Christina Woodling
Affiliations
Professional Details
I am a Retirement Strategist and Registered Social Security Analyst (RSSA) through the National Association of Registered Social Security Analysts (NARSSA). I work with individuals and families to help them understand Social Security benefits, Medicare options, estate-planning considerations, and life insurance as part of an integrated retirement strategy.
My focus is on education and clarity—helping people make informed decisions, avoid common planning mistakes, and better understand how their benefits and protection strategies work together. I frequently collaborate with other professionals to support long-term planning and legacy goals.
I am committed to professionalism, transparency, and serving the community through education and trusted relationships.
In the News
Newsweek | Some Americans Could Get New Social Security Numbers Under Bill
December 2, 2025
Christina Woodling, a Registered Social Security Analyst and the Founder of Five Star Freedom Group, experienced the troubles that can arise after her child’s Social Security number was stolen and… Read More
Upcoming Events
5 Ways to Exit Your Business
Thursday, October 15, 2026 7:00 PM ET
https://us02web.zoom.us/j/81439183373
Description: You are in business today. One day, you will be out of business.
one of five ways:
o Death, o Disability, o Retirement, o Voluntary Sale, o Bankruptcy.
• My job is to help you exit your business with the maximum profit for you and your family.”
Estate Planning Education ( Wills and Trusts)
Tuesday, October 27, 2026 11:00 AM ET
Greater Sarasota Chamber of Commerce
Description: An estate plan is vital for any individual, couple, or family that owns a home and has assets.
Ensure that your estate planning is in good order by reviewing the methods families use to avoid the delays and legal fees of probate court.
Learn various methods and best practices to protect your family from unnecessary costs and wasted time in probate.
You will learn the following topics in easy-to-understand terms: • The advantages and disadvantages of wills and living trusts
How powers of attorney work and don’t work (some may not be valid if you are disabled or pass away) •
How Probate Court works and why you may want to avoid it for your family
Why putting property in your children’s names may be a mistake • Common missteps by families raising children with challenges, disabilities, or special needs
Protecting your home from being swallowed up by the costs of nursing home care.
Protecting your heirs’ inheritance from lawsuits, divorce, and spendthrifts.
Best practices for naming retirement accounts and life insurance beneficiaries
Estate Planning Education ( Wills and Trusts)
Thursday, October 29, 2026 11:00 AM ET
Greater Sarasota Chamber of Commerce
Description: An estate plan is vital for any individual, couple, or family that owns a home and has assets.
Ensure that your estate planning is in good order by reviewing the methods families use to avoid the delays and legal fees of probate court.
Learn various methods and best practices to protect your family from unnecessary costs and wasted time in probate.
You will learn the following topics in easy-to-understand terms: •
The advantages and disadvantages of wills and living trusts:
How powers of attorney work and don’t work (some may not be valid if you are disabled or pass away) •
How Probate Court works and why you may want to avoid it for your family
Why putting property in your children’s names may be a mistake • Common missteps by families raising children with challenges, disabilities, or special needs
Protecting your home from being swallowed up by the costs of nursing home care.
Protecting your heirs’ inheritance from lawsuits, divorce, and spendthrifts.
Best practices for naming retirement accounts and life insurance beneficiaries
Real Stories from Real People
Most People Leave Money on the Table
96% Don't Optimize
Very few people get all the Social Security they’re entitled to.
$111,000 Average Lost
The average household is losing $111,000 in potential income.
1 Chance To Claim
Social Security gives you one chance to get it right – forever.
Maximize Your Benefits
Discover important information for your situation.
Married
If you are married, you may be able to collect up to one-half of your spouse’s Social Security benefit. This won’t affect your spouse’s checks. Ask an RSSA® for details.
Divorced
If you are divorced and 62 or older, you may qualify to receive Social Security benefits from your ex-spouse — in addition to your own Social Security payments. Ask an RSSA® for details.
Widowed
If your spouse has passed away, you may be eligible for a survivor benefit. The extra money may be essential for you. Ask an RSSA® for details.
Single
If you are single, and solely responsible for your retirement, making the optimal Social Security claiming decision is particularly important. Ask an RSSA® about your options.
Self-Employed
As a self-employed person, you may be able to decrease your payroll taxes — yet still receive the maximum income from Social Security. Ask an RSSA® for details.
Disability
Social Security can provide valuable disability benefits if you qualify, but these benefits — and how you qualify for them — are often misunderstood. Ask an RSSA® for details.
Immigrant
If you are a lawful permanent resident, but not yet a citizen, you may still qualify for Social Security benefits. Ask an RSSA® for details.
