Amy discovered the photo above a few weeks ago, and it's stirred up a host of memories from a pivotal period in my life that I feel compelled to document here--I don't expect anyone to read all this, but I suspect I'll enjoy re-reading it myself some day. The photo shows the two of us in 1991 in our first apartment in San Francisco. It was $750 a month for a nice one-bedroom on the Panhandle. She was--and is--completely adorable, and I look at that face and fall in love all over again. I have no excuse for my haircut and no explanation for what we're doing with our hands.
The Fender Bandmaster amp in the background was given to me by Charles Thompson, aka Black Francis of the Pixies, when he and I were dishwashers together in a Boston restaurant for a few months in 1986-87, while I was a student at the School of the Museum of Fine Arts and he was launching the band. Charles was friendly and funny and a good colleague in a shitty job, and I really wanted to see his band, but I was under 21 and didn't have a fake ID and the Boston clubs were strict about carding.
By early 1988 I knew that art school and life in Boston had helped me grow up in some critically important ways, but I also wanted to continue my education in a more conventional setting. I'd spent my freshman year at Duke, and although I'd enjoyed aspects of it immensely and had close relationships with many people there, I felt that I had changed too much to go back and feel at home there again. I decided to apply to Brown, which affords students a great deal of freedom in charting their path, and although I considered some other schools, ultimately I applied only to Brown. It's not that I was confident of my acceptance--I wasn't--but I knew that if I were to return to school successfully I would have to retain the independence I'd enjoyed in Boston. I spent the summer of 1988 living with my (very patient and supportive) Mom and Dad and working construction, waiting and wondering what I would do if I didn't get in. Somehow, I did.
After moving to Providence that fall I came up to Boston regularly, and I finally got to see the Pixies at the Rat in Kenmore Square in December 1988. I was practically sitting on the stage, and it was one of the greatest shows I've even seen. Kim Deal wore a dress and high heels and deftly dodged the crush of people. The previous year Amy and I and a pair of friends decided to skip the Hüsker Dü show at the Orpheum, and I will go to my grave regretting that decision, but at least I saw the Pixies at the Rat, and I'll hold on to that one forever.
Amy and I were friends in high school and started seeing each other shortly after she graduated. I had decided to leave Duke before she and I got together, but I chose the SMFA because it was near Dartmouth, where Amy was headed. We were deeply committed to each other, but we were also teenagers, and I was obviously filled with uncertainty. With the benefit of hindsight, the turmoil we went through over the next few years was predictable, but at the time it was also quite painful.
In early 1989, shortly after seeing the Pixies, I was thinking about calling Charles and asking him if I could travel with the band and help out in some way over the summer. I was a terrible guitar player, but I could tune, and I was willing to work for free. I have no idea if he would have said yes--I had his phone number, but didn't know him well. But then I realized that if he did say yes, I probably would have gone, and who knew how a summer apart would have affected me and Amy?
So I never made that call, and instead Amy and I decided to spend the summer together in Washington D.C. She had her shit together and landed an internship at a law firm--it wasn't the greatest job in the world, but it paid enough to allow her to save for senior year, and it provided a grownup-looking line on a resume. I most definitely did not have my shit together and arrived in D.C. unemployed, eventually finding a job as a sandwich maker at a deli in Georgetown. To save the money I needed for senior year, I bought a bucket, a pole, and a squeegee, and after work I roamed the neighborhood offering to clean the storefront windows of local businesses, and eventually I developed a regular clientele.
Washington was in the midst of a profound homelessness crisis in the late '80s, and as I walked to and from Georgetown and along my window-washing route I would pass dozens and dozens of people living without shelter. At the deli where I worked we threw out large boxes of unsold muffins at the end of each day, and eventually I convinced the managers to let me take them home with me so that I could distribute them to the people I passed--this also turned into a regular route.
