skills, but more due to the preparation recommended by others. Those same lessons can be applied to the business world, and daily life in general.

Try Something that you are Not Sure that You Can Do

I had never ridden a bike more than 10 miles when our daughter said she was going to do RAGBRAI for a second time. In a weak moment, I said “I’m in.” She recommended a bike to purchase, along with an indoor trainer and I started riding in my basement in January. I also posted on social media that I was going to attempt the ride as a means of self-motivation. Once you say that you are going to do something, the challenge is to keep your word! Have you avoided trying something in your career or at work because you weren’t sure that you could do it? Or maybe because “it hadn’t been done before.” Get out of your comfort zone, try something with no guarantee of success, and see if you and your team rise to the occasion.

Overcoming Challenges

The weather did not cooperate that spring, and I wasn’t able to start riding outside until late April. Riding on a trainer is much different than riding outside, and I found that not waiting until the street cleaners had cleared off all the sand and gravel from winter was a problem. I fell numerous times because I wasn’t aware that sand on the road is not much different than ice. I learned to become more observant, and stayed on trails because they were safer. Three weeks before heading to Iowa, I found out the hard way that my padded riding shorts were not up to the task. (Use your imagination here!) I spent the next 10 days walking instead of riding to keep up my stamina, purchased better shorts, installed a new seat, and did a bike fitting. That’s a lot of changes very close to the event, but all turned out to be beneficial. We face challenges in our lives every day. Some big and some small, but all with consequences. How will you approach your next challenge?


A friend who had completed six RAGBRAI rides told me that if I trained at least twice the amount of mileage as the week in Iowa required, that I would be fine. That was the best advice that I received about preparation, and that is the biggest reason that I did not labor during the week on the road. Completing 900 miles in training, helped me to be able to complete the 407 course miles in seven days of back-to-back rides. I also had a riding buddy who helped me learn how to ride in a group, when we completed a July Fourth ride with hundreds of other bikers. In another blog, I wrote about military and government entities spending time to “practice scenarios” so as not to be caught off guard when something serious happens like the lights going out in New York City recently or a hurricane hitting New Orleans. Businesses do not have a track record of following suit. Have you completed a situational analysis of you biggest risk with your team at work? Why not?


In order to complete the 900 training miles, I needed a plan, which fortunately was provided by the ride organizers. If you complete so many miles per week and keep increasing the number of miles ridden each time, you’ll be ready. Because I started late due to the weather, that made it more challenging. I found that finishing several 25 miles rides helped me with stamina. Completing 40-50 mile rides helped me with endurance. It required getting on the road at 5:30 a.m. on workdays and spending at least one weekend day on longer rides. All that effort paid off in the end. Being physically and mentally fit are things that we all aspire to attain. Be disciplined enough to not only make a commitment, but then keep yourself accountable to meeting or exceeding that commitment. Better yet, have an accountability partner help keep you on track.

Find Your Lane

Riding with hundreds of people isn’t the same as riding with tens of thousands. The sight of thousands of bikers in front and behind you “as far as the eye can see” is not something that pictures can do justice. It is equally daunting to safely navigate through or around. You need to find your rhythm and ensure that you don’t make a lane change without looking and anticipating what other riders might do. I wasn’t the most experienced rider, but I found out that I wasn’t the least experienced either. Never presume what an inexperienced rider might do right in front of you, and without warning. There is a difference between trying something that you have never done before and trying something that is out of your sweet spot. If you are good at leading startup companies, you are likely not comfortable doing the same for a billion-dollar firm. Nether is right or wrong, but if you are self-aware, understand where your strengths lie, and know what gives you the most joy, you’ll find your lane.

We completed the seven-day ride without incident, although I did see a few nasty spills and avoided at least one myself. Finishing RAGBRAI was something that I was not sure that I could accomplish, and I am glad to say that is was a fun experience. I gained four pounds during the week which I attribute to eating too many pieces of pie that church groups sold every day! The number one question people ask is “will you do it again?” My answer is NO and not because I didn’t have a great experience. It is because after two days of hot, humid weather, and an overnight thunderstorm, we enjoyed five days of 75-degrees, and low humidity. The year before, it was over 100 degrees most days, and the year after it was cold, rainy and windy. Not that I’m not up for a challenge, but having experienced RAGBRAI under close to optimal conditions, I guess I’m just spoiled!! Send me an email if you’d like to hear more about applying these lessons through executive coaching. I’d love to chat!

You Worked Hard To Reach The Top

You Worked Hard To Reach The Top

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