By Brian Britton French
Growing up in Connecticut, our family was blessed with a teenage friend who possessed a rare and remarkable gift—the ability to see the world not as it was, but as it could be. His name was Jim W., and my mother, with her usual knack for perfect observation, crowned him with a title that would stick forever: “the eternal optimist.”
Jim had this extraordinary way of reframing everything. On days when the Connecticut sky hung heavy and gray, when the cold seemed to seep into your very bones, Jim would look up at those oppressive clouds and say with genuine conviction, “I’m sure tomorrow will be bright and sunny.” At first, you’d shake your head at the seeming naivety of it. But over time, you began to understand—Jim wasn’t denying reality. He was choosing hope. He was consciously deciding that the future held promise, and in doing so, he somehow made that future a little brighter for everyone around him.
As the years went by, Jim’s relentless optimism became something of a family joke—but the kind of joke that’s wrapped in affection and admiration. We’d exchange knowing glances when he’d launch into one of his sunny predictions, but beneath our gentle teasing was a profound appreciation for what he brought to our lives. In a world that often feels weighted down by cynicism and doubt, Jim was a walking reminder that perspective is a choice.
But Jim’s optimism was never passive. It wasn’t just about seeing the glass as half full—it was about actively filling it up. This became crystal clear when Jim was working as a salesman for a screw manufacturer, of all things. It was honest work, necessary work, but not exactly the stuff of dreams. Yet even there, Jim remained engaged with life and the people around him.
One of his friends was a guy named Scott, someone who was fascinated by the emerging world of digital photography and Adobe Photoshop. Now, most people, when presented with a friend’s wild idea about teaching Photoshop seminars around the country or writing a book about it, would politely nod and maybe offer some cautionary advice about the challenges ahead. They’d talk about the saturated market, the financial risks, the improbability of success.
But when Scott came to Jim with what must have seemed like an insane proposition—quitting stable jobs to travel the country teaching software and maybe write a book about it—Jim’s response was pure, undiluted Jim: “Absolutely! That’s a great idea. Let’s do it. We have everything to gain and nothing to lose.”
Think about that for a moment. Here was a screw salesman telling his friend, “Yes, let’s build a media empire.” Most people would have laughed it off. Jim said yes. And not a tentative, hedging yes—but an enthusiastic, all-in affirmation that believed in both the idea and the person behind it.
That leap of faith, that willingness to see possibility where others saw risk, helped give birth to Kelby Media. Scott Kelby went on to write more than fifteen books on mastering Adobe Photoshop. He became one of the most recognized names in digital photography education. And while Scott’s talent and work ethic were undoubtedly the driving force, I can’t help but wonder: would it have happened without Jim’s immediate, unconditional belief?
Here’s the beautiful irony: Jim W. retired twenty-five years ago, in his early forties. Being an optimist, it turns out, can be monetized—and the universe has a way of rewarding optimists a thousandfold. While others stayed in their comfortable positions, calculating risks and protecting what they had, Jim took the leap. He believed in possibilities, he invested his faith and energy in them, and that faith came back to him in abundance. His optimism wasn’t just a personality trait; it was an investment strategy, a life philosophy, and ultimately, the key to his freedom.
This is what eternal optimists do. They don’t just see the bright side—they become the catalyst that helps others take the leap. They provide the emotional and psychological foundation that allows dreams to become reality. When everyone else is calculating the odds of failure, they’re already imagining the victory celebration.
Being an optimist can be a tremendous asset in life, perhaps one of the greatest assets of all. Optimism isn’t about being naive or ignorant of challenges. It’s about believing that challenges can be overcome. It’s about seeing obstacles as temporary rather than permanent. It’s about understanding that failure is often just a detour on the way to success. Research has shown that optimists live longer, enjoy better health, have stronger relationships, and yes, achieve more of their goals. But beyond the statistics and studies, there’s a simpler truth: optimists make life better, not just for themselves but for everyone around them.
They give us permission to dream. They remind us that tomorrow really could be bright and sunny, even when today is cold and gray. They show us that saying yes to a crazy idea isn’t foolish—it’s brave. They teach us that we really do have everything to gain and nothing to lose when we pursue what matters to us.
I miss my friend Jim W. I miss his unshakeable belief that good things were always just around the corner. I miss his willingness to jump into the deep end with both feet, pulling others along with him through sheer enthusiasm. I miss the way he could take the edge off a difficult day with nothing more than a sunny prediction about tomorrow.
But more than missing him, I’m grateful for him. Grateful for the example he set, the joy he brought, and the reminder he provided that life is better when we choose to see its possibilities rather than its limitations.
Everyone needs an eternal optimist in their life. Someone who will tell you your wild idea isn’t crazy—it’s brilliant. Someone who sees the sunny day hiding behind the clouds. Someone who genuinely believes that you have everything to gain and nothing to lose. These people don’t just make our lives more pleasant; they make our lives more possible. They help us become the best versions of ourselves, not through criticism or coaching, but through the simple power of unwavering belief.
Jim understood something profound that many people never grasp: the future is largely unwritten, and our attitude toward it shapes how it unfolds. By choosing optimism, by choosing belief, by choosing yes—he didn’t just change his own life. He changed the lives of everyone fortunate enough to know him.
So here’s to Jim W., the eternal optimist. May we all find someone like him in our lives. Better yet, may we all strive to be someone like him for others—someone who looks at the gray skies and predicts sunshine, someone who hears a crazy dream and says “absolutely,” someone who reminds us that we have everything to gain and nothing to lose.
Because in the end, Jim was right. Tomorrow really can be bright and sunny—if we believe it can be, and if we have the courage to act on that belief.
About the Author
