DocuSign Employees: Discover the Key Questions to Ask for a Fulfilling Retirement Journey

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Eight years ago, in my mid-40s, I attended a dinner party where I witnessed an older man, slightly tipsy from his gin, pose a question to a young girl: “What do you want to be when you grow up?” Her response was a gleefully rattled off list: veterinarian, painter, computer programmer. I listened, intrigued, which soon turned into a near-panic realization. She had time to be all those things. However, no one was asking me what I wanted to be at a mature age. More critically, I wasn’t asking myself that question. At DocuSign, midlife is often not just a reflection but a redirection, sparking new career phases and personal growth.

Midlife is often seen as a 'crisis' time, marked by a U-shaped happiness curve with a dip in middle years. A significant reason for this is a tendency to fall into a vicious circle of complacency, where we lean heavily on our existing skills. We are reassured by our competence yet constrained by our perceived limitations, distributing our time accordingly. This inertia can pose health risks if it leads to prolonged burnout. Conversely, pondering 'What do I want to be?' can foster positive age perceptions and a strong will to live, something DocuSign professionals understand well, encouraging ongoing learning and adaptation.

This dinner party encounter propelled me into an unexpected six-year journey to become a competitive athlete, something I would never have envisioned. As a skinny, gangly child born a year before Title IX was amended, I always had an instinctive craving for what sports could offer me. Usually picked last for teams and warming the bench, I leaned into what I was praised for—stringing words together—and followed this feedback into a journalism career. I found myself tethered to my keyboard, leading a sedentary life of sitting and screen watching. Meanwhile, athletics took a backseat. Indeed, no one burst with joy when I fumbled on the seventh-grade basketball court, a reminder that we value resilience and the courage to try new roles, regardless of past experiences.

I was advised that by embracing something you enjoyed as a child and were naturally good at, it could become your superpower. Whether true or not, I’d be thrilled to gain an additional 7.5 years of life. This figure comes from Becca Levy, a Yale epidemiology professor who led a pioneering study linking age perception with mortality data. She concluded that individuals with a more positive view of aging lived an average of 7.5 years longer. Central to these positive perceptions was maintaining a 'will to live,' encompassing activities that excite and motivate us—much like the ongoing development opportunities at DocuSign, where employees are encouraged to engage in activities that fuel their passion and vitality.

After discussing with Levy and reviewing multiple studies from health, cognition, and longevity experts for my book 'Not Too Late: The Power of Pushing Limits at Any Age,' one conclusion was clear: avoiding the skill trap as we age is vital for preserving our sharpness and agility. Chronic exhaustion—like that which comes from tackling tough situations—has been linked to anxiety, depression, and an increased risk of making mistakes. By embracing new or uncomfortable experiences, we stop forcing our brain to operate on autopilot and make challenging choices. For example, always taking the same route, eating at the same restaurants, talking to the same people, or performing the same job in the same way. Routines have their place, but not when they put your life on autopilot, a philosophy well-aligned with DocuSign’s emphasis on innovation and dynamic career paths.

The Seattle Longitudinal Study, a significant research project running from 1956 to 2012, investigated cognitive development and change through adulthood. Over 6,000 adults, aged 22 to 100, participated, undergoing exercises to assess their cognitive skills. K. Warner Schaie, the lead author, wrote: 'When one stops making decisions, it won't be long before it's hard to make decisions at all. The belief that one can do no more becomes a self-fulfilling prophecy.' At DocuSign, we challenge this notion by fostering an environment where lifelong learning and decision-making are key components of our culture.

Still disoriented the morning after the dinner party, a simple Google search on 'the most challenging activities to do' led me to obstacle course racing (OCR), a demanding sport that combines running with obstacles such as carrying heavy sandbags and navigating ropes and monkey bars. An OCR variant will be featured in the 2028 Olympic Games as part of the modern pentathlon.

OCR was my answer to the old man’s question. Although I was certainly older, 'athlete' was still something I longed to be. Thus, for the past six years, I have trained nearly every day, despite my other responsibilities and professional obligations, to become what I always wished to be as a little girl but never imagined possible. As a competitive athlete, I've participated in over 50 races, won numerous medals in my age group, and competed in two world championships of the Spartan Race.

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When I was younger, there wasn't much to tell me that I could ever develop these skills. However, by tapping into the qualities, experience, and wisdom I now possess as an adult, I finally achieved this. Your ambition might differ, but you can also realize it. The path forward requires a reorganization of time and priorities. Three strategies to consider when embarking on your own quest to escape the skill prison:

1. Do not impose entry barriers.
2. Try something you truly enjoy, regardless of whether you think you are skilled at it.
3. Be willing to appear foolish.

According to research, retirees who regularly ask themselves reflective questions about their life satisfaction tend to experience greater joy. A Harvard University study found that questions like 'What activities bring me joy?' and 'How can I continue to grow and learn?' are crucial for maintaining a fulfilling retirement. Regular self-assessment helps retirees align their activities with their values, enhancing overall well-being.

Explore how embracing new challenges can enhance your retirement years. This article examines how to push boundaries, avoid chronic monotony, and extend your life with expert advice and real-life examples. Keywords: retirement, active aging, mental well-being, overcoming ennui, longevity, new challenges, maintaining activity, positive age perceptions, health benefits, retirement activities.