Dream Big: 10 Lessons Learned from Skydiving

By Christine Smith

On Monday, I had the opportunity to jump out of a plane from 10,000 feet in the air at 120 miles per hour. Yes, that’s right, I went skydiving! If you’ve seen my bio on the NRMC website, you would know that it was an item on my bucket list. To say the least, skydiving was an awesome experience and has definitely been a highlight of my 19 years of life thus far.

For those of you out there that are risk-averse, I’m sure you think I am absolutely insane—which is understandable. On the other hand, I know there are some of you out there who love taking risks! Clearly, I am one of those people. Even though the way down was a mere 6 minutes, the memories I made will last a lifetime. Along with the memories, I learned several helpful lessons relevant to my journey as a Risk Champion.

  • Don’t overanalyze: After signing the required waivers, it was tempting to turn around, get back in my car, and drive as far away as possible. But since I already paid a deposit, I told myself that walking away would be a foolish waste of money. I tend to overthink things and analyze the minute details of every situation, but I’m also frugal! Risk leaders can learn to let go and not overanalyze by enabling their team members to make decisions. A July 2017 McKinsey & Company article, “Culture for a Digital Age” by Julie Goran, Laura LaBerge, and Ramesh Srinivasan, includes findings from McKinsey’s survey of global executives, who identified “shortcomings in organizational culture” as a barrier to organizational effectiveness in today’s digital world. The authors provide a helpful perspective on how leaders sometimes impede risk-taking: “Regardless of industry, the critical question for executives concerned with their organization’s risk appetite is whether they are trusting their employees, at all levels, to make big enough bets without subjecting them to red tape.” The authors note that managers may need training on how to step back and truly delegate decision-making authority. Managers must not overanalyze; staff should be allowed space to experiment with interpreting and applying the organization’s risk appetite.
  • Learn how to be comfortable with the uncomfortable: Life-changing personal and professional growth happens when you step (or jump!) out of your comfort zone. You learn more about yourself and realize that you are much more capable than what you ever imagined. Risk leaders often struggle to help their peers become comfortable with candidly assessing organizational challenges and failures. The authors of “Culture for a Digital Age” echo this, explaining that “Building a culture where people feel comfortable trying things that might fail starts with senior leaders’ attitudes and role modeling. They must break the status quo of hierarchical decision making, overcome a focus on optimizing rather than innovating, and celebrate learning from failure.”
  • Stop fearing ‘fear’ itself: Once up in the air, I knew I was going to jump. I made a conscious decision to stop being afraid and start enjoying the experience. Don’t let your mindset hold you back, or let life-changing experiences slip away due to fear. Risk Champions are not guided by fear of what could go wrong; instead they ask, “what must go right in order for us to achieve our objectives?” Change the risk conversation from one based on fear to one focused on advancing your nonprofit’s mission.
  • Always have a Plan B: A skydiver always has a backup parachute in case the first one fails. Make sure your nonprofit also has a backup plan for the downside risk events you worry about. It’s better to be safe than sorry! The NRMC team often references how risk management enables nonprofit leaders to remain nimble when the future doesn’t turn out the way they expect it to. Contingency planning prepares you to adapt to multiple possible outcomes—rather than just a single outcome you hope will occur.
  • Make a choice and commit to it: I am proud of myself for completing something I’ve hoped to do for a long time. Some NRMC clients have struggled with a phenomenon, shiny penny syndrome, and they feel they are constantly changing direction and chasing after the next big thing. While nonprofit leaders must be agile enough to identify and leverage sudden opportunities, we also need the grit to persevere with a choice we have made. While planning for a new initiative or opportunity, anticipate milestones and checkpoints throughout the implementation phase. Don’t abandon your commitment without rigorous reflection during these checkpoints. Develop criteria to guide your thoughtful decision to either persevere or purposefully wind down your new initiative.
  • Once you achieve a dream, conceive another: I’ll be the first to say that it can be a bit depressing to return to normal daily routines after doing something that you were looking forward to. Although I’m thankful and so happy to have experienced jumping out of a plane, I’m sad that it’s over. Now, I’m letting this feeling of excitement push me to find another goal to achieve. Let this be encouragement for you too! Once you achieve a goal, whether it be personal or work-related, find another to keep you going. The discipline of risk management is constantly evolving, as are the environments that our nonprofits operate in each day. Each time you set new dreams and objectives for your organization, be sure to keep your risk program up to par.
  • Take time to reflect and enjoy the serenity: The few minutes after the free fall were easily the most enjoyable minutes of my life. After having wind rushing at you at 120 miles per hour, the calmness and the silence after the wind stopped was indescribable. Sometimes it’s hard to find the serenity as a risk leader, because we can’t always identify when we have helped prevent a crisis from occurring. If you can’t determine specific events your work has influenced, then focus on the big picture. Ask, “how has our risk management program helped us make better decisions as a team?” When your team members start making risk-aware decisions—even small decisions day-to-day—you can pause to reflect and enjoy the serenity and support your risk management program has brought to your mission.
  • Surround yourself with the right people: One of my best friends went skydiving with me and I was so thankful to have her there. The support we gave each other was priceless. I learned that keeping encouraging and loyal people in your life will only bring positivity and joy. Life is too short to be in toxic relationships with negative people. Risk Champions are sometimes perceived as the negative people in their organizations. If this has happened to you, then reflect honestly on your interactions with your team members. Read our recent article about Risk Champions to learn about the charismatic qualities you can showcase as a risk leader, and how to inject positive language into your peer-to-peer conversations about risk.
  • Say yes more often: As an introvert, personal time is essential. There are surely times I’d rather stay at home reading a good book than going out and interacting with people. While there are times when staying home and relaxing is more than okay, skydiving helped me learn that we have only a finite time to experience this life. We should be comfortable with spontaneity and seek it out at times! This world has so much to offer us and we must take advantage of it before time runs out. The same holds true for Risk Champions, who exist to move their nonprofit missions forward—not hold them back with webs of red tape and risk aversion. Be the risk leader who says “yes!” when your team members share out-of-the-box or risky ideas. Instead of stopping bold new ideas in their tracks, say yes and share how risk management can help the ideas take shape, so they lead to the desired outcomes.
  • Release the need for control: No one likes a control freak. I will admit, I am sometimes a control freak. After skydiving, I can say that letting go and jumping was one of the most liberating things I’ve done. There are some things in life that cannot be controlled, and that is okay. Acknowledging this fact is a huge milestone in living a life full of liberation, and in convincing your nonprofit team that “risk happens” and sometimes it’s right to take risks. As Helen Keller said, “Security is mostly a superstition… Life is either a daring adventure or nothing.”

Even though jumping out of a plane may not be everyone’s cup of tea, there are times when it is beneficial to drink the tea anyways. I realized that the truly beautiful moments in life come from taking leaps of faith. Find what encourages your team to take those leaps of faith and ignite a spark within the soul of your nonprofit.

“If you can dream it, you can do it.” – Walt Disney

Christine Smith is a Summer Intern at the Nonprofit Risk Management Center. She supports ongoing consulting projects and the development of a new web app, My Risk Assessment. For questions, comments, or to hear more about skydiving, you can reach Christine at Christine@nonprofitrisk.org or 703.777.3504.