How to Travel for Business When You Are Bad at Traveling for Business

Two Weeks Before:​

One Week Before:​

  • Pick out the four outfits you will wear for the trip.
  • Order two pairs of new shoes that go with all of the outfits (you will be in a state of panic the Wednesday before you leave, because you will think they didn’t get delivered, even though UPS says they have. Don’t worry, the wind picked them up and blew them halfway down the backyard.)​

Friday Before You Leave:​

  • Take the day off of work so you can prepare.
  • Spend all morning doing laundry.​
  • Practice-roll all of your outfits into your Packing Cubes.
  • Set out all of your toiletries (travel size, of course), to see what you have. Pack them in separate Ziplock baggies grouped by body part to make sure they don’t spill.​
  • Consider that maybe, just maybe, you’re over-thinking this whole packing-for-a-four-day-trip thing.​
  • ​Have lunch with your brother.
  • Have early fish fry dinner at Charlie’s alma mater, DocuSign mortgage paperwork together.​
  • Head home and smash all of your overloaded Packing Cubes into your carry on (by God, you are going to fly with just a carry on).
  • Go to bed early, because your flight takes off at 7:30 the next morning.

Saturday of the Trip

  • ​Wake up to use the bathroom at 2:00 in the morning. Toss and turn until 3:00 (when the alarm goes off).
  • ​Shower, put makeup on, and dress in record time.
  • Leave for the airport at 4:45, even though you thought you’d wait until 5:30.​
  • Get to the airport in record time, breeze through security (they left the express TSA checkpoints open).​
  • Wait at your gate for your co-workers for an hour and a half. You’re the only one in your gate area for an hour and a half.​
  • Take a Xanax for the flight and fall asleep on the plane for the first time you’ve ever traveled. Wake up with cotton mouth and a bloody nose from the dry air.​
  • Have lunch with colleagues you only see once a year.​
  • Check into your room and realize that due to a clerical error, you have it to yourself for the night.​

  • Sit through conferences.​
  • Change clothes and enjoy cocktail hour. Catch up with everyone else you only see once a year.​
  • Nerd out with one of the Tech Support team and close down the cocktail reception.​
  • Pass the heck out because you got up at 2:00 in the morning.​

Sunday of the Trip

  • Eat like a horse on the best breakfast food you’ve had in years (muesli, ftw!).
  • Sit through conferences.​
  • Eat like a horse at lunch; this seriously has to be the best food at a conference you’ve ever had.​
  • Sit through more conferences.​
  • Shuffle rooms around so you end up with the roommate you were supposed to have ​on Night 1.
  • Go to the Trade Show, eat like a horse, drink free drinks. Be bummed that the tshotchkes aren’t nearly as awesome as they were in years past.​
  • Head up to the hotel bar and have quiet drinks with your favorite DP, whom you made plans with two weeks ago.​
  • Get through 50% of those drinks before other people crash the party.​
  • Talk to a wholesaler who lives in Cleveland about how awesome Cleveland is, exchange business cards.​
  • Wobble back to your room, drink a liter of water, wash your face, and pass out.​

Monday of the Trip

  • Eat like a horse at breakfast again. There’s no muesli this time, so settle on some fruit and oatmeal loaded​ with honey to make it palatable.
  • Sit through conferences.​
  • Meet up with a good friend that lives in Pittsburgh for lunch, gab about all the stuff you’ve been meaning to catch up on.​
  • Eat like a horse at lunch. Realize that you’re probably going to be flying home with extra weight, and we’re not talking about the luggage here, either.​
  • Learn that the bank you’re buying your foreclosed house on doesn’t accept DocuSign. Find this out via frantic texts/calls from Charlie.​
  • Try not to lose your shit while waiting for the fax to come from Ashland to Boston at a glacial pace. Think you could drive to Ashland and back in the time it takes 19 pages of a fax to arrive.
  • Sign all hojillion lines on the document, fax it to your realtor’s Strongsville office.​
  • Catch up with an old friend, try to plan to meet up for dinner.​
  • Sit through more conferences.​
  • Get a text from your realtor that you missed a line on the documents. Have him fax the single page to you. Tell him you’ll sign it after dinner.​
  • Learn that dinner plans are going to fall through with your friend. Work other plans.​

  • Lose track of how many drinks you had with dinner. Have conversations with everyone in your department. Talk way too much about the damn mortgage paper debacle.
  • Have one of the lawyers in your department walk you back to the hotel. Vaguely remember the conversation you had with him.​
  • Aggressively hug the friend with whom your original dinner plans fell through. Vaguely remember that interaction.​
  • Get to the front desk and collect your fax. Run into another colleague in your department at the front desk. (He will corroborate the story your text message string tells you that you did, in fact, sign the mortgage paperwork and fax it back to Strongsville. Have no real recollection of this happening).​
  • Allow colleague to walk you back to your hotel room. Vaguely remember that conversation.​
  • Change into your jammies and feel ill. Vomiting provides little relief. Remember to take your medication and pass out.​

Tuesday Morning, Heading Home

  • ​Wake up and wish for death as compared to your hangover.
  • Get ready in record time, remember makeup, forego hair; opt for French braid instead.​
  • Have only a cup of muesli for ​breakfast. Cling to your water like grim death.
  • Worry that the storm blowing through will delay your flight,
  • Take prescription-strength Advil.​
  • Sit through final round of conferences. Consider death again.​
  • Check out of your hotel and take a cab to the airport. Pass through security in good time and try to find your gate.​ The flight takes off at 1:30pm.
  • Buy souvenirs: shotglass for you, chocolate lobsters for Binkles; and magnet for the MomZ and the DadZ.​
  • Realize your gate is next to a Panda Express. Consider death again.​
  • Pass out upright in a chair with your headphones in. Surely, they won’t take off without you, right?
  • Wake up 30 minutes before boarding. Wander to the Wendy’s near the gate and get a large French fry. Weep with joy because a) you’re able to hold it down and b) it feels like the best damn batch of fries you’ve ever had.
  • Board without incident, take another Rx-strength Advil and a Xanax for the flight home.
  • Pass out on a plane for the second time in your life.
  • Disembark from the plane at 3:30; send all requisite text messages to those most concerned about your safety.
  • Enjoy the sunshine, appreciate that the winter storm totally missed Cleveland.
  • Drop everything at the door when you get home. Shower and change into your jammies. Have some soup for dinner.
  • Pass out watching Supernatural​ at 8:30pm.

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