Polishing up your professional online profile, tweaking your resume — these tasks can often feel tedious and dull, the kind of thing you put off as long as possible. But keeping your headshot fresh — which, if you're a professional, entrepreneur, or creative type, is just as important as keeping your resume current — doesn't have to feel like a chore at all. Turns out, it can feel like a party.

My brother and a few friends needed new headshots for LinkedIn, Facebook, and various work websites, so we came up with the idea of holding a 'Headshot Hangout' to get all the pictures taken and make an event out of it.

I headed into Chicago to set up an impromptu photo studio at Mike's apartment. He made some pizzas for everyone to snack on. Josh, who runs a wine business, brought something to drink. Our friend Mark, a stylist at Trunk Club, helped all the guys dress the part.

Over the course of 3 hours, everyone ate, drank, enjoyed great company, and spent some quality time in front of the camera. It was a fun afternoon and the shots look great. I follow several of the guys on Facebook and it’s been cool to see the comments they get when they post their new photos as profile pics.

Sound like fun? If you're interested in hosting your own Headshot Party in Chicago or Lake County, drop me a note — I'd love to help!