Ranking the year-end tax data-gathering process for $2M to $8M retirees from easiest to hardest to build an accurate fall income tax projection before December 31st.

Episode 50 of Retirement Tax Matters reviews the numbers behind the latest Social Security Trust Fund report and what the possible projected 2032 reserve depletion means for retirees between $2M and $8M. Garrett Crawford, CFP® and Adam Reed walk through the report details, noting that while trust fund reserves are projected to run out in the fourth quarter of 2032, ongoing payroll tax revenues may still cover approximately 78% of scheduled benefits.

Avoid the April 15th tax surprise. Today’s conversation centers on three areas we see where high-net-worth retirees can get tripped up and experience a larger-than-expected tax bill come tax filing day.

Could staying at your desk for just six extra months be worth 30 years of previous savings? Discover an interesting math discussion behind a 2018 NBER study called The Power of Working Longer and why it’s important for high-net-worth retirees to take note. In this episode of Retirement Tax Matters, Garrett Crawford, CFP® breaks down the three levers of One More Year Syndrome and the proactive tax-return-driven strategies you might consider if you encounter this.

Episode 12 of Retirement Tax Matters focuses on Social Security optimization for Hign-Net-Worth retirees, framing it as a critical spousal protection and legacy tool rather than a simple break-even calculation…

The passage of the recent tax legislation, One Big Beautiful Bill Act (OBBBA), has created significant confusion around how Social Security will be taxed. Many retirees are asking if their benefits will now be tax-free. In this episode, Garrett Crawford breaks down the reality of the new law, explaining that the primary change is not to Social Security taxation itself, but the introduction of a new, substantial "Senior Deduction." We'll cover who qualifies for this deduction, the specific income phase-outs that could affect HNW retirees, and the critical planning dilemma it creates when considering strategic Roth conversions.