Helping Children Take Appropriate Risks for Great Rewards

Almost anyone who has ever asked another person to spend the rest of their life with them can likely still feel that interminable pause between the question and the answer. The fact of the matter is that any significant “ask” often carries with it the fear of rejection.

The risk to connect beyond ourselves is one of the most challenging undertakings we ever make. No matter our age, we never completely absolve ourselves of that twinge of trepidation at the uncompromising reality of looking in the mirror to see if it really is that person we hold in high regard (Denzel Washington in my case) staring back at us or simply some lesser reflection of our truer self. Much of our self-image is inextricably tied to the affirmation we receive from others, so these moments are fraught with tension and uncertainty. Whether winning a big case, landing a coveted position, closing on a 30-million-dollar deal, or making a new friend, experiencing this anxiety and joy is part of what it means to be human.

And being human in a new and diverse environment, without its comforting familiarity and predictability, is harder still. My experience has been that this type of change always seems to fall on the continuum of difficulty, varying in position but continually present. The skill, therefore, is not in eliminating this difficulty but in effectively managing it. Our gift to ourselves and our children then is to develop the tools in them to engage these difficulties, feeling the fear and doing it anyway, to quote Dr. Susan Jeffers.

We try to coach and guide our young people from the beginning of their formal, social schooling to practice the language and behaviors that will help them make connections and friends. Yet, it is one thing to teach; it is quite another to witness the evidence of what they have actually learned. And for the children themselves, putting lessons into practice is a sometimes daunting unknown. How can they be sure that the risks are worth it and the promised rewards will really materialize? How can they be sure that they will be accepted and welcomed when they reach out to new people in new situations?

For some of us, the fear of the unknown can paralyze us. I’ve been victim to this thinking on occasion. What I’ve realized, however, is that the only guarantee is that not trying guarantees never achieving. As Teddy Roosevelt said, the credit belongs to the men and women who are actually in the arena. If exercising this kind of courage can be hard for adults to muster, how can we expect our children to do the same? As I used to tell my math students, the answer is not easy, but it is simple. We teach them the skills of appropriate risk-taking; we check for their understanding of the same; we give them guided opportunities to demonstrate their learning; we encourage them to apply these skills in real time in the real world; and then we engage them in conversation to reflect upon and refine their behaviors. And, as Paul Laurence Dunbar said, “That is life.”

The power of this lesson really hit home for me with an experience my younger son had in first grade. He had switched schools (this was his third school in three years, after graduating pre-school and leaving a small, separate kindergarten program) and found himself on the playground at morning recess on the first day of school. He knew none of his classmates and he was commuting to a school in a different city from where we lived. This son, mind you, is an observer, a patient and cautious participant who rarely, if ever, dives headfirst into anything unfamiliar.

But on this day my son saw two “veteran” boys on the playground playing soccer, which was not a game he really knew or played well. Yet something compelled this cautious child to take a risk and ask these two boys if he could play this new game with them, in this new space, in this new school, and they said “yes!”

I’m not sure how long it took for them to answer or if my son felt the same pit in his stomach that I felt 16 years ago in mine when I asked my girlfriend to marry me and be with me for the next 50 or 60 years. But in my father’s heart, I agonized every millisecond for him. What I know now is that my child, through no force of mine, fortuitously chose to ask two boys with big hearts, kind spirits, and skills of inclusion, if he could play ball with them. What I know now is that my child took an unusual risk on his own, in a new school. What I know now is that my spirit leapt for him beyond my conscious mind—because they said yes.

What I also know is that years later these two boys remain my son’s best friends, and my wife and I are eternally grateful that they all found each other. Destiny is frequently unpredictable, but blessings are often unforgettable. For the forces that came together that day, we are all eternally grateful. And we also recognize that kismet partnered with intentionality that fateful day to help shape my son’s experience. Our encouragement to him and those of his early teachers did not fall upon deaf ears. The lessons and values taught to his friends were not offered in vain. And the most fitting rewards often do come as a result of the most appropriate risks.

It was true for me 16 years ago, it was true for my son in first grade, and it can be true for each of us in our own right moments.

But if we never take the risk and exercise the courage to ask, then we can never experience the moment when “they” say yes!

Robert Greene

Robert Greene is a husband, father, and independent school parent. In his professional life, he often consults with corporations, schools, and other educational organizations on leadership, organizational development and strategy, cutlural competency, and more. He can be reached at