How to set boundaries with annoying male coworkers (and still get ahead)
Navigating offsite drinking with older male colleagues when it's uncomfy but worried it's a bad look to skip
Hi please advisers (hmm don’t think I like that),
I feel like a lot of women in many different professions will (unfortunately) be able to relate to this week’s reader email. If you’ve been in a situation like this, and especially have come up with a method around it, please share in the comments. Diving in.
Hi Aleen!
I work in sales and just got back from a 4 day trade show - think intense 10 hour days mostly on your feet and interacting with people constantly. My team is mostly male average ages between 45-60, I’m a 28 year old female. Most nights we would have a client dinner lasting until 9-10ish and then our team would go to another bar to have drinks for a couple of hours. I felt pressure to attend these “after parties” (both external and self-imposed pressure) but often found myself uncomfy by either the topics of conversation or behavior of my colleagues.
Things like sexually suggestive conversations, personal overshares, speaking negatively of spouses or even just giving me unsolicited advice on finances, relationships, having kids, etc. Not to mention that I’d rather be getting the additional sleep and charging up for the next day of the show. In essence I would love some advice on how to navigate the pressure to attend work social events and form these relationships with colleagues while also taking care of yourself. Thanks.
Hey hey,
Yeah this is tough, I totally hear you. Being the only woman on a team of all men (or any team where you’re the odd one out) is definitely jarring at first – I’ve been in plenty of these rooms in my career – but it’s often the character of those men (or people) that will determine your experience. In your case, it seems like 1) you don’t want to be spending time with these guys in the first place because they kind of suck, and 2) you don’t feel confident enough in how you’re perceived that if you were to skip out, it wouldn’t hurt your job performance somehow. And unfortunately, some industries really are structured so that showing face in certain situations is necessary, if not explicitly required.
Sales is both high pressure and all about relationships, so I understand why skipping the “after-after” drinks might feel like putting yourself on the outside of the inner circle. But let’s be real… you’re a grown woman in a high-performance field, not a contestant on The Bachelor. You're allowed to protect your boundaries and your *literal* energy, both of which you need to feel good and do well in the long run in this job.
I understand that this isn’t all about fomo and that your absence might put you at a career disadvantage. But at the end of the day, most sales jobs come down to how close you are to your quota, not your teammates’ opinions of how well you can hang.
As much fun as it is to talk shit about these guys and feel (justifiably) frustrated by the situation, here’s how I would approach it:
1. Pick Your Party Nights
You don’t have to go to every bar, every night. Show up sometimes, stay for one drink, and leave. People remember your energy while you were there, not that you didn’t close it down. Maybe invent a point system for when you’re not sure if it’s worth it. For example, is a client there? +1. How many? +1 for each additional. Will this appearance do more for achieving your sales goal than the rest you’ll get at home? +2. What senior management is going? Award points depending on importance. If you get past 5 points (or however you design this), it may be worth the time. If not, there’s no need to feel guilty or second guess your decision. Remember, sometimes being the one to close it down is a gateway to a bad reputation, even in industries that party hard.
2. Set a Natural Exit
Blame an early call, a workout, or even just needing rest, whatever feels authentic to you. Say it once and with confidence. “I’m going to head out, early morning tomorrow. This was fun!” It’s only as awkward as you deliver it. Most people won’t question it. If they do, that says more about them than you.
3. Redirect or Opt Out Gracefully
Having fun with your coworkers does not have to mean pretending you’re okay with creepy jokes or comments. You don’t have to be super serious all the time, but draw your boundary clearly around work appropriateness. When the talk turns inappropriate or just exhausting, steer it back or excuse yourself to the bar, the bathroom, to catch up with someone else or check your phone. If the same guys keep crossing a line, take mental notes. This is valuable intel. You don’t have to call it out every time, but you do get to decide what you tolerate.
4. Build Relationships Your Way
Not all connections have to happen over beer at 11 PM! Grab a coffee the next morning. Set up a lunch next week to debrief the trade show. Show them you’re serious about work and being a reliable teammate.
5. Remember This: Opting Out Isn’t Opting Out of Success
You’re not “missing out” by skipping a round of scotch and soul-baring from men who don’t know how to respect boundaries. You’re choosing to show up clear-eyed, energized, and professional. That’s a power move.
Essentially: you’re allowed to say “this doesn’t work for me” and still be taken seriously. Anyone who implies otherwise probably isn’t someone whose approval you need to win.
You don’t need to drink to belong. You need to deliver your quota, build trust, and stay sharp. And you’re already doing all of that.
You so got this,
Aleen
Dm or email me your question at @aleen or hi@aleen.com