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Living Without a Net: An Odyssey into Self-Employment (Part VII): It's Good to Be the Boss

Growing up, I wanted to be a dentist, though it was only temporary. I liked the cool instruments the dentist used, and I liked the orange-flavored toothpaste. Once that fantasy faded I wanted to be a teacher. Believe me, there wasn't some inherent form of altruism guiding the desire; I was too young to ponder my legacy, and had I known then about the money that would have been it. Rather, in my limited, five-year experience with life, teachers were influencers, they were leaders. I didn't know how to describe it at the time, but that's what I wanted to be--a leader.

Eventually I dropped the teacher fantasy as well. When someone asked me what I wanted to be, I said, quite simply, "I wanna be the boss!" It didn't matter in what arena. I just wanted to be Top Dawg.

My parents never put the kabosh on anything. They encouraged me and my sister to join sports teams and male-dominated organizations in school. They never told me not to do something because it was for boys (not even the Dungeons and Dragons club; though after two meetings I had to put the kabosh on that one). In eigth grade my sister and I were cast as twin boys in the school play because, well, we looked like boys, and no one was the wiser.

I was this flat-chested, lanky thing, and my Mom bought me this ugly little training bra--wireless, more like a two hankies sewn together, one cup was red, the other was blue, I suppose, in case I forgot my right from my left.) I refused to wear the thing; it never occurred to me that I needed to start looking like a girl. It never occurred to me that I couldn't be the boss.

Living Without a Net: An Odyssey into Self-Employment (Part VI): Forgiving the Defectors

One of my former neighbors came to see me yesterday. We used to live in the same apartment building in San Francisco--I lived on the fourth floor, he lived on the first. When I met him I had just moved into the building and was very nervous because I'd just signed the lease and then lost my job the same week. He had just left his business development position at one of the more successful companies in the Valley. Both of us were single. Needless to say, we had a lot of free time on our hands.

It was San Francisco during the Dot Com bust. Our yuppie neighborhood was like the unemployed version of Melrose Place. It teemed with professionals that had just lost their jobs. They hung out in cafes and kept the local eateries busier during the week than they were on the weekends. Some folks were experimenting with alternative lifestyles. One of my friends, formerly a marketing executive with an MBA, was leaving for art school in London. Another friend, a computer engineer, was training to become a personal coach. A neighbor on my floor, a laid off banker, used his time training for an Iron Man competition; when he wasn't training he delighted in long bouts of daytime sex.

The groaning that came from the other side of the wall didn't so much irritate me as much as it aroused feelings of deprivation. Not only was I starved of a paycheck, I was starved of attention and companionship, something that cubicle mates unwittingly provide. Whenever the groaning got loud enough to distract me I'd call my friend on the first floor.

"Lo?"

"Hey it's Jory."

"Sup?"

"They're at it again."

"Wanna go get coffee?"

"Yeah." 

We established an oddly platonic partnership, inviting each other to parties and introducing each other to potential date material. He'd call me in the middle of the day to see if I was up for hanging out at one of the local coffee shops. I came over in the evening to watch shows on his wide-screen television. He'd busted his knee a few months earlier and had arthroscopic surgery, resulting in several months of limited mobility. I came over to bring him groceries. He took me out to dinner at places where we would never have found parking had he not qualified to have a temporarily disabled sticker on his car. We talked about relationships (about not being in them, mostly) and, most often, about leaving the security of a steady paycheck.

Limit My Options, Please!

I’m writing while flying back from the Land of Agita—also known as New York City. I used to live in this glorious place, one with which I’ve had a love-hate relationship for over a decade, this place of manic derision and freedom.

The crush began when I was a sophomore in college and I interned for a summer at the book publisher Little, Brown and Company. The father and stepmother of my high-school pal, Justine, hooked me up big time, helping me to land the internship and providing a relatively autonomous arrangement for us; Justine and I stayed at their friends’ apartment—a charming one-bedroom that they vacated in the summer—on the Upper West Side.

