Retirement planning involves more than reaching a savings goal. Once you begin turning those savings into income, decisions about Social Security, taxes, Medicare, and investments start working together. A choice that looks sensible on its own can create unexpected costs elsewhere in your plan.

Some decisions can be adjusted later. Others have deadlines, tax consequences or restrictions that make a second chance difficult. You do not need to get every detail perfect, but you do need to understand the tradeoffs before you act. Here are five decisions worth a closer look as you approach retirement or review your current plan.

1. When to claim Social Security

It can be tempting to claim Social Security as soon as you are eligible, especially when you are ready to leave work. But you don’t have to start claiming social security the day you retire.

Starting before full retirement age generally means a lower monthly benefit. Waiting beyond full retirement age increases your retirement benefit through age 70. A larger monthly check, however, does not automatically make waiting the right choice for every household. Your health, other income, cash needs and family circumstances all deserve attention. Social Security explains the claiming rules here.

You have limited options to withdraw an application or suspend benefits, but each has specific requirements and consequences. Make your claiming decision carefully, because you can’t easily reverse it.

2. How much to convert to a Roth IRA

A Roth conversion can be appealing when you are thinking about future taxes. The amount you convert and the year you choose matter as much as the idea itself.

When you convert money from a traditional IRA to a Roth IRA, previously untaxed amounts generally become taxable income for that year. Amounts representing after-tax basis are treated differently. Converting a large balance without reviewing the tax impact can create an unwelcome bill.

Under current rules, you can’t reverse a Roth IRA conversion through recharacterization. That is different from the rules for certain regular IRA contributions. The IRS outlines these distinctions in Publication 590-A.

Before converting, compare the current tax cost with possible future benefits. Include how you would pay the tax and whether the additional income could affect Medicare premiums. A smaller conversion, a conversion spread across years, or no conversion may each deserve consideration. None is automatically best.

3. How income affects your Medicare premiums

Your Medicare premiums can reflect financial decisions made before the bill arrives. Higher-income beneficiaries may pay an income-related monthly adjustment amount, commonly called IRMAA, on top of their regular Part B and Part D premiums.

Social Security generally uses income information from two years before the premium year. That means a taxable Roth conversion or other income increase can affect premiums later, even if your current income has fallen. SSA explains the lookback process here.

IRMAA is not necessarily permanent. If a qualifying life-changing event, such as stopping work or reducing work, lowers your income, you may be able to request a lower determination from Social Security.

The practical lesson is this: review projected income and Medicare costs together. A tax strategy may still make sense with higher premiums, but be sure to put that cost in the comparison before you move forward.

4. Choosing which accounts to spend first

Two withdrawals of the same dollar amount can leave you with different amounts to spend after taxes. Money from a traditional IRA, a brokerage account and a Roth IRA does not necessarily receive the same tax treatment.

Traditional IRA withdrawals generally create taxable income, except for any applicable after-tax basis. Qualified Roth IRA withdrawals are tax-free. With a brokerage account, selling an investment can generate a taxable gain rather than making the entire sale proceeds taxable.

Required minimum distributions also limit how long you can leave money untouched in certain retirement accounts. The IRS explains RMD requirements and tax treatment here.

There is no single withdrawal order that fits every retiree. The useful question is which combination of accounts supports your spending while accounting for current taxes, future distributions and other income. Review that combination regularly, especially when a large expense or change in household circumstances comes along.

5. Taking investment risk that does not fit your income needs

An investment approach that felt comfortable while you were earning a paycheck may feel different when the portfolio must help pay your bills.

If you need to sell investments during a market decline, you will have fewer assets available to participate in any later recovery. But becoming overly conservative brings another concern: inflation can reduce what your money buys over a retirement that may last decades.

Your investment mix should reflect both near-term spending needs and longer-term goals. Consider how much income comes from other sources, how flexible your spending is and how much market volatility your finances can accommodate. Diversification can help manage risk, but it does not guarantee a profit or prevent losses. FINRA discusses these retirement portfolio tradeoffs here.

Look at the decisions together

These choices overlap. A conversion can affect taxes and Medicare premiums. Your Social Security timing can change how much you need to withdraw. Those withdrawals can influence the investment risk your plan can support.

Before making your next retirement decision, take a step back and review the connections. If you would like to discuss your questions with our team at RGA, contact us to start a conversation.

This material is for general educational purposes and is not individualized investment, tax or legal advice. Consult qualified professionals about your circumstances. All investing involves risk, including possible loss of principal.

