Success Stories

Why Clients Choose Thinking Outside the Box Law, Inc.

Dual Focus = Broader Solutions:

By combining bankruptcy and tax knowledge, the firm can craft strategic solutions that deal with all creditors—including the IRS—under one roof.

A Strategic, Personalized Approach:

Each case is approached with careful planning, timing, and legal insight. No cookie-cutter solutions—just well-executed strategies tailored to each client’s unique financial picture.

Trusted Results:

With a flawless 5.0-star rating and consistent elite praise, the firm has helped people shed hundreds of thousands in debt—even in cases other attorneys declined.

I’ve been working with Thinking Outside the Box Law in Naperville for about five years, and I can’t recommend them highly enough. A couple of years ago, they refiled several years of tax returns for me and ended up getting me thousands of dollars back. Jon and his team are communicative, excellent at their craft, and consistently make time for me. It’s rare to find a legal team that blends skill, integrity, and genuine care the way they do. They’re serving their clients – and their community – at a different level.

Hannah Billingsley

★★★★★

This attorney and his staff are highly skilled, knowledgeable, and trustworthy. They helped walk me through a complicated situation with grace and dignity. I am so relieved and forever grateful for their legal help, kindness, and wisdom. I highly recommend this law firm to anyone who needs legal advice and financial solutions. Don’t hesitate. Give them a call.

Patti Ann

★★★★★

Jon and his team are lifesavers! Two years ago my husband and I were in a bad place with our finances and the IRS due to mistakes we made when we started our own business. We contacted Jon and he immediately reassured us everything would be OK and came up with a plan. He accomplished what we never would’ve been able to do ourselves. Not only did he straighten things out with the IRS, he helped us completely turn our financial situation around and establish a system that would keep us on track in the future! I can’t recommend him highly enough!

Kimberly Gallo

★★★★★

Bankruptcy went very smoothly. Attorney Jon Dowat ensured I knew what was occurring every step of the way and made the entire process painless.

Saquoya M

★★★★★

Jon and his team are the best of the best at what they do. Guided me in relieving me of $450k in tax debt thru bankruptcy. Something no other firm offered or even knew was a possibility. Top it all with the upmost professionalism and kindness makes this firm the only choice for help with your tax, debt or combination troubles! Thank you Jon and staff!!!

Adam Toddy

★★★★★

Jon and team are fantastic! He helped me and my former wife navigate a tough season in our lives, and I am here to tell you that his experience, and easy going manner, got us through it. You can get your life back, and Jon helps you get there!

Timothy Goebel

★★★★★

I have worked with Jon and his staff for over a decade. He is very pleasant, extremely knowledgable, and knows the laws inside and out. Jon and his staff are always available or will call you back quickly. I am extremely pleased with all their support and Jon has helped me through difficult times and now with my taxes!!! I so appreciate your humor, honesty and advice! I know I can rest easy that my taxes will be done perfectly!! I would recommend Thinking Outside The Box to anyone who needs financial help or tax services done to the best extent of the current laws!! Thank you!

Susan Jamison

★★★★★

Do you know that dreaded feeling when you must deal with the IRS?! DO NOT stress, call John at Thinking Outside the Box, Law and ALL your stress of dealing with the IRS will be over. In 2015 I had a very complicated tax issue that caused me great stress. I was referred to John and after meeting him I handed the ENTIRE case, and process to him to handle. I no longer had to answer calls, worry and no stress AND he fixed my entire situation and I received a $18,000 reimbursement check from the IRS! THEN AGAIN this last year I had to deal with the IRS for almost $30,000. I tried to handle this myself thinking it would just be one phone call. After going round and round I contacted John again and he completed took over my case, no stress and I no longer owe the $30,000. PLEASE don’t attempt to deal with the IRS yourself, John has been in the industry for so long, he is professional, kind, efficient and a great man of integrity to. Thank you John and to your wonderful staff for being there for me!! Nancy

Nancy Conley

★★★★★

I was referred here after getting to the end of my rope and having already seen many different attorneys in which I realized were giving me bad advice and dragging things out because they didn’t have time to deal with my complicated situation. When I went to see Jon and Julianne they took my situation serious, gave me good advice and I left feeling a weight lifted because they really seemed to know what they were doing and were trustworthy. If you are in over your head and have financial problems come to see them because they can and will help you because they are skilled in their professional expertise and they care.

Dan

★★★★★

Attorney, Jon Dowat and staff are extremely knowledgeable in all aspects of tax and bankruptcy law. Jon is not only an attorney he is also a CPA. He has successfully discharged over $180,000 in FEDERAL TAXES!!! We HIGHLY recommend anyone with any kind of tax or financial problems to call his office. You will NOT be disappointed!!!

Frank Sutherland

★★★★★

Jon and his staff were amazing to work with. They answered all of our questions and were very thorough. He even found extra money in my old tax returns. I am so happy I found him! It’s been such a relief to work with a company that made a scary and stressful process less scary and stressful.

Christopher Roach

★★★★★

I had a debt to the IRS that John and the the office at TOTBL took care of for me. He successfully filed an offer in compromise. I had talked to other attorneys, accountants etc. and no one had an answer for this. John took care of it and now were done. I can’t say enough about their professionalism and attention to detail. Thank You John and all at Thinking Outside The Box Law.

Jim Massoth

★★★★★

Jon Dowat knows his stuff. This is the second time we’ve worked with him. He is professional AND easy to talk to. Most legal issues are confusing. Jon cuts through all that stuff. Meet him; you’ll like him.

Margaret Field

★★★★★

Jon and Julianne did an excellent job for me. they settled my taxes i dont have to look over my shoulder anymore and I got my first refund in ten years. Great job guys.

Robert McCarthy

★★★★★

Jon helped us with multiple issues successfully. He and his friendly staff are a pleasure to work with in difficult situations. We highly recommend their services!

Scott Duncan

★★★★★

From the second I met them, I knew I was in good hands. All the time I spent worried about what was going on, and finally was working with someone the knew what to do, how to do it, and give me peace of mind which is what I needed the most. Very professional, extremely knowledgeable, and very good at what they do. Highly recommend!!

Dan Alsteen

★★★★★

Lawyer was very professional and honest in his advice. You rarely see this happening in the real world when the mercenary lawyers want to take anything they possibly can from an already struggling defendant.

Aryan Chandhok

★★★★★

Beautiful experience with a Christian-based practice! I will be forever grateful for all they did for me.

Patricia Heffern

★★★★★

I have had a positive experience with this firm and would recommend them.

Dan Wyllie

★★★★★

Jon and his team are the best of the best. They relieved me of $450,000 in tax debt through bankruptcy—something no other firm even thought possible.

Verified Review, BirdEye

★★★★★

I walked into Jon’s office feeling hopeless. After our second meeting, I had confidence and a clear path forward.

Client Testimonial, Website Reviews

★★★★★