“Outliers are those who have been given opportunities — and who have had the strength and presence of mind to seize them.” – Malcolm Gladwell
This blog post could be 10 pages long if I listed each failure of the last 5 years. You could say I’ve somewhat perfected the art of “failing fast” only because I’ve done it so many times 😂. Strangely, I find Leaders have a difficult time admitting their failures let alone writing about them. Enter… Me 🙋🏾♀️
Malcolm Gladwell is one of my favorite authors. The simplistic yet curve-bending way he can visualize what others overlook I find magnetic. His theory on 10,000 hours to mastering a skill is quoted and cited extensively. So why is this even a topic for Whispers? Well, if I could point to the greatest successes of my career they’ve followed points in which I allowed Myself to fail fast.
My first big speaking event many years ago was in Indianapolis, Indiana. I was asked to speak to a group of clinicians whom recently underwent changes to their operating model. I quickly accepted the invite without asking many questions. I was eager to show my skills and how good of a speaker I was. I chose my best outfit, made the drive to Indy, and was introduced on the stage in a way that made even me flush. As I think back on my time on stage, I don’t even think anyone in the crowd cracked a smile. They were angry, and I represented everything involved in their job change. My topic was completely irrelevant to them, and in Q&A they ripped it to shreds. As I walked off stage my colleague put her arm on my shoulder and said “next time”… clearly signaling my failed engagement. 🤦🏾♀️ Why do I tell this story? Because, it’s important to know what you see today came from failing fast and refining. Although I could’ve wallowed in self-pity and vowed never to assume speaking publicly again I was willing to right to the event boothe where attendees could ask questions 1:1. By the enf od the day I earned their respect for being willing to listen and shared their feedback with the Team that invited me. This experience was a pivotal moment in my Career.
As I move to the next example, don’t get me wrong. Failure stinks… it’s not fun and can certainly cause physical and emotional stress. It’s effect on you is something you must weigh against the associated risks as each opportunity presents. However it also can be incredibly enlightening and propel you forward in the overall journey, what I’ve learned is that when I’m conscious to the journey I’m able to fail fast. I don’t sit in the failure, but rather assess the journey with a sense of urgency that allows me time to pivot. In the article Why the Most Successful People Fail Most Often Jeff Bezos speaks of failure; “failure to be a part of the game — and knows a home run is well worth the wait. He advises, “Given a 10% chance of a 100-times payoff, you should take that bet every time.
I created the cycle below to proide a visual of the process that’s worked for me. It’s very simple yet effective. Each arrows point continually as they cycle doesn’t stop and quite possibly shouldn’t. The cycle also never gets easy. I’m constantly reminding Myself failure is a part of the process to make progress…..

How about one more recent example for good measure? Most recently I’ve been trying to find the right formula for a “Whispers Meet Up”. I’m naturally an introvert, but desire to create a community that allows space for conversation similar to what I post each week. One month I finally gatherer the courage for a test run. I just knew the event would be a success. I planned (and over planned) the “test” event for weeks. I kept the invitees very small, but took great care in every logistical detail. You probably can see what’s coming… it flopped 😧. When I begun to refect internally and externally I realized I spent so much time on logistics, I didn’t pay attention to what mattered most… THE PEOPLE! What I quickly realized is that failure was part of the journey. It’s what will make the next attempt 1% better.
Anyone that’s had any success will tell you failure must be part of the journey. Failure is the teacher along the way. “Smooth seas never made a skilled Sailor”.
In peace,
Judith
Resources:Why the Most Successful People Fail Most Often
