Our planning process

The Southshore System

A simple breakdown of what it looks like to work with a financial planner

1

Onboarding

Establish login credentials with RightCapital. We gather information surrounding your current financial state with the ability to upload documents like tax returns, social security statements, investment statements, insurance declaration pages and estate planning documents.

01

2

Design Meeting

Meet to discuss the vision and goals questionnaire that each completed. It’s a great way to get to know each other and create space for each individual to share what is important to them in retirement.

02

3

Investment Planning

Meet to discuss your preferences for risk, volatility, and returns. We talk historical risks/returns of stock and bond markets. Then discuss why our investment philosophy revolves around low-cost index and factor-based (DFA/Avantis) ETFs.

03

4

Strategy Session

Meeting to explore and compare alternative scenarios in Income Lab. I’ll show different timing for retirement, tax strategies (bracket management with Roth conversions), and spending levels

04

5

Delivery Meeting

Meet to deliver and evaluate planning strategies in all 7 retirement planning areas. I provide a bullet-point executive summary of ideas, with supplemental sections. We will discuss and prioritize top-tier recommendations.

05

"...Chris did an exceptionally thorough job analyzing my full financial picture. He uses a very organized, step-by-step planning process that includes a series of focused meetings, which allowed us to thoughtfully build a plan together. The final product was detailed, refined, and well thought out. It addressed cash flow projections, tax considerations, Roth conversion strategies, Social Security timing recommendations for both spouses, and asset allocation with appropriate adjustments....."

Testimonial Disclosure

Our 7-Point Retirement System

Before looking at a single number, we focus entirely on the life you want to build. We help you map out your retirement "must-haves" alongside those big, exciting bucket-list dreams. Together, we use these personal aspirations to design a customized roadmap.

Common Questions We Answer:

How do I balance my immediate bucket-list dreams with my long-term financial security?

How do I reconcile different retirement goals with my spouse?

How do I transition mentally from a lifetime of aggressive saving to suddenly relaxing and enjoying my life?

Transitioning from saving money to spending it can be one of the most stressful phases of retirement. We help you build a reliable "retirement paycheck" that you are comfortable with. Our dynamic plan is structured to prevent both overspending and underspending, letting you confidently enjoy life to the fullest.

Common Questions We Answer:

Where exactly will my monthly income come from once my salary stops?

How will my income plan adapt if the stock market goes through a sudden downturn?

When is the most optimal and tax-efficient time for me to claim Social Security?

Taxes will likely represent one of your single largest expenses throughout your retirement years. Unlike traditional tax preparation that only looks backward at last year, our planning proactively focuses on forward-looking strategies. We look for smart opportunities to minimize your total lifetime tax liability so you keep more of your wealth.

Common Questions We Answer:

How can I lower the taxes I pay when withdrawing from my IRAs or 401(k)s?

Does it make sense for me to do Roth IRA conversions, and if so, when?

How will my retirement income level impact my Medicare premiums (IRMAA)?

Health care is often the single largest wildcard and a confusing aspect of retirement, which is why we model health care and long-term care expenses directly into your plan. We also have partners who can assist with bridging the pre-Medicare health insurance gap, enrolling in Medicare, or selecting optimal supplemental policies.

Common Questions We Answer:

What are my health insurance options if I want to retire before Medicare starts?

Will I be automatically enrolled in Medicare when I turn 65?

Is Long-Term Care Insurance (LTCI) actually worth the premiums, or is it better to self-insure?

We believe in designing evidence-based portfolios tailored to your financial goals. By educating you on how different market climates impact investments, we establish an asset mix that balances your personal risk tolerance with your retirement needs. From there, we manage or recommend investments across all your accounts to keep you aligned with your long-term plan.

Common Questions We Answer:

Is my current investment portfolio too risky—or too conservative—for retirement?

How do I transition my portfolio from a "growth" focus to a reliable "income" focus?

How do I protect my portfolio from Sequence of Returns Risk?

As a fee-only advisory firm, we do not sell insurance products or earn commissions from referrals. This independence allows us to provide an entirely unbiased, professional review of your existing insurance coverage. We identify potential gaps and give you a clear checklist to review with your agent.

Common Questions We Answer:

Am I currently overpaying for insurance coverage I no longer need in retirement?

Do I have any hidden gaps in my homeowners or auto policies?

Do I need an Umbrella Liability Policy in retirement?

A great estate plan ensures your wishes, your care, and your legacy are fully protected if you cannot make decisions yourself. We review your current wills, trusts, and power of attorney documents to ensure they align with your actual goals. If your plan needs to be created or updated, we connect you with trusted estate attorneys or services to complete the process.

Common Questions We Answer:

Who will handle my financial and medical decisions if I suddenly become incapacitated?

How do I prevent my heirs from going through the complex, costly, and public probate court process?

What happens to my Traditional and Roth IRAs when I leave them to my heirs?

"...We've been clients of Southshore Financial Planning for the past 4 years and felt it has been well worth the investment. We have a somewhat complex financial profile with multiple businesses including our primary business being highly seasonal and commission based . . . Beyond his wealth of knowledge, Chris down to earth, very approachable and accessible to bounce ideas or talk through implications to our overall financial plan at a moment's notice outside of scheduled meetings he normally coordinates...."

Testimonial Disclosure

Winter Spring Fall Meetings

"I’ve been with Chris for several years and he is outstanding in what he does. He listens to your goals and offers practical advice/solutions for your needs. Because of him and his efforts I can breathe easy in retirement and not worry about paying for better healthcare needs or living expenses."

Testimonial Disclosure

(813) 406-0544

(855) 949-3718

hello@southshorefp.com

We deliver tailored solutions to help you live your best life through dedicated financial planning and investment management strategies that are personalized to your needs, goals and lifestyle.

Talk with an Advisor

Office: 1600 E 8th Ave., Ste. A200 Tampa, FL 33605

Additional Location: 200 Central Ave. St. Petersburg, FL 33701

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Southshore Financial Planning LLC (“Southshore Financial Planning”, “Southshore”) is a registered investment advisor offering advisory services in the State of Florida and in other jurisdictions where exempted. Registration does not imply a certain level of skill or training. The presence of this website on the Internet shall not be directly or indirectly interpreted as a solicitation of investment advisory services to persons of another jurisdiction unless otherwise permitted by statute. Follow-up or individualized responses to consumers in a particular state by Southshore Financial in the rendering of personalized investment advice for compensation shall not be made without our first complying with jurisdiction requirements or pursuant to an applicable state exemption.

All written content on this site is for information purposes only. Opinions expressed herein are solely those of Southshore Financial Planning, unless otherwise specifically cited. Material presented is believed to be from reliable sources, and no representations are made by our firm as to other parties’ informational accuracy or completeness. All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation.