About Jon
Jon Dowat built a career at the intersection of tax law, accounting and federal practice. He moved from numbers to courtroom papers over the course of two decades. The combination of an economics background and later legal training shaped a practice that crosses both advisory and litigation work.
He earned a Bachelor of Arts in economics and mathematics from Indiana University Bloomington, completing that degree in 1982. Years later he returned to school for law, taking coursework in tax law at Chicago-Kent College of Law and receiving his J.D. in 2004. The academic path reflects an early grounding in quantitative analysis followed by formal training in the tax field.
Soon after law school he stepped into a dual professional role. Since 2005 he has served as managing lawyer and accountant at Thinking Outside the Box Law, Inc. That title captures the hybrid nature of his work: overseeing a small firm while providing both legal counsel and tax-oriented accounting insight. Colleagues and clients have encountered him in negotiating settlements and in formal proceedings.
His admissions cover a range of federal and state tribunals. He is licensed in Illinois and holds memberships that allow practice in the United States Tax Court and several federal district and bankruptcy courts, including the Central District of Illinois, the Northern District of Illinois (Eastern Division), the Eastern District of Wisconsin and the United States Bankruptcy Court for the Northern District of Illinois, Eastern Division. He is a current member of the State Bar of Illinois.
Matters that come through his office tend toward tax controversies, bankruptcy-related proceedings and civil litigation in federal courts. He handles case preparation, client counseling on tax consequences, and appearances in bankruptcy hearings. The work combines technical tax knowledge, evidence gathering and courtroom procedure.
He describes his role as bridging the technical demands of tax and accounting with the procedural rigors of litigation. He has run a small practice that serves individuals and businesses navigating complex tax assessments and insolvency issues. He continues to practice at Thinking Outside the Box Law, Inc., concentrating on tax, bankruptcy and related federal matters.
