Teaching My Children to Risk and Fail

Alexandra Kuykendall essentials


(Even When I Don’t Feel Like It)

“Be careful.”

“I’m not so sure about that.”

“Don’t fall.”

The words come out like a reflex, their meaning gone even as I say them. It’s the mama bear in me combined with my low risk tolerance pushing them out, giving cheap warnings that ultimately pass over my children’s heads without notice. It’s as if the words I’m speaking become the adult “Waa, Waa” of Charlie Brown’s grown-ups. They are the background noise of my daughters’ childhood.

Here’s the dilemma. I don’t want my children to see playing it safe is the prescription for life. But my fears as a mom often pop up as a deterrent to allowing, even encouraging, them to take risks. So if I don’t naturally let my girls try things that feel dicey, but I know that very risk taking is good for them, how do I encourage them to make the leap?

I practice a lot of self-talk.

I remind myself failure is opportunity. Opportunity for my kids to learn how to cope with their feelings. How to understand perseverance. How to find where their true talents lie. And really opportunity to learn some serious life skills that will serve them well as healthy, functioning adults.

I am prepared to walk through failure with them.

I’m not going to let my children crash and burn and flail alone. I’m there to show empathy, to comfort, to talk through both feelings and approach for getting up and trying again. I am their encourager. Their champion. Their number one cheerleader. And I am prepared to cheer them on through the hard stuff.

I remember their failure is not my failure.

When we get overly enmeshed with our children, we forget where we end and they begin. Allowing them to have their own failures and wins frees me from the pressure of needing them to succeed (however success is defined.) Each of my daughters is her own person, and we are in the beginning of a lifelong dance of them taking risks and failing and me giving them the freedom to do so.

I surround myself with parents who push me.

Nothing inspires me more than another parent who models where I want to be in my mothering. So spending time with parents who are less guarded than I am, instinctively pushes me in the right direction. Even my marriage offers another parenting perspective that is often (okay, really often) more risk tolerant than I am.

I take risks.

Nothing teaches healthy risk-taking and gracious failure than watching someone else walk through it. As our children’s number one model on how to do grown-up life, they are watching and learning from us in this area. So though I am risk averse, I push myself past my comfort zone and then talk about how I am feeling with my girls. They need to know the very nature of risk is the uncertainty, and I’m willing to sometimes jump in feet first.

Part of parenting (the most difficult part from what I hear) is letting go. The good thing is we don’t do it all at once. We take baby steps right along with our babies. And big girl steps with our bigger kids. Letting our children take some safe risks where they can fail, while we are there to coach them through the process is part of our responsibility, and when done well, even our joy.


Alexandra Kuykendall
As a mom to four girls, ages 3 to 12, Alexandra Kuykendall’s days are spent washing dishes, driving to and from different schools and trying to find a better solution to the laundry dilemma. She writes to capture the places where motherhood meets everyday life to remember the small, yet significant moments in the midst of the blur. She is the author of The Artist’s Daughter, A Memoir , a contributor to this year’s Be you, Bravely, An Experiment in Courage and acts as the Specialty Content Editor for MOPS International. A city girl at heart, she makes her home in the shadow of downtown Denver. You can read more of Alex’s everyday thoughts and connect with her at AlexandraKuykendall.com.