How To Fail And Feel Okay About It

Like most people I know, I’ve wished long and hard for countless things to happen in my life that didn’t end up happening.

I can think of half a dozen specific examples: Not winning over a particular guy in high school, not getting into my first choice of college, not landing a big project or client, or not getting my book proposal picked up by a publisher on the first round.

And there are many more where those came from.

At the time and in the moment, failing at each one of those aforementioned aspirations caused me a significant amount of disappointment and suffering. I had a hope or dream in my mind, I worked tirelessly to realize it, and it didn’t happen.

However, in each and every one of those scenarios, if I waited long enough—several years in most cases—the failure eventually led to something even greater than the original dream.

In 1995 I was devastated when I wasn’t admitted to the University of Virginia. I had my sights set on that school when I was a young girl and getting that rejection letter not only hurt deeply, but convinced me I wouldn’t get other things I wanted in life.

Six years later, I found myself saying “I do” to the man of my dreams, Richard, who I’d met my sophomore year at James Madison University., “Why didn’t I get into UVA?” quickly turned into “Thank God I didn’t get into UVA”. That rejection letter didn’t limit the possibilities in my life, it ended up changing the trajectory of my life in the most positive way possible.

11110746_10154137812169848_8852297068664809670_nAnd the same is for most of the failures in my life.

The rejection from the high school guy made room for Richard in my life (my parents are very grateful). The rejection from one client made room for a bigger and better project from one of their competitors. And even my inability to get pregnant for a long time made room for me to help dozens of women through the same issue.

The list goes on, and it’s filled with deep disappointment that later turned to genuine gratitude.

Except one example: my book publishing deal. I’m still in the middle of that turnaround moment. Earlier this year I put together a book proposal for a self-help book that I’m writing for mothers. My literary agent shopped it around to 13 different publishers, and every single one said nope, nada or no thank you.


Normally, I’d be devastated by this development, but if history repeats itself — and I expect that it will — one day the very relevant and very positive reason for the rejection will reveal itself when an even better opportunity knocks at the door.

Maybe the reason will be revealed a week from now, maybe it will lie dormant for the next ten years, but I know, without a doubt, that one day a full-circle moment will happen and I’ll say to myself, “So that’s why the first round of the book deal didn’t happen.” And I have all the trust in the world that I’ll follow that sentiment with, “Thank God the first round of the book deal didn’t happen.”

It’s a waiting-to-exhale moment that’s just waiting to happen.

I’ve seen the way this movie ends enough times to trust that my current situation is turning out this way for a very positive reason that I am simply unable to see right now.

One day I know that I’ll be able to breathe a sigh of relief for my unanswered publishing prayer. And until that day comes, I’ll keep trying and keep failing without all the fear that comes with feeling that failure is the end of the road. Sometimes it’s just the beginning of a new, hidden path.

Wait for it.




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Katherine, it was great seeing you last night and hearing the wisdom you and John shared. I have spent my lunch hour catching up on your blog–so many awesome articles! One great tidbit I’ve learned from my mentor is “Every adversity carries with it the seed of equal or greater benefit.” Adversity–not getting into UVA. Greater benefit–JMU and Richard. Sometimes it just takes a while for that seed to come up, but it will. Your book is going to make a great impact and help tons of moms and mom-adjacents when it gets published. I’ll look forward to reading it and getting a copy for my mom 🙂

Katherine Wintschreply
– In reply to: Essie

Thank you for the wise words, Essie 🙂 I appreciate it. I’m crossing my fingers on the book front. Thank you for reading.

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