Amy and I made it through another challenging year as a couple--my fault--and shortly before graduation we decided to take a wild leap and move to San Francisco, which I had visited with my family years previously and remained a sort of magical place in my imagination. Most of our peers were headed to entry-level professional jobs in New York and Boston, and we weren't quite ready for that--we wanted to have an adventure in this city that seemed so welcoming to people who didn't quite fit into the ordinary categories elsewhere. It's not lost on us that two history majors would not be able to do this today--and that a great deal of privilege enabled us to do it then. So that summer we hitched a U-Haul trailer to my Camaro--yes!--and drove across the U.S., surviving on Denny's in the morning and Domino's at night.
Once again, Amy had her shit together and followed her interest in public health education and her actual experience as an HIV peer educator at Dartmouth into a grownup job with the California Medical Association, which would ultimately lead her to law school, corporate practice, legal librarianship, and the leadership role she holds today as the director of the Zief Law Library at the USF School of Law.
And once again, I did not have my shit together and was really at a loss as to what to do professionally. But my history degree qualified me to serve as a cub reporter for the (now-defunct, of course) San Carlos-Belmont Enquirer-Bulletin, an old-school local weekly that was part of a small chain of area papers owned by Jerry Fuchs, an equally old-school publisher. I landed the job by passing this test with Jerry: after asking me some perfunctory questions, he turned the tables and told me to interview him, then put me in a room with a typewriter and had me write up my notes as a feature on the spot. It was the most true-to-life job interview experience I've ever had.
After a few months covering anything and everything in the charming, sleepy town of Belmont, Jerry promoted me to County Editor and allowed me to write about a broader range of issues affecting the region. My experience in Washington D.C. had stuck with me, and I was keenly aware of the extent of homelessness in San Francisco, and a little investigating made clear that the issue was also a problem on the Peninsula. Homelessness wasn't as visible as it was in SF because there were relatively few panhandlers, but if you knew where to look you could find the quiet streets where people were living out of cars and RVs, and even the occasional encampment.
There was much I loved about being a journalist--I had a great deal of freedom in choosing what to write about and how to spend my time, and much older people in positions of authority treated me with respect (and answered my naive questions graciously), and seeing my name in print each week was always a thrill. The money was terrible, even then, and I had to write the occasional piece of hackwork on an important advertiser--it was very much a business, and I knew that.
But I couldn't stop thinking about homelessness, and I wanted to work on the issue directly, not from the sidelines as a writer. I told Jerry I was quitting, and although as an old RFK supporter he understood my motives, he also made one last offer to try to keep me--he'd give me a weekly column. This was incredibly tempting, and I've often wondered what my life would look like today if I'd said yes. The most likely conclusion is that I would have had an amazing experience as a Bay Area writer in the '90s and '00s, only to be laid off in the '10s.
So I sold my Camaro for $3,000 to finance a job search, eventually landing a role as the intake worker at a drop-in crisis center operated by Compass Community Services (then known as Travelers Aid.) The woman who interviewed me, Kathy Taylor Gaubatz, became one of my most important mentors and a personal role model, but (she told me years later), she almost didn't hire me because I wore a coat and tie to the interview, which (along with my total lack of experience) made her wonder if I'd be able to fit into a world where coats and ties looked out of place, to say the least.
I spent a little over a year in that job--every day, at 9:00am and at 1:00pm, I would interview a long line of people seeking help ranging from a cot in a shelter to a long-term bed in a rehab center, from treatment for mental health issues to a bus ticket home. We could help some of them, but we couldn't help all of them. And even when we could help, we couldn't accommodate everyone, and I had to turn away most of the people I talked to, and I tried to do it with compassion and respect. I failed with one guy, though, and he spit in my face. I took the rest of that day off, and went to the childcare center that our agency operated in the Tenderloin, and I just hung out with the little kids and their teachers to decompress.
Then I was hired by a coalition of the city's family and domestic violence shelters to help launch the Homeless Children's Network, which would provide therapy and counseling to children in these shelters (and which is still in operation). I was responsible for management and fundraising, and my counterpart who initially provided our services and ultimately led the clinical team was Erica Kisch, a gifted counselor and another special colleague.
