Robert L. Field, CF2™, CFS, NSSA, IRMAACP
Robert L. Field
NSSA® · IRMAACP · CF2® — Social Security & Medicare planning specialist at Nelson Financial Planning

Rob Field is a Partner and Financial Planner at Nelson Financial Planning, Inc. and a FINRA Registered Representative with Nelson Ivest Brokerage Services, Inc. He joined the Nelson team in September 2015, bringing with him more than three decades of experience across some of the most recognizable names in the financial services industry.
Rob has become the firm's go-to resource for two of the most complex — and most misunderstood — areas of retirement planning: Social Security strategy and IRMAA. He holds the National Social Security Advisor (NSSA) designation and the IRMAA Certified Planner credential, making him one of the only advisors within 50 miles of Winter Park to hold both at the same time. Social Security and Medicare premiums are deeply intertwined, and the decisions clients make about income and withdrawals in the years before and after retirement can have a lasting impact on what they actually take home each month.
Beyond Social Security and Medicare, Rob brings deep expertise in portfolio analysis, asset allocation, mutual fund strategy, income distribution, and legacy planning. His background includes nearly a decade as Regional Vice President at Nationwide Financial Services and roles at Trinity Financial Services and in life settlement portfolio analysis — giving him an unusually broad, practical understanding of how money moves across a client's full financial life.
FIDUCIARY COMMITMENT
At Nelson Financial Planning, every advisor is a Certified Financial Fiduciary™ — not because it's required, but because we believe there's no other way to practice. Rob's advice is always, exclusively, in your best interest.
Father of twins Robert and Elizabeth, and grandfather to Maisie and Graham. Rob enjoys golf, tennis, and Florida's beaches — and says grandfatherhood has given him a new appreciation for long-term planning.
Rob is active in the community, staying involved with the Paralyzed Veterans Association, Fresh Start Ministries, and the SPCA.
We offer complimentary consultations - no minimums, no pressure. Book your conversation today!
What Rob Helps Clients With
Understanding why your Social Security check is smaller than expected
Planning withdrawals to stay below IRMAA Medicare surcharge thresholds.
Appealing an IRMAA surcharge after a one-time income event.
Coordinating Social Security timing with Medicare enrollment.
Portfolio analysis and asset allocation for retirement income goals.
Income distribution - sequencing IRAs, SS and investments efficiently.
RMD planning and coordination across accounts.
Legacy and estate coordination across asset classes.
Rob Featured on Dollars & Sense Financial Podcast
Medicare Advantage Secrets & Divorce Money Traps | What Retirees Must Know
Market Boom & Social Security Shakeup | What It Means for Your Retirement
7 Investment Mistakes that Could Destroy Your Retirement
6 Retirement Milestones You Can’t Afford to Miss (Most People Forget These!)
Credentials & Designations
IRMAA Certified Planner
IRMAACP
Specialized training in Medicare's income-related premium surcharge system - covering minimization strategies, the SSA-44 appeal process, and proactive income management.
One of the only advisors within 50 miles of Winter Park to hold this alongside the NSSA.
National Social Security Advisor
NSSA®
Certification in Social Security optimization - benefit timing, spousal coordination, WEP/GPO rules, and integration with Medicare and retirement income.
Certified Financial Fiduciary™
CF2®
Demonstrated commitment to the fiduciary standard. Every recommendation is made solely in the client's best interest. Every Nelson advisor holds this designation by choice.
Certified Funds Specialist
CFS®
Advanced training in mutual funds analysis, portfolio construction, and investment selection matched to individual goals and risk profiles.
Series 6 · FINRA
Investment Company and Variable Contracts license, held with Nelson Invest Brokerage Services, Inc.
B.B.A.
Bachelor of Business Administration - Sam Houston State University, Huntsville, TX






