Struggling Forward
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Struggling Forward

How and Why to Make Failure Your Friend

Embrace it and you will always be rewarded

Photo by marc liu on Unsplash


It is the most feared word in human language. In business, in school, in relationships, in life.


Is it because we hate to lose?

Is it because we fear embarrassment?

Is it because we are afraid to feel inadequate?

While the answers to these questions may all be yes, there is an even larger problem. We are afraid to fail because we are afraid to try again. In our culture, the number of times we try is often equated with the number of times in which we were made to feel less. It is a measure of the experiences in which we were viewed as fools, losers, and with shame, when in reality, we should be quantifying these experiences as ones which created opportunities to learn and discover.

How You Should View Failure

I want to urge you to embrace failure, overcome adversity, not be afraid to feel embarrassed, feel beaten, lose, take a risk, get shut down. You can get rejected 100 times, and you still should never feel like a failure as long as you have gained just one thing from each experience. At the end of the day, success is not about getting everything — it is about getting ONE thing.

Let’s do even more than not let the fear of striking out keep us from playing the game.

Striking out is the largest mistake you can make as a batter in baseball. It is the large failures we are afraid of that keep us from pursuing our dreams. But it is the small mistakes, the risks we are ambivalent about but don’t end up pursuing; the pop flies, the groundouts, the foul tips, which keep us from playing the game to our full potential.

A Failure Letter

Below is an email that I sent to a college professor of mine a year after I FAILED her class.

Hi Sara,

I don’t know if you remember me, but I was in your Gender Economics class Fall 2015. I actually failed your class, which was the first time that has happened to me in my life.

I just want to thank you for that experience. Since that class, I have focused on perspective and overcoming adversity, and have even shared my own story of failing to help others who think getting a bad grade is the end of the world. I have achieved so much since then and have really turned what seemed like a destructive experience, into one that has only benefitted me.

I wrote about learning from failure in my essay which got me into my current Masters program, I talked about it in the interview that landed me my dream job, and I have shared it with friends who need a pick me up story during tough times.

So thank you again. We are all going to face extreme obstacles in our lives, and it is how we react to them and persevere through them, which determines the people we ultimately become.

All the best,


Her Response:


That’s quite a story of achievement. I’m very happy to hear that you have come a long way and that you turned that one failure into a story of success. It makes me very happy to know that you are trying to help others and to spread a more positive message about learning from our mistakes.

Wishing you all the best moving forward,


What that email did for me was awesome. It gave me the opportunity to prove to somebody my accomplishments, circle back on a relationship, and make somebody else happy! She must have been thrilled to receive this email and start her day knowing that somebody was grateful for her and the influence she had on his life.

If you don’t want to do this for you, then do it for them!

People love being appreciated.

Provide somebody else the opportunity to start their day on a positive note by making them know the positive impact they have had on your life. If you think this is strange to send to a friend, family member, friend of a friend, coach, then start by saying, “Hey, I’m trying this new thing where I reach out to unbelievable people in my life. It really helps me start my day on the right foot!” or you can say, “Don’t be alarmed, I’m doing great, but I just wanted to send you this note to get both of us to have an awesome day.”

It will feel awkward, but it will be beneficial for the both of you in the short and long run. It is an acknowledgment of an experience in your life that will benefit both you and somebody else.

Final Words

The most important lessons in life are learned at some of our lowest moments. Like I mentioned in my email, we are all going to face extreme obstacles in our lives, and it is how we react to them and persevere through them, which determines the people we ultimately become.

Tim and I urge you to share your stories with us. We guarantee that this is a judgment free, supportive environment to share, reflect, and receive feedback about the moments in your lives where you may have felt less. However, with the vulnerability and courage you unleash by sharing your story, and through the thoughtful feedback of this community, you will overcome, you will conquer your setbacks, you will thrive, and you will struggle forward.


Jordan & Tim

This article was published in Struggling Forward. Struggling Forward is a community that helps each other to go through the struggle on the way towards our dreams.




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Jordan Gross

Jordan Gross

Son, Grandson | Reimagining Personal Development | “What Happens in Tomorrow World?” Publishing Spring 2021, BenBella Books, Matt Holt Books

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