Alright, let’s talk about this fuzzy line between work and fun, something I bumped into quite a bit over the years. It’s this whole “gray zone business or pleasure” thing.

I remember this one time, years ago, I got an invite to a conference. Sounded fancy, important even. The catch? It was in a city I’d always wanted to visit, like, properly visit, not just see the inside of a convention center.
The Decision Point
So, first thought: Work trip! Perfect excuse. My boss at the time was pretty chill, mostly cared about results. I pitched it purely on the business benefits:
- Networking opportunities galore.
- Learning the latest industry buzzwords.
- Bringing back valuable insights, blah blah blah.
He signed off on it. Easy peasy. But in the back of my head, I was already thinking about the other stuff. The museums, the food, maybe catching a local band.
The Actual Trip – How It Went Down
I booked my flights. Added an extra day at the end. Used my own dime for that, figured it kept things cleaner. Hotel was covered by the company, standard procedure.
Once I got there, the first couple of days were pretty much by the book. I went to the keynotes, sat through some panels. Took notes, even. Shook hands, swapped business cards, did the whole dance. That was the business part, clear cut.

But then… the evenings. Official conference dinners? Yeah, went to one. Found it kinda stiff. The other nights? I wandered off. Found this little backstreet diner, amazing food. Met some other conference folks there, also ditching the official stuff. We talked shop, sure, but mostly just shot the breeze. Was that business? Kinda. Was it pleasure? Definitely.
Then came the sessions I wasn’t super interested in. Honestly? Skipped a few. Went to that museum I wanted to see instead. Felt a tiny bit guilty, then figured, hey, my brain needs a break to absorb the useful stuff, right? Rationalization is a powerful tool.
My extra day? Pure tourist mode. Walked for miles, took photos, bought some tacky souvenirs. No pretense of work whatsoever. That was clearly pleasure.
Looking Back – The Gray Zone Reality
So, when I got back, I filed my expenses for the flights (minus the extra day’s cost difference, trying to be fair), the hotel for the conference duration, and some meals that were “networking dinners” (even the one at the diner felt justifiable-ish). It all got approved.
But the whole experience sat firmly in that gray zone. Was it a boondoggle? Not entirely. I did make some decent contacts. I did learn a few things. Did I maximize every second for the company? Hell no. Did I enjoy myself? Absolutely.

I realized this happens all the time. People tack on vacation days to work trips. People use company events to socialize and relax as much as they network. The lines get blurred because, well, we’re human. We want to enjoy life, even when we’re supposed to be “on the clock.”
My takeaway? It’s a balancing act. You gotta deliver something work-related to justify the “business” part. But kidding yourself that these trips are 100% work or 100% pleasure is usually wrong. It’s almost always somewhere in between, deep in that gray zone. And honestly, maybe that’s okay. Maybe those relaxed moments, the “pleasure” side, actually lead to better connections than forced networking ever could.