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.”

Join us for a free informational session with guest Speaker, Mary Stallings, of the Alzheimer's Association. Bring a lo...
06/10/2026

Join us for a free informational session with guest Speaker, Mary Stallings, of the Alzheimer's Association. Bring a loved one with you. Ideal for caregivers or those who just want to know more.

If you’re looking to ease into retirement, some good-paying jobs can be done on a part-time basis.
06/10/2026

If you’re looking to ease into retirement, some good-paying jobs can be done on a part-time basis.

If you’re looking to ease into retirement, some good-paying jobs can be done on a part-time basis.

Today is a good day to remember that work doesn’t last forever. Come talk to us about retirement strategies that are des...
06/09/2026

Today is a good day to remember that work doesn’t last forever. Come talk to us about retirement strategies that are designed to help achieve goals and build rewarding retirement lifestyles. Visit https://www.dowlingretirement.com/ or call 708.479.8771 to learn more.

National Best Friends Day reminds us that the best relationships are built on trust, honesty, and showing up when it mat...
06/08/2026

National Best Friends Day reminds us that the best relationships are built on trust, honesty, and showing up when it matters most. Your financial life deserves that too.
A strong plan should help you feel supported through every stage of life.

A recession shouldn't spell doom for your retirement goals. Here's how to position your nest egg to weather any economic...
06/05/2026

A recession shouldn't spell doom for your retirement goals. Here's how to position your nest egg to weather any economic cycle.

A recession shouldn't spell doom for your retirement goals. Here's how to position your nest egg to weather any economic cycle.

The Guide to Avoiding 401(k) Rollover Mistakes could help expensive mistakes be avoided. Get the guide today by calling ...
06/03/2026

The Guide to Avoiding 401(k) Rollover Mistakes could help expensive mistakes be avoided. Get the guide today by calling us at 708.479.8771!

You might live three decades in retirement. Are you prepared?
06/01/2026

You might live three decades in retirement. Are you prepared?

You might live three decades in retirement. Are you prepared?

This is an article about some of the top-rated methods used to create and follow a retirement savings plan.
05/29/2026

This is an article about some of the top-rated methods used to create and follow a retirement savings plan.

Use these top-rated methods to create and follow a retirement savings plan.

IRAs and 401(k)s, RMDs and 1099s. There’s a lot to manage on the way to retirement, some of which is easy to understand ...
05/27/2026

IRAs and 401(k)s, RMDs and 1099s. There’s a lot to manage on the way to retirement, some of which is easy to understand and some of which isn’t. The good news is we’re here to help make a little more sense of it all.
Visit https://www.dowlingretirement.com/ or call us at 708.479.8771 to begin navigating retirement today.

05/26/2026

During this episode, we'll walk through the key rules and strategies around traditional IRA withdrawals and how timing your withdrawals could make a meaningful difference in your overall retirement picture.

Listen here: https://bit.ly/43xElp0

Check out this show and our other shows on Apple Podcasts, Spotify, and Amazon Music by visiting: https://dowlingretirement.com/media/radio/index.html

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

Website

Alerts

Be the first to know and let us send you an email when Dowling Legacy & Retirement posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Shortcuts

Share

Category