Racing Wisely: Choosing an Event

This excerpt from my latest book, Racing Wisely, prompts you to consider what you are going for when you commit to an event. Find a downloadable race planning questionnaire at

Before Francesca’s 40-miler

Your personal best race is one where you meet your goals while maintaining a positive outlook according to your intention. The fact that this happens in a race is important. Racing puts something on the line. It raises the stakes in a way that demands we bring our personal best effort to the table. Being timed; comparing ourselves to the field of competition, or even just to the time on the clock someone else has started and stopped; having the results posted online: all this makes it more real. Compared to heading out for a training day on a Saturday morning, toeing the line of the race is far more intense and requires strong focus. Racing commits you to paying attention, which is hard to do in our daily life, which is full of distractions. In a race, you don’t stop at a convenience store for a sports drink, or pause by the side of the road to check your text messages. In a race, you are totally in the moment.

In a race, there is a concrete goal: crossing the finish line. The parameters of having a start and a finish give us a standard against which we test ourselves. By this testing, we learn where our limits are, and often that they lie far, far beyond where we believed they did.

This testing also makes us vulnerable. We’re open to failure just as much as we’re open to success. But without such a step, we can’t experience the fullness of what it means to be human. We have to be open to losing control. When we mitigate our capacity for risk, we also mitigate our capacity for joy. Without taking chances—running only 20 miles before your first marathon, for example, or going fast over rocky, rooty singletrack trail—you’ll never have the opportunity to enjoy the stupendous feeling of surpassing your perceived limits. This is why we race: the many ways in which we can fail make achieving our goals feel that much sweeter. Without the chance of losing, of being embarrassed, of finding that our best is not, in fact, good enough, the myriad minor victories that happen in the course of any hard effort would be bland. As Truman Capote said, “Failure is the condiment that gives success its flavor.”

Your personal best race, then, is one where you have committed fully, despite the possibility of failure. Knowing what might go wrong, you’ve managed all the contingencies you can. This frees up energy for pushing when you need to, and for coping with the things you can’t control—for fighting against the possibility of failure. Choose a race that inspires you to throw your whole self into the challenge, a race where the reward is worth the risk.

After Francesca's 40-miler
After Francesca’s 40-miler

Visualize exactly how you want to feel as you cross the line. Imagine what it will take for you to cross feeling satisfied. From there, you can start to discern your specific intentions and goals, which we’ll discuss in chapter 3.

As you think though the variables, you’ll develop a better picture of what kind of race environment will suit you. It could be a large race with cheering spectators and a sense of history; it could be a small event in the woods with very little support. Ultimately, you need to decide on what matters most to you. When you make race choices based on your own desires, not on what others in the sport consider important, you are best positioned to develop skills that apply in all areas of your life and to learn about your own abilities and limits.

My best friend Francesca, approaching her fortieth birthday, wanted to run 40 miles for the first time. She chose to create her own event instead of signing up for a race. She chose a day, mapped a course, invited friends to join her, and did it on her own. Francesca may have learned more about her own strengths by staging her own event than by buying in to someone else’s vision. Because she was clear on what she wanted, all the rest was easy.

Find a downloadable race planning questionnaire at