About Our Firm

Our Mission

To restore hope and stability to individuals and small businesses through thoughtful, strategic legal solutions that address the full scope of financial distress—especially when taxes and debt collide.

Thinking Outside the Box Law, Inc. is a modern law firm committed to helping individuals and businesses overcome serious financial challenges. Specializing in tax resolution and bankruptcy law, we use the power of the Tax Code and the Bankruptcy Code to eliminate debt, settle back taxes, and help clients get caught up when they’ve fallen behind on filing returns.

We’re not just legal technicians—we’re problem solvers. Every case is different, and our approach is tailored to each client’s unique situation. It’s this mix of math, timing, and strategy—and when you get it right, it’s like unlocking a secret exit for your client. That’s what we do every day.

At Thinking Outside the Box Law, Inc., we don’t believe in cookie-cutter solutions. We think creatively, act strategically, and guide our clients toward a brighter financial future with compassion and clarity.

Our Services Include:

IRS and state tax debt resolution
Chapter 7 and Chapter 13 bankruptcy filings
Offers in compromise and installment plan negotiations
Assistance with unfiled tax returns
Asset protection and credit rebuilding strategies

We’re here to relieve the stress, clarify the confusion, and chart the most effective path forward. If you’re feeling stuck, let’s find the exit—together.

Who We Are

Thinking Outside the Box Law, Inc. is a results-driven law firm based in Naperville, Illinois, serving clients across DuPage, Kane, Kendall, Will, and Cook Counties. With extensive experience in both bankruptcy and tax law, the firm stands out for its ability to offer powerful, integrated solutions to individuals and small businesses facing serious financial challenges.

The firm takes a unique approach that blends timing, legal strategy, and financial precision—a method that allows for creative, effective relief from all types of debt, including IRS obligations. This synergy between tax and bankruptcy law gives the firm more tools than traditional firms to address the full spectrum of creditor issues.

Practice Areas

Bankruptcy Law

Skilled in Chapter 7, 11, and 13 filings, the firm helps clients eliminate or restructure debt, protect assets, and stop creditor actions—often in conjunction with tax relief strategies.

Tax Law

Offering comprehensive tax representation, including audit defense, settlement negotiations, offers in compromise, and resolution of back taxes with the IRS and Illinois Department of Revenue.

Small Business Support

From entity formation to financial restructuring, the firm supports small businesses with practical legal guidance grounded in real-world financial experience.

Let Us Help:

Customer Stories

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Hannah Billingsley profile picture
Hannah Billingsley
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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.
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Patti Ann profile picture
Patti Ann
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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.
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Saquoya M profile picture
Saquoya M
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Bankruptcy went very smoothly. Attorney Jon Dowat ensured I knew what was occurring every step of the way and made the entire process painless.
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Adam Toddy profile picture
Adam Toddy
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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!!!
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Patricia Heffern profile picture
Patricia Heffern
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Beautiful experience with a Christian-based practice! I will be forever grateful for all they did for me.
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Timothy Goebel profile picture
Timothy Goebel
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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!
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Scott Duncan profile picture
Scott Duncan
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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!
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Aryan Chandhok profile picture
Aryan Chandhok
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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.
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Margaret Field profile picture
Margaret Field
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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.
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Kimberly Gallo profile picture
Kimberly Gallo
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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!