You ever try to mix business and pleasure and then immediately regret it halfway through the second drink? Like, why wouldn’t you want to have a good time while working? But then someone brings up Q3 projections while you’re halfway into a margarita, and suddenly everything feels… off.
But here’s the thing. People do mix the two all the time. It’s not some big scandal. It’s actually kind of common, especially now that work doesn’t always mean an office and a suit and some soul-crushing fluorescent lights. People take meetings over brunch, talk shop at weddings, close deals on the golf course, which honestly just seems like a weird place to do anything serious, but whatever. To each their own.
There’s this blurry line now between what counts as “work” and what counts as “personal time.” You answer a few emails while you’re on vacation. You grab drinks with a client who also kinda feels like a friend. You throw in a little small talk during a meeting and suddenly it turns into a 30-minute chat about weekend plans and your favorite sandwich spot. That line? It’s gone. It’s been gone for a while.
Some people love it. They feel like it makes work more human. More relaxed. ” And I get that. There’s something refreshing about not needing to switch into some stiff version of yourself just because it’s “work time.” You can be real. Joke around a little. Laugh. Talk about your dog. Whatever.
But not everyone’s into it. For some people, mixing business and pleasure feels messy. Risky, even. What happens when the business part crashes but the pleasure part is still around? Or vice versa? What if you’re too friendly and they start taking advantage? Or you take things too far and it gets awkward? And let’s not even get into dating coworkers or clients. That’s a whole other level of “maybe don’t.”
Still, people do it. All the time. Especially in industries where networking is basically everything. Think entertainment, tech, fashion, even real estate. In those worlds, the social scene is the work scene. You go to events. You hit happy hours. You talk business, but you also laugh and drink and vibe. And yeah, some of the biggest deals get done while people are halfway distracted by appetizers and background music.
I think the trick is knowing your boundaries. Like, can you handle it if the lines get blurry? Can you stay professional even when the setting isn’t? If someone’s telling you a funny story about their weekend, are you gonna weirdly pivot into a sales pitch? Please don’t. No one wants that. You’ve gotta read the room. Timing matters. Tone matters. And if you’re gonna mix business with pleasure, you better be really good at keeping them separate when things go sideways.
Also, let’s be honest. Some people try to use “pleasure” as an excuse to escape the stress of “business.” Like, they’ll slap a company name on a vacation and call it a “work trip.” You flew to Miami, took one meeting, then spent four days at the pool. That’s not a business trip. That’s a tan with a receipt. Not saying you can’t enjoy yourself while working, but if you’re just gaming the system to feel less guilty about relaxing, just own that. No need to pretend.
On the flip side, there’s the idea of turning your pleasure into your business. Now that’s a whole different vibe. People start side hustles based on stuff they love. Baking, photography, travel, video games, whatever. Suddenly your hobby’s got invoices and tax forms. And at first, it’s amazing. You’re doing what you love. You’re your own boss. You’re excited. Until one day you realize you haven’t done the thing just for fun in months because now it’s tied to deadlines and money and client expectations.
That’s the downside no one talks about. When pleasure becomes business, it can start to lose its magic. Like, you used to bake cookies because it made you happy. Now you’re baking 300 of them for a corporate event and you’re dead tired and don’t even want to look at another chocolate chip for the next six months. It’s wild how quickly the thing you loved can turn into just another job.
So yeah, mixing business and pleasure isn’t always glamorous. It can be fun. It can be useful. Sometimes it’s the only way things get done. But it’s also messy and confusing and sometimes you don’t realize it’s a bad idea until it’s way too late.
Still, not all mixed moments are disasters. I’ve had great conversations with coworkers over drinks. Some of my best ideas popped up during casual chats, not in some formal meeting. I’ve seen friendships form out of work relationships and work partnerships form out of random social settings. It’s not all doom and awkwardness. There’s some magic in the overlap too.
At the end of the day, we’re all just trying to figure out how to do the work, make some money, and still have a life that doesn’t feel like a spreadsheet. If that means sometimes mixing things up, so be it. Just try not to pitch your startup idea at your cousin’s wedding. Or if you do, at least wait until after the cake.
