Jon Dowat

Jon Dowat, Esq., leads Thinking Outside the Box Law, Inc., as its founder and managing attorney, focusing on the intersection of bankruptcy law and tax law. With more than two decades of experience, Jon is recognized for crafting innovative, practical solutions for individuals and small businesses encountering significant financial hurdles.

Prior to his legal career, Jon gained valuable experience as a broker and investment advisor, where he honed skills in financial planning, tax strategy, and debt management. His interest in these areas led him to earn his law degree from Chicago-Kent College of Law, with a concentration in taxation. Early in his legal journey, Jon identified the strategic use of bankruptcy law as a potent method for addressing tax debt and achieving financial stability, which became the cornerstone of his practice.

Jon assists clients with Chapter 7 and Chapter 13 bankruptcies, tax planning, tax controversies, and negotiations with the IRS and state tax authorities. His methodology integrates bankruptcy and tax laws to maximize leverage and reduce liabilities, often achieving outcomes unattainable through tax resolution alone.

Clients consistently describe Jon as trustworthy, knowledgeable, and composed under pressure. He is adept at simplifying complex financial and legal matters, ensuring clients feel respected during stressful times. His guiding principle is straightforward: financial challenges require solutions, not judgment, and every client deserves a fresh start based on sound strategy and honest counsel.