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.”

Learn how a mega backdoor Roth works and whether it fits with your retirement goals.
09/01/2026

Learn how a mega backdoor Roth works and whether it fits with your retirement goals.

Learn how a mega backdoor Roth works and whether it fits with your retirement goals.

Market ups and downs can feel more stressful near retirement. A thoughtful strategy can help you stay focused on your lo...
08/31/2026

Market ups and downs can feel more stressful near retirement. A thoughtful strategy can help you stay focused on your long-term goals. To get started, call our office at 708-479-8771.

Here's some retirement savings withdrawal strategies that could potentially help reduce taxes and penalties.
08/28/2026

Here's some retirement savings withdrawal strategies that could potentially help reduce taxes and penalties.

Here's how to withdraw retirement savings and reduce taxes and penalties.

August is National Golf Month, and retirement planning has more in common with your short game than you might think.Both...
08/26/2026

August is National Golf Month, and retirement planning has more in common with your short game than you might think.
Both require patience, a steady strategy, and the ability to adjust when the wind picks up.
Market shifts, tax changes, inflation, and life events can all throw off your line, so it helps to have a plan that keeps you on course.
Let's review your financial plan and get you ready for the next round.

Since 2009, Gradient Gives Back Foundation has provided over 1,100 months of housing payments to families in need across...
08/25/2026

Since 2009, Gradient Gives Back Foundation has provided over 1,100 months of housing payments to families in need across 21 states. 🌟 With nearly $1 million given and 85 families helped, this program continues to inspire charitable giving and unity in communities nationwide.

We’re proud to support this mission. Do you know a family who could benefit? Nominate them today at dowlinggivesback.com

10 Reasons to Save for Retirement in a Roth IRA.
08/24/2026

10 Reasons to Save for Retirement in a Roth IRA.

Roth IRA benefits include tax-free retirement income and other valuable tax advantages.

Life, markets, and financial goals can change. Regular reviews can help keep your retirement strategy on track. Visit ou...
08/21/2026

Life, markets, and financial goals can change. Regular reviews can help keep your retirement strategy on track. Visit our website at www.dowlingretirement.com.

Learn about the common pitfalls people find themselves in when Medicare doesn’t cover the cost of care.
08/19/2026

Learn about the common pitfalls people find themselves in when Medicare doesn’t cover the cost of care.

Learn about the common pitfalls people find themselves in when Medicare doesn’t cover the cost of care.

Before choosing your retirement date, we believe you should consider these three questions:1. How much will I need each ...
08/17/2026

Before choosing your retirement date, we believe you should consider these three questions:

1. How much will I need each month?
2. Where will that income come from?
3. How will my plan respond if circumstances change?

Retirement planning is not about predicting the future perfectly. It is about preparing for a range of possibilities.

Schedule a retirement readiness conversation with us at 708-479-8771.

Exciting news! Ron Dowling will be a Guest Speaker at SSSRA Family Resource Night on August 31.With more than 35 years o...
08/16/2026

Exciting news! Ron Dowling will be a Guest Speaker at SSSRA Family Resource Night on August 31.

With more than 35 years of experience, Ron will help families understand the fundamentals of special needs planning and the steps they can take to create a thoughtful, protective plan for a loved one’s future.

The event is free and available both in person and virtually.

📅 Monday, August 31
⏰ 6:00 p.m.

Register now to save your seat! https://sssra.networkforgood.com/events/103782-sssra-family-resource-night-august-2026

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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