How to Be Strategic With Your Retirement Withdrawals
To make your savings last, you need to know how to draw from the right investment … at the right moment.

Consider, for a moment, your approach to investments.
Are you an active investor, adjusting your strategy as the market tides shift? Or are you passive, going with the flow even when the flow carries you into a precarious situation?
In retirement, it pays to have a plan that allows you to adapt to new conditions, making decisions that best align with the particulars of the present. This doesn’t mean you need to be a day trader, constantly monitoring the S&P 500 and buying and selling by the hour.

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.
But, since retirement is when you begin to spend the money you devoted decades to saving, you want to draw on that money in a strategic manner so you stretch your dollars as far as possible. After all, retirement should be a happy time of traveling, taking up new hobbies or spending more time with grandchildren. For too many, though, retirement can be a time of anxiety as they struggle to make their finances line up with their vision. Too often, it seems, bringing the two into alignment is a challenge.
But one way to keep your retirement on track is to be an active participant — not just when creating a retirement plan, but also when implementing it. When you’re engaged with your plan, you can align your decisions to the market conditions of the moment.
Get tactical with your withdrawals
Let me elaborate.
Sometimes people take a “set it and forget it” approach to their retirement finances. The market churns along with its ups and downs, and they pay no attention to what those ups and downs mean to them — or to their precious savings and investments.
This inattentiveness is a bad idea. When it comes to investments, what you don’t know definitely can hurt you.
If you monitor the market, though, you give yourself the opportunity to be strategic when you make withdrawals from particular accounts because the timing for your withdrawals can make a difference.
This is why I recommend retirees divide their money. Keep some in the market where the potential for strong gains is possible. Invest another portion in an annuity that is not susceptible to the lowest lows of market volatility. If the market is strong, you can draw on your burgeoning brokerage account to help with your monthly retirement income needs. In a down market, you can turn to your annuity.
Make decisions from a position of strength
Generally, when people think of annuities, they think of something that provides a lifetime income. You pay a lump sum to an insurance company, and in return, they make regular monthly payments to you, much like a pension.
That is one way an annuity works. But it’s not the only way.
Some annuities can also be liquid. In other words, you can have access to at least a certain portion of your money, making withdrawals to help with your income needs. You can get a guaranteed stream of income while still allowing your principal to be invested for growth. If you add an enhanced liquidity rider, if you don’t draw from the annuity one year, you can take more from it the next. Another great thing about these annuities is while they have growth potential, they are also guaranteed against loss, so they don’t carry the same risk as investing in the stock market.
Of course, there are limits to the gains you can make as well. This is why you want some of your money in the market, where there is potential for greater growth. Then you can be intentional with when and from where to make withdrawals.
If the market is on an uptick, you should peel off money from some of the stock investments that have provided a good return. A down market, when selling a stock could result in a loss, is a good time to draw from the annuity.
With such a back-and-forth strategy, you are always drawing on your savings from a position of strength rather than a position of weakness.
This approach also gives you a chance to stay active in the market. When the market drops, that’s an opportunity to take advantage of the liquidity of your annuity and buy stocks at low prices. Then, when the market rebounds and the value of those stocks grows, you can capitalize on your gains and draw on those, rather than from the annuity. (If that sounds like the classic “buy low and sell high” concept, that’s because it is.)
True, making the right move at the right time can get tricky. But a financial professional who has a good understanding of this approach will be able to give you proper guidance, so you can make decisions with confidence and get back to turning your retirement vision into your retirement reality.
Ronnie Blair contributed to this article.
The appearances in Kiplinger were obtained through a PR program. The columnist received assistance from a public relations firm in preparing this piece for submission to Kiplinger.com. Kiplinger was not compensated in any way.
Securities and advisory services offered only by duly registered individuals through Madison Avenue Securities, LLC. (MAS), Member FINRA & SIPC, and a registered investment advisor. Dynamic Wealth Strategies and MAS are not affiliated entities.
Annuity guarantees rely on financial strength and claims-paying ability of issuing insurance company. Annuities are insurance products that may be subject to fees, surrender charges and holding periods which vary by carrier. Annuities are not FDIC insured.
Related Content
Get Kiplinger Today newsletter — free
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.
Adam Tau is the co-founder and Wealth Manager at Dynamic Wealth Strategies. He began his financial career on Wall Street just after the 2008 financial crisis. Later, he decided to create an independent practice with his wife and co-founder of Dynamic Wealth Strategies, Rebecca Miller. He has a Bachelor of Science in Psychology from Salisbury University.
-
Ask the Editor: Four Reader Tax Questions
Ask the Editor In our new Ask the Editor series, Joy Taylor, The Kiplinger Tax Letter Editor, answers questions related to filing of tax returns and paying taxes.
By Joy Taylor Published
-
These Eight States Have the Most Expensive Home Insurance in 2025
If you live in one of these eight states, you’re probably paying $1,000 or more above the national average for home insurance.
By Rachael Green Published
-
Retiring With a Pension? Four Things to Know
The road to a secure retirement is slightly more intricate for people with pensions. Here are four key issues to consider to make the most out of yours.
By Joe F. Schmitz Jr., CFP®, ChFC® Published
-
How to Teach Your Kids About the Tax Facts of Life
Taxes are unavoidable, so it's important to teach children what to expect. Also, does your child need to file a tax return for 2024? Find out here.
By Neale Godfrey, Financial Literacy Expert Published
-
Revocable Living Trusts: The Good, the Bad and the Ugly
People are conditioned to believe they should avoid probate at all costs, but when compared with living trusts, probate could be a smart choice for some folks.
By Charles A. Borek, JD, MBA, CPA Published
-
How to Plan for Retirement When Your Child Has Special Needs
When your child has special needs, your retirement plan should include a plan for when you'll no longer be able to care for them yourself. A five-step guide.
By Christopher M. Butterworth, ChSNC®, CRPS, CLU® Published
-
Tax Advantages of Oil and Gas Investments: What You Need to Know
Tax incentives allow for deductions and potential tax-free earnings — benefits accessible only to accredited investors in small producer projects.
By Daniel Goodwin Published
-
Charitable Contributions: Five Frequently Asked Questions
Make the most of your good intentions by understanding the ins and outs of charitable giving. A good starting point is knowing what's deductible and what isn't.
By Stephen B. Dunbar III, JD, CLU Published
-
Financial Leverage, Part Two: Don't Say We Didn't Warn You
A lesson in how highly leveraged investments can benefit the first movers and crush the next round of buyers.
By Stephen P. Harbeck Published
-
Taxes in Retirement: What ESOP Participants Need to Know
Most Employee Stock Ownership Plans (ESOP) participants transfer company stock to an IRA starting around age 55, so taxes on that money have been deferred.
By Peter Newman, CFA Published