The Wild Blue Yawn-der

Robert Held laughs when asked about leaving behind the thrills of flying jets for his current full-time focus on trust and estate law.

“I know that it always sounds like the grass is greener on the other side,” says Held, 51, who was a pilot for an international airline throughout law school and during the first seven years of his legal career. “The truth is that airline flying is exceedingly boring. If you pilot a flight to Europe, you have a minute or two during takeoff where it’s interesting, but then you’re flying over the ocean at night and the plane is on autopilot. Then you have a couple of minutes during the descent and landing itself that I would describe as ‘fun’ and then you walk off the plane and it’s over.”

That’s not to say that Held doesn’t look back fondly on his days in the cockpit, which ended in 2005, two years after he left Lord, Bissell & Brook to start a firm with Lou Harrison, one of his law professors from DePaul.

After earning his pilot’s license and graduating from SUNY-Buffalo in 1980, Held entered the Air Force. He served as a military pilot for seven years, three of which he spent stationed in England in an  EF-111A unit. His squadron flew one mission during the 1986 raid on Libya, losing two fellow airmen in combat.

Upon leaving the service he worked for a commercial airline, but his drive for new experiences led him to pursue a law degree. Throughout his studies he continued to fly full-time. His typical route took him from Chicago to cities in Western Europe—London, Paris, Milan—and back again.

“I would arrange my schedule so that I would leave Friday evening, fly to Europe and arrive Saturday morning,” says Held, who became good at sneaking naps during breaks and mastering sleep cycles. “Then I would fly back on Sunday and, as an associate, I had to be right back in the office early Monday morning.

“I wouldn’t do it again,” he adds with a laugh.

Harrison & Held just celebrated its fifth anniversary and has grown to 23 lawyers and six paralegals, while expanding beyond its original specialty of estate planning and estate/trust administration and into the fields of corporate, real estate and general litigation.

“To me, it’s exciting and particularly intellectually challenging to work on client matters that have a high level of complexity,” he says. “When you’re solving problems and working with a tremendous group of people, you really enjoy what you do.”