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Thinking Outside the Box Law, Inc. BBB Business Review

Connect the dots between two of the most powerful legal systems available to individuals and businesses in distress: the Tax Code and the Bankruptcy Code.

Want to work with one of the most trusted tax law attorneys in Illinois with a proven track record for helping people in your situation with our tax services?

Services

Tax Debt Resolution

Drowning in tax debt? We negotiate directly with the IRS and state tax authorities to slash your balances, set up affordable payment plans, or settle for pennies on the dollar with an Offer in Compromise.

Bankruptcy Services

Facing foreclosure, garnishments, or bank levies? Bankruptcy could be the solution to giving you breathing room and a chance to rebuild.

Other Services

At Thinking Outside the Box Law, our primary mission is to help individuals and businesses resolve serious tax and debt challenges.

Tax Service

Why Choose Thinking Outside the Box Law

When it comes to serious tax debt, years of unfiled returns, or IRS collections, you can’t afford to gamble on flashy marketing or sales-driven “tax relief” companies. There’s too much at stake—and too many ways to make things worse.

I’m Jon Dowat, attorney-at-law. I have deep expertise in both tax and bankruptcy law. For years, I’ve been helping clients across the country resolve complex tax problems, stop aggressive IRS actions, and get back on solid ground with trusted tax services.

What sets us apart

When you reach out to us, you’re not getting a call center or a commissioned salesperson. You’re getting direct, experienced legal help from a licensed attorney who knows how to combine tax law and bankruptcy law to deliver real, lasting relief.

And we have the track record to prove it:

  • Discharged $1 million in business
  • Settled $3 million IRS debt for just $2,600
  • Stopped foreclosure with a second bankruptcy filing

We’re not here to sell you. We’re here to fix it.

If you’re overwhelmed by unfiled returns, crushing tax bills, levies, garnishments, or the threat of foreclosure, we know exactly where to start – and how to end it.

We offer clear, compassionate solutions so you can finally have peace of mind. Let’s turn the chaos into a fresh start.

Tax Service
Tax Service

What sets us apart

When you reach out to us, you’re not getting a call center or a commissioned salesperson. You’re getting direct, experienced legal help from a licensed attorney who knows how to combine tax law and bankruptcy law to deliver real, lasting relief.

And we have the track record to prove it:

  • Discharged $1 million in business
  • Settled $3 million IRS debt for just $2,600
  • Stopped foreclosure with a second bankruptcy filing

We’re not here to sell you. We’re here to fix it.

If you’re overwhelmed by unfiled returns, crushing tax bills, levies, garnishments, or the threat of foreclosure, we know exactly where to start – and how to end it.

We offer clear, compassionate solutions so you can finally have peace of mind. Let’s turn the chaos into a fresh start.

Recent Posts

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
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
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
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
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!

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