A guy who calls himself “Sarge” and I, accompanied by 9 fellow cyclists and a support crew, spent about 17 hours riding 250 miles to the beach in 3 days, just last week. Sharing the common traits of strong endurance and moderate speed, Sarge and I opted to stick together on this charity ride: he, a 70-year-old retired Master Sergeant-U.S. Army (Vietnam War-2 tours, 200 paratrooper jumps) and inner-city teaching veteran (ROTC Instructor, high school cross-country coach) and me, a suburban mom of 2. Here’s what I learned.

Loyalty means commitment to team success and personal accountability.
Being part of a team, whether it is a technology group implementing a new system or a couple saving for a down payment on a house, means commitment to achieving well-defined and mutually agreed upon goals. Team members should work together to overcome unforeseen obstacles (programming code glitch) and individual setbacks (a spouse’s job loss). Though loyalty implies that you stand together no matter what, it doesn’t erase the need for personal accountability—making sure you have the right training and dedication so that you can be a contributor and not just enjoy the fruit of someone else’s labor.

We stuck together for the entire ride. There were times when one of us needed to slow down and recover, and others when one felt stronger but being a team meant we stayed together rather than breaking away or setting an undoable pace. Still, there is an understanding that if you decide to participate in such a ride that you are physically and mentally ready to handle the challenges, and have a shared awareness and commitment to safety that protects everyone.  

Persevere but know when you need to change directions.

When the stock market and your investments are down, a project is off track, or financial results are not in line with the business plan, you may need to just persevere through rocky times. Or, you may need to re-evaluate your plan, and make adjustments ranging from slight modifications to your portfolio or shutting down an entire business unit.

Our longest day was 115 miles, starting at 7 a.m., traveling through a mountainous area, and ending at after 6 p.m., meaning that we need to persevere despite fatigue. Knowing that Sarge has made this particular trip 7 times previously gave me confidence that he could make it an eighth time and that he was familiar with the route. Some road detours and changes, though, along with a cue sheet that was nearly impossible to follow, caused one potentially serious problem. When we ended up on a newly rerouted highway (four lanes, yikes!), I tried to ask him if we were going the right way; about that time, he said the route didn’t look familiar. Fortunately, the back-up van was nearby and carried us back to a less-traveled road and correct route.  
 

Know what is happening around you but don’t let your surroundings control you.

It’s always a good idea to have some idea of your circumstances and what other people are doing, even if you don’t have an immediate reaction. Monitoring tax legislation, competitive activity, and housing market fluctuations are all useful. You might not make a move at all but your awareness will help you make better decisions; and if your boss asks about why your division isn’t introducing a new product to counter-balance your competitor, you’re likely to have a response that shows you are aware of the market and can champion your viewpoint in an intelligent, informed way.

Most cyclists like to know whether an intersection is approaching, a car is following close behind, or a dog is waiting to chase. In some cases, I might go ahead and slow down (just in case I may need to stop at the intersection) or speed up (so that I can outrun the dog); in others, I will just keep doing what I normally do such as riding reasonably close to the shoulder of the road. But it is helpful to know what is happening around me so that I can make good decisions about what I should or shouldn’t do next.

Get the right equipment and make sure it’s in top condition.

Whether you are creating a website or constructing a skyscraper, the right equipment is essential. Work is easier and safer, and you can more quickly find the source of any problems if you know that you are using the right equipment as well as appropriate materials and tools. And, in the end, you’ll be more confident about your results.

I had my bike checked out before the trip and my tires were pumped to at least 100 lbs air pressure before heading out each day. There were times that I thought I might have a low-air tire but then realized it was me, and not my bike, that was dragging.

Make a list and follow it.

Whether you are creating an annual business plan, writing a grocery list, or making tomorrow’s at-work to-do list, it helps to plan ahead rather than throw things together or make decisions at the last minute. Setting priorities and planning your day when you have time to reflect is preferable to making decisions when you are dealing with crises or trying to move quickly from one task to another. 

I packed a couple of days ahead of time but forgot to include my moisture-wicking socks and my toothbrush. Sarge recommended a packing list and gave me an idea to deal with my packing-related Achilles Heel: create a separate toiletries bag for trips only rather than waiting to get completely ready and then grabbing my shampoo, toothpaste, etc.

Push your limits but don’t be foolish.

Significant accomplishments often require physical and mental stamina. Working long hours may be necessary for a certain length of time (few days to several years) but time for rest and recovery are essential. You might be surprised at what you can accomplish with a few hours of extra effort each week but too many hours at the office can diminish your productivity and wreck your personal life. (also learned from the book "Executive Stamina")

The ride length was challenging but doable. We stopped for rest breaks and meals every 15-30 miles. We drank plenty of water and took in electrolytes via bananas, Gatorade, gel, and Endurolytes (recommended by a fellow cyclist and physician).

Anticipate disaster.

No matter how well you prepare, you can’t control every circumstance and situation. Some risks can be controlled but not eliminated: you can hold cash and not just equities to protect yourself from market drops, you can buy a house with a mortgage payment that is 25% rather than 45% of your take-home pay so that all of your money won’t be tied up in your house, and you can keep working a day job while you start a new business to generate positive cash flow. Insurance (homeowners/renters, health, life) are also useful in case of unlikely but potentially devastating events.

I noticed that Sarge kept his ID (driver’s license) tucked in his helmet. Though he expected a safe ride, he was prepared for an accident. 

Pace yourself.

You can't reach long-term goals overnight. If you are moving ahead (that is, you’re on track for paying down debt, progressing in your career, getting your graduate degree, or building your investments), don’t let the fact that there are likely others ahead bother you. Keep the pace that you know you can handle for the long haul.

Though I enjoy going fast when I can, a reasonable pace is suitable for an endurance event. We averaged 14 mph over 250 miles.

Be confident, not arrogant.

I think the confidence vs. arrogance question has been a stumbling block for me as braggadocio is frowned upon in my family and to a certain extent, my (Southern USA) culture. But I’ve learned that it is okay to calmly list accomplishments relevant to topic of conversation so that a reasonable person can draw conclusions about your capabilities and strengths.

Right before we drove to our starting place, Sarge told my husband that we’d be back on Saturday. Since I had a mild anxiety about being on the road for such a long time, I found his confidence in our ability to safely and successfully complete the ride comforting.