That summer Justine’s parents exposed me to all of the great aspects of New York. They held dinner parties with other writers and literary folks whom I could listen to forever. They served wine that didn’t come in a fruity flavor. They took us to cool off-Broadway shows in the Village, sidestepping Les Mis and touristy Times Square entirely. They took us to bistros in Soho, Little Italy, and the West Village, often paying with several $100 bills. They taught me things critical to surviving in New York, such as arriving at dinner parties ten minutes late—no later and no earlier; writing thank you notes and sending thoughtful gifts; properly chilling a sauvignon blanc; coordinating the entertainment of guests while cooking a meal; being provocative and appropriate; being a New Yorker.

I went back to college in the fall, back to Champaign, Illinois, where the preferred libation was watered-down Natural Light, determined to get the hell out of the Midwest as quickly as possible. I had seen the light, or the penthouse on Central Park West, so to speak. I was convinced I had found my home.

I managed to graduate from college a semester early. With $700 in my bank account I flew to New York, determined to enter the world of publishing as an editorial assistant, slowly—but without question—working my way up the commercial publishing ladder.

My father dropped me off at the airport and said quite bluntly: “If you need money, don’t ask me for it.” He wasn’t joking, actually.

“Geesh,” I thought to myself, “What’s he getting all worried about.” I had, after all, already been to New York. I knew all about it, and most importantly, I knew how to survive.

“Remember,” he said to me, getting back into his car, “they take out taxes.” I wondered, what the hell is he talking about?

Needless to say, my introductory summer to New York City, while heady and hypnotizing, hardly prepared me for the realities of living in Manhattan. I learned quickly that, while people in publishing generally have snooty taste, the entry-level ones can only afford the vapours of affectation. I’d sipped and sampled all of the delectables of the City a year before, but I wasn’t to do so again until “Wait staff, Bennigans” moved further down on my resume. Even those who had paid their dues, I learned, those who had been in the industry for five to ten years, often had a roommate, or a rent-controlled-slum of an apartment, or wealthy parents to get them through the rough times.

Fortunately I was all-about adversity. I usually need a significant amount of challenge in order for my accomplishments to feel deserved. But what was painful was the disappearance of the options I’d enjoyed that summer I was an intern in New York: The plays, the restaurants, the good wine with dinner I would not enjoy for several years—and even then I had to pick my opportunities carefully.

Therein lies the rub: New York offers one so very much, but also so very little leeway to pursue these options. Thus the nervousness I felt when I landed in New York, with a weekend’s worth of discretionary income: I could now have my way with the City.

Coffee Thought #2

I've been searching for the most advantageous coffeehouses in my neighborhood, as I need a specific environment to get my work done. Sure home is fine for writing, but I find that I need to get out at least once a day, to be in another environment, preferably a caffeinated one.

There are three or four coffeehouses that I frequent regularly, each with it's own sense of charm and personal amenities. I'm all for supporting the neighborhood Mom and Pop place, but I've encountered some issues that keep pushing me toward Starbucks:

--Internet availability: I get that this is a perk, not a requirement, and not all places want to attract a crowd of people who don't talk but just stare at screens all day. Still, it's nice to not have to go home just to check your email.

--Seating limits: Two places that I like to frequent have time limits on their customers. One flat out says that patrons cannot sit for more than and hour and a half per order. The other suggests that sitting in the place for three hours and not buying anything more significant than a cup of coffee is rude. Now I feel rather self-conscious. Should I order a slice of quiche and keep these boys happy?

It will probably just be a matter of time before Starbucks imposes similar limits, but to my pleasant surprise, they haven't kicked me out yet. In fact, they come around and offer me samples of the Chantico--that new, very likely illegal, chocolate substance that puts me in a sugar coma after the first sip. Damn, it's good. Hell, there's even a man I notice who comes in at the same time every day and just falls asleep. They offer him Chantico too, if he's up.

I want to tap him in the shoulder and tell him "No loitering!" but I realize it's just a measly $1.65--the cost of a Grande--that keeps me from being just like him. Hell, throw in the Chantico and I'm probably worth only $1 to them.

And yet, Starbucks makes money. There are enough people who run in for lattes and $3 mochas to basically subsidize the few of us who don't need to be anywhere anytime soon.

As wireless accessibility develops, so do the rules. When will Internet access be a must have? When will we have to start feeding the food meter at these places to justify our staying at them for hours at a time?

I wonder if Starbucks needs a consultant ...

