The older I get, the more I believe the key to happiness and success is being willing to fail. This doesn’t mean you have to seek out failure, but rather it’s about learning how to fail in a way that propels you forward and helps you learn.

I grew up a smart kid. I was placed in gifted programs, and getting outstanding grades in High School was smooth sailing. I wasn’t an all-star athlete, but I played on the varsity basketball team as the starting point guard.

For the most part, I just didn’t have to try that hard to succeed because I was blessed with gifts that worked well for me in my early life.

But once I got to college, and then work in the real world followed by motherhood? Things changed.

I graduated college with a 3.0, I had a tendency to skip a lot of morning classes, not study and cram at the last minute, and be up all night before turning in a paper exactly on the deadline.

These tendencies followed me to my jobs, and these mixed with depression, being a new mom, and other personal issues led to me being fired from a job I worked for most of my 20’s.

When I look back, I don’t really regret anything because at this point in my life I am very happy. Life isn’t perfect, but it is damn close. BUT, the thing that tortured me more than anything until I hit my 30’s was a need for perfect AND a fear of failure.

I had so many things I wanted to try in my 20’s, like quitting my job to go to law school, or grade school. I wanted to quit my job and travel the world or break up with that boyfriend. But I was too afraid.

The unknown had me paralyzed. And that paralysis kept me trapped in relationships and jobs I didn’t enjoy anymore.

Luckily, life finds a way to push you out of the nest. Ironically my fear of failure is what created failure in my life by way of one engagement breaking up and getting fired. Two things that I lamented at the time, but I now see as incredible blessings in my life.

My fear of failure was also part of the reason my marriage almost ended in divorce.

My husband and I had a very romantic start to our life together. Within six weeks of getting together, my then-new boyfriend was suddenly proposing to me on a beach in Puerto Rico, where we traveled to pretty much on a whim. Nine months later we were married.

But it just seemed too good. And as much as I wanted to believe in our relationship, part of me holding myself back from being totally IN the marriage because I just couldn’t believe something that good could just happen to me. I was afraid it would fail, and so behaved in ways that almost ensured the failure.

The reason I had an almost phobia of failing was that I never had really failed in my past, and never learned an important skill… resilience.

This is one of the virtues I am most keen to help develop in my children.

My daughter doesn’t like to lose. She has a bit of a fit when someone beats her in a game or she falls off the monkey bars. My message to her? Losing/Failure is part of the process.

I don’t try to make her feel better about her attempts. I don’t sugarcoat the truth, that she came up short. I admit that yes, that try didn’t go so well, but she has another shot at it. She can either accept defeat or keep practicing until she masters what she wants.

I’ve been a big fan of Brené Brown for many years now. Her work has been instrumental in my transformation from perfectionist to resilient myself. I think this quote sums up the lessons I hope to instill in my kids:

“Vulnerability is not winning or losing; it’s having the courage to show up and be seen when we have no control over the outcome. Vulnerability is not weakness; it’s our greatest measure of courage.”
― Brené Brown, Rising Strong: How the Ability to Reset Transforms the Way We Live, Love, Parent, and Lead

Reading that quote I realize that what I was truly missing for so long was courage. The thing that is required to get over the fear of failure and to actually find the strength to be resilient is courage.

Ironically, it is motherhood that has taught me courage. Because as a mom you have no real choice but to be courageous, model that courage, and teach it to your children.

Hell, even the very act of bringing children into this world can be terrifying! It takes a lot of courage to give birth, no matter how you give birth.

And I guess it is also the only way to truly teach our children resilience, courage, and the willingness to fail.

The way is to model it. To do it ourselves.

So that’s what I’m doing. Teaching my kids resilience and how to fail by doing it myself first.

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