Retirement Roulette? Letting It All Ride on Stocks May Not Be Best
For those in or near retirement, gambling too hard on today’s record-setting bull market could be more risk than they bargained for.
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.
You are now subscribed
Your newsletter sign-up was successful
Want to add more newsletters?
Delivered daily
Kiplinger Today
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more delivered daily. Smart money moves start here.
Sent five days a week
Kiplinger A Step Ahead
Get practical help to make better financial decisions in your everyday life, from spending to savings on top deals.
Delivered daily
Kiplinger Closing Bell
Get today's biggest financial and investing headlines delivered to your inbox every day the U.S. stock market is open.
Sent twice a week
Kiplinger Adviser Intel
Financial pros across the country share best practices and fresh tactics to preserve and grow your wealth.
Delivered weekly
Kiplinger Tax Tips
Trim your federal and state tax bills with practical tax-planning and tax-cutting strategies.
Sent twice a week
Kiplinger Retirement Tips
Your twice-a-week guide to planning and enjoying a financially secure and richly rewarding retirement
Sent bimonthly.
Kiplinger Adviser Angle
Insights for advisers, wealth managers and other financial professionals.
Sent twice a week
Kiplinger Investing Weekly
Your twice-a-week roundup of promising stocks, funds, companies and industries you should consider, ones you should avoid, and why.
Sent weekly for six weeks
Kiplinger Invest for Retirement
Your step-by-step six-part series on how to invest for retirement, from devising a successful strategy to exactly which investments to choose.
Have you ever watched somebody playing roulette at a casino – or maybe just in a movie?
The chips pile up as the person gets lucky. And then he starts to get greedy.
You, of course, see the inevitable coming, and so you wonder: Why doesn’t he play it safe and set at least some of that aside? When the tide turns, and he loses everything, you shake your head.
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
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.
But there’s a chance you’re doing the same thing with your investment portfolio.
With an eight-year bull market and a series of record-setting highs, it’s hard not to be – let’s not say greedy, but definitely enthusiastic.
If you (understandably) moved from more conservative financial vehicles to stocks to grow your wealth – or just to keep up with inflation – it may be time to take some chips off the table as you close in on retirement.
Yes, it’s fun watching your account balances grow month to month and year to year. But at some point, the market will have to correct, and there could be a serious downturn. If you’re in retirement – or close to it – when that happens, you may not be able to recover.
The stock market appears to love our new president, but that doesn’t mean record growth is guaranteed to continue. Not to mention that we’re in a global economy and our future is intertwined with dozens of other countries. Moves to protect our borders, slow immigration, disrupt trade agreements and perhaps impose tariffs are bound to have some effect on the marketplace. And then there’s terrorism, threats from emerging nations and anxiety among some of our longtime allies.
Change – good or bad – can be unpleasant.
Start by developing a plan
So, how can you help protect yourself from the pain and still make the most of the current market?
Do some math. Figure out how much income you’ll need to get by every year in retirement. (And plan for a lot of years. It could 20 or 30, or longer.) Then add up the income streams you know you can count on: a pension, if you have one, Social Security and other stable sources that aren’t dependent on the vagaries of the general marketplace. If there’s a gap between those numbers – and if you’re a Baby Boomer, there probably is – you’ll have to find a way to fill it.
Should you need to pull a chunk from your retirement accounts every month, make sure that money is positioned in a way that can help make sure it won’t take a massive hit if there is a market correction.
There are myriad vehicles out there that can help lower your risk, including:
- Dividend-paying stocks
- Annuities
- Municipal bonds
If you don’t have a pension, you can create your own guaranteed income stream to help complement your Social Security income, so you hopefully don’t have to spend your days worrying and watching CNBC.
Have a frank talk … together
Talk to your financial professional about which solutions might be a good fit for you. But before you go, heed this bit of advice: Both spouses need to take part in the conversation.
That guy at the roulette table who loses all his money? He seldom has his wife at his side. She’d probably stop him – or grab a couple of stacks and run back to their hotel room. After all, it’s her money, too.
At our firm, we’ve found that many women are prudent when it comes to finances and value smart planning. They know the odds, and if their spouse dies, they want to remain financially independent.
Once the two of you have developed your retirement income plan, if there’s something left over, you can head back to the market. And let the chips fall where they may.
Kim Franke-Folstad contributed to this article.
Investment advisory services offered only by duly registered individuals through AE Wealth Management, LLC (AEWM). AEWM and Your Own Retirement are not affiliated companies. Investing involves risk, including the potential loss of principal. Any references to protection benefits, safety, or guaranteed income generally refer to fixed insurance products, never securities or investment products. Insurance and annuity product guarantees are backed by the financial strength and claims-paying ability of the issuing insurance company.
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.

David Hickey is a managing director at Your Own Retirement in Cranberry Township, Pennsylvania. He has over 30 years of experience in the insurance, finance and investment industry. Hickey has earned the Certified Property and Casualty Underwriting designation from the American Institute. He has a Bachelor of Arts degree in English from the University of Pittsburgh. Hickey has contributed his time to coaching baseball and ice hockey; part and parcel of raising five children with his wife of 31 years, Susan.
-
How Much It Costs to Host a Super Bowl Party in 2026Hosting a Super Bowl party in 2026 could cost you. Here's a breakdown of food, drink and entertainment costs — plus ways to save.
-
3 Reasons to Use a 5-Year CD As You Approach RetirementA five-year CD can help you reach other milestones as you approach retirement.
-
Your Adult Kids Are Doing Fine. Is It Time To Spend Some of Their Inheritance?If your kids are successful, do they need an inheritance? Ask yourself these four questions before passing down another dollar.
-
The 4 Estate Planning Documents Every High-Net-Worth Family Needs (Not Just a Will)The key to successful estate planning for HNW families isn't just drafting these four documents, but ensuring they're current and immediately accessible.
-
Love and Legacy: What Couples Rarely Talk About (But Should)Couples who talk openly about finances, including estate planning, are more likely to head into retirement joyfully. How can you get the conversation going?
-
How to Get the Fair Value for Your Shares When You Are in the Minority Vote on a Sale of Substantially All Corporate AssetsWhen a sale of substantially all corporate assets is approved by majority vote, shareholders on the losing side of the vote should understand their rights.
-
How to Add a Pet Trust to Your Estate Plan: Don't Leave Your Best Friend to ChanceAdding a pet trust to your estate plan can ensure your pets are properly looked after when you're no longer able to care for them. This is how to go about it.
-
Want to Avoid Leaving Chaos in Your Wake? Don't Leave Behind an Outdated Estate PlanAn outdated or incomplete estate plan could cause confusion for those handling your affairs at a difficult time. This guide highlights what to update and when.
-
I'm a Financial Adviser: This Is Why I Became an Advocate for Fee-Only Financial AdviceCan financial advisers who earn commissions on product sales give clients the best advice? For one professional, changing track was the clear choice.
-
I Met With 100-Plus Advisers to Develop This Road Map for Adopting AIFor financial advisers eager to embrace AI but unsure where to start, this road map will help you integrate the right tools and safeguards into your work.
-
The Referral Revolution: How to Grow Your Business With TrustYou can attract ideal clients by focusing on value and leveraging your current relationships to create a referral-based practice.