Happily Retired, but Financially Anxious: Susan and David

After decades of purposeful work, David as a corporate attorney and Susan as an educator, the couple stepped into retirement with optimism and enthusiasm. They were eager to travel, volunteer, and spend meaningful time with their growing family. They had done the hard work of saving and planning. They were, in every sense, happily retired.

Yet beneath their cheerful outlook lay a quiet uncertainty of whether their wealth could support their goals and maintain their independence. Their former advisor had been attentive during their accumulation years but offered little structure or strategy once paychecks stopped. Without a coordinated plan for cash flow, Susan and David found themselves guessing which accounts to draw from, paying more in taxes than necessary, and juggling statements from a handful of custodians.  David’s pickleball partner suggested that they reach out to Rockwood for guidance, as their current advisory relationship did not inspire the confidence they sought.

During our discovery process, we began with a deep exploration of their priorities: dependable income that adjusts with inflation, simplified finances that reduced administrative burdens, and a plan to balance travel, family gifting, and philanthropy without ever worrying about “running out.”

We restructured their portfolio into a globally diversified, low-cost allocation engineered to generate consistent, tax-efficient cash flow. We helped them establish a strategic distribution plan that drew intentional proportions from taxable, tax-deferred, and Roth assets, smoothing their lifetime tax liability. We also coordinated with their estate attorney to refresh their trust documents and implement a gifting strategy that allowed them to witness their generosity in action—funding their grandchildren’s education and supporting their favorite literacy nonprofit.

To bring simplicity and organization, we consolidated their investment accounts and automated their monthly cash flows, transforming a patchwork of accounts into a cohesive system they could easily understand.

Today, Susan and David have the confidence to enjoy their lifestyle—extended stays at their lake cottage, travel abroad with friends, and the joy of funding their grandchildren’s education and the clarity to stop second-guessing whether they should or shouldn’t. They embody what it means to be happily retired: secure, intentional, and present in every moment, with the comfort of knowing their wealth is fulfilling its purpose.