(This is chapter 32 of my ongoing memoir of the Internet industry.)

I got my first assignment in my new role as Director of Product Development at iVillage. It was a big one.

IVillage had always grown through acquisitions. The company had launched in 1995 with a site on America Online called ParentSoup, but its presence in the parenting community more than doubled when it bought a sprawling message-board site called ParentsPlace, run by a married couple in Berkeley who now flew into New York City every other week to attend management meetings. An awful amount of the site’s traffic came from Astrology.com, created by and acquired from another married couple from Australia, who flew in less often. The ParentsPlace and Astrology acquisitions brought in traffic that was critical to iVillage’s early growth, but the stock market also wanted to see e-commerce, so right around the time I joined iVillage it was busy completing its acquisition of iBaby.com, an online store that was supposed to become the Amazon.com of diapers, baby bottles and high-end onesies (though, unlike ParentsPlace and Astrology, this idea never really panned out and the store eventually faded into nonexistence).

These acquisitions led to the successful stock market debut, which then made more acquisitions possible. In July we bought Lamaze, the company that promoted natural childbirth, which seemed strange to me and a lot of people because Lamaze was a trusted name in the medical field but nobody imagined it was a for-profit company available to be acquired. Well, apparently it was, and we acquired it. Then, after I joined the marketing department my new boss Alexandra told me that we were about to buy another company, a small but innovative community software company with a unique family focus, and I was going to lead the integration effort.

I was glad to have something to look forward to, because things hadn’t been going particularly well since I’d moved from the technology department into the marketing team. My official responsibility was to manage our various user features: email, personal web pages, message boards, chat. A new entry-level employee named Margaret Chan had been hired to join the product development team just before I moved in, and now I was supposed to be her manager. But I’d barely figured out yet how to approach my own new responsibilities, and when she came to me for guidance and direction I didn’t have much to offer.

I didn’t realize at first how fundamentally different my new role was from any role I’d played before. Still thinking like a techie, I wanted to move slowly and deliberately to improve our products. I didn’t realize that in the marketing/product development side of the company we were expected to talk up our plans and engender group discussion more than we’d ever do on the tech side. Here, “slow” was a dirty word, and the quiet, deliberate process of grappling intellectually with a problem left everyone involved with the problem feeling anxious.

Margaret, though new to the business, was more naturally suited for this type of work than I was, and she quickly became frustrated with my aversion to quick action. Within my first couple of weeks in this new position I realized I was losing control of my only employee.

Then, the acquisition Alexandra had told me about was suddenly announced. We were buying a small company called FamilyPoint.com, which created private online family “clubs” including photo albums, genealogy charts, message boards and chats, all of them private and invitation-based. It was an early stab at social networking, and the founder Russ Kelly had certainly done an impressive job of putting the software together and kicking the product off, though it was unclear whether or not many families were actually using the service. The company was based in midtown Manhattan, just ten blocks from our office, and on the day of the acquisition I went to meet Russ, a brusque and plain-speaking serial entrepreneur, and his team of about twelve developers and product managers.

We’d just paid $30 million dollars for FamilyPoint.com, and now it was my job to figure out how to integrate the service into our company, and how to turn this notion of “private clubs” into a profitable addition to our community package.

A $30 million acquisition, as my first project on this side of the business? It was a hell of a way to start. I said I’d wanted something exciting, and I got it.

During my first few weeks in the marketing department I spent a lot of time walking the streets of New York City, because my new office was in the middle of a very public “playpen” and I didn’t have the privacy I was accustomed to. I wasn’t feeling a lot of pressure yet — that would come soon — and so I took the liberty of spending many hours away from the office, trying to think my way through the problems I’d been given to solve without being interrupted.

