Rocking Chairs and Reflections: Are You Creating Moments to Remember?

Several years ago, a chance meeting introduced me to Linda, a woman whose business acumen was as sharp as her life wisdom was profound. With years of experience in the fast-paced telecom industry, Linda had a knack for cutting through the noise and offering advice that resonated deeply. One piece of her wisdom, in particular, has stuck with me – her perspective on risk-taking, framed through what she called “rocking chair moments.”

What exactly are rocking chair moments?

Imagine yourself in the golden years, perhaps sitting in a comfortable rocking chair on your porch, gently swaying as you reflect on the tapestry of your life. These “rocking chair moments” are those snapshots of time that flash through your mind. The question Linda posed was stark and simple: when you look back, will your inner voice whisper, “Gee, I wish I had done that?” or will it resonate with a confident, “Damn, I’m glad I did that!”?

The essence of rocking chair moments lies in this very reflection. Most of us, deep down, yearn for a life story filled with “Glad I did” chapters. This “rocking chair test” can be applied to any significant decision, whether it’s a personal leap of faith like skydiving, or a career-defining move such as accepting a challenging promotion or relocating your family across continents for an opportunity. It’s about evaluating choices against the backdrop of your future self, comfortably seated in that rocking chair, contemplating your journey.

Siobhan Smith, a leader at Coca-Cola European Partners, shared a powerful “Glad I did” moment that perfectly illustrates this. Early in her career, she faced the daunting prospect of taking an international position. It was a significant family decision, fraught with uncertainty. However, Siobhan recognized the untapped potential in the situation. As she recounted, “I consider myself lucky that the IT function was not viewed well and that there were many opportunities to improve the state of the business and the relationship with the business team. When we arrived in our new location, my husband said ‘You are going to be working non-stop. This is terrible.’ I said, ‘This is great. This is an opportunity I can really get some quick wins and gain credibility.’ It truly set me up for fast promotions after that.”

Siobhan’s courageous decision, viewed through the lens of her rocking chair, was undoubtedly a moment she was glad she embraced.

But the beauty of rocking chair opportunities is that they aren’t always grand, life-altering events. They often present themselves in the everyday.

In my work with executive development, I’ve observed countless accomplished leaders grapple with confidence at pivotal moments. Katty Kay and Claire Shipman, in their insightful book The Confidence Code, succinctly define confidence as “turning thought into action.” In our Signature Select program for female leaders, we dedicate considerable time to cultivating the ability to project confidence, even when self-doubt creeps in. These women often share stories of meetings where they wished they had voiced their ideas but remained silent, relegated themselves to the periphery, or hesitated to seek guidance from senior leaders, lacking the confidence to ask for their time.

The fear of vulnerability, of taking action that might expose us to potential failure, is a universal human experience. We are often wired to focus on the negative, on what could go wrong, rather than the possibilities of success. Yet, time and again, executives I’ve worked with have been surprised by the positive responses they received after simply reaching out to senior leaders for a coffee or a conversation. That initial “yes” often acts as a powerful catalyst, building the confidence to take further steps.

Fear of failure is a common thread that runs through us all. We inadvertently construct our own barriers to achievement, even when evidence suggests otherwise.

When I embarked on the journey of creating Signature Leaders, I was navigating uncharted territory, completely on my own. In that initial year, the question, “What if I fail?” echoed frequently in my mind. Fortunately, failure didn’t materialize; the first year exceeded expectations. However, the fear didn’t vanish entirely; it simply shifted its form. Doubt morphed into, “What if I was just lucky, and can’t replicate that success?” But just as before, the second year proved equally, if not more, successful. Even now, years into entrepreneurship, with a portfolio of thriving programs, that nagging self-doubt can still surface, momentarily dimming my confidence.

Stephen Hunt’s impactful quote, “If you are not living on the edge you’re taking up too much space,” rings true. Growth is inextricably linked to risk-taking, to embracing failures as learning opportunities. In today’s dynamic business landscape, organizations need individuals who are willing to venture to the edge. Innovation is born from experimentation, and companies thrive on fresh perspectives and approaches that are actively tested. As a CEO faculty member in our Signature Program aptly stated, “I’m hiring an executive that wants to play to Win. I don’t need an executive that plays ‘not to lose.’”

This necessitates a culture of risk-taking, of continuous stretching and growth.

So, as you navigate your career and life’s journey, pause and apply the rocking chair test before making significant decisions. Ask yourself: will this be a moment you’ll look back on with pride and joy? Will your future self, perhaps in a rocking chair, wish you had been bolder, taken more chances? Or will your memories be a collection of “Damn, I’m glad I did that’s”? My hope is for the latter. Embrace the rocking chair test, and you might find yourself taking calculated risks that pave the way for profound personal and professional growth, creating a life story rich with fulfilling “Glad I did” moments.

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