Client Journeys / Confident Retirement Case Study
From Complexity to Clarity — Planning a Purposeful Retirement
Client Profile:
Two high-achieving professionals in their early 60s, referred by their trusted tax advisor.
Client Vision
After decades of building successful careers — one as a physician and business owner, the other as a mortgage broker — this couple began to look toward the horizon. Retirement was no longer a distant idea; it was becoming a near-term reality. As they began thinking more seriously about the future, their vision came into focus: simplify their financial life, live intentionally, and ensure their wealth could support not just their lifestyle, but also their children, grandchildren, and the causes they cared deeply about.
But they were looking for more than just a retirement “number.” They wanted clarity and confidence. They wanted to feel secure in the decisions ahead, and to have a trusted partner who could help them make sense of the moving pieces, offer thoughtful perspective, and walk alongside them every step of the way.
Disclaimer:
This case study is presented anonymously. All names and identifying details have been changed or omitted to protect the privacy and confidentiality of the individuals and organizations involved.
Living the Plan: Fragmented Finances to a Fully Aligned Future
The
Challenges
Wealth Without Coordination
Despite their strong earnings history and significant assets, their financial picture was complex — and in many areas, misaligned with their goals. Over the years, they had accumulated a wide array of accounts and assets:
Several retirement plans, including a defined benefit plan
Multiple real estate properties (residence, vacation home, family property, medical office)
A 529 college savings account
Life insurance policies and annuities from a prior advisor
Rental income, Social Security benefits, and a lingering mortgage
Some pieces had gone untouched for years. Their 529 plan was sitting entirely in cash. Their investment portfolios were overly concentrated in stocks. And their long-term care insurance premiums had recently increased significantly, creating additional concern.
Their wealth had grown — but it wasn’t working in harmony. What they needed wasn’t just technical help. They needed a big-picture view, thoughtful strategy, and a steady hand.
Our
Approach
We began with one essential step: listening.
Our initial meetings were designed not just to gather documents, but to truly understand their lives — their hopes, their concerns, and the legacy they wanted to build. Only then did we begin the work of financial planning.
Our process included:
Account consolidation and investment alignment: We restructured their portfolios to reflect their actual risk tolerance, improve diversification, and consider tax efficiency.
Insurance review: We evaluated their variable life insurance, annuity, and long-term care policy to determine what was worth keeping — and what wasn’t serving them.
Social Security and income planning: We created a customized strategy to time benefits in conjunction with their defined benefit income and annuity payments, helping to reduce risk and create reliable income.
Education funding reallocation: When their son opted out of college, we updated the 529 plan beneficiary to their grandson — keeping the funds growing tax-efficiently.
Real estate strategy: We analyzed whether to sell or retain the vacation property and medical office. Together, we discussed how to use equity to support their retirement goals and gifting plans.
Tax-aware gifting and generosity planning: We facilitated Qualified Charitable Distributions and explored donor-advised funds, aligning their giving goals with smart tax strategies.
Throughout this process, we worked in collaboration with their CPA to ensure every decision fit into a broader, cohesive plan.
The Journey
This was not a one-and-done financial plan.
Over the course of several years, their life — and therefore their plan — evolved. We adjusted as they sold their medical practice and prepared to retire fully. We modeled different timelines for property sales, accounted for capital gains taxes, and reserved cash for short-term needs — including a down payment gift to help their daughter purchase her first home.
Later, when they found their dream oceanfront property, we worked through the financial and emotional considerations of purchasing it. Our role was to help them feel confident in the “yes,” knowing it fit within their plan and wouldn’t jeopardize their future security.
The Outcome
Today, they are living the retirement they envisioned — and more.
Their accounts are simplified and aligned to support long-term goals
They’ve maintained the insurance policies that made sense and released the ones that didn’t
They’ve reduced their tax burden through strategic charitable giving
They’ve supported their children and created a path for legacy giving
And perhaps most importantly, they’ve stepped into this next phase with peace of mind
They know their financial life is no longer something to manage alone — they have a trusted partner by their side.
Reflections
& Wisdom
Wealth isn’t just about what you’ve accumulated — it’s about how you live with it.
This case is a reminder that financial complexity often comes not from lack of resources — but from lack of alignment. As advisors, our greatest value often lies in simplifying the tangled, reframing the journey, and creating a clear, intentional path forward.
Why Choose Skyline Advisors?
We help guide your financial future—we’re your dedicated advisors for life, not salespeople.
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