6 Key Questions to Ask as You Approach Retirement
Retirement used to mean collecting a pension, receiving Social Security, and coasting into your golden years. But today’s retirees are facing more decisions—and more complexity—than ever before.
As you get closer to that next chapter, asking the right questions now can help you enter retirement with greater clarity and confidence. Here are six important questions to consider before you take the leap.
1. When should I claim Social Security?
The age at which you file for Social Security can have a big impact on your monthly benefit—and your long-term income. While you can start collecting as early as age 62, doing so can reduce your benefit by up to 30%. On the other hand, delaying until age 70 could increase your monthly check by 24% or more.
Ask yourself:
Do I need the income right away?
Am I in good health with a family history of longevity?
How will my filing age affect a spouse or survivor?
Coordinating your filing strategy with your other income sources can help you get the most out of your benefit.
2. How much income will I need? And where will it come from?
Retirement isn’t just about your total savings but rather how those savings will be used. Start by estimating your monthly spending needs, including:
Housing and utilities
Healthcare
Travel and leisure
Taxes
Inflation
Then identify your income sources: Social Security, pensions, rental income, annuities, investment withdrawals, or part-time work. A financial professional can help you turn your nest egg into a reliable income stream that supports your lifestyle.
3. What’s my strategy for healthcare?
One of the biggest retirement surprises? Healthcare costs. Even with Medicare, many retirees are surprised to learn just how much they pay out of pocket.
According to recent estimates, a retired couple may spend over $300,000 on healthcare during retirement. That includes:
Medicare premiums
Deductibles and copays
Prescription drug costs
Long-term care
Be sure to explore Medicare Advantage or Medigap plans, and consider long-term care insurance or other protection options. Planning ahead now can help you avoid unexpected medical expenses later.
4. How will taxes impact my retirement income?
It’s easy to assume your tax bill will go down in retirement, but that’s seldom the case. In fact, without a thoughtful tax strategy, you could end up paying more than expected and shrinking the very income you’ve worked so hard to build.
Not all retirement income is taxed the same way. For example:
Traditional 401(k) and IRA withdrawals are taxed as ordinary income.
Roth withdrawals are tax-free.
Social Security benefits may be taxable depending on your total income.
Without a clear tax strategy, you could end up paying more than you need to. A tax-smart withdrawal plan can help you keep more of what you’ve saved—and potentially stretch your assets further.
5. What do I want this next chapter to look like?
It’s easy to focus on the numbers, but retirement is about more than finances. It’s a chance to redefine what your days look like and what they feel like. Think about:
How you’ll spend your time
Where you want to live
What brings you meaning and purpose
Maybe you’ve always dreamed of traveling more, spending extra time with grandkids, or diving into a passion project that’s been on the back burner. Perhaps you want to give back through volunteer work, start a part-time business, or simply enjoy the freedom of unstructured days.
Retirement is the process of defining a new, deeply personal chapter. The clearer you are about what you want this season of your life to include, the better you can align your financial strategy to support it.
6. Who’s helping me with this?
Retirement can feel overwhelming, but you don’t have to go it alone. We want to help you clarify your goals, create a strategy you feel good about, and move forward with confidence knowing you have a trusted professional by your side. With us you can:
Estimate your income and expenses
Create a personalized Social Security strategy
Navigate Medicare and healthcare planning
Build a sustainable withdrawal plan
Prepare for the “what-ifs” that life might throw your way
You’ve worked hard to get here. With the right questions (and the right guidance), you can retire with clarity, confidence, and a sense of purpose.
Ready to start answering these questions for yourself?
Let’s talk. Schedule a no-obligation consultation and let’s build a retirement strategy that works for you.
Whether you’re five years away from retirement or thinking about stepping away sooner, now is the time to get clear on your options. We’ll help you make informed decisions, avoid costly mistakes, and feel confident about the road ahead.
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Investing involves risk, including the potential loss of principal. The information provided is for general educational and informational purposes only and is not intended to serve as specific financial, investment, or tax advice. Individual circumstances vary, and you should consult with a qualified financial or tax professional before making any financial decisions.
