Many lawyers have left Big Law careers behind to start their own business ventures, whether they be stateside or overseas.

Timothy Duffy, a former litigation partner at Kirkland & Ellis in Chicago, has taken what some would call a road less traveled in his own backyard. In addition to setting up his own solo legal practice and working on a food distribution startup, Duffy, along with his wife Bette Anne Duffy, are the owners of an eyelash extension franchise just outside of Chicago called Deka Lash.

“Like most guys I had no idea you even did this or this was a thing,” said Timothy Duffy of his new enterprise in the Windy City suburb of Glenview, Illinois. “But when [my wife] told me she was going to a salon and spending about $500 a month on eyelashes and she couldn't get an appointment because the place was so booked up, I thought, 'Well, maybe there's something to this.'”

Duffy and his wife opened up their first Deka Lash location in August 2017. The business has done so well that they're in the process of opening up a second location near Chicago in February and have two more locations in the works, Duffy said.

Owning and operating an eyelash extension franchise is a bit of a departure from Duffy's former career as a Kirkland litigator. Duffy first joined the Am Law 100 firm in 1995, following a clerkship with the U.S. Court of Appeals for the D.C. Circuit. His practice encompassed all areas of litigation, but had a particular focus on accounting, commercial and mass tort litigation, as well as corporate governance work.

Duffy had a role in some of Kirkland's most notable cases throughout the years, including its representation of General Motors Corp. pertaining to its ignition switch defect, British energy giant BP plc in litigation emanating from the Deepwater Horizon oil spill and accounting giant PricewaterhouseCoopers in a $55 million settlement with victims of Bernard Madoff's massive Ponzi scheme.

But after more than 20 years at Kirkland, a friend approached Duffy to help in the creation of CeresNexus LLC, a suburban Denver-based startup that attempts to simplify the way food companies and other buyers acquire food products from vendors. Duffy said the more he began taking an active role in the business' development, the more he saw himself doing something different.

“As soon as you start thinking about doing something new it's like, 'Oh gee, well my normal job is kind of boring,'” he joked.

In early 2017, Duffy switched to an of counsel role at Kirkland before officially exiting the firm in November. Duffy said that he is still working alongside his former Kirkland colleagues in some ongoing matters for former clients, but does so through his solo practice in the Chicago suburb of Northfield, Illinois. (Duffy's law office is a mere 10-minute drive from the nearest Deka Lash.)

While he holds a fondness for his former firm and time in Big Law, Duffy said his new endeavors have presented him with a unique challenge that have allowed him to be a bit more creative, strategic and sensitive to how he spends his time. That has also caused him to reflect on the culture that Big Law creates and the priorities it can sometimes encourage.

“You have a lot of smart people putting a lot of effort into making their third and fourth million dollars, and if that's what you want to do that's fantastic, but I think a lot of people end up doing that even though that's not really what they want to do,” said Duffy, adding that such pressure often has less to do with dollar figures than a feeling of not measuring up to colleagues. “And I really think it leads to good smart people [being] trapped by their own ambition in a way they never really expected.”

Since leaving Big Law behind, Duffy said he's been approached by many people who have said they wished they could do something similar and pursue different endeavors. But to that end, Duffy said he challenges them to pause and look at their own career trajectories.

“You can do whatever you want, but it might require you not doing what you've been doing for the past 20 years,” he said.