Retirement Planning: The Right Questions to Ask at Every Stage of Life

Justin Clark, CFP®,
Senior Wealth Manager

Retirement isn’t something you suddenly start thinking about a few years before you leave work. Every stage of life brings decisions that shape the options you’ll have later.

The good news is that you don’t need to have everything figured out from the beginning. The habits you build in your 20s are different from the decisions you’ll make in your 50s or 70s, but each one lays the groundwork for what’s next.

Rather than focusing on retirement as a distant finish line, it helps to think of it as an ongoing process. As your career, family, and priorities change, so will the questions worth asking.

Your 20s and 30s: When Should I Start Planning?

Answer: As soon as you start earning a paycheck.

At this stage retirement may feel a lifetime away, but time is one asset you can never replace. By starting early you give your investments more years to grow.

This is also when good financial habits begin to take shape. Contributing to a retirement plan, setting up a tax-advantaged Health Savings Account (HSA), building an emergency fund, managing debt responsibly, and investing consistently can make a much bigger difference than trying to catch up later.

If your employer offers matching 401(k) or 403(b) contributions, be sure to contribute enough to receive the full benefit. It’s one of the simplest ways to boost your savings.

Your 40s: How Much Will I Need?

Answer: That depends on the lifestyle you want to achieve in retirement.

By your 40s, retirement often starts to feel more real. It’s also when career demands, raising children, supporting aging parents, and paying down a mortgage can all compete with saving for the future.

As your income grows, look for opportunities to increase your retirement contributions. It’s also a good time to review your insurance coverage and consider asset protection strategies, including trusts and LLCs.

While saving is important, so is thinking about the retirement you want to create. Do you want to travel? Split time between two homes? Leave your business to your children? Start a family foundation? Gradually transition away from work?

Your answers will help determine how much income you’ll need and shape a retirement plan built around your unique goals.

Your 50s: When Can I Retire?

Answer: When your savings, income, and spending plan make work optional.

At this stage, retirement starts to feel close enough to picture. Instead of asking, “Am I saving enough?” the question becomes, “Can I actually retire when I want to?”

The answer depends on more than your investment account balance. Areas to review with your advisor include:

  • Your projected retirement income and expenses
  • Social Security claiming strategies
  • Healthcare, insurance, and estate planning
  • Catch-up retirement contributions
  • Tax-efficient saving strategies

Running your plan under different scenarios can also be valuable. How would retiring two years earlier affect your income? What if markets decline just before retirement?

Understanding those possibilities now can help you make decisions with greater confidence later.

Your 60s: How Long Will My Savings Last?Answer: The goal is to create an income strategy that can support you throughout retirement.

Retirement often begins during this decade, bringing a different set of financial decisions. After years of building your portfolio, you’re now relying on it to provide income.

With people living longer—especially women—it’s important to make sure your savings can support a retirement that may last 30 years or more. Work with your advisor to identify any potential gaps in your income plan, reassess your investment mix and risk level, and review Medicare and long-term care planning.

As you begin drawing on your savings, how you withdraw your money can be just as important as how you invested it.

Coordinating distributions from different account types, taking IRA withdrawals during lower-income years, gifting appreciated stocks, and managing trust distributions can help reduce taxes and avoid unintentionally moving into a higher tax bracket.

Your 70s and Beyond: What Do I Want This Next Chapter to Look Like?

Answer: One that supports the life you want and the people you care about.

Retirement planning doesn’t end once you’ve stopped working. As your focus shifts from building wealth to using it, your financial decisions should support both your lifestyle and the legacy you hope to leave.

Required Minimum Distributions (RMDs) become an important part of the conversation, and their timing can affect your taxes. If you have an IRA, Qualified Charitable Distributions (QCDs) may help satisfy RMD requirements while supporting the charitable causes that matter to you.

This is also an ideal time to review your estate and trust documents to ensure they continue to reflect your family, your wishes, and your long-term intentions.

Most importantly, this stage of life is about enjoying what you’ve worked so hard to build. Whether that means traveling, spending more time with family, supporting the next generation, or giving back to your community, your financial plan should make it all possible.

Live for Today. Prepare for Tomorrow.

Retirement planning is about making thoughtful choices as your life evolves.

The questions you’ll ask at 25 are very different from the ones you’ll ask at 65, and that’s exactly how it should be. Every stage brings new opportunities, new priorities, and new decisions.

Let’s talk about where you are now and where you want to be.

Frequently Asked Questions

How do I know if I’ve saved enough?
Your retirement needs depend on the lifestyle you want to maintain, expected longevity, healthcare costs, and your legacy goals. It’s not about a single target number.

Is it ever too late to start planning?
No. While starting early offers advantages, meaningful progress can still be made later in life through disciplined saving and a well-designed financial strategy.

How can I mitigate taxes in retirement?
Strategies such as tax-loss harvesting, Roth conversions, charitable giving, gifting appreciated securities, and planning for RMDs can help reduce lifetime taxes and preserve more wealth for you and your heirs.

This presentation is not an offer or a solicitation to buy or sell securities. The information contained in this presentation has been compiled from third-party sources and is believed to be reliable; however, its accuracy is not guaranteed and should not be relied upon in any way whatsoever. This presentation may not be construed as investment, tax or legal advice and does not give investment recommendations. Tax laws are subject to change and may differ by jurisdiction. Consult your tax professionals regarding your specific circumstances. Any opinion included in this report constitutes our judgment as of the date of this report and is subject to change without notice.
 
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