Drowning in debt?

We’re your judgment-free path to a fresh start.

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

Bankruptcy Misconceptions

Bankruptcy Misconceptions

There are a lot of common bankruptcy misconceptions out there. Fears caused by these bankruptcy...

Customer Stories

Ready for experienced tax help

YOU CAN TRUST?