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.

Day 35: Road Construction is Not Your Friend

This trip has reminded me of something that I don’t miss from the regular working world: getting up at six in the morning. I remember when I worked for Spleak, a startup company that was based in both Copenhagen and San Francisco, I typically woke up at five thirty in the morning just so I could chat with my Danish friends on MSN Messenger before I jumped on the bus to head downtown to our main office. Now I’m lucky if I can get up before eight without hyperventilating.

We’ve felt sad leaving pretty much everyone that we’ve visited on this trip, but I felt particularly blue about waving goodbye to Jason and Rebecca. Maybe it was the cheap champagne at the Loading Zone, the bountiful food spread at Camille’s, or the suspicious way Jason checked over his shoulder to see if we had Fox New cameras hidden somewhere. I sincerely hope that we all join up again in the near future, whether it be in Wisconsin, California, or points in between. Maybe their kids will have even gotten over being afraid of us by then.

We pointed Roxy due south and started our tour of the lower part of Wisconsin. On our way to see a gang of golden retreiver puppies in Chicago, we took a detour through Madison. While we were only there for about twenty minutes, I am here to tell you that contrary to popular belief, it is not fun to play Dodge the Road Construction before you’ve had your morning coffee. Apparently, summer is THE time to tear up the roads around the University of Wisconsin, leaving cars to drive in slow circles around state monuments saying things like “Big Ben, kids, Parliament.” If you don’t get that movie reference, consider yourself off my Christmas card list.

Madison was just as Madison-y as I expected, with a beautiful view of the capitol in clear focus as we drove into the city. Located between two lakes, there is plenty of waterfront property, which makes the area especially appealing on a warm summer day. Of course, I wouldn’t know what that is, because it’s basically been raining since we arrived in the state two days ago.

A friend of mine asked if Madison is like Austin. I’d have to say on first glance, no. While Madison has architecture that screams Mike Brady era, Austin is a mix of southwestern funk and retro fabulousness. Madison may want to be Austin, but it isn’t yet.

Don’t take it from me, however. I haven’t had my morning coffee yet.