Walking along 5th Ave – Pittsburgh – this morning, traversing the four or so blocks from the Holiday Inn to Craig Street, triggered a flood of memories. That was no surprise: the first time I’d made this walk, eleven years ago, I was pretty sure I was walking into the opening page of the next big chapter of my life. The Menlo Park startup I’d been with for the past three years was ready to implode, and I’d been lured to Pittsburgh for an interview with a small research lab that many of my friends extolled as utopian.

If the idea of leaving California for P…p…Pittsburgh weren’t bad enough, it meant taking my 5th-generation California wife (and 6th gen Cali daughter) with me to this city that evoked the collapsed rubble of abandoned steel mills. But Andrew, Dayne, Rich and Shumeet swore that they’d make me a convert – “Just come visit,” they said, “and make your own decision.”

On that walk from the Holiday in to JPRC’s office just off Craig Street, I probably hadn’t fallen in love yet. But as looked up at the gothic Cathedral of Learning, past St. Paul’s Church, around the corner and past the quirky bookstores and indecipherable shops of Oakland (“Haircut and talking – $9!”), it must’ve been starting.

When I got home two days later, I explained to Devon that, somehow, it felt like “home” there. We went out a second time, together, and by the time we touched down back in California, we agreed to make the move.

Found a home in Mr. Rogers Neighborhood. Literally. He lived a few blocks from the Malvern Ave corner where we bought our house, and his daughter lived just down our street. Our house was known as the “school bus house”, because kids would wait on our porch for the bus when the weather was particularly bad. We later learned that, when Devon had been in kindergarten, she’d lived four blocks up on the same street while her father finished grad school.

We were a block from the sprawling urban woods of Schenley Park, with broad lawns and dark leafy mysterious walks that traversed Panther hollow on old stone bridges. A few more blocks from CMU and the Carnegie Museums. Kid-loving neighbors who everyone addressed as “Mr. and Mrs.” – mulberry trees and yards to run through.

Of course, I know I’m embellishing a little as the years pass, but D and I decided that this was the place we were going to raise our kids and grow old. Who could’ve known that four years (and three failed startups) later, we’d be packing our bags for a return to California.

JPRC started to crumble soon after we arrived – the Japanese stock market had tanked, and our parent company, a Japanese software house, was under seige by Microsoft. Just over a year after we arrived, the Lab shut its doors. D and I surprised each other by wanting to stay, so I joined a couple of other JPRC survivors in opening the Pittsburgh office of a Burning Glass, a San Diego startup that needed some machine learning chops.

That lasted another year before they needed to retrench and retreat, after which I jumped to DigitalMC, a tiny CMU-based startup that was just coming off the blocks. Those were heady times. We were small, agile and naive. We knew we were probably doomed, but like the proverbial hotrod burning down the open highway, the ride was just too good to stop.

When DMC ran out of money in early 2002, we kept working for three months out of our CEO’s attic. We lived off our savings and took side jobs to postpone the inevitable. Finally, the savings were gone, the industry was clearly still dead, and it was time to get a real job. The economy was still dragging through the scuppers, and our choice was to hang on in hopes of a faculty position at Pitt the next spring (a long shot), or declare defeat, and move back to California to join one of a few tech companies that seemed to be weathering the storm.

When we left, we literally mourned leaving. Packing up the house where we had planned to grow old was, saying goodbye to the neighbors who had welcomed us so warmly – these were tear-filled affairs. I’d moved many times before, but this time it was for keeps, and it hurt.

…

That was seven years ago. Life in the intervening time has been good to us. We have a nice house in Palo Alto with friendly neighbors. I have – in my humble estimation – the best job on the planet, and get to bike to work along the Baylands, past herons, rabbits and pheasants. Our kids can walk to the library and city pool. We’re close to family. I can’t complain, or shouldn’t.

But walking along 5th Ave this morning brought me back to the promise of that time, over ten years ago, when I first stepped out into this strange city, knowing that it likely held the key to my future, but when I didn’t yet know how much I would come to love it, nor how much I would miss it when this chapter of my life ended.