wedding road trip

O Chicago

After a morning of road construction, golden retriever puppies, and the great Dave Davis, we pulled into Oak Park,  Chicago, for the much anticipated reunion with our friends Olivia and Jafer and their three-month-old daughter Camilla.  I say reunion because they moved away from San Francisco in January and haven’t looked back.

For our Bay Area readers who cannot fathom leaving Fog City, let me share this with you: Olivia and Jafer rent a five bedroom house in an inner-ring suburb loaded with Frank Lloyd Wright buildings, a very short walk from shops, movie theaters, and an El station, with the train offering a 15 minute ride to downtown Chicago. It’s as convenient as Noe Valley, but in a bigger city with more culture (and let’s face it, the arts scene in SF is sort of on life support), all for the cost of their old two-bedroom apartment in Burlingame. Makes one think…

Seeing Olivia is extra fun for me, because she’s one of my urban planner friends, so we can talk excitedly about floor-to-area-ratios and streetscape design while Jaime’s eyes glaze over. Even so, over dinner we got to the good stuff: relationship lessons.  My favorite tip came from Jafer, who explained how it’s great to take risks together (moving, kids, investments, trying blowfish sushi, etc.). This idea is coupled with a phrase I admittedly had not heard before “the harder you work the luckier you get.”

For many people, such as Warren Buffett (who is surely reading this website), “work hard and take risks” would not be astounding advice.  However, I’m traditionally a risk-adverse person and have usually just done the “work hard” half of the equation. But Jaime’s been lobbying me to take more leaps of faith – she calls it the magic of believing – that are grounded in preparation and confidence. And I am marrying her in part because she’s very good at setting high goals and fulfilling them. Even so it’s not easy to just change a lifelong behavioral pattern. I’ve been slowly realizing what Olivia and Jafer said so succinctly – take risks together. Jaime isn’t expecting me to jump off the high dive by myself. Which is good… because I’m afraid of heights.

Tags: Day 35 wisconsin to chicago, marital advice, wedding road trip chicago