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.”

The journey to retirement can be full of excitement and worry, obstacles and windfalls, ups and downs. We’re here for al...
07/20/2026

The journey to retirement can be full of excitement and worry, obstacles and windfalls, ups and downs. We’re here for all of it. Visit https://www.dowlingretirement.com/ or call us at 708.479.8771 to begin the discussion about building a map to retirement today.

07/19/2026

Stop Emergency Fund Anxiety: Link Cash to Your Goals!

Investment Behaviors That Can Hurt Your Retirement | Live Long Retire Strong Ep 1

Full Episode: https://youtu.be/txkrbhfcjhs

07/18/2026

Your Investment Policy Guide 🧭

Investment Behaviors That Can Hurt Your Retirement | Live Long Retire Strong Ep 1

Full Episode: https://youtu.be/txkrbhfcjhs

07/17/2026

Systematic Rebalancing: Maintain Risk and Outcomes

Investment Behaviors That Can Hurt Your Retirement | Live Long Retire Strong Ep 1

Full Episode: https://youtu.be/txkrbhfcjhs

Early retirees can learn new skills, read more, take free college or community classes, or try new hobbies.
07/17/2026

Early retirees can learn new skills, read more, take free college or community classes, or try new hobbies.

Research links retiring early to cognitive decline, while continued work is associated with stronger cognition.

07/16/2026

Not All Retirement Dollars Are Taxed the Same

Investment Behaviors That Can Hurt Your Retirement | Live Long Retire Strong Ep 1

Full Episode: https://youtu.be/txkrbhfcjhs

Dementia doesn't just affect the individual; it affects the whole family. ❤️Join Karen Dowling and the Dowling Legacy te...
07/16/2026

Dementia doesn't just affect the individual; it affects the whole family. ❤️

Join Karen Dowling and the Dowling Legacy team for a day of community support and education. Whether you're a caregiver or just want to be prepared for the future, you belong here.

Register online: https://bit.ly/4thd7gO

Market volatility is inevitable, so are you ready to build a strong strategy to help weather the ups and downs? Give us ...
07/15/2026

Market volatility is inevitable, so are you ready to build a strong strategy to help weather the ups and downs? Give us a call today at 708.479.8771 or visit our website to schedule a complimentary consultation at www.dowlingretirement.com.

Flights, hotels and rental cars all cost more in 2026, but travelers who stay flexible can still find deals.
07/13/2026

Flights, hotels and rental cars all cost more in 2026, but travelers who stay flexible can still find deals.

Flights, hotels and rental cars all cost more in 2026, but travelers who stay flexible can still find deals.

One of the hardest parts of a health journey is knowing how to start the conversation with your doctor. 🩺Our 2 PM sessio...
07/13/2026

One of the hardest parts of a health journey is knowing how to start the conversation with your doctor. 🩺

Our 2 PM session on July 23rd specifically covers how to talk to medical professionals about memory concerns. Don't navigate this alone—let us help you take the next step.

🔗 Sign up here: https://bit.ly/4thd7gO

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

Alerts

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