Profile
A couple in their late 50s. He's a senior executive at a large financial services company earning approximately $950,000 per year. They have two adult daughters and are planning to retire within the next year.
The Situation
After decades of building wealth at the highest levels of corporate America, this couple was ready for a transition — but that transition was anything but simple. They were planning to sell their primary residence and a property in Telluride, relocate to the Mountain West, and leave behind an executive role that had defined much of their adult life.
Each of those moves came with a cascade of financial questions. How would they handle health insurance before Medicare? What should they do with the 401(k), 457(b), HSA, and HRA accounts tied to his employer? Should they purchase their new home with cash or take out a mortgage? What about the cost basis and estate handling for their digital assets? How could they give charitably in the most tax-efficient way? Should they keep or drop their life insurance policies? And when was the right time to update their estate plan to reflect all of these changes?
The questions weren't just financial — they were deeply personal. This was about leaving a career behind, building a new life in a new place, and doing it all with clarity and intention.
Statement of Financial Purpose
“We desire financial independence so that we can be comfortable and live peacefully.”
What the Plan Focused On
- ●Selling two properties and purchasing a new home, including a detailed cash-versus-financing analysis
- ●Exiting the executive role with a clean, well-planned transition
- ●Dedicating year one to travel and exploration
- ●Settling into a new community — finding a church, building friendships
- ●Funding two daughters' weddings at approximately $50,000 each
- ●Updating their estate plan and legacy structure
- ●Establishing a charitable foundation
- ●Being open and accessible for family
- ●Making the most of the next ten years
- ●Priority order: Faith, then Family, then Self
Action Items
- ●Comprehensive expense audit to establish a baseline for retirement spending
- ●Review 401(k), 457(b), HSA, and HRA accounts for rollover and distribution planning
- ●Analyze new home purchase: cash versus mortgage, capital sourcing strategy, and capital gains exclusion timing
- ●Establish cost basis documentation for digital assets
- ●Develop a tax-efficient charitable giving strategy
- ●Health coverage gap analysis for the period before Medicare eligibility
- ●Life insurance evaluation — keep, reduce, or drop existing policies
- ●Structure and establish a charitable foundation
- ●Year-one travel logistics and budgeting
- ●Beneficiary review across all accounts and policies
- ●Comprehensive estate plan update
- ●Introduction to a CPA for coordinated tax planning
Why This Story Matters
For a couple at this income level, the question was never “Do we have enough?” The real challenge was orchestrating a complex, multi-step transition without leaving anything to chance. Selling two homes, buying a third, relocating across the country, leaving behind an executive career, managing employer-tied accounts, and launching a charitable foundation — all at the same time.
Without a coordinated plan, any one of those decisions could have created unnecessary tax liability, gaps in coverage, or misaligned timing. With a plan, every piece moved in sequence — and this couple was able to walk into their next chapter with the same confidence and clarity that defined their careers.