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Dare to Fail Greatly

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“Only those who dare to fail greatly can ever achieve greatly.” – Robert Kennedy

After an unusually mild summer in St. Louis, last weekend brought with it a return of heat and humidity and the opportunity to take my kids swimming.

Keeping an eye on my older three sons, I worked with my daughter on jumping from the side of the pool into my arms. Since Grace had just learned to swim, this was a bit scary for her.

With her blonde, wet hair dripping and her her pouty eyes looking at me she said, “Dad, I don’t think I can. What if it doesn’t work? What if I fail?”

These words were shared by a nervous three-year-old.

Moments later she ignored her own question, took the massive risk, left the safety of the pool deck and jumped into the water, into my arms. Successfully.

Let’s review these words: “I don’t think I can. What if it doesn’t work? What if I fail?”

Don’t we also use these words to explain why we don’t take chances in life? These words ultimately crush our ability to truly thrive in relationships, professionally and in life.

Today I am giving you three life-giving thoughts to replace these possibility-crushing ones:

1. I think I can. Most of us have a little voice in our ear that whispers throughout the day how the world is against us, it won’t work, they don’t want us to call them, we’re not good enough. Replace that voice with one that breathes hope and possibility into each moment. These words aren’t just some rosy, self-help banter. They’re not just for a little choo-choo train going up a big hill. No, this is an imperative conversation that we must have with ourselves – and one that must be owned intentionally throughout each day. I think I can.

2. So what if it doesn’t work? When I take a big risk in any area of life, I always ask two simple questions: What’s the best thing that can happen if it works and what’s the worst thing that can happen if it doesn’t? Very quickly these questions free me to make an educated choice with a strong level of confidence…and frequently, I discover that the possibility of success far outweighs the fear of failure. So instead of asking as a victim, ask this question as a victor: So what if it doesn’t work!

3. What’s the worst thing that can happen if I fail? Ok. So the worst thing has happened. It didn’t work out. We failed brutally in the project, the trial, the rehearsal, the date, the job interview. Now what? How do we bounce back from this? I always feel liberated when leaning into the words credited to John Lennon: ‘It’s going to be okay in the end…so if it’s not okay, it’s not the end.’This most recent failure, whatever it might have been for you, is not the end. More than likely, it’s the end of one chapter; a chapter that taught you a great deal, and now frees you to begin writing the next, best chapter of your life.

My friends, leading a radically inspired life requires not just the willingness to dare greatly, but to know that when we fail – and we will fail – to remain positive in spite of it, learn lessons from it, lead better because of it, and be confident regardless of it.

This is your day to embrace the truth that only those who dare to fail greatly, can ever achieve greatly. This is your day to live inspired.

So jump in.


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