The Psychological Side of Retirement: How to Transition from Executive Life to Leisure

By Roxanne Martens, MS, CFP® 

Many executives understandably view retirement as a financial transition. It’s a time when their resources for everyday living significantly change. But the psychological aspect of retirement is just as pertinent and poignant.

After years of overseeing teams, maneuvering through crises, and making impactful decisions, the specter of retirement might look like a sudden void that needs to be filled. Making the adjustment involves rethinking and reframing. Here are some ways to think through that transition.

From Structure to Freedom

Often, executives look forward to retirement as a reclamation of freedom from the grind. But when that freedom finally comes, some newly retired people find themselves lost, not knowing what to do with it.

They find out that for all of their working years, they had depended on the daily rhythm and cadence of work life for structure. Responsibility defines the life of executives. When meetings, deliverables, and leadership are no longer part of everyday life, they can feel a little disoriented.

Some executives are surprised by how their performance and title informed so much of their self-worth and identity. Now that “freedom” is imminent, the needed adjustment is just as much psychological as practical.

Retirement and Repurposing

Here’s the mindset shift: just because you retire doesn’t mean you have to stop working. Instead, you now have the means to work on what you care about the most.

Whether it’s mentoring budding entrepreneurs, devoting time to nonprofits, or finally getting around to writing that book, retirees defy passivity by pursuing personal goals. That sense of purpose is crucial in staying satisfied.

Consider launching a post-retirement career as a consultant or advisor. You have decades of experience and knowledge that future generations genuinely want to hear about.

This is more than staying busy. It’s about keeping purpose at the center of your life—even if the context has changed.

Rebuilding Community and Connection

One unexpected challenge of retirement is the sudden loss of built-in social networks. For decades, colleagues, clients, and work-related events have shaped your daily interactions. When that disappears, it can lead to a quiet sense of isolation—even for the most independent people.

That's why it's important to be intentional about rebuilding your community. That could mean spending more time with family, joining local boards or interest groups, or volunteering in ways that put you in touch with like-minded people.

Many retirees find great joy in forming new connections that aren't tied to professional status. Instead of being introduced as “the VP of…” you get to show up simply as yourself. It’s a return to authenticity and a powerful reminder that relationships matter as much in retirement as they did in your career.

A strong social circle doesn’t just enrich your life emotionally, it can support your mental and physical well-being for years to come.

Reframing Work

The prospect of not working is one of the biggest hangups many have about entering retirement. Retiring doesn’t mean you have to stop functioning, engaging, or being productive. Now, the reward comes from contributing in a way that’s aligned with your values, not your job description.

Think of it this way. For years, you’ve been relied upon to deliver results. Now that retirement has arrived, you can think of your work as something to contribute out of your own initiative.

You’re not on the clock anymore. There’s no pressure from higher-ups to produce. Now you can offer perspective and knowledge in ways others can benefit from. You can develop and invent initiatives that reflect your professional passions. By doing so, you can reframe retirement as an evolution in your life, not an exit.

Defining the Future

Many executives are hopeful and optimistic about their retirement years. But some retirees can feel a sense of being exiled—and that’s heartbreaking.

Retirement doesn’t equal abandonment. It’s about putting your life activities in context. You’ve gotten where you are by being a leader, a builder, and a strategist. You can still use all those skills in retirement, on a smaller scale with less pressure. And it can all be in service to the purpose you’re most passionate about.

Plotting Your Next Steps With CGN Advisors

CGN Advisors specializes in helping executives craft solid retirement plans. We’ve worked with execs from Walmart, J.B. Hunt, Tyson Foods, Caterpillar, Meta, Salesforce, Expedia, and other companies to build meaningful and rewarding retirements.

When professionals contact us, we take all their professional and personal priorities into consideration to form plans that are both sustainable and aligned with the life they want to lead.

To schedule a meeting, call our Manhattan, KS, office at (785) 340-3434 or our Rogers, AR, office at (479) 335-1034.

About Roxanne

Roxanne Martens is a CERTIFIED FINANCIAL PLANNER® professional and serves as a Lead Financial Advisor on the team at CGN Advisors, a Fee-Only, financial advisory firm based in Manhattan, Kansas. Roxanne works out of CGN’s Arkansas location, serving clients in the Rogers, Bentonville, Springdale, and Fayetteville areas. An advisor since 2020, she works with corporate executives, young professionals, and those approaching retirement by helping them utilize their growing income efficiently and facilitating strategic cash flows once their regular earned income ends. She enjoys using her skill set to educate and guide clients through life as they make financial decisions and set goals. Roxanne says, “Comprehensive financial planning and investment management takes a lot of trust from the client, and I don’t take that lightly. I genuinely want each of my clients to succeed.” Her favorite aspect of her role is connecting with clients on a personal level, providing clarity and peace, and being able to witness them realize their dreams.

Roxanne obtained her master’s degree in personal financial planning from Kansas State University and holds the CFP® designation. Prior to becoming a financial advisor, she taught in the Personal Financial Planning program at Kansas State University for seven years. As a mom with young children, most of her free time is spent with her husband, John, and two sons, Johnny and Judd. They enjoy living life outdoors—bike rides and spending time at the lake or pool. To learn more about Roxanne, connect with her on LinkedIn.

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