Giving Our Children the Gifts of Freedom and Failure

Let’s start with this premise: parenting is hard.

There is no roadmap, except the one left behind by our own parents, which so many of us try desperately to avoid.

There is no test of one’s qualifications, and if there were, who would administer it and set the standards? Would we measure intelligence? Aptitude? Compassion? Experiences? One’s moral compass? The subjectivity of the matter in question makes such a qualification nearly impossible to equitably construct, so we are resigned to the simple fact that it doesn’t take much for someone to actually become a parent. Parenting effectively is a different matter entirely.

With our need for perpetual learning and self-improvement, there is no shortage on parenting advice and tools these days, and well-intended parents, eager to craft the perfect experience for their children, are depriving them of two of life’s essentials: freedom and failure.


From the time we are mobile, most of us spend our early years running away from our parents. Those first steps, spurred on by a sense of independence that eludes us in the safety of our parents’ arms, are marked by a sense of pride and curiosity—look what I can accomplish; I wonder what’s just around that corner. And while we certainly get a lot from the safety and security of our parent’s embrace and watchful eye, there is something else we achieve in being free from it: the ability to explore, create our own experiences, and satiate our natural curiosity.

Parents who script every experience for their child are depriving that child of this freedom.

As we work to ensure that their resumes will stand out in a sea of competitive college and job applicants, perhaps we have robbed them of this opportunity at defining the very thing that we are trying to manufacture for them: that something that will bring success, purpose, and joy to their lives.

I once had a friend share with me her response to her kids’ proclamation, “I’m bored,” which I thought was simple yet brilliant: “Only boring people get bored.”

Boredom is what spurs creativity, relaxation, and initiative. It allows us to daydream and get enveloped in our own completely useless thoughts so that we can recharge. It encourages us to create a comic strip or video game. To call up a friend to go for a bike ride or to explore the creek. To write a story that sets us on the path to crafting the next great American novel or, perhaps equally important, the next collection of stories in a set of notebooks that will go forever unread except by the collection’s author. 

Life, after all, is so much more than the sum total of our accomplishments and accolades, a message that is often lost in our uber-competitive world that might sometimes have us believe otherwise.

By the time our children head off to college, they should already have at their disposal lessons they’ve learned from freedom. Being home by themselves; traveling without mommy and daddy; the ability to select for themselves the interests and passions they’d like to pursue; choosing their own friends.

You see, in this freedom and independence they get to practice decision-making skills about courses to take, how to navigate a difficult situation, how to surround themselves with a positive peer group, and how to advocate for themselves…all while the stakes are relatively low. In the absence of such experiences, college will be a much more daunting place, as they set out to tackle these challenges alone and in a sea of newness that can feel all-consuming.


You cannot have freedom without failure. They are inextricably linked, not necessarily in every experience, but certainly in the essence of what they are.

Having freedom means that you will naturally take risks and taking risks means that you will fail. Failure is a part of life that can be awful. But failure is the birthplace of opportunities and junctures that will largely define one’s character.

In our attempt to protect every child’s self-esteem, we have created a participation-trophy culture, wherein every kid succeeds equally until they don’t. Last summer, while volunteering at my daughters’ swim meet, I discovered that the league provides ribbons for the top 16 finishers. That’s right- 16. I didn’t even know that ribbons came in such a myriad of colors to support 16 finishers.

Come high school and then eventually college, a much harsher reality is unleashed, and too many children are ill-prepared for disappointment so that when they get their first C or D or they don’t get into their top choice for school, they lack the coping skills and foresight to understand the larger picture, that this is but a blip in the stories that will ultimately unfold as their lives.

As children and adolescents, they need to learn through experience that sometimes the most valiant effort will be met with what seems to be a crushing blow of failure. Because in being rejected by a boyfriend or girlfriend, getting a failing grade, and being teased, they can understand the value of resiliency. 

They can come to know the possibility of rebounding from this failure, with the support and encouragement of mom and dad, but not their rescue. Entering college armed with these experiences and the lessons and tools that emerge from them will undoubtedly make them better prepared for the challenges they will face as young adults and beyond.

Letting go and watching our children fail is an easy topic for me to write about; it is a much more difficult practice to implement. But in the end, we have to recognize that only one of our goals is to support our children as they apply to college. Another is to make sure they are equipped to handle the stress and pressure of being away from home, of making good decisions, of failing and bouncing back.

After all, college is but a snippet of a life that is hopefully filled with success and accomplishments but also freedom and failure.



Savena Allen

Savena Wright

Director of Undergraduate Admissions at
Savena has her MS in Education from the University of Pennsylvania and served as a high school guidance counselor prior to her role at Admit Advantage and

Get more admissions help at

Author: Savena Wright

Savena has her MS in Education from the University of Pennsylvania and served as a high school guidance counselor prior to her role at Admit Advantage and Get more admissions help at

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