The Top 10 Most Important Retirement Plan Questions to Ask Yourself

Retirement isn’t just about leaving the workforce. It’s about entering a new phase of life with purpose, clarity, and financial confidence. In a recent episode of the Investors Row podcast by IRA Club, President Dennis Blitz and Sponsor Care Manager, Kasia Baldus, explored essential questions everyone should ask before retiring.

Whether you’re years away or right around the corner from retirement, these reflections can help you plan for a fulfilling and financially sound future. Here’s what you should be thinking about now. If you prefer to listen, check out the episode here.

Let’s Clear Up Some Things First

Before diving into retirement planning, let’s address a common misunderstanding: the so-called “$6,000 Social Security increase.” Contrary to headlines, this isn’t a cash boost.

Here’s the truth:

• It’s a $6,000 income tax deduction, not an increase.
• If you’re over 65, this deduction lowers your taxable income.
• In a 20% tax bracket, it might save you about $1,200/year.
• It’ not for everyone. It phases out at $175,000 (single) or $250,000 (married filing jointly).
• This deduction is temporary, ending after the 2028 tax year.

So, remember, the $6,000 social security deduction is just that, a deduction for those who qualify for it, and not an extra boost of cash. Now that we have cleared that up, let’s dive into the top 10 essential questions to ask yourself before retirement.

1. What Do I Plan to Do in Retirement?

Retirement is a big step for all of us when the time comes. Too many people focus solely on ending their careers without planning for what comes next. Instead, consider:

• Do I want to travel? How often and how far?
• What does my travel budget look like?
• Will I pick up a hobby, spend time with family, or pursue a new skill?

Planning how you’ll spend your time gives retirement structure and meaning.

2. Will I Continue Working Part-Time?

A part-time job can offer supplemental income, routine & social interaction, and a smoother transition into retirement. Even a rough idea of your potential part-time earnings can help shape your retirement budget. So, ask yourself:

• Will I work part-time?
• What might I earn if I were to work part-time?

Again, this is just a rough idea. It’s ok if it’s not exact; you’re just building a picture.

3. What Do I Want to Accomplish During Retirement?

This is your time. Set goals that fulfill you:

• Learn a new language or musical instrument
• Restore classic cars
• Write a book or take up painting

There are many things you could be working towards while you’re in retirement. Having clear personal goals can provide a deep sense of satisfaction.

4. Do I Want to Volunteer During Retirement?

Volunteering brings purpose to an individual and has proven positive health benefits, including:

• Slows cognitive decline
• Improves sleep and emotional well-being
• Strengthens your community

There are countless ways to get involved, especially with all your new free time. Start thinking about the causes you care about.

5. Will I Stay in My Current Home?

Housing can be one of your largest ongoing expenses. Ask yourself:

• Is my mortgage paid off?
• What are my property taxes, insurance, and annual maintenance costs?
• Will my home suit my needs as I age?

Even if your home is paid off, those “hidden” costs, such as repairs and appliance replacements, can add up.

6. What Family Responsibilities Might I Have?

Family needs can shape your financial plan:

• Are you or a loved one facing significant medical expenses?
• Are you supporting a child, ex-spouse, or aging parent?
• Do you have special needs dependents?

Medical expenses alone can range from $200,000 to $300,000 in retirement. Planning early can help reduce surprises.

7. What’s My Expected Life Span?

Government life expectancy charts don’t reflect individual lifestyles. Consider:

• Your personal health history
• Family longevity
• Habits (diet, exercise, alcohol use, seatbelt use)

You may live longer than you expect, so plan for a long, healthy life.

8. What Retirement Savings Do I Have?

Take inventory of your:

• Employer-sponsored plans (401(k), 403(b), TSP)
• Personal IRAs
• Other investment accounts

Write down:

• Current balances
• Estimated value at retirement
• Expected annual withdrawals

This helps you understand how long your funds will last. Also, if you have a pre-tax retirement account that requires minimum distributions, ensure you are calculating the required minimum distribution you’d need to withdraw each year starting at the age of 73.

9. What Will My Social Security Benefit Be?

Don’t rely on the average ($1,918/month)—you’re not average. Use the official Social Security estimator tool to:

• Calculate your projected benefit
• Explore how delaying retirement (up to age 70) increases payouts
• Consider how it fits into your total income picture

You can find this tool on the Social Security website here.

10. How Do My Income and Expenses Compare?

Create a rough annual budget:

• Total income from savings, Social Security, IRAs
• Total expected expenses (housing, medical, travel, food, etc.)

If expenses (X) are higher than income (Y), it’s time to strategize.

The Role of IRAs in Retirement

IRAs are more than just a savings account; they’re a tool for financial freedom.

Benefits of self-directed IRAs include:

• Tax-deferred growth
• Flexibility to invest in alternative assets (like real estate, private equity)
• Control over when and how you pay taxes

If your IRA doesn’t yet hold enough for a large investment, don’t worry, you’re not locked out. Schedule your free consultation with an IRA Club new account specialist to discuss how you can find ways to make big investments possible with limited funds.

At the End of the Day, it’s More Than About Money.

Retirement isn’t just about whether you’ve saved enough; it’s about designing a life that fulfills you. From budgeting for future travel to planning for family needs, asking the right questions now makes all the difference later.

And remember: there are factors you can’t control (inflation, taxes), but there are many you can. Start now.

IRA Club does not provide investment, tax, financial, or legal advice, nor do we endorse any products, investments, or companies that provide such advice and investments. All parties are strongly encouraged to perform due diligence and consult with the appropriate professional(s) licensed in that area before entering any investment. Performing due diligence helps protect against fraud. IRA Club discloses that it may receive an investment holding/technology facilitation fee for each member who invests through the Investor’s Row platform.