Living Beyond the Rearview 

“Glory Days” is a deceptively upbeat anthem about people lingering in the glow of their past. The characters in the song—an aging athlete, a single mom, and Springsteen himself—are caught in the gravitational pull of their former triumphs. They get together, have a few beers, and talk about the way things used to be. While there’s warmth in their memories, there is also a creeping sense of stagnation. 

It’s a story that resonates because it’s deeply human. We all have chapters that shine: a career peak, an athletic high, a creative breakthrough, or a time when our house was full of family. These moments matter, but when they become the standard by which we measure everything else, they can also be obstacles to a happy future. 

When the Past Defines the Future 

Hanging on to former success is rarely about arrogance. It’s about identity. Something worked. Something clicked. It made you feel like the best version of yourself. And so it’s tempting to chase that same magic again. But as the world shifts, what once seemed just right may no longer be. 

Marlon Brando, for example, struggled for years after early acclaim with films like The Wild One and A Streetcar Named Desire. He reemerged many years later in The Godfather by embracing his age and evolving his craft. 

Organizations face similar traps. Kodak, once the king of film photography, also invented one of the first digital cameras (in 1975) and earned patents for numerous imaging technologies in the 1980s and 1990s. Yet faced with the choice between digital and analog, it clung to its film legacy. The result? Lost leadership and missed opportunities. 

The same pattern shows up in our everyday decisions. A former executive in search of a part-time retirement job might hold out for a title, salary, or perks that no longer fit. An investor might chase yesterday’s returns. An amateur athlete might stop playing the sport they love just because they can’t achieve their former personal best. 

The risk is directional. Looking backward too long makes it harder to move forward. It keeps us thinking about our former selves, without a full view of who we are, here and now. 

The Psychology of Staying Stuck 

Nostalgia can be powerful and productive. It buffers us against anxiety and reminds us of our potential. But when it becomes the lens through which we make decisions, it can also distort our judgment. 

“When you’ve made it once, you know exactly what it takes to do it again,” says Wilson Hoyle, a CAPTRUST senior executive and inspirational speaker to organizations across the country. “That knowledge can motivate or paralyze you.”  

In his long career, Hoyle has led thousands of employees and watched many more clients and colleagues retire, redefining who they want to be and moving into new phases of life. He also speaks frequently to professional sports teams and to players who are often in the middle of their glory days.  

When people hang on too tightly to the past, he says, they’re falling prey to three key cognitive behaviors: 

• Status quo bias. We naturally prefer what’s familiar, even if the environment has changed. But avoiding change for the sake of comfort can limit growth. 
• Loss aversion. We feel the sting of loss more intensely than the pleasure of gain, making us overly cautious or protective against perceived risks that may no longer apply. 
• Anchoring. We latch on to old benchmarks and can’t let them go. Opportunities that don’t match that standard may get dismissed, even if they align more closely with our current needs, goals, or values. 

These are natural biases that our brains have developed to try to keep us safe. They help us avoid making bad decisions. They can also keep us stuck in the past. Two empty nesters might find themselves unable to enjoy their years of independence and freedom. Or a person might hold on to weight goals and beauty standards that are now unreasonable and downright damaging. 

Letting Go, Not Losing Ground 

Letting go of past success doesn’t mean rebuffing it. It means recognizing that success today might require a new definition.  

“The people who transition well after early success are the ones who can do two things: turn the page and start from the bottom, with no sense of entitlement,” says Hoyle. “It’s not about rejecting your past. It’s about not being beholden to it.” 

Americans are living longer than ever now, spending an average of 25 to 30 years in retirement. This reality forces a reevaluation of what it means to be productive, fulfilled, and financially secure later in life. Holding on to outdated assumptions can create a mismatch between goals and resources. 

“Sometimes, you need to be willing to go backward to go forward,” says Hoyle. “And that takes humility.” His advice: Reexamine what you need to feel satisfied today, not what made you feel fulfilled in the past, so you can set new goals that match your current goals and needs. 

The Cost of Clinging 

What once felt like stability can quietly become resistance. In a world that demands adaptability, a refusal to evolve can quietly erode career prospects, financial resilience, and personal well-being. Being anchored to the past can show up in subtle but consequential ways: 

• Turning down opportunities. Waiting for a role that matches a past salary or job title can lead to long employment gaps or diminished offers. Time passes, gaps widen, and financial strain sets in. 
• Fighting a pivot. Clinging to old friends or a now-dysfunctional marriage, refusing to downsize when you know you need to, and continuing old hobbies that no longer bring you joy are three examples of how we reject adaptation. In doing so, we fight our own evolution. 
• Straining relationships. Holding on to an old identity can create tension at home. For example, one spouse might continue spending to maintain a lifestyle no longer supported by current earnings. Over time, this friction creates stress and chips away at emotional well-being. 
• Avoiding necessary adjustments. Whether it’s downshifting your career, retooling your fitness regimen, reskilling, or revisiting your financial plan, delay compounds risk. The longer someone tries to sustain a former version of success, the harder it becomes to adjust with intention. 

In each case, the issue isn’t nostalgia. It’s inertia. 

Four Ways to Move Forward 

Letting go is easier with a plan. “There’s no shortcut to building something meaningful,” says Hoyle. “The ones who remember that are the ones who succeed a second time.”  

Here are four strategies to help you move from looking back to moving ahead: 

• Name what you’re holding on to. Ask yourself: What part of the past am I trying to re-create? Is it influence, recognition, empowerment, security? Naming it helps shift the narrative. 
• Reframe risk. Growth lives just outside of your comfort zone. A pay cut for purpose or a bold lifestyle pivot might feel like a step down but could be your best investment in the long run. 
• Update your success metrics. What mattered then may not matter now. Redefine success around who you are today. Flexibility, autonomy, fulfillment, and impact are all valid metrics. 
• Craft a new narrative. Replace “I peaked back then” and “That was the best time of my life” with “That season prepared me for what’s next.” Your past isn’t the ceiling. It’s the foundation of your next level. 

Hoyle also mentions the importance of friends and family: “The ones who move forward the most consistently tend to be surrounded by support—not voices telling them they’re above starting over. That kind of environment makes it easier to embrace humility and begin again.” 

Building on the Glory, Not Living in It 

If you’re looking for positive role models, consider LeBron James and Joni Mitchell. James achieved early success on the basketball court but continues to evolve in business and through activism. Mitchell didn’t stay in folk music forever, although it was the genre that made her famous. In the late 1970s, she pushed into jazz and experimental sounds, willing to risk commercial success to keep growing. 

Whether you’re navigating a career shift, a relationship change, a financial transition, or personal reinvention, it’s worth asking: Am I looking backward to feel safe, or forward to make progress? Clinging to the past can limit your ability to build something new. The most resilient people are those who honor their history without being bound to it. 

Celebrate your wins, but don’t stop there. Your next success might not look like your last one. And that’s not just OK. It’s essential. 

“You don’t need to peak again to move forward,” says Hoyle. “You just need to get started.” 

Written by John Curry

Have questions? Need help? Call the CAPTRUST at Work Desk at 800.967.9948, or schedule an appointment with a retirement counselor today.