Dowling Legacy & Retirement

Dowling Legacy & Retirement We empower you to navigate today’s complex financial world. We customize a plan to fit your individual and family needs. Ronald R.

Our Team

Dowling Legacy & Retirement serves Orland Park, IL and surrounding communities. Our mission is to provide the families and businesses we serve with innovative financial strategies, solutions and planning that result in financial clarity, security and overall financial health. Making strong commitments to our clients and building life-long relationships are tenets of success at our firm. Dowling Legacy & Retirement provides investors custom-tailored strategies to meet short and long-term needs. Our goal is to help our clients realize their financial dreams by offering creative solutions through an open and transparent process utilizing innovative solutions to achieve financial independence. We customize a plan to fit your individual and family needs, as well as the needs of your small or large business. Call us for your Complimentary Consultation and receive our latest book. Karen Prescia Dowling, CEO/President

Karen is CEO/President of Dowling Legacy & Retirement. She received her Bachelors in Accounting in 1981 from Loras College, Dubuque, Iowa and her Masters in Business Administration (MBA) in 1987 from the University of Nevada, Las Vegas. Karen is a Licensed Life and Health Insurance agent and a Certified Estate Planner (CEP), specializing in Legacy, Long Term Care and Retirement Planning. As an Investment Advisor for Chancellor Financial Services, Inc., Karen develops investment strategies designed based on client’s investment goals. With over 25 years as a Business Consultant, and over 35 years as an Accountant, she has helped both small and Fortune 500 companies improve their bottom line and streamline operations through budgeting, monitoring and analyzing financial performance. Being a Certified Life Coach, Karen has coached individuals through life transitions, guiding them, both personally and financially. Whether your goal is to accumulate wealth, maximize social security benefits, acquire life insurance, set up a trust or retire with confidence, Karen is passionate about building plans that help organize client assets while protecting them for the next generation. Primary and paramount is her mission to assist clients towards planning a retirement they have always dreamed of, one that will provide them peace of mind & financial freedom throughout their lifetime. Dowling, Advisor

Ron is a Strategic Consultant and Advisor for Dowling Legacy & Retirement. Ron has been in the Insurance and Legacy Planning industry for over 35 years. As a Consultant and Certified Estate Planner (CEP), Ron specializes in Legacy, Medicaid and Retirement Planning. He has been featured in Forbes Magazine for two consecutive years and has co-authored the book, “Getting Your House in Order”, which addresses how to organize the financial and legal areas in your life that can give you the confidence to retire successfully and ensure your affairs will be handled according to your wishes. Ron speaks at educational seminars and workshops for corporations, private groups, local residents and organizations at many well-known restaurants around Chicago and the surrounding suburbs. Ron has made it his mission to educate individuals on how to protect their assets and plan for a prosperous, stress free retirement. “I’m addicted to helping people. It’s about the self-satisfaction of helping people and building plans to protect people and their assets.”

What's your biggest question about Social Security or Medicare? Drop it in the comments!Then join us this fall, where we...
10/10/2026

What's your biggest question about Social Security or Medicare? Drop it in the comments!
Then join us this fall, where we'll cover claiming strategies, Medicare enrollment, and common mistakes to avoid.
-October 19, 21 or 28 -6:00 to 7:30 p.m.
Lincoln-Way Central, 1801 E Lincoln Hwy, New Lenox, IL 60451
Register here: https://events.afceducators.org/K4YTK9

If you’re required to take minimum distributions from your retirement accounts, it’s worth confirming that your withdraw...
10/09/2026

If you’re required to take minimum distributions from your retirement accounts, it’s worth confirming that your withdrawals are on track for the year.

Taking a few minutes to review your plan now can help you stay ahead of year-end deadlines. Call our office at 708-479-8771.

Turning 65 soon? Your Medicare Initial Enrollment Period is a seven-month window: it starts three months before the mont...
10/09/2026

Turning 65 soon? Your Medicare Initial Enrollment Period is a seven-month window: it starts three months before the month you turn 65 and ends three months after.
Missing it could mean late enrollment penalties that last as long as you have Medicare.
Learn how enrollment works, and when it doesn't apply to you, at our educational class.
-October 19, 21 or 28 -6:00 to 7:30 p.m.
Lincoln-Way Central, 1801 E Lincoln Hwy, New Lenox, IL 60451
Register today: https://events.afceducators.org/K4YTK9

You don’t need to panic yet about Social Security, but you should stay informed.
10/07/2026

You don’t need to panic yet about Social Security, but you should stay informed.

You don’t need to panic yet about Social Security, but you should stay informed.

Retirement comes with a lot of decisions, but two of the biggest are when to claim Social Security and how to enroll in ...
10/07/2026

Retirement comes with a lot of decisions, but two of the biggest are when to claim Social Security and how to enroll in Medicare.
Join us for a clear, practical class designed to help you better understand both.
We'll cover: -How your Social Security claiming age can affect your benefit -How Medicare Parts A, B, C and D work -Important Medicare enrollment periods -Common mistakes that could cost you money in retirement
Choose from one of three class dates: -October 19, 21 or 28 -6:00 to 7:30 p.m.
These classes will be held at Lincoln-Way Central, 1801 E Lincoln Hwy, New Lenox, IL 60451.
If retirement is getting closer, this is a great opportunity to get informed before making these important decisions.
Register for the event here: https://events.afceducators.org/K4YTK9

Consider your eligibility and the impact of removing retirement dollars before dipping into your 401(k) plan.
10/05/2026

Consider your eligibility and the impact of removing retirement dollars before dipping into your 401(k) plan.

Consider your eligibility and the impact of removing retirement dollars before dipping into your 401(k) plan.

December can get busy fast. Your financial planning doesn’t have to get squeezed in at the last minute.Starting your yea...
10/01/2026

December can get busy fast. Your financial planning doesn’t have to get squeezed in at the last minute.

Starting your year-end review early gives you time to ask questions, explore your options, and determine which strategies may make sense for your goals. To get started, contact our office today at 708-479-8771.

Annuities can provide guaranteed income, principal protection or market-linked growth, but costs, risks, tax treatment a...
09/30/2026

Annuities can provide guaranteed income, principal protection or market-linked growth, but costs, risks, tax treatment and withdrawal rules vary widely.

Annuities can provide guaranteed income, principal protection or market-linked growth, but costs, risks, tax treatment and withdrawal rules vary widely.

Is there a financial decision you’ve been meaning to make?Maybe it’s updating an account, reviewing a strategy, adjustin...
09/28/2026

Is there a financial decision you’ve been meaning to make?
Maybe it’s updating an account, reviewing a strategy, adjusting a savings goal, or finally addressing something that’s been sitting on your to-do list.
Now is a good time to organize those outstanding decisions and determine your next steps. A little clarity today can help you head into the new year with fewer financial question marks.

To get started, give us a call at 708-479-8771.

Address

10727 Winterset Drive
Orland Park, IL
60467

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

Telephone

(708) 479-8771

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