By the time we got HCN up and running, Kathy had become Compass's executive director, and she asked me to return as her first associate director, and later Erica joined us to manage the organization's main family shelter program. (Erica would eventually succeed Kathy and is still running Compass today.) Over the next three years we opened Clara House, a transitional housing program for families; expanded the childcare program that I mentioned earlier, enabling it to double in size; and were asked by the city to establish a centralized intake system for all family shelters. I raised over $1 million to help support this work, a sum that seems trifling today, but which had a big impact in that setting at the time, and I wore a bunch of different hats as I helped Kathy and the rest of our management team turn these projects from ideas into realities.
I didn't have any formal training as a technologist, but thanks to my family and education I'd had more exposure to personal computers than the typical person working in social services in the 1990s, and I was reasonably adept at learning the often-clunky office productivity software of that era. I also began using email intensively in 1994 in order to plan a long-distance motorcycle trip with a friend who lived across the country. These experiences helped me see what a huge opportunity there was for nonprofit organizations to employ technology more effectively, in uses ranging from service delivery to fundraising.
Then in 1996 I met Melinda Tuan, an MBA student at Stanford who was considering an internship at Compass, and the following year I visited the school's Graduate School of Business to attend a conference on entrepreneurship that Melinda had organized. At that conference I saw a passionate, blunt, and wickedly funny talk by Jed Emerson, who was the CEO of the Roberts Enterprise Development Fund, one of the first efforts to fund social ventures. (Melinda went on to work for Jed and later succeeded him at REDF, and Jed went on to become one of the leading thinkers in the world of impact investing.)
I'd been thinking about graduate school but was leaning toward a public policy degree, when a conversation with Kurt Taylor, Kathy's husband, changed my perspective dramatically. He said something like, "You seem to enjoy starting new ventures and getting things done, and I don't think you want to write white papers--you should consider business school." With this in mind, and with the realization that mission-driven people like Melinda and Jed were welcome at Stanford, which was obviously a hotbed of entrepreneurship and technology, I decided to apply to business school. Many people who knew me found this inexplicable.
Around this time Amy graduated fifth in her class at U.C. Hastings, which led to an offer to join the healthcare practice of a San Francisco firm. While I wasn't the best boyfriend in college, I take pride in being an outstanding law school husband. I had so much practice helping Amy prepare for the bar that I honestly believe that I would have had a 50/50 shot at passing it myself.
While waiting to hear my fate, I quit my job at Compass and trained my successor as associate director--no matter what the B-schools thought of me, the application process had made me realize that after 7 years in social services it was time for something different. I was proud of the organizations I'd been a part of and the work we'd done, and I felt grateful for what I'd learned and the sense that I'd made a meaningful contribution. But I also knew that this wasn't the work of a lifetime for me, and if I stayed any longer the feelings of cynicism and futility that had begun to erode my commitment to that work would get the better of me.
And then I got the call from Marie Mookini, Stanford's dean of admissions at the time, welcoming me to the GSB. I was surprised, but not nearly as surprised as I remain today, looking back more than two decades removed. As an MBA student I would discover organizational behavior with Roberto Fernandez and interpersonal dynamics with Mary Ann Huckabay, two of the most gifted teachers I've ever known (and I've been blessed with many); these were the foundational learning experiences that would eventually lead me into executive coaching. I would explore a rich variety of post-MBA paths, which was inevitable in the near-frenzied atmosphere of 1999-2000. I would graduate with offers from four startups, only to conclude that I didn't think I could give them my best effort, leading me to re-launch my job search in the summer of 2000. And I would return to my original reason for attending business school--helping nonprofits use technology more effectively--and eventually be asked to serve as the first executive director of the Nonprofit Technology Network. (My work in the nonprofit technology sector from 2000 to 2006, before I launched my coaching practice, deserves its own post, if I'm ever similarly inspired by a photo from the '00s.)
This walk down memory lane has left me feeling a little wistful, mildly embarrassed, and profoundly grateful. Everyone mentioned above--especially Amy and my parents--played an essential role in the lengthy, uncertain process of helping a well-meaning but deeply confused young man finally get his shit together, and I will always be in their debt.