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BETHANY J LONGFELLOW

Director of Client Engagement

862.207.3891

bethany@ronaldgelok.com

 

Bethany works remotely from her home in southwest Missouri. Bethany handles all the creative aspects for RGA, marketing, webinars, and connect with webinar participants just discovering our firm. Her goal is to help ensure RGA is available to everyone who wants personalized planning to live their dream retirements.

When Bethany’s not working, she rides competively in the jumper ring with her two horses, Sassy & Jax, and enjoys spending time with her three dogs, Banjo, Heidi & Roo. 

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TAMMIE BARONE

Director of Client Services

862.207.3841

tamara@ronaldgelok.com

 

Tammie has over 20 years’ experience working with and assisting financial advisory firms and has been a dedicated team member at RGA for nearly 10 years. As the Director of Client Services at the firm, she is the “go to” for all of our clients’ needs. Tammie maintains her Life and Health Insurance license in NJ, is dearly cherished by our clients, and if you ask any one of them, they will tell you that her passion is helping people.

Born and raised in Morris County, Tammie currently resides in Essex County, where she enjoys any outdoor activities, cooking and spending time with family, friends and her 2 dogs.

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CHRISTIAN VIVAS

Financial Advisor

862.207.3851

christian@ronaldgelok.com

 

Christian is a New Jersey native and received his Bachelor’s and Master’s Degree from Rutgers University in 2007 and 2010 respectively. He is an intricate member of the Financial Planning Team whose primary focus is on Income & Expense Projection and Lifetime Income Needs. He provides our clients with a comprehensive and educational explanation of the solutions that RGA provides that is easy to understand. Christian developed our Income Tax Reduction Analysis and spearheads strategic research initiatives for new, innovative solutions to retirement planning. Christian also oversees all marketing content and procedures while assisting with business development initiatives.

Outside of the firm, Christian spends his time teaching group fitness at YMCAs and private gyms. At home he unwinds by listening to music, taking care of his Guinea Pigs, and spending time with his wife Sarah, and their dog Chimichanga.

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ALINA ESTRIN

Executive Assistant to Brian Ginty

862.207.3868

alina@ronaldgelok.com

 

Alina was born in Russia, so she is fluent in English and Russian. Prior to joining RGA, Alina worked for the NJ State after carrier with Lehman Brother. Additionally, Alina has a PhD in economics. As Executive Assistant to Brian Ginty, Alina prepares applications, reviews documents, and analyzes illustrations prior to Brian presenting them to our future clients.

Outside of RGA, Aline continues her many years a Yoga, Thai Chi, and Pilates instructor.

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CHRISSY BODEN

Strategic Initiatives Coordinator

862.207.3866

chrissy@ronaldgelok.com

 

Chrissy (Gelok) Boden serves as Strategic Initiatives Coordinator at Ronald Gelok & Associates. In this role, she leads the coordination and execution of the firm’s key strategic initiatives, including innovation and AI-driven projects. She ensures priorities move forward with clear next steps, defined ownership, and structured timelines — keeping projects organized, aligned, and advancing.

Chrissy earned her Bachelor’s degree from Messiah College in 2012 and a Master’s degree in Counseling from Eastern University in 2014. She began her professional career in education as a school counselor and academic registrar, where she developed expertise in communication, systems management, and client-centered support.

Today, she applies that background to operational leadership at RGA, strengthening internal execution, enhancing organizational communications, and supporting a seamless client experience. Her work helps ensure that the firm’s strategic priorities translate into consistent, high-quality service for clients.

Chrissy is a New Jersey native and enjoys spending time with her husband and their three children, along with extended family and friends. When she has a quiet moment, she enjoys reading, biking, discovering new music, and brewing a great cup of coffee.

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BRIAN T GINTY, CSSC

Financial Advisor & Certified Structured Settlement Consultant

862.207.3843

brian@ronaldgelok.com

 

Brian was a Senior Vice President for The Halpern Group, a company which facilitated the establishment of trusts for plaintiffs in personal injury disputes. In addition to The Halpern Group, Brian has held senior management positions both at AIG Domestic Life Companies and Prudential Financial. He was also National Sales Director and Senior Vice President of Corporate Development at two of the largest structured settlement brokerage firms.

During his career, Brian has successfully negotiated more than 1000 cases throughout the United States and Canada.  He has been a leader in integrating trust and other financial vehicles to provide comprehensive financial strategies for tort victims. 

Brian is a regular speaker at legal seminars and meetings including the American Association for Justice, the North Carolina Association for Justice and the New Jersey Association for Justice.

Brian is a veteran of the United States Navy where he served as a cryptologist in Misawa. Japan.  During his three years in Japan, Brian played for the base soccer team as well as coached the high school team.  He also taught English and attended the University of Maryland, Far East Division.  He graduated magna cum laude with a dual major in Business Management and Psychology.  Upon his discharge Brian enrolled in Rutgers Graduate School of Management while he began his career in the financial services industry. 

