So this year, he and a similarly self-employed friend, Mike Snyder of Snyder Online Marketing, decided to reclaim the ritual: Wednesday they're throwing a Freelancers Holiday Ball, a night for office-party orphans to call their own.
Snyder said those who make up Philly's vibrant gig economy deserve to feel appreciated.
"A third of the workforce in Philadelphia is somebody who's a freelancer or small-business owner or contracts their services: Web designers, DJs, even Bitcoin entrepreneurs, or people like myself in online marketing," said Snyder, 38, of Queen Village. "There are so many people that this time of year are going to holiday parties, and we felt like: Why should we feel left out?"
About 70 people had signed up by last week at PhillyFreelancer.com. Lekkas said he would not make money from the free event at Khyber Pass Pub, but saw it as a chance to network.
In a subtle way, it's also a statement in defense of the Form 1099-filers of the world, at a time when "freelancer" is sometimes construed as a euphemism for "underemployed."
"People who work the standard 9-to-5 don't understand how we do what we do," Snyder said. "The term entrepreneur is taken very loosely these days. . . . We feel like, the guy who's in his basement 12 to 14 hours a day, banging out good-quality work - they're the true entrepreneurs, and they deserve the recognition."
If all goes well, Lekkas wants to make the party an annual tradition, and could envision it becoming more elaborate.
For a blueprint, he could look to freelancer-saturated Brooklyn, where a group of bloggers have been throwing their own No-Office Holiday Party for the last three years.
The event - which usually attracts a few hundred cubicle refugees for live-band karaoke, comedy, and drink specials - has all the trappings of a classic office party. (Well, almost all: They've never managed to bring in a copy machine for the requisite lewd photocopies. "Nobody wants to rent us one, because we're obviously going to break it," said Tim Donnelly, a contributing editor at the blog Brokelyn and one of the organizers.)
Why go to all the trouble? Donnelly admitted it's partly just a good excuse for a night out.
But more than that, he said, "It's kind of a pushback against this idea of the office-job economy. . . . The need to have that office culture has disappeared. In a way, it's a celebration of that idea that people don't want to be in an office anymore."
And, it's a chance for people who normally work in isolation to develop connections.
That's the appeal for Nico Westerdale, 37, of Old City, who's planning to attend the Freelancers Ball. He's president of a small company, the software daily-deal start-up Bits du Jour, but his coworkers are scattered around the globe. So, Westerdale has been trying to make connections in the Philly start-up scene.
He said that, in his sector, business connections and friendships are nearly indistinguishable.
"It's so different from corporate networking," Westerdale said. "You just want to talk to interesting people doing interesting things. Maybe you'll be able to work together, maybe you won't - but it's fun. I think the best business ideas and the most exciting stuff comes from people getting together, having fun, and creating something good out of it."
If that doesn't work out, at least the Freelancers Ball will offer a better beer selection than your average company outing: Virginia's Starr Hill Brewery is offering free tastings.
As a bonus, attendees can avoid those typical office-party pitfalls: uncomfortable chitchat with the woman from accounting whose name you never learned, getting tipsy in front of your boss, or the hungover return to your desk the next morning.
After all, said Lekkas, when you're your own boss, "You can't fire yourself if you get too drunk."