Dog-sitting in Chicago for most of May felt like a no-brainer to me. For the last few months, I’ve had a flexible, freelance, remote job working on TripSavvy.com, which just launched on May 15. I could either work from the various libraries in and around my hometown, or I could work while staying for free in the city of Chicago. I have a few friends in the city and had plenty I wanted to see, do, and eat that I’d missed from my first long weekend there. The fact that I’m obsessed with puppies was another bonus.

The pups were definitely a little more work than I expected, but I found plenty of time to get out and explore. My frousin {friend + cousin}, Christie, visited for a few nights and we had a few whirlwind days on and off the tourist track. I got together a lot with my friend who moved to Chicago from a block away from me in NYC a few years back. We sat through half of a freezing cold 18-inning Yankees vs. Cubs game at Wrigley Field and spent two days wandering around Madison, Wisconsin {US State #22 for me}. An old coworker and I had drinks on the 95th floor of the Signature Room at John Hancock Center then met up unexpectedly in a salad shop and toasted a few glasses of champagne afterward. I had an essentially free dinner with my sister’s best friend because they forgot about our burgers for about an hour and got to meet her adorable baby girl beforehand.

And then, just like that, I was home for Memorial Day and my summer began. When you’ve grown up at the beach, these big summer weekends are special. Even if you’re wearing a hoodie and elephant pants from Myanmar that have a huge hole in the crotch because they were $3, sitting in front of the ocean with your family and a good book (Alexander Hamilton, in my case) for the 32nd MDW in a row, give or take a few years in the middle, means the WORLD.

Posts on 10 Miles Behind Me in May (only two – eek!):

• Hotel Review | The Edgewater in Madison, Wisconsin
• Europe | Why You Should Travel by Bus Instead of by Train

Bonus:

• My REDBOOK Magazine article, also available on June newstands (where they added THREE years to my age accidentally)

What’s next?

I spent this past weekend in Newark, Delaware for my TEN YEAR COLLEGE REUNION which feels like a long time when you say it but doesn’t feel like a long time when you’re drinking in the sunshine, dancing to the music of horrible DJs, and laughing until your abs hurt with some of your favorite people.

I’ll be heading up to NYC twice in one week for a few travel events and one more dog-sitting gig in Jersey City for Jackson, the pup I watched during the worst (and coldest) snow (and ice) storm in January. In the sunshine, it’ll be a piece of cake.

In the middle of June, I’m heading back to the Midwest for about a week. I was accepted into #Bloghouse, a blog conference where I will take classes on how to make this blog better which hopefully will result in a site redesign one of these days. This year, #Bloghouse is in Indianapolis, where my godparents live, so I’ll spend some time with them before and after the conference.

The rest is still unwritten {which is a line from a song that a horrible DJ this past weekend did not have in his collection which means a lot to me and my college buddies}.

xx