About Us
Servicing Dupage, Kane, Kendall, Will, and Cook CountiesCredit card companies. Banks. Hospitals. The IRS. Illinois Department of Revenue. Let us take the weight of these organizations off of your shoulders. We use bankruptcy law and tax law to help individuals and small businesses deal with these institutions and regain their financial footing.
Leverage our knowledge, experience, and creativity. Your finances are an ecosystem. The combination of our bankruptcy law and tax law experience allows us to do more for our clients than a bankruptcy-only or tax-only firm.
Take control of your personal finances. We can help you find the right legal tools to deal with your individual situation. We have helped our clients with tax preparation, credit card debt, medical bills, delinquent taxes, foreclosures, personal judgments, and more.
Take control of your business finances. We can help you navigate your business taxes and debts.
Do it right the first time. If you are just starting your business, we can help you figure out your best incorporation strategy and help you put a tax system in place to avoid problems down the road.
If you feel like your financial situation is overwhelming and you don’t know where to turn, call Thinking Outside the Box Law for a free evaluation of your case.
Meet the Team
Jon Dowat
Esq.
Julianne Di Benedetto
CP®, AACP, ILAP
Jon Dowat, Esq.
I started my career as a broker and investment advisor. During my career, I ended up doing accounting for my clients. I became interested in the tax laws because helping my clients reduce their taxes was an area that made a huge difference in their lives.
I felt I could help my clients more if I studied the tax laws. I quit my full time job and enrolled in law school where I primarily studied taxation.
After I got my law degree I was helping my clients prepare tax returns and settle tax debts with the IRS. I did not plan to practice bankruptcy law. I discovered the bankruptcy laws gave me more leverage over the IRS when resolving my clients tax problems.
Internal Revenue Code (tax laws) make up a large part of the Bankruptcy laws. Bankruptcy law allows a taxpayers greater control in resolving tax issues and can allow taxpayers to discharge penalties or pay back some taxes for “pennies on the dollar.” In some instances bankruptcy can completely discharge Federal and State income taxes.
My practice utilizes bankruptcy and tax laws to help individuals and businesses resolve their financial problems. This combination taxation and bankruptcy gives clients a greater range of options in relieving the stress related to their financial problems (primarily tax and debt issues).
Julianne Di Benedetto,
CP®, AACP, ILAP
Julianne is the Executive Law Office Administrator and Senior Supervising Paralegal at Thinking Outside the Box Law, where she has worked since 2016. In addition to managing the office, Julianne prepares business and personal bankruptcy petitions, drafts Offers in Compromise for tax settlement, prepares business and personal tax returns, performs accounting services, and incorporates businesses. She is a certified paralegal with both state and national organizations, and she is a registered tax return preparer with the Internal Revenue Service. Julianne is certified in QuickBooks.
Julianne earned her associate’s degree in paralegal studies from the College of DuPage in Glen Ellyn, Illinois, and graduated with High Honors. As a student, she was the president of the LEX Paralegal Honor Society, the vice president of Paralegal Club, and the paralegal student representative to the program’s Advisory Council. She was inducted into both the LEX Honor Society and the Phi Theta Kappa Honor Society.
After graduation, Julianne earned the ILAP credential from the Illinois Paralegal Association, the Certified Paralegal® credential from NALA, and the Certified Paralegal credential from the American Alliance of Paralegals. Since her graduation, Julianne has given presentations to college paralegal programs and to paralegal organizations on various topics, including bankruptcy law, tax law, and navigating paralegal certifications. Julianne has been featured on the American Bar Association website and the College of DuPage website as a paralegal graduate success story. Julianne’s article on paralegal regulation and licensure was published in the Paralegal Reporter, a paralegal magazine distributed by the National Federation of Paralegal Associations (NFPA). Julianne was named the 2021 Rising Star in the paralegal field by NALA, one of the leading national paralegal associations, for “exemplary service to the paralegal profession.” In 2023, Julianne was invited to work with NALA to update its paralegal certification exam. She contributed to the newly adapted bankruptcy section of the exam and co-authored the bankruptcy chapter in NALA’s certification exam book. In 2023, Julianne was selected to join NALA’s inaugural LEAD leadership development program, which she successfully completed in 2024.
As a firm believer in education, Julianne returned to the College of DuPage to pursue additional certificates in accounting, office technology, and management. She also completed her second degree. As a returning student, Julianne is the vice president of both Paralegal Club and LEX. She is a permanent member of the paralegal/legal studies program Advisory Council and is the Coordinator/Peer Reviewer Coordinator of the College of DuPage Paralegal Studies Expo. She has also served as the Vice-Chair of the DuPage County Bar Association Paralegal Section.
Currently, Julianne is studying for the NFPA paralegal certification exam. She plans to continue her interest in lifelong learning by pursuing additional degrees in formal education.
Let Us Help:
Friend,
If you’re reading this, chances are you’re overwhelmed.
Maybe you’re getting threatening IRS letters or collection calls. Maybe you haven’t filed taxes in years and don’t know where to start. Maybe your wages are being garnished, your bank account has been drained, or you’re afraid you could lose your home or your business.
You are not alone—and you are not out of options.
At Thinking Outside the Box Law, we help people in crisis take back control of their financial lives. With deep expertise in both tax law and bankruptcy law, we offer solutions most firms can’t. We don’t just negotiate with the IRS—we use the full power of the legal system to:
– Stop IRS levies, garnishments, and foreclosures immediately
– Discharge or reduce state and federal tax debts
– Reconstruct years of unfiled tax returns
– Set up court-supervised payment plans with little to no interest
And when you hire us, you never have to face the IRS alone. We step in as your representative, shield you from the chaos, and create a clear path toward resolution and relief.
If you’re ready to take the first step toward a fresh start, click on the button below to take your first step. Discover why I’ve been called “The Most Trusted Tax Attorney in DuPage.”
PS — If you’re speaking with other firms, ask them one critical question:
“Can you represent me in both tax resolution and bankruptcy court?”
That one question can make the difference between a dead-end plan and a real solution.
PPS — Already know you’re ready for help?
Reach out today. Our schedule fills fast, but if you call us at (630) 225-9840 or Email Us, we’ll give you options for getting started right away. We promise—this experience will feel different from what you’ve been through before.
Talk soon,
Jon Dowat
Attorney at Law
