Jessie Oleson is a writer, illustrator, gallery owner and cake anthropologist who runs Cakespy.com, an award-winning dessert website. Her first book, CakeSpy Presents Sweet Treats for a Sugar-Filled Life, which was featured on the Today show, came out in October 2011; she is currently at work on her second book. She loves classic rock and beatniks. And she's not above the Jersey Shore or driving six hours for a cupcake.
What's in your bag? When you pack for a trip, in your handbag, in the pockets of your jeans...?
For a trip: a sketchbook and my favorite pencils and pens; in my handbag, always a book to read and usually carrots to snack on; in the pocket of my jeans, sidewalk chalk (I am a compulsive and very enthusiastic sidewalk-chalker).
You have five minutes to pack up -- for a trip of which the duration you're not sure. What do you take?
My laptop, my passport and my pug.
What is your most essential article of clothing?
It's an accessory, but a valued one: my Cartier trinity ring. I never take it off.
What are the top five songs you need to have access to hearing at all times?
"The Only Living Boy in New York" by Paul Simon; "Home/Naive Melody" by the Talking Heads; "Ana Ng" by They Might Be Giants; "Sweet Jane" by the Velvet Underground; "Tangled Up in Blue" by Bob Dylan.
What is your preferred hummingbird beat/cities you like to frequent?
My regular orbit circles around family and friends and includes Seattle, San Francisco, NYC, the Jersey Shore and Philadelphia.
What's something crazy that you did to follow your passion? (Like, did you live out of your car for a month? Drive 10 hours to pick up a certain, weird material you needed?)
I once drove six hours because someone said they'd make me cupcakes if I came to visit. They were really good cupcakes.
What is one tip you have for traveling -- a beauty tip, a survival tip, a culinary tip... ?
If you go to a chain restaurant, I will seek you out and smack you. Ask the locals where to eat! You get the best suggestions this way.
What makes you a good house guest?
I always try to make plans that they can include themselves in, or opt out of. We don't need to be joined at the hip the whole visit!
What's a recent or favorite meal you had while bouncing around the globe?
I really enjoyed the scientific whimsy of eating at MOTO in Chicago.
Where have you had your best night's sleep?
I always sleep almost stupidly well on my friend James's sofa in Astoria, Queens.
Who would you like to travel with -- three people (you guys can caravan together or on separate trips)?
Woody Allen, Jack Kerouac and Anthony Bourdain. Maybe not all at once. Although then again, maybe that would be a great sitcom: Three Oddball Men and a Little Lady.