Work Trips and Happy Hours: The Complete Guide for Your First Corporate Events

Just back from his first company offsite, Josh Felgoise learned some valuable (and expensive) lessons about navigating work trips and office happy hours. If you're in your 20s and facing your first corporate travel or after-work events, this guide will help you avoid the mistakes he made while making the most of these crucial networking opportunities.

Work Trip Essentials: What Nobody Tells You

1. Arrive 15 Minutes Early to Everything

Josh's biggest shock? Showing up "on time" at 8:59 AM, only to find everyone else had been there for 15 minutes.

"I rolled up at 8:59 and was like, 'what's up everybody?' But you should be there early."

Why this matters: Those extra 15 minutes are prime networking time. People are relaxed, making small talk, and setting the tone for the day. Missing this window means missing valuable relationship-building opportunities.

2. Master the Dress Code Game

Work trips often involve mixed activities—meetings in the morning, company hike in the afternoon. Josh's solution? Lululemon pants (not sponsored, just enthusiastic).

Pro tip: Invest in versatile pieces that work for both professional and casual activities. You'll look put-together without needing multiple outfit changes.

3. Phone Etiquette: Stay Present

Most companies now have explicit "phone-free" periods during offsites. Even when phones are allowed, Josh recommends:

• Make a conscious effort not to check texts or your Apple Watch

• Step out of the room if you need to use your phone

• Be genuinely present with your colleagues

The payoff? You'll be seen as engaged and professional, setting you apart from those constantly distracted by their devices.

Company Dinners: The Unspoken Rules

Order Smart, Not Expensive

The golden rule: Watch what your boss orders before you order.

"If they're getting the steak, then you can get the steak too. But if they're getting pasta that's less expensive than the steak, I wouldn't get the steak."

How to handle it:

• If the waiter comes to you first, say "Please, you go first"

• Follow the lead of people above you in the hierarchy

• When in doubt, choose something mid-range

The Two-Drink Rule

Josh's hard-learned wisdom: Stick to 1-2 drinks maximum at company dinners.

Why this matters:

• You're still at work, even if it feels social

• You need to stay in control of what you say

• Exception: If senior people leave early and it's just peers, you can have one more

Know your tolerance: If one drink affects you significantly, consider not drinking at all.

Expenses: Know Before You Go

Perhaps Josh's most expensive lesson: He spent well above his per diem, only to learn his startup doesn't even have one.

Before traveling, clarify:

• What the company will cover (flights, hotel, transportation)

• Your daily expense limit (if any)

• What requires pre-approval

• Receipt requirements

What's typically covered:

• Flight and airport transportation

• Hotel accommodations

• Ubers to/from company events

• Not always covered: Personal meals, entertainment, shopping

Work Trip Social Dynamics

Trust Carefully

The relaxed atmosphere can make you feel like you're hanging out with friends, but remember: you're still at work.

Josh's advice: "Be careful with who you trust and who you can't. Anything can get back to anybody."

Key principles:

• Don't bad-mouth colleagues or bosses

• Avoid sharing sensitive company information

• Remember that even trusted colleagues might repeat things

• Keep some professional boundaries intact

Make Time for Yourself

Work trips are exhausting because you're "on" 24/7. Josh found himself going to bed at 10-11 PM (early for him) because the days were so draining.

Self-care strategies:

• Block out 20 minutes daily for yourself

• Call friends or family

• Maintain your routine (journaling, exercise)

• Don't feel guilty about taking breaks

Happy Hour Mastery

The Same Two-Drink Rule Applies

"Don't be that person" who gets too excited about free drinks and loses control.

The progression:

1. Stick to 2 drinks while senior people are around

2. When they leave, you can have more with peers

3. Always know your limits regardless

For Non-Drinkers

Josh acknowledges this can be challenging. His suggestions:

• Hold a seltzer or soda to blend in naturally

• Go for 30 minutes minimum to show face

• Focus on the food and networking

• Leave when you're comfortable—you're not obligated to stay

Networking Gold Mine

Happy hours offer unique access to people you wouldn't normally interact with.

Strategy:

• Wait for natural breaks in conversations

• Introduce yourself to senior people when they're free

• Ask about their work and show genuine interest

• Follow up the next day with LinkedIn or email

Sample follow-up: "Hey, it was great chatting with you at the happy hour. Would love to grab coffee and learn more about your work."

What Not to Do (The Horror Stories)

Josh has seen it all. Avoid being the person who:

• Gets blackout drunk at company events

• Shares confidential information after a few drinks

• Bad-mouths colleagues or management

• "Twerks on the wall" (yes, this happened)

• Orders the most expensive item when everyone else is being modest

The Bigger Picture: Why These Events Matter

Work trips and happy hours aren't just about free food and drinks. They're about:

Relationship Building: Creating connections beyond Slack and Zoom calls

Career Advancement: Getting face time with decision-makers

Cultural Integration: Understanding company dynamics and unwritten rules

Skill Development: Learning professional social navigation

Key Takeaways for Your Next Work Event

Before You Go:

1. Research the company's expense policy

2. Pack versatile, professional attire

3. Plan to arrive early to everything

During the Event:

1. Stay present—put your phone away

2. Follow social cues from senior colleagues

3. Network strategically but authentically

4. Maintain professionalism even in casual moments

Remember:

• You're representing yourself and building your reputation

• These people will influence your career trajectory

• Balance is key—be social but not sloppy

• Everyone is watching—especially when they think you don't notice

The Final Word

Work trips and happy hours are unique opportunities disguised as simple social events. The colleagues you meet, the impressions you make, and the relationships you build during these events can significantly impact your career trajectory.

As Josh learned (sometimes the hard way), success at these events isn't about being the most outgoing or drinking the most. It's about being professional, strategic, and genuinely interested in your colleagues as people.

The bottom line: Show up early, dress appropriately, drink responsibly, network authentically, and remember that your future career might depend on how you handle that seemingly casual Tuesday night happy hour.

Navigating your first corporate job? Subscribe to Guyset for more honest advice about the unspoken rules of professional life in your 20s.

I went on a work trip last week and I live to tell the tale. Also what better time to talk about happy hours, dinners, and drinking with your coworkers than now? 

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Send anything you want me to talk about or any questions you have to advice@guyset.com. You can reach me on Instagram DMs HERE or email josh@guyset.com. See you next Tuesday!