Some Questions I Have Before Going On A Business Trip With My Boss

Some Questions I Have Before Going On A Business Trip With My Boss

For the past six months, I’ve been subtly hinting at the idea that I should be traveling more for work. This was mostly done out of a selfish nature because it’s winter in Chicago and my side of the company mostly operates out of cities that are, you know, warm. Mainly Phoenix. Do I think I could contribute to their site’s culture and help standardize best practices? Of course. Despite how much I screw around at work, I’m actually pretty decent at my job. But more than anything else, I just want to get away.

Yes, I know I could just take some vacation days and go to Southern California or plan a weekend trip to Vegas with some friends, but the caveat there is that I would have to be the one paying for it. If I’m traveling for work, I can expense it and tell the big wigs upstairs that the 2 a.m. runs to In-N-Out Burger were pre-meditated tactics that showed a huge boost in morale and company culture.

Anyway, I’m sure you’ve heard the cliché, “Be careful what you wish for.” That couldn’t ring more true. I got my wish. In February, I’ll be traveling to Phoenix for a full week… and sharing an Airbnb with my boss during the whole trip.

I’m not sure what I was expecting. I’ve never traveled on business before, so I’m sure this was precautionary—rightfully so, based on the aforementioned 2 a.m. In-N-Out trips. Since it’s all so new to me, I have some questions before we leave.

How much of the trip can I post on social media?

We’re traveling for work, but Phoenix is so drastically different from Chicago that I kind of want to treat it as a vacation. That includes doing some hiking, a lot of drinking — some of which can be done pool-side – and maybe I’ll even bring my golf clubs. I don’t know. What I do know is that I’m definitely the kind of douche that wants to make everyone jealous as they stare out their cubicle at a grey sky and mid 20-degree temperatures.

How often can I drink?

If I had it my way, I’d be going out every night while we’re there. I’ve never been to Phoenix as an adult and I’ve heard that there are a lot of cool bars and breweries there. Sure, I know this isn’t a vacation. The issue is that, this is something I do on a regular basis at home. You know how you lie to your boss/coworkers about what you did over the weekend? I do that shit all the time. I honestly don’t plan on changing, so I may just have to hide it or get my boss involved.

To piggy-back off that…

How drunk can I get?

I’m not saying I’m going to be blacking out every night, but, like…is one night okay? No? Yes? I’ll read the room.

What if I have an opportunity to hook up with someone?

I’m not going to not take that opportunity while traveling on business. That’s content for days. There’s no way I’m taking her back to our Airbnb, so I’d have to go back to her place. But then I would have to explain to my boss where I was the night before, and then he might start judging my lifestyle. Not that I think there’s anything that could affect my career with that as long as I’m still at 100% the next day. I’m mostly just concerned with it being awkward.

What if he hooks up with someone at the Airbnb?

Holy shit. I don’t even want to think about it. Hearing headboards against the wall in combination with any grunts and slaps that might come with it…I would probably just leave.

Do we have to sit next to each other on the plane?

I really hope we don’t. I like to think that my boss has a high opinion of me, so the thought of him seeing me clench my fists, turn white, and start breathing heavily at the first sign of turbulence leads me to believe that he’ll see that as a sign of weakness. Sorry that flying gives me anxiety, man.

Much like any Bumble date I’ve ever been on, I’m probably overthinking this. But please, please, please, if you have any advice on how to pull this off, hit me up. Slide into my DMs. Whatever. Just help me out.

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Using sarcasm as a defense mechanism since 1993. At any given moment I'm either tired, drunk, or stressed out. Get at me at or whatever.

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