Retirement is often viewed through a financial lens, defined by savings goals, investment strategies, and a projected date for when work will end. But ask anyone who’s approaching that milestone, and a different reality often emerges: Retirement planning can be just as emotional as it is financial.

Cindy Giovacchino, a seasoned financial planner and the founder of Gio Financial, encounters this emotional aspect of retirement planning regularly. While spreadsheets and strategy are important, she believes the process should also include space for deeper reflection on identity, purpose, and the kind of life someone hopes to build after their working years.

These aren’t questions most people are accustomed to asking themselves. Fortunately, a thoughtful financial planner like Cindy Giovacchino can guide clients through them. In fact, much of her work involves helping clients step back and consider not only what they can afford, but also what they truly want this next phase of their life to look like.

“Who Am I Without My Job?”

For many, work has offered more than a paycheck—it has shaped their identity. Whether you’re a business owner, a nurse, or a tradesperson, stepping away from your career can sometimes feel like stepping into the unknown.

Some clients don’t struggle with the numbers; they struggle with the psychological shift. Retirement may signal a loss of structure or purpose, which can feel unsettling. But when financial planners like Cindy Giovacchino raise questions like this, it can help clients think ahead about how to build a fulfilling life beyond work.

“Is My Lifestyle Helping or Hurting My Long-Term Plan?”

Even high-income earners can find themselves facing challenges if spending outpaces planning. Consider someone with multiple properties, expensive tastes, and a $20,000/month lifestyle. On paper, they may seem secure, but projections might suggest a different outlook. Reducing monthly spending, even by a few thousand dollars, could extend their assets significantly.

The challenge isn’t just the math—it’s navigating values and trade-offs. This is where an advisor’s role becomes critical. Someone like Cindy Giovacchino can help guide the conversation with clarity and respect, helping clients understand the long-term implications of their current habits.

“Can I Retire Now—or Should I Ease Into It?”

For those with modest savings, the retirement question is often about timing. A client who spent decades in a hands-on trade might want to travel or slow down, but they aren’t certain if full retirement is realistic just yet. Part-time work or phased retirement can offer a helpful bridge between financial stability and personal fulfillment.

A financial planner can model these different paths and discuss how each option aligns with specific goals, helping clients feel more confident in whichever timeline they decide to pursue.

“What Do I Want My Legacy to Be?”

Legacy is about more than money. It can be about family, community, or a cause close to your heart. Many people may not think to ask themselves about their legacy until they’re already retired. An advisor like Cindy Giovacchino often introduces this question early, helping it shape not only estate plans but also meaningful financial decisions throughout retirement.

Retirement Is More Than a Financial Plan

Cindy Giovacchino approaches retirement planning as both a technical process and a personal journey. Her work emphasizes the reality that people aren’t just planning for the end of work—they’re preparing for a new chapter of life. And that requires more than projections. It requires the opportunity to ask and be guided through the right questions.

By working with a financial planner who recognizes the emotional side of this transition, individuals can approach retirement with more clarity, confidence, and a plan that supports not just their finances but their future selves.

About Cindy Giovacchino

Cindy Giovacchino is a dedicated financial planner with over 25 years of experience, passionate about helping clients work toward financial security. She offers personalized, hands-on guidance, whether working with high-net-worth individuals or those just beginning their financial journey. Giovacchino is known for building lasting relationships.

Cindy Giovacchino is an Osaic Institutions Financial Professional. Securities offered through Osaic Institutions, Inc. Member FINRA/SIPC. There is no assurance that investing through a financial professional will improve net results.

Disclaimer: This article is for informational purposes only and does not constitute financial, legal, or tax advice. Readers should consult with a qualified financial advisor or other professional to discuss their individual circumstances before making any financial decisions.