I also spent a lot of this time guiltily not thinking about the problems I was supposed to solve at work, but instead thinking about whatever I wanted to think about. I visited several parks and museums. One Wednesday early afternoon I found myself strolling on Sullivan Street in Greenwich Village when I saw a line outside a theater and realized the matinee of the long-running Off-Broadway musical “The Fantasticks” was about to start. I’d seen this great show as a kid with my father, and on an impulse I bought a ticket, went in, enjoyed myself for two hours, and then got back to the office around 4:30 to face the emails I didn’t know how to answer and the employee I didn’t know how to manage.

I was feeling very random these days, these months. Meg and I tried to plan a summer trip with the whole family, but I was too busy at work and things were tense between us, so instead she took Elizabeth to San Francisco as a present for Elizabeth’s 14th birthday while Daniel and Abby went to stay with my parents on Long Island. I spent that week going to work as usual, and hanging around Manhattan at nights before going home to Queens, also as usual. I didn’t do anything good with my “solitary week”. I wasn’t getting any writing done these days, and wasn’t doing anything new on LitKicks at all.

I remember that after Meg and Elizabeth got home it felt strange that they’d been in San Francisco without me, and it turned out they didn’t see any of the beatnik spots I would have taken them to — they didn’t go to City Lights bookstore, didn’t see the Turkish rug shop on Fillmore Street that had once been the Six Gallery, didn’t drive through Big Sur. This was the summer that Daniel’s obsession with Pokemon cards reached a peak, and I remember him pleading and pleading until we finally agreed to give him thirty dollars to buy the card he wanted the most, a Charizard, at the local comic book/card store on Austin Street in Forest Hills. Abigail played along like she was obsessed with Pokemon cards along with Daniel, but we could tell she was more interested in talking about them with him than in the cards themselves. Whenever we bought them both a pack, he would immediately claim the best ones in her pack as well as his, and give her all of his unwanted energy cards and doubles and triples, and she happily accepted.

I remember the hot movie that summer was The Blair Witch Project, the first movie to become a hit through an internet-based marketing campaign. I went to see it with Meg and Elizabeth, and we all thought it was cool. It would turn out to be the last movie Meg and I would see together.

I can’t explain what happened on Friday evening, September 3, 1999. I know that when I woke up that morning I had no idea I would end my marriage before the sun went down. Around 3 pm that afternoon we got in an argument on the phone over whether or not I would stop at the supermarket on the way home from work. It was that trivial a fight. I remember putting the phone down and thinking to myself “it’s time to end this.”

I had no plan. I hung around the city for a while, nervous. I got home around 8:30, Daniel and Abby’s bedtime, and I took Meg into the bedroom and said “Let’s move on. Let’s stop this cycle.” She didn’t react as positively as I had expected. We’d discussed the possibility of divorce several times this summer, usually at our tensest and most unhappy moments, and she always said “I’m ready”. It turned out she was bluffing.

I can’t explain why I so completely botched the part where we tell the kids, even though I knew how important it was to handle this with sensitivity. Instead, we punted miserably. After we talked for a while about my plan to leave Meg challenged me: “why don’t you tell Elizabeth?” So I called Elizabeth in and blurted it out. She didn’t take it the way I hoped either.

I thought I had it all worked out in my head, as concrete as a well-written computer program. The kids would be happy because now they’d get to spend every weekend doing exciting things with me. Nothing bad would happen, nothing they liked would go away, and we were moving on to a new two-household configuration in a mature and happy way, and everything would be great. But I could see it on Elizabeth’s face as soon as I started blurting my garbled plans out that she wasn’t taking it that way.

The three of us agreed that I would go sleep somewhere else and they wouldn’t say anything to Daniel and Abigail when they woke up in the morning and found me not there. Meg and Elizabeth would calmly say that I had to leave early to deal with a problem at work. I later found out that this didn’t happen as we planned it either.

I walked out the door and walked down to the Forest Hills train station to catch the Long Island Railroad into Manhattan. I got a room at the Hotel Pennsylvania across the street from Penn Station, where I watched TV and stared out the window and tasted a new taste in my mouth — bitterness — that I’d never precisely tasted before.