Okay, first...get your heads out of the gutter.
Working Naked Day is the creation of Lisa Kanarek and is intended as a celebration of the ability to work "naked," as in free of the usual corporate hang-ups such as the daily commute, irritating coworkers, office politics, difficulty managing work/life balance...and yes, dress codes.
And while there are some who do indeed go...ahem, full monty for the day, I will not. Sorry...it's too friggin' cold, and it would make walking the dog a bit awkward.
But Working Naked Day means more than a different interpretation of "Business Casual," at least to me. It's also working without a safety net—no backup or support staff to cover when you're sick, go on vacation, or are simply overwhelmed; no pal in the next cubicle to brainstorm or kvetch with; no HR reps to help you pick the right medical plan; and having to deal with all the other nagging fears and doubts that come with the freelancer lifestyle—and MAKING IT HAPPEN. (And that wouldn't be the case without all my clients and clients-to-be, so thank you, thank you, and thaaaaank you!)
So, as I said from the start, Working Naked Day is not for dwelling on the "what ifs" and looking down to see there isn't any net. Instead, it's about celebrating me, my awesome clients, and the fact that I am indeed making it...and doing it while wearing comfy sweats and a Batman T-shirt. Maybe even the cape; I haven't gotten that far yet in today's decision-making...
Happy Working Naked Day, y'all!!