Clarify Your Retirement Goals with These 4 Questions
Before you get wrapped up thinking about savings, income and taxes, you need to think a little harder about what you really want from your retirement. Setting some life goals will give you and your financial planner a clear direction.


What’s important to you about money?
I ask clients and potential clients this question all the time, and I’ve learned — after having had thousands of these conversations — that few people give the topic much thought.
That’s unfortunate, because the answer — or answers — will help you focus on what matters to you most.

Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Investors (and many financial professionals) tend to put all the emphasis on growing their nest eggs for retirement and not focusing on whether the money you amass while you’re working will last after you’ve retired. But there’s so much more to a comprehensive financial plan than just the beginning and the end.
You should be using your money as a tool to achieve your goals. And your adviser can’t help you reach those goals if you don’t even know what they are, or if you can’t articulate them, when you’re discussing retirement strategies.
Here are some questions to help you get started. (If you’re married, be sure to include your spouse.)
Who do you want to help with your money?
Answering “myself” or “ourselves” is a perfectly acceptable answer. But if you have others you want to include — parents or children or anyone else you’ll need or want to take care of — be specific about what you’d like to be able to do for them. You could and should be exploring how you’ll cover those costs now and in the future.
Do you have any specific “bucket list” items you wish to achieve?
Have you and your spouse dreamed of traveling, moving or changing your lifestyle in any way? When do you want those things to happen? Have you considered and included the costs of these activities in your financial plan?
You can’t take it with you, so do you want to live large or leave some behind?
Is it OK to spend every penny you have during your lifetime, so that the last payment to the funeral home barely clears, or does leaving a financial legacy matter to you? Which people or organizations should receive your money? Your adviser can help you set up a course of action (a will, a trust, life insurance, etc.) to help you achieve your legacy goals in the most tax-efficient manner possible.
What would happen if you or your spouse became sick or disabled?
Have you talked about what kind of care you’d prefer if it’s required (e.g., skilled care in your home, adult day care, an assisted living facility)? How would you pay for care, and how would your choices affect your loved ones in the short and long term?
Money is a very personal topic, and sharing your thoughts on these issues can be uncomfortable — particularly if you and your spouse disagree on your various goals. But if you’ve never thought about your money in this way before, this can be a powerful and revealing exercise. Complete it thoughtfully, and discuss your options with the people affected.
Then you’ll be ready to build a truly comprehensive financial plan.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Les Goldstein is the founder and president of Personal Financial Strategies Inc., a branch office of Securities America Inc., member FINRA/SIPC. Personal Financial Strategies and Securities America are separate entities. As an Investment Adviser Representative with Securities America Advisors Inc. in the greater Chicago area, he helps clients create a retirement lifestyle for themselves and leave a meaningful financial legacy for their loved ones.
-
Stock Market Today: President Trump Reboots the Tariff Trade
A broad consensus that markets hate uncertainty more than anything else is being tested on an almost daily basis in 2025.
-
Electric Car Owners Can’t Avoid Road Taxes in 2025
New Taxes Hawaii launched its new EV road usage fee in July. Here’s why some states are implementing similar new electric vehicle taxes across the nation.
-
The Hidden Costs of Caregiving: Crisis Goes Well Beyond Financial Issues
Many caregivers are drained emotionally as well as financially, leading to depression, burnout and depleted retirement prospects. What's to be done?
-
Cash Balance Plans: An Expert Guide to the High Earner's Secret Weapon for Retirement
Cash balance plans offer business owners and high-income professionals a powerful way to significantly boost retirement savings and reduce taxes.
-
Five Things You Can Learn From Jimmy Buffett's Estate Dispute
The dispute over Jimmy Buffett's estate highlights crucial lessons for the rest of us on trust creation, including the importance of co-trustee selection, proactive communication and options for conflict resolution.
-
I'm a Financial Adviser: For True Diversification, Think Beyond the Basic Stock-Bond Portfolio
Amid rising uncertainty and inflation, effective portfolio diversification needs to extend beyond just stocks and bonds to truly manage risk.
-
I'm a Retirement Psychologist: Money Won't Buy You Happiness in Your Life After Work
While financial security is crucial for retirement, the true 'retirement crisis' is often an emotional, psychological and social one. You need a plan beyond just money that includes purpose, structure and social connection.
-
Retiring Early? This Strategy Cuts Your Income Tax to Zero
When retiring early, married couples can use this little-known (and legitimate) strategy to take a six-figure income every year — tax-free.
-
Ditch the Golf Shoes: Your Retirement Needs a Side Gig
A side gig in retirement can help combat boredom, loneliness and the threat of inflation eroding your savings. And the earlier you start planning, the better.
-
Roth IRA Conversions in the Summer? Why Now May Be the Sweet Spot
Converting now would enable you to spread a possible tax hit over more than one payment while reducing future taxes.