Jon Dowat

Jon Dowat, Esq., is the founder and managing attorney of Thinking Outside the Box Law, Inc., where he focuses his practice on the intersection of bankruptcy law and tax law. With more than two decades of experience, Jon is known for developing creative, practical solutions for individuals and small businesses facing serious financial challenges. Before becoming an attorney, Jon worked as a broker and investment advisor, gaining hands-on experience with financial planning, tax strategy, and debt management. That background led him to pursue his law degree at Chicago-Kent College of Law, where he concentrated on taxation. Early in his legal career, Jon recognized that bankruptcy law—when used strategically—can be a powerful tool for resolving tax debt and restoring financial stability. This insight became the foundation of his practice. Jon represents clients in Chapter 7 and Chapter 13 bankruptcies, tax planning, tax controversy matters, and negotiations with the IRS and state taxing authorities. His approach emphasizes using bankruptcy and tax law together to maximize leverage, reduce overall liability, and create realistic paths forward—often achieving results that would not be possible through tax resolution alone. Clients consistently describe Jon as trustworthy, knowledgeable, and calm under pressure. He is known for explaining complex financial and legal issues in plain English and for treating clients with respect during what is often one of the most stressful periods of their lives. His philosophy is simple: financial problems deserve solutions—not judgment—and every client deserves a fresh start built on sound strategy and honest advice.