Five Questions to Ask Yourself Five Years Before Retirement
Blog post description.Retirement is exciting, but it can also bring a lot of decisions. If you’re about five years away from retiring, these questions can help you picture the life you want and build a plan to support it.
Huyen Nguyen
8/6/20263 min read
As a CFP® professional, I believe retirement planning should feel personal, practical, and reassuring, not overwhelming. My role is to help you connect the numbers with the life you actually want to live, so each decision supports your values, your family, and your long term peace of mind.
One of the most helpful first steps in retirement planning is to imagine your future clearly. Where will you live? How will you spend your time? What kind of lifestyle feels meaningful and sustainable? The answers to those questions shape your spending plan, your retirement income strategy, and the adjustments you may want to make while you still have time.
The goal is not to predict every detail perfectly. It is to avoid major surprises later by making thoughtful choices now. Whether that means working a little longer, saving more, adjusting your lifestyle, or simply getting more organized, the five years before retirement can be a powerful planning window.
1. Where will you live?
Your location affects much more than your address. It can influence housing costs, taxes, travel, access to healthcare, proximity to family, and your day to day lifestyle. As you think about whether to stay put, downsize, relocate, or split time between places, consider what matters most to you.
· Do you want to be closer to children, grandchildren, friends, or community?
· Will your preferred location make retirement more or less affordable?
· How important are climate, recreation, culture, and access to medical care?
· If travel is part of your dream, will your home base make that easier?
· If you plan to work, consult, or start a business, does the area support those goals?
2. What will you do with your time?
Retirement is not just a financial transition. It is a lifestyle transition. How you spend your days will have a direct impact on how much income you need. Some activities add expenses, while others may generate income or simply bring fulfillment at a low cost.
· Expense generating activities: Travel, hobbies, dining out, entertainment, home projects, and family experiences can all be wonderful parts of retirement, but they should be included in your spending plan.
· Income generating activities: Part time work, consulting, teaching, or starting a small business can provide purpose and income. Even volunteer work can be valuable if it brings structure, connection, and joy.
If you dream of launching a business or pursuing a passion project in retirement, remember that it may take time and possibly some upfront investment before it becomes profitable. Planning for that runway now can make the transition smoother.
3. What does “living well” mean to you?
There is no single retirement lifestyle that fits everyone. For some people, living well means simplifying, spending less, and enjoying more time at home. For others, it means travel, dining, experiences, and finally doing the things they postponed during their working years.
· A simpler lifestyle: Cooking at home, gardening, walking, reading, biking, and spending time with loved ones can create a rich retirement without a high price tag.
· A more active lifestyle: Travel, hobbies, entertainment, charitable giving, and family support may require a larger income plan, but may be exactly what makes retirement meaningful to you.
A helpful exercise is to separate your future spending into “needs,” “wants,” and “dreams.” That makes it easier to see which expenses are essential and which ones can flex if markets, health, or family circumstances change.
4. How long should your money last?
No one can know exactly how long they will live, which is why longevity is one of the biggest retirement planning challenges. A plan that only covers the “average” life expectancy may fall short if you live well into your 90s. For many households, it can be wise to test whether income, savings, and insurance strategies could support a retirement that lasts to age 95 or 100.
This is also a good time to look at Social Security timing, pension options, withdrawal strategies, tax planning, healthcare costs, and long term care considerations together, not as separate decisions, but as parts of one coordinated plan.
5. What surprises should you prepare for?
Even the best plan needs room for the unexpected. Health changes, family needs, market downturns, inflation, natural disasters, and major home repairs can all affect retirement security. Building flexibility into your plan can help you respond with confidence instead of panic.
· Health: Medicare, supplemental coverage, out of pocket costs, and long term care planning all deserve attention before retirement begins.
· Family: Aging parents, adult children, grandchildren, or other loved ones may need emotional, practical, or financial support.
· The economy: Market downturns and inflation can test a retirement income plan, especially early in retirement.
· Emergencies: Insurance coverage, cash reserves, estate documents, and a disaster plan can help protect both your finances and your peace of mind.
The bottom line
Five years before retirement is a wonderful time to pause, dream, and plan. You do not need every answer today, but you do need a thoughtful process for turning your retirement vision into a sustainable income plan.
If retirement is on the horizon, I’d be honored to help you think through the next chapter with clarity and care. Together, we can review your income sources, investment strategy, tax picture, healthcare planning, and lifestyle goals, so you can move toward retirement with confidence, flexibility, and a plan designed around what matters most to you.
Inclusive Wealth Financial Planning LLC is a Registered Investment Advisor (RIA) registered in Pennsylvania and Texas. We may also serve clients in all other states pursuant to the de minimis exemption.
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