First World Problems

When I learned about this work thing I needed to attend in Boston, I immediately snapped into action. The work thing required me to be in Massachusetts for a grand total of 18 hours: 4 hours of meetings, a dinner, a good nights sleep, and then home on the train the next morning.

Boston -  Destination for the Work Thing

I booked a hotel within walking distance of the train station. 

Then I decided I wanted to actually walk the walking distance. 

Then I made the daring call to *not* take my rolley-bag. I would eschew the rolley-bag. Because simply, who could disagree that rolley-bags on sidewalks suck if you’re going more than like 10 feet?

I decided I would take my work backpack and my handbag, which is a tote-style affair. That’s it. And exactly then ... the whole endeavor became a full-on OCD challenge: How do I pack for one night’s stay in Boston with everything I need for work still in my work backpack, but then also manage to stuff in there all I need to stay overnight?

Immediate Contingency Alert! What if the train comes in late and the timing means I need to go directly to the meeting? And then to dinner right after? Do you see the danger here? I do not show up at business meetings looking like I have a campsite jammed in my backpack.

Luckily I had an entire week to plot my strategy.

As they say, when tackling an overwhelming challenge, break it down. One thing at a time in order of importance.

First things first. I contemplated what to wear to the big meeting I’d attend directly upon arrival. I considered tackling it “rent-the-runway” style and shipping my meeting clothes back from Boston instead of carrying them. This, however, seemed excessive after I evaluated the logistics using charts and graphs.

Ultimately, I decided on a Diane Furstenberg wrap dress because it rolls up very small. Definitely not pants and a jacket for chrissakes. That would also require a shirt and seriously. Shudder. I’d need a magic wand or an as-seen-on-tv-vacuum contraptions to get all those square yards of fabric in my backpack for the ride home.

Next up: What to wear the morning after the meeting? It might seem logical to just wear the same thing Day 2 that I wore Day 1. But. Danger. What if I see someone from the meeting also at the train station? Diane Furstenberg wrap dresses are not exactly low-key. The patterns tend to be eye-catching. Hashtag embarrassing.

Diane Furstenberg - Not Subtle.

So the Day 2 problem remained. I needed a train-ride-home outfit involving the lightest possible fabric in the smallest possible configuration. I considered jeans (no way, heavy and bulky) or a skirt (would also require a shirt). Finally I picked out this satin short dress. I would wear it with leggings.

Leggings! Also known as a fantastic idea. I could also wear said leggings in the hotel room for my morning exercise libations.  Revelation! I would also take a double duty camisole! I started feeling like MacGyver triumphing over a spacial relations quest.

Meanwhile, shoes. I had discussed the crucial shoe decision with Renya and Kate at brunch last week, and so had thoughts going in. Fluevogs to the rescue. Look good, but able to cover moderate distances on foot without proactively bandaid-ing the entire metatarsal region. 

With these major checkboxes checked, the rest of the docket fell neatly into place.

End of the day Post Mortem Report:

Ha HA! Snaps. The plan came together perfectly. The triumph is real.