By Steve Seals
Imagine waking up five years from now with no alarm clock, no meetings, and the freedom to spend your time exactly how you want. Maybe it’s traveling, volunteering, or simply enjoying slower mornings. That vision of retirement may feel close, but turning it into reality requires careful preparation.
The five years before retirement are some of the most important in your financial life. It’s the time to tighten your plans, assess your options, and make intentional decisions.
So, how do you know if you’re on the right track? Start by asking yourself these five questions. They can help you identify blind spots and build a solid foundation for the years ahead.
1. What Do You Anticipate for Your Retirement Income?
Start by creating a complete picture of your expected income streams. These may include:
- Social Security
- Pensions
- 401(k) and IRA distributions
- Investment or rental income
- Part-time work or consulting
Understanding when each income stream becomes available (and what taxes might apply) is essential. For example, withdrawing from a traditional IRA before age 59½ may trigger a penalty, while delaying Social Security past full retirement age can significantly boost your monthly benefit.
Even if retirement is a few years off, it’s worth running projections now. You may uncover opportunities to increase your income or optimize your withdrawal strategy.
2. What Will Your Retirement Expenses Be?
Many people underestimate how much they’ll spend in retirement. While some expenses, like commuting or work-related costs, may go down, others can go up, especially healthcare and travel.
Create a detailed retirement budget by including:
- Monthly living expenses
- Travel plans
- Health insurance and out-of-pocket costs
- Hobbies or new pursuits
- Financial support for adult children or grandkids
- Home renovations or downsizing costs
Don’t forget to factor in inflation. What costs $4,000 per month today could easily be $5,500 in a decade. And always leave room for the unexpected: emergency repairs, medical bills, or helping a loved one.
3. When Should You Actually Retire?
Just because you can retire at a certain age doesn’t mean it’s the right time for you. This is a deeply personal decision that blends financial readiness with emotional and psychological preparedness.
From a numbers perspective, even working one or two additional years can help:
- Boost your savings
- Increase your Social Security benefit
- Delay withdrawals from your retirement accounts
But also think beyond the balance sheet. Are you ready to step away from your work? Do you have hobbies or goals that will bring you purpose and joy in retirement?
For more on this topic, read our guide: When to Retire: December, January, or Mid-Year?
4. What’s Your Healthcare Plan?
Healthcare is one of the biggest and most complex expenses in retirement. If you’re retiring before age 65, you’ll need a plan to bridge the gap until Medicare kicks in.
Once eligible, take time to explore:
- Medicare Parts A, B, and D
- Medigap or Medicare Advantage plans
- Employer-sponsored retiree coverage (if available)
Costs to consider include premiums, deductibles, copays, prescription costs, and dental or vision care not covered by Medicare. And don’t forget about long-term care planning, a major financial blind spot for many retirees.
Understanding your options in advance can prevent last-minute surprises and help you get the coverage you need.
5. Have You Discussed Your Plans With Loved Ones?
Retirement doesn’t happen in a vacuum. It affects your spouse, family, and even close friends. Whether you plan to travel, move, or spend more time at home, it’s important to communicate your vision.
Start with your spouse or partner: Are you aligned on your retirement timeline, spending plans, or big goals? Then expand the conversation to your adult children or others who may be affected by your choices.
Discussing your plans early can help set expectations and foster support as you enter this exciting chapter.
Planning Ahead Gives You Freedom Later
Retirement means stepping into a new way of life. It’s a transition that involves your finances, your identity, and your vision for the future.
Remember that you don’t have to go it alone. At Seals Financial Planning & Investments, we’re your dedicated partner on the road to financial clarity and confidence. For those approaching retirement or already in the midst of it, we recognize the unique financial decisions this phase brings. Our team is here to guide you every step of the way—with tailored retirement planning and investment strategies that align with your specific goals, lifestyle, and circumstances.
Our team can help you navigate the shift from accumulation to distribution and craft a strategy that empowers you to retire on your terms.
Want to talk through your timeline? Please give us a call at (859) 230-3476 if you would like to schedule a time to meet.
About Richard Stephen (Steve) Seals
Steve Seals is owner and independent Registered Investment Advisor Representative at Seals Financial Planning & Investments VI, LLC, a financial planning services firm based in Lexington, KY. As an independent Registered Investment Advisor Representative with about two decades of experience in the investment and insurance industries, Steve’s firm is founded on getting to know each client personally, allowing him to provide sound financial advice throughout their career and into retirement. With the mission of guiding clients on the path of success, Steve is fueled by his commitment to excellence and goes the extra mile to make sure clients are fully satisfied. He believes in maintaining a positive mindset, creating partnerships with a purpose, and always striving for significant outcomes.
Born in Jenkins, Kentucky, Steve grew up with a love for basketball and serving his community. After high school, he served nine years in the United States Marine Corps, then earned a bachelor’s degree in accounting. He was eventually able to put his degree and desire to help others to work as a fiduciary financial planner. Prior to founding his own firm in 2014, Steve learned from working with Edward Jones, US Bank, University of Kentucky Federal Credit Union, and CUSO Financial. He also received his Security Series 63 and 65/66 through Keystone Financial Group, LLC, and holds various life, health, and variable insurance licenses.
Steve and his wife, Angie, have three daughters (Lauren, Peyton, and Ashton) and two grandsons (Kenyon and Kai). Steve holds a private pilot’s license, and the family enjoys sports, spending time at the lake, and traveling. To learn more about Steve, connect with him on LinkedIn.
