Four Ways to Prevent Feeling Regret in Retirement
Making financial plans for decades into the future can be daunting, but focusing your efforts is key to achieving freedom, financial and otherwise, in your golden years.


As a working American, you’ve likely dreamed of the day when you can finally hang up your hat for good and retire. Some dream of traveling the world, or moving to a tropical area, or simply spending time indulging in hobbies. Unfortunately, that’s not the reality for many retirees.
A recent study from MedicareFAQ found 59% of respondents are concerned about their financial situation in retirement. Meanwhile, 60% say they wish they would have started saving for retirement earlier or contributed more to their retirement savings.
Fortunately, there are steps working Americans can take now to achieve financial security in retirement and avoid living with regret.
From just $107.88 $24.99 for Kiplinger Personal Finance
Be a smarter, better informed investor.

Sign up for Kiplinger’s Free 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.
Trying to financially plan for life decades into the future is overwhelming. Health care costs, longer life expectancies, inflation and cost-of-living increases are just some of the considerations when you’re figuring out how much money to save. These four tips can help you prevent regret in retirement:
1. Decide how you want to spend your golden years.
To start, make a plan for how you want to spend your retirement. Do you dream of traveling the world, or purchasing your dream home, boat or RV? Developing goals for retirement can help you get an idea of how much money you’ll need to save to achieve those goals. Making a bucket list can also be helpful. You might find you can start crossing items off your list during your working years, thus reducing the financial burden you could face in retirement.
2. Save early and often.
Saving is obviously another key step when planning for retirement, but unfortunately, a lot of people don’t begin saving early enough.
When it comes to saving for retirement, don’t wait. Time and compound interest are on your side. The sooner you begin saving, the more time your money has to grow.
If you haven’t already, check to see if your employer offers a 401(k) and company match. You can also open up an IRA, making contributions to it whenever possible.
If you can, figure out ways to make passive income during your working years. Investing in real estate and a high-yield savings account or CDs are other saving vehicles you have at your disposal.
3. Take care of your health.
It may not be top of mind, but maintaining your health during your working years can help you in retirement. According to the same MedicareFAQ report, 82% of respondents say they didn’t prioritize their health during their working years. Carving out time to exercise, eating a nutritious diet and developing healthy habits can lower your risk of illness later in life.
These illnesses may require you to undergo costly treatments or move into a long-term care facility, which can be expensive.
Being proactive about your health in the now not only increases your chances of a longer life, but it can also help you save on health care costs as you age.
Plus, it will increase your quality of life in the present.
4. Consider taking on a side hustle.
If you want to generate more income for retirement, consider tapping into today’s gig economy. Picking up side jobs, starting a small business or providing services that align with your skills and talents are all great ways to generate income on top of your regular salary.
The extra income can help you cover current expenses, pay off debt or increase your retirement contributions, which will only benefit you in retirement.
During our working years, many of us look forward to life in retirement. The additional free time allows us to slow down and enjoy life, giving us time to reflect and explore ourselves and the world around us. Don’t let financial burdens limit you or fill you with feelings of regret during one of the most precious phases of life. Preparing for retirement now will allow you to fully enjoy it when the time comes.
Pat Simasko is an investment advisory representative of and provides advisory services through CoreCap Advisors, LLC. Simasko Law is a separate entity and not affiliated with CoreCap Advisors. The information provided here is not tax, investment or financial advice. You should consult with a licensed professional for advice concerning your specific situation.
Related Content
- How Getting Married Affects Your Social Security Benefits
- How Lower Interest Rates Could Affect Older Adults
- The Five Stages of Retirement (and How to Skip Three of Them)
- Six Financial Actions to Take the Year Before Retirement
- Five Things I Wish I’d Known Before I Retired
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.

Patrick M. Simasko is an elder law attorney and financial adviser at Simasko Law and Simasko Financial, specializing in elder law and wealth preservation. He’s also an Elder Law Professor at Michigan State University School of Law. His self-effacing character, style and ability have garnered him prominence and recognition throughout the metro Detroit area as well as the entire state.
-
Savings Goal Calculator
Tools Want to know how much you need to save each month to reach your financial goals? Our calculator helps you build a realistic savings plan.
-
Cash vs. Mortgage: How to Pay for Your Second Home
Should you buy your second home outright or finance it with a loan? Weigh the pros, cons and tax implications before making the leap.
-
Gray Divorce Can Throw Your Retirement a Curveball: What to Know
If you're entering retirement and going through a divorce at the same time, you've got some work to do to shore up your long-term financial security.
-
I'm a Real Estate Investing Expert: Optional 721 UPREIT DSTs Can Be the Best of Both Worlds
Before investing in any 721 UPREIT exchange, look for one that offers a straightforward, investor-friendly exit.
-
How an Expired Passport Thwarted Blackmail (and What Other Important Documents You Should Keep)
An optometrist produced his expired passport to foil a blackmail attempt by the daughter of a former employee. After proving he was out of the country on the date of a forged diary entry, he took it a step further.
-
Optimize, Grow, Retain: The Power of Annual Client Reviews
Financial advisers can use annual reviews to help enhance client outcomes, strengthen relationships and build their practice.
-
I'm a Real Estate Investing Pro: This Is What Investors Should Know About Truck Stop Investments
Truck stops might seem like good investments, but they can actually be a risky gamble due to unstable fuel prices, unreliable operators and coming changes in transportation. Instead, consider safer options like industrial or residential properties.
-
Don't Disinherit Your Grandchildren: The Hidden Risks of Retirement Account Beneficiary Forms
Standard retirement account beneficiary forms may not be flexible enough to ensure your money passes to family members according to your wishes. Naming a trust as the contingent beneficiary can help avoid these issues. Here's how.
-
This Is How Life Insurance Can Fund Your Dreams Now
Beyond a death benefit, life insurance can provide significant financial value and flexibility through 'living benefits' while you are still alive, helping with expenses like education, business ventures or retirement.
-
Potential Trouble for Retirees: A Wealth Adviser's Guide to the OBBB's Impact on Retirement
While some provisions might help, others could push you into a higher tax bracket and raise your costs. Be strategic about Roth conversions, charitable donations, estate tax plans and health care expenditures.