Jacobson has been recognized by his legal peers as a Wisconsin “Super Lawyer,” and he served as president of an eleven-lawyer firm in La Crosse in the mid-2000s. He has litigated disputes involving environmental law, business matters, insurance, employment, personal injury, real estate, stray voltage, contracts, construction defects, and corporate governance, including multiple jury trials to successful completion. He represented Wisconsin commercial corn growers as part of $110 million settlement of nationwide class action with claims arising from genetically-modified “StarLink” corn. With co-counsel from multiple firms, he helped achieve a multimillion-dollar settlement of an environmental class action against the Burlington Northern Santa Fe Railroad on behalf of 300 La Crosse property owners. He successfully appealed circuit court decisions, including obtaining a victory before the Iowa Supreme Court and defeating an opponent's petition for certiorari before the U.S. Supreme Court in a wrongful termination case. He also served as board president of Midwest Environmental Advocates, a public interest law firm based in Madison. He’s a member of the board of directors of Wisconsin Wetlands Association and a past board member of Gathering Waters Conservancy.

In addition to his legal work, Jacobson is the Emmy Award-winning executive producer of the documentary film Mysteries of the Driftless, he’s the best-selling author of the novel The Kurchatov Penetration, and he’s a landscape photographer. Additionally, Jacobson is a Major in the U.S. Air Force Auxiliary (Civil Air Patrol), where he has served as a Mission Pilot and Squadron Legal Officer. Also, he earned a black belt in karate.

Jacobson got his start in the practice of law in La Crosse in 1992, and is now in his 25th year as an attorney. He worked in La Crosse law firms for 14 years, and then served as executive director of Mississippi Valley Conservancy from 2006 to 2013. In 2013, Jacobson married a Boscobel, Wisconsin kindergarten teacher, Lisa, and relocated there. While in Boscobel, Jacobson was engaged in organizational consulting and economic development work. He also co-founded the nonprofit group, Sustainable Driftless, Inc., and is in the midst of producing a feature-length documentary film about the beautiful landscape of the Driftless Region.