How to Prevent An Awful First Business Trip in Five Easy Steps

When I took my first ACTUAL business trip, I wasn’t sure what to expect. Would it be boring, or exciting? Would I have too much free time, or not enough? Would I be lonely, or networked out of my mind?

As it turns out, there was a single answer to all of these questions: Sorta.

The conference itself was fantastic; I learned a lot of cool stuff – some of which may even be beneficial to non-millennials with “real jobs.” In particular, I learned exactly what I’d do differently on the next go-round.

Here are five travel tips that will keep your own first business trip from becoming a disaster.

Step 1: Don’t Cheap-Out on the Flight

Although corporate travel costs were covered by my agency, I didn’t opt for business class on a major carrier like veteran business travelers might. No. I decided to use one of those just-get-me-there sites that mix and match airlines to secure the lowest fare. I put on my patented “prices only – I’ll deal with the times later” blinders, and chose my fate. This resulted in my 5:30 A.M. arrival at the Spirit Airlines kiosk in Ft. Lauderdale-Hollywood International Airport.

Fun fact: This particular terminal is actually the ninth circle of Hell (Google it).

After approximately 15-20 tries, I gave up on using the electronic check-in machine to get my travel documents. I then trudged to the end of a 1.375 mile line full of equally-chipper travelers. Five minutes before the final boarding call, I found myself confronted with a customer service representative who informed me I somehow was both registered and not registered for my flight. I was then pleasantly surprised by a $55 carry-on baggage fee.

I was the very last person to board the plane – which I’m almost certain was actually an old Chevrolet Beretta with some fancy bodywork and wings.

Step 2: If Given the Option, Always Choose San Diego

This one is simple. Not all business travel destinations are created equal. If you ever have the opportunity for business travel to San Diego in the spring, do everything short of auctioning off your first-born to get it. Your second is fair game, though.

The city is beautiful in a post-WWII-meets-SoCal-casual-luxury-meets-Hipster kind of way. During my business trip, the temperature varied between “comfortable” and “perfect.” The obvious American military influence everywhere left me with the feeling that the United States is already pretty great; and I never got tired of stepping out of the business meetings to stare at the stunning views of either the bay or the sublime Gaslamp Quarter.

Step 3: Bring Workout Gear

For those of you who don’t know, Florida is somewhat flat. The closest thing we have to mountains are the acrid piles of trash barely disguised as grass-covered hills along the turnpike.

On the other hand, San Diego’s Cortez Hill, the neighborhood home to the small Days Inn hotel room where I stayed, had an actual hill. This work trip offered me the perfect opportunity to run up, down, and around this massive (to me) incline and work up a morning sweat. Unfortunately, I’d bitten off a bit more than my legs could chew; I’d conveniently forgotten that I needed to walk over to the convention center, then spend a full day walking through it, before walking back to my hotel room. Still, it was a unique and gratifying way to experience a new locale.

And for those that would prefer not to make their business trip any more strenuous – bring along a couple pairs of shorts, sneakers, and tank tops anyway. At least everyone in the security line watching the TSA agent rifle through all of your perfectly-packed belongings will be impressed by your unwavering commitment to fitness.

Step 4: Don’t Give Your Wife A Chance to Miss You

Nearly all of my time was spent with a laser focus on the business purposes for my trip — rushing from workshop to workshop to lunch to workshop to networking event to dinner…rinse, lather, repeat. Any remaining free time was spent testing out new mobile video techniques, or transcribing my hastily scribbled notes into cohesive sentences.

Unfortunately (and predictably), this meant I neglected to stay in constant contact with my wife throughout the day.

This was an issue, because normally if I fail to text an ill-conceived emoji once every few hours, she’ll assume I’ve perished in a horrific accident. Or worse, in this case: that I’d met a mesmerizing Mexican mistress and hightailed it to Tijuana. Of course this never would have happened (my Spanish is passable at best) but it COULD have, and that’s the point…I guess?

What I realized though (as she was detailing all the super-fun things she was worried I might be doing), was my family was an entire country away and missing me. Although I was experiencing and learning new things, back home, a huge part of their daily lives was missing.

Make the time to call home. A lot.

Step 5: Don’t Book The Red-Eye. Ever.

This is one of the most important business travel tips. I can’t sleep on planes. I can’t throw my head back onto the seat. And I can’t fold myself forward and sleep on the little tray table. I’m not quite charming enough to talk a stranger into letting me drool on their shoulder. Normally this isn’t a problem, because I’m smart enough to avoid late-night flights.

Remember step 1? I didn’t. I booked a red-eye.

Going east.

On a Tuesday.

Miraculously, I managed to secure about 20 total minutes of sleep. I distinctly remember considering the possibility of lying down in the aisle, daring an air marshal to make me move. There were only two things which, when combined, nearly made the entire fiasco worth it:

1. The sunrise over the Florida Everglades
2. The fact that I’d somehow managed to nab a Virgin Atlantic flight

I’d only had one prior experience with Mr. Branson’s airline – and it was many years ago. I remember it being pleasant. But since then, I’m convinced Virgin has stepped up its game up in a big way. Some might find it hokey, but I enjoyed the cool purple lighting everywhere, the impeccably choreographed safety video, and my seat’s valiant attempts to keep me comfortable. I’m seriously considering making Virgin our family’s exclusive air-travel solution. Raphael knows what I’m talking about:

“Delightful” is a word I only use when I’m “delirious”

My first business trip was undoubtedly a success – despite my best efforts to sabotage it from the beginning. The entire episode was one big learning experience, and I hope any fellow newbies were able to find at least one piece of advice to follow when the opportunity arises.

And when it does, don’t try to be a goody-two-shoes kiss-ass and try save your employer a couple dozen bucks on your flight.