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HELENA MATTIOLI-KING

Operations Coordinator

862.207.3846

helena@ronaldgelok.com

 

As RGA's Operations Coordinator, Helena ensures the company functions efficiently and effectively on a day-to-day basis. She is a vital part of both the Operations and Retirement Planning Teams. With both her Bachelor's and Master's degrees from Ramapo College, Helena continues to use her education and prior work experience to continue to go above and beyond for RGA and our clients.

Outside of RGA, Helena enjoys spending time with her beloved cats, Rosie and Jelly. She also enjoys reading and spending time with her family.

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THOMAS J SMITH, MBA, JD, LLM

Director of Tax Reduction Planning

862.207.3846

tom@ronaldgelok.com

 

Bio coming soon.

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MORGAN KELLY WINTRINGHAM

Director of Operations & Certified Financial Fiduciary

862.207.3808

morgan@ronaldgelok.com

 

With sixteen years of experience in the financial services industry, Morgan plays a central leadership role in ensuring every client experience reflects precision, clarity, and care. Having spent more than a decade with the firm, she partners closely with the Advisory and Leadership teams to translate thoughtful retirement strategies into seamless execution. From overseeing client onboarding to strengthening internal infrastructure and developing team members, she helps maintain the high standards and concierge-level service the firm is known for. As a Certified Financial Fiduciary®, she is committed to upholding the structure, accountability, and stewardship that support each client’s long-term success.

Outside of the office, Morgan has been married to her husband, Stephen, for four years and is the proud mother of their one-year-old son, Ronan, who keeps her joyfully busy. Family is at the center of everything she does, and much of her time outside of work is spent creating a warm home and fully embracing this season of motherhood.

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GINA RUSSO

Wealth Management Coordinator

862.207.3847

gina@ronaldgelok.com

 

Gina Russo is based in New York and has a deep appreciation for both learning and connection. She is an avid reader who enjoys exploring new ideas through books and loves discovering new restaurants and experiencing different cuisines, always eager to try something new.

Above all, Gina values spending quality time with her family and friends, whether that means sharing a meal, having meaningful conversations, or simply enjoying each other’s company. She believes that balance, curiosity, and strong relationships are what make life truly fulfilling.

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DAN SHERMAN

Financial Advisor

862.207.3860

dan@ronaldgelok.com

 Dan Sherman is a seasoned financial advisor with two decades of experience in wealth management. A native New Yorker, Dan earned his MBA from New York University in 2007. He specializes in comprehensive financial planning, retirement strategies, and investment management, helping clients navigate their financial futures with confidence.


Away from the office, Dan is an avid athlete who enjoys tennis, long-distance running, and surfing. He splits his time between New York and Connecticut with his fiancée, Olyia. Deeply committed to his community, Dan is a dedicated volunteer Suffolk County firefighter and an ocean lifeguard on Fire Island, a place he has summered since childhood.

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LEAH SCHMIDT

Office Administrator

862.207.3801

leah@ronaldgelok.com

 

Leah is the Office Administrator who enjoys supporting the team behind the scenes and helping keep everything running smoothly. Known for her organization, reliability, and attention to detail, Leah takes pride in being someone others can count on. Leah is committed to professionalism and creating a positive, efficient office environment for both colleagues and clients. Born and raised in New Jersey, Leah is a big family person and a dog lover at heart.

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ASHLEY STANICH
Client Onboarding Manager
862.207.3842
ashley@ronaldgelok.com

ASHLEY STANICH

Client Onboarding Manager

862.207.3842

ashley@ronaldgelok.com

 

Ashley joins the RGA team as a Client Onboarding Manager, where she partners closely with the advisory team to deliver a smooth, organized, and client-focused onboarding experience. With a strong passion for supporting advisors, she has built her career in operations, where she excels at managing details, streamlining processes, and keeping multiple priorities moving forward with precision. She takes pride in being a reliable point of coordination and ensuring nothing falls through the cracks.

Outside of the office, Ashley enjoys life with her fiancé and their puppy, Shortcake. She is currently embracing the excitement (and occasional challenges) of homeownership while planning her upcoming wedding. A passionate traveler, Ashley loves exploring new destinations, immersing herself in different cultures, and discovering local food scenes around the world. Whether it’s a weekend getaway or an international adventure, she’s always looking for her next destination and the experiences that come with it. A true foodie at heart, she enjoys restaurant pop-ups, trying new cuisines, and turning every trip into a memorable culinary experience.

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