Lindsay O'Leary. Soaring.
Lindsay enjoying a beautiful soaring ride 30 miles south of Pittsburgh last summer with her partner and pilot Tom.

Director of web communications and social media at Carlow University, an MBA student in the evenings, a remodeler of quirky living spaces and an artist/glassblower, Lindsay O’Leary is carless, clumsy and happily living with her partner Tom in the neighborhood of S’Liberty Morning Park (living within a block of Highland Park, East Liberty and Morningside).

Monday, February 2

Morning: Anxiously await the news about the forecasted snowstorm and Punxsutawney Phil’s shadow. Hop on the 75 with a mid-ride stop at Prantl’s on my way into work. Mondays are invariably chock-full of meetings at the university, so the day will be eased by devouring teeny tiny chocolate burnt almond tort cups.

Night: Head downtown to see Tom Sarver’s latest curatorial creation—the Sideways Museum in the window of Space Gallery on Liberty Ave. As is the fashion these days with our new fancy and ever-needy pedometers, I walk at least 10,000 steps a day, so I’ll spend some time sliding around on slippy sidewalks gazing up at the Point’s unique architecture. Afterwards, I’ll spend a couple of hours catching up on guilty pleasure TV with friends in Regent Square.

Tuesday, February 3

The founder of Vermont’s Bread and Puppet Theater, Peter Schumann, is giving a talk at CMU’s School of Art at 5 p.m. As a former diehard Black Sheep Puppet Festival volunteer, this is exceedingly exciting.

Head over to Artists Image Resource (AIR) on the North Side for our bimonthly board meeting with a bunch of good folks and for one last look at the impressive Printwork 2014 show.

Wednesday, February 4

Morning: Order Web Design Day tickets. I missed out on ordering them during the pre-sale by seconds, so I have about a dozen alarms/alerts set to remind me to snag tickets for myself and Carlow’s talented web and social media content editor, Dane Horvath. I went to the last one and it was top-notch.

Afternoon: Spak Brothers for lunch with Liz Keller, director of pre-college art programs at CMU. I’ll likely pick up some sandwiches from Spak Brothers because I am enamored with their seitan Pittsburgh Steak sandwich.

Night: Walk a few blocks to dinner at Teppanyaki Kyoto on Bryant Street with glass artist Lyla Nelson and author/professor Nicole Peeler, two close neighbors and even closer friends. Yes, it’s Japanese, but, nope, not known for sushi. When you go, get the okonomiyaki, a delicious, delicious giant grilled savory pancake.

Thursday, February 5

Morning: A cold and hard jog with Maya Henry, Pittsburgh’s new ‎nighttime economy manager. Oddly enough, we mostly see each other before 8 a.m. We have a loop we like to do through Morningside down to a dead-end street that overlooks the Allegheny River. If we’re lucky, we’ll run into our favorite 80-something-year-old St. Raphael Church parishioner yelling “Looking stronger than ever, ladies!” in the quiet morning air.

Afternoon: Lunch at the packed Red Oak Cafe in Oakland with my old Mattress Factory office mate, Abby Vanim. What was that? You haven’t had their brussels sprout hash? I’m pretty sure I could eat a five-gallon bucket of it in one sitting.

Night: Head over to Concept Art Gallery during their Thursday evening hours to catch Vanessa German’s most recent show, The Ordinary Sacred. Her art leaves me breathless. I’m in the middle of getting my MBA from Carlow University, so like most nights, it’s a school night, and I’ll be meeting with my teammates for our Decision-Making for Leaders class. It’s notoriously the toughest class in the program, but my team is amazing.

Friday, February 6

Night: Unblurred on Penn Ave. Hang out at Assemble and check out the giant Color Me Pittsburgh map, which raises questions about social justice and race in our city. Then swing by old Penn Ave. gallery favorites such as ModernFormations and The Clay Penn.

Late Night: The Grand Budapest Hotel at Row House Cinema. With full-time work and school, I haven’t been catching many movies on my must-see list, so I’ll down a couple espressos to catch Mr. Anderson’s latest at this midnight showing with one of my oldest Pittsburgh friends, Jim Foreman.

Saturday, February 7

Morning: Jog to Highland Park and around the reservoir a few times. After I exit the park and run down Highland Ave. past the giant row of ginkgo trees, stop at Tazza D’Oro for coffee, a sfogliatelle pastry and friendly faces.

Afternoon: Drink good beer and buy good gifts at the first-ever Crafts & Drafts Valentine’s Artist Market at East End Brewing organized by the always surprising and inspiring artist/DJ/organizer Matthew Buchholz of Alternate Histories.

Oscar Nominated Shorts: Animation at Regent Square Theater at 2 p.m. An annual favorite of mine is to catch these short films while my brain explodes from the quality of animation and the improbable storytelling.

Night: Go and pick up Tom at the airport. He will have been away in California for two weeks, so having him home is going to be extra fantastic.

Sunday, February 8

Morning: Convince jet-lagged Tom that we must head to e2, my favorite spot in the city for brunch. Try to tell myself I don’t need the “omg berry white doughnuts” and a main course, but order ‘em anyway.

Afternoon: Visit the discordant and delightful sloth at The Aviary. I’m sure we’ll bump into a bird or two while we’re there. Tom is a sailplane pilot and president of the Pittsburgh Soaring Association, so we’ll take a long drive and head out to a regional airport to see what’s shakin’ with the powered plane pilots and daydream about flights for the soaring season ahead.

Jennifer has worked at the Mattress Factory, Brooklyn Museum of Art and Dahesh Museum of Art and is co-author of Pittsburgh Signs Project: 250 Signs of Western Pennsylvania. She also is co-coordinator of Handmade Arcade. Musically, she is in a band called The Garment District and is a founding member of Brooklyn's The Ladybug Transistor.