The Stunning Paradox of Failure

The Stunning Paradox of Failure

Categorized under: technology education for kids

“Success is a lousy teacher. It seduces smart people into thinking they can’t fail.” - Bill Gates

Although most of us would agree with this quote by Bill Gates. In many ways, we try to spare our kids from failure because we know how it feels. Failure can be painful. Failure can be demotivating. Failure can be difficult. So, we erroneously think that if we can orchestrate their friends, classes and extracurricular activities that we can have them move from success to success without any of these challenging feelings.

The College Admissions Scandal

Unfortunately, this approach does not prepare kids for the harsh realities that await them once they move beyond environments that we as parents can influence or control. The college admissions scandal that has ensnared many rich and famous people is a perfect case study on this. Despite being able to provide everything for their kids that money can buy, the parents who have been accused of paying admissions counselors and universities for their kids to attend top colleges and universities are admitting that they didn’t believe that their kids would be able to make it into these schools on their own. And, either the parent or the child psychology would be damaged in the process. To counterbalance this potential failure, these parents decided it would be better to cheat the system.

As some parents have accepted responsibility for their actions, their statements to the judges has been surprisingly similar. In nearly all cases, they have talked about the harm to the parent and child relationship that has been done by not allowing their kids to have an opportunity to fail during the college admissions process. Along with this statement, the parents acknowledge a fundamental and concerning truth about their kids - mom and dad don’t believe in my capability to be successful on my own.

For parents, this is unsettling. While the majority of parents will never go to the extremes that the parents in the college admissions scandal went to; the reality is we do try to create the right boundary conditions for our kids every step of the way. However, often our boundary conditions are designed to enable our kids to be successful. Instead, we need to create more opportunities for our children to fail. By enabling our kid to fail early and fail often, we can better contextualize to them that failure is a necessary and useful part of life.

We can demonstrate by our responses to them not achieving a meaningful goal that we still love them and care for them. We can show them that when they fall short, the only time they don’t grow is when they don’t learn and improve. We can prove that we when have failures in our lives that it’s OK to talk about it. By avoiding failure or pretending like failure doesn’t happen, we create a warped sense of reality within our kids where they became less resilient to handle something that is relatively commonplace in life.

The Unique Role of Technology

Within technology, we believe that there is a unique ecosystem that lets kids feel what it is like to safely fail. The nature of computers is that they can only do exactly what we tell them to do. And, because there is often a disconnect between what we what a computer program to do and what it actually does, those who are learning how to build with technology can get first hand experience with failure in safe environment.

By starting with small projects or features within projects, students begin to get a sense of what it feels like when something doesn’t work. As they gain experience with debugging and troubleshooting more complex problems, they begin to see how difficult it can be to find an issue within their lines of code.

Even as we are teaching our students how to build with technology, we try to increase their ability to wait before they ask questions. In essence, we want them to talk through what they are trying to get the computer to do. And, to see if they can figure it out on their own without instructor guidance. In an increasingly consumer oriented world, this can be difficult. We are used to streaming movies on demand, ordering items online and having them delivered within a few hours and being able to text our friends with near instant responses. 

On the other hand, problem solving can be circuitous and non-linear. Sometimes, you have to experiment to see how a change in one part of the code impacts the output. To do this, you have to hypothesize and test to see the result. If kids are only comfortable running tests with deterministic outcomes, then that’s not really a test at all. A true experiment is when you have a hypothesis about the outcome but don’t really know until you’ve collected data whether or not your guess was valid. So, if we can encourage students to build their patience then they can see as bad as not finding an error in the moment is that if they keep working on it eventually they will figure out what the issue is.

While this approach may initial feel uncomfortable for kids who are used to having their parents create fertile boundary conditions for their continuous success. The reality is that our kids will be faced with problems that do not have easy solutions. The world around them is increasingly become disrupted by technology and innovation. If we truly want our kids to be successful, they must build the muscle to understand how to navigate a world where problems will have to be broken down to first principles and solutions will have to be constructed based on that knowledge.


From a professional standpoint, projects don’t work out. New business are started that don’t gain traction. Great accomplishments are not rewarded with compensation increases or promotions to increased responsibility. Client proposals which meet all the needs aren’t accepted. Recruiting of a talented team member ends in an offer being accepted at a competitive firm. Companies lay off employees due to constantly changing business conditions. There are numerous everyday examples that we can think of in which failure is an inevitable part of life. It’s about time that we started sharing this reality with our kids so that they can truly become successful in the long term.

About the Author: Omowale Casselle is the Co-Founder & CEO of Digital Adventures.