Mr. Osborn was admitted to the Illinois Bar in 1980. He is also admitted to the United States District Court - Northern District of Illinois. He is a member of the Illinois State and Whiteside County bar associations. He served as the President of the Whiteside County Bar Association in 2003-2004. In addition, he is a member of the Illinois Bankers Association and the American Bankruptcy Institute.

Mr. Osborn has been involved with the Illinois State Bar Association, including serving as a member of the Commercial Banking and Bankruptcy Section Council, 1994-2002, Chairperson 2000-2001. He was reappointed as a member of the ISBA's Family Law Section Council and Continuing Legal Education Committee, for which he served as Chairperson from 2007-2009.  

Mr. Osborn has been a featured speaker at numerous continuing legal education seminars on bankruptcy and family law matters, and has also lectured at Illinois Bankers Association meetings. After the passage of revisions to Article 9 of Illinois' Uniform Commercial Code, he made presentations on the effects of the revisions.  He also has made numerous presentations to Northwest Illinois bankers on tipics ranging from BAPCPA, participation agreements, letters of credit and the Equal Credit Opportunity Act.  In October 2004, he presented programs in Chicago and Bloomington on creative drafting in marital settlement agreements. In April 2005, he spoke in New Orleans on cross-examination techniques; January 2006 in Bloomington, Illinois on dissolution for farmers; October 2006 in Collinsville and Chicago, Illinois on avoiding pitfalls in marital settlement agreements; and in December 2007 in Chicago and Springfield on discovery techniques.  In June 2008, he moderated three programs on professionalism at the annual meeting of the ISBA in St. Louis.  In 2009, he has made presentations at seminars in Edwardsville and Chicago and moderated the ISBA's Basic Skills programs for new admittees.  He was appointed by then-ISBA President Bob Downs to serve on the Special Task Force on continuing legal education. 

Locally, Mr. Osborn served for over 10 years on the board of Winning Wheels, Inc., a residential facility for physically disabled young people. He is also the immediate past President of the Sterling Schools Foundation, which operates an auditorium on the campus of Sterling High School, issues scholarships, awards minigrants to teachers, sponsors Distinguished Alumni awards and publishes a newsletter distributed to alumni at no cost to them.