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When Is the Right Time to Retire?

Get Your Financials in Order, Gain Financial Freedom, and Get the Most Out of Retirement

​Budgeting for retirement is based on a projected retirement date.  But when most people start their retirement income planning, they may not be sure exactly when they will want to step away from their job—and as they age, their planning for retirement may change. If you are thinking about accelerating your retirement plans, you are not alone.

CERTIFIED FINANCIAL PLANNER™ practitioners work hard to make sure their clients are ready for retirement. When people change their minds about when they want to retire, their retirement income planning does, too. Sudden changes in fortune or lifestyle can prompt people to wonder if they can reach financial freedom sooner than they expected, like coming into a big inheritance, a generous severance package near the end of a career or a big offer to sell your company, or even a health scare or a spouse’s retirement.

If you feel you may be reaching financial freedom sooner than you thought, we are always ready to explore your options for an early retirement.

So, when should YOU retire? Not before you can answer “yes” to the four questions below!

1. If I retire now, is my healthcare—and that of my spouse—covered?

When you think about your road to financial freedom, do you think about your personal health? You should. If you are like most working people, you have a health insurance plan that is covered or partially compensated by your work. Retiring tips don’t often talk about health care because they assume you have reached the age of 65 and are eligible for Medicare plans.

If you retire today, how will you get healthcare for yourself and for your family? Depending on your retirement plans, you may need to pay for your health insurance plan out of pocket for years—and potentially for your spouse and for any children under age 26 currently on your healthcare plan as well. A high-quality healthcare plan that goes beyond catastrophic coverage can be costly, depending on your age or any pre-existing conditions. (Don’t fall for low-cost, Medishare-style junk plans that do not provide adequate coverage!)

Healthcare challenges can strike at any time and turn your financial freedom into a financial disaster. At Oak Street Advisors, our fee-only financial advisors recommend strategies to protect your finances from catastrophic healthcare expenses while concurrently also minimizing taxes and potentially realizing tax-free investment growth if you choose to retire before you are eligible for Medicare.

If I retire now, can I get by without my social security benefits?

Most retirement strategies rely on social security benefits on some level. During your retirement income planning, your financial advisor helps you decide the optimal time to begin drawing your social security income. Most try to find ways for you to postpone taking social security until you reach at least full retirement age—as late as 67 years old, depending upon your birthdate, if not age 70.

If your retirement income planning relied on receiving social security (or receiving the maximum amount of social security) and you are not yet eligible to draw payments, can you replace that income or get by without it until you reach the appropriate age?

If I retire now, am I truly debt-free?

Financial planning after retirement usually assumes you have paid off all of your credit cards, any outstanding medical or educational debts, and—hopefully—your home. Most CERTIFIED FINANCIAL PLANNER™ practitioners encourage all of our clients to make a debt-free retirement a high priority. You cannot retire with confidence if you are still making credit card, car, boat, student loan, or mortgage payments.

Why? Peace of mind. When your home is paid off, your retirement income planning needs to cover taxes, insurance, and general home maintenance, not costly mortgage payments.

If I retire now, do I have a personal or professional goal?

Financial freedom tips fail to ask what, exactly, you plan to do with that newfound financial freedom. When you begin planning for your retirement, you should think about what your hopes and dreams for this incredible phase of your life might be.

Getting away from the daily grind can sound wonderful when we are in the working world. But if you do not have ideas or plans for how to spend that new free time, you may find it weighs more heavily on you than you had imagined. Your retirement plans should include more than retirement income planning. Retirement planning should include new challenges, opportunities for learning and personal growth, restorative rest and relaxation, community involvement, family connections, travel … whatever is meaningful and motivating for you. Your road to financial freedom needs a destination.

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Christina Norwood​

Christina Norwood​

Operations Manager

Born and raised in Maryland, I moved to South Carolina in 2023 and joined Oak Street Advisors’ Myrtle Beach office in 2024 as the firm’s Operations Manager.  I’ve worked in the financial service industry most of my career, including ten years for a large brokerage firm and the last two years as a Client Relations Specialist at a similarly sized RIA. 

I enjoy working hand-in-hand with our clients on all administrative and operational needs. Client satisfaction and planning efficiency are my top priorities — as I take pride in providing proactive service to every client household at Oak Street Advisors.
 
While not in the office, I enjoy quality time with my family, walking my rescue dog, Auggie, on the beach, cooking, and exploring South Carolina.

Ryan cooper

Fiduciary Financial Advisor

​I joined Oak Street Advisors’ Myrtle Beach office in 2021. I currently serve as a fiduciary financial advisor and associate financial planner. I hold the Series 65 and am working towards obtaining my CERTIFIED FINANCIAL PLANNER (TM) accreditation. 

I strive to provide clients diligent and proactive service while assisting the team with planning, investment strategies, and recommendations.
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While not in the office, I enjoy running, golfing, fishing, going to the beach with my wife Natalie and our son Bennett, and watching my beloved Green Bay Packers play (I even own stock in the team!).

BRYAN TAYLOR, CFP®

Owner & President  | Fiduciary Financial Advisor

I graduated from Clemson University and began my financial planning career shortly after with a small advisory firm on the ground floor — learning the basics of financial and tax planning and running a financial advising business.

At the same time, I enrolled in the University of Georgia Terry College of Business’ Executive Program in Financial Planning and completed the coursework at nights and on weekends. Soon after, I completed my CFP® certification and joined the family business.

A year after I joined the firm, we opened our second location in Mt. Pleasant, SC where I reside with my family. Over the next 10+ years I cherished the opportunity to learn and grow the family business with my father. We worked hard to build the firm into what it is today — something we’re both proud to say we accomplished together.

Today, I serve in a Senior Advisor and Planner role, working together with our team on all financial plans and strategies. By collaborating we provide fiduciary financial and tax planning and asset management to our clients within a fee-only business model — which reflects our conviction of putting our clients’ interest above the next dollar.

When I’m away from the office, I enjoy playing golf, boating, pulling for the Clemson Tigers, and relaxing on the beach with my wife, Laura, and daughters Riley and Ramsey.

Links:
NAPFA – National Association of Personal Financial Advisors
Certified Financial Planner© Professional
LinkedIn
Fee Only Network