Coffee Thought #1

I broke my favorite coffee mug. I know, I know, big whoop. But this was an extraordinary coffee mug. I received it as a gift when I left my first real (read: salaried) job.

The other lowly assistant editors in my department who, like me, spent their weekends poring over reams of paper, each donated a dollar to pay for it, not an insignificant thing when you're making $19k a year--in New York City, no less. They were smart--they knew I needed a mug with good capacity to keep me caffeinated enough throughout the day.

It was a simple, painted mug; and it was quite sturdy. It weathered being packed up and moved nine times, to different job situations--corporate, start-up, self-employed. It got me through long meetings and tense deadlines. I moved it from New York to San Francisco, wrapping it with special care, lest I start my new job on the wrong cup.

I figured the demise of this mug would be from something dramatic--a tornado, perhaps, or a scheming co-worker who wanted it for herself, or from me throwing it at someone in anger at someone worthy of pulling me away from my daily caffeine infusion. But it didn't end that way. I suppose it was best that neither of us knew it would happen. It happened not at any job, but at home, the first week of my transition into self-employment

I was at home writing something and felt my brain drying out. I'd just finished my usual mug of coffee, but wanted more. There was just enough chalky sediment at the bottom of the French press to pour a third of a cup and stick it in the microwave. As I pulled the mug out I hit it against the sink and next thing I know, Ginger (our cat) is licking up the remaining Costa Rican roast amidst shards of ceramic glass.

I was paralyzed, unable to move while the b-friend began to mop the mess up.

"What do you think this means?" I said. "This mug has always weathered being knocked into things before. This time it just shattered. Why now? ... Perhaps it's a sign. The coffee mug that took me through nine different jobs, seemingly different lives, now shattering. Perhaps my real career is about to begin."

The b-friend said, "That, or maybe you shouldn't have gone for that second cup of coffee."

Living Without a Net: An Odyssey into Self-Employment (Part V): Learning to Improvise

(This is the fifth part in a series about living the Entrepreneurial Life)

This summer I went on a personal development retreat up in Mendocino, CA. It was one experiences where your mind is so filled with possibility at the end of it that you don’t remember how you got home, or how you got to your office that Monday morning, or how you could stand to work another day for someone other than yourself.

But I’m getting ahead of myself. I didn’t leave this retreat thinking I needed to quit my job; rather, I left thinking about something that would lead to my eventual decision to work for myself. I learned that I am—quelle surprise—a bit of a control freak, but not the usual garden variety take-a-Valium kind; more the paranormal kind. I am such a control freak that I foster a form of clairvoyance, imagining what people are going to say or do before it happens. I supposed I like to be prepared.

My b-friend thought I lived in La La Land, but that wasn’t it. I was actually living a few minutes into the future. If he didn’t understand me, I told him, wait a few minutes and he would get what I just said. My responses were simply reactions to something I predicted he would do or say.

Needless to say, this became very confusing for those who lived in real time, or who might not have done or said what I thought they would. My reactions were completely useless to them, and to me. For example; I’d been writing a book for two years but was going to let it languish on my hard drive because I was fairly certain of what an agent would think of it, or what the public would think of it if I snowed the agent and got the damn thing published. It’s very hard finishing things when you already imagine others negatively receiving them.

At the retreat, after I was called out on this little habit of mine, I was given a homework assignment that I promised to fulfill within a week: Sign up for an Improvisation Course. I felt so blissed out and in the moment that I didn’t think about how unappealing I would find this idea in the future.

It was almost eerie, how one week later, homework left undone, I met up for lunch with a friend I hadn’t seen in a long time. She’d been in a relationship with a man and was living with him now.

“How did you meet this guy?” I said.

“We met in an improv course,” she said. I swallowed hard. As she started to tell me about how much fun they’d had in their course together, I realized I was being told all this for a reason.

“Who teaches this course?” I asked my friend.

“His name is Dave. Here’s his number.”

Living Without a Net; An Odyssey into Self-Employment (Chapter IV): Making Your Luck

I had breakfast with a blogger/entrepreneur the other day, the now netless Andy Lark. Andy just left his position as head of global marketing at Sun Microsystems. He liked the work, he says, but it seemed that there were too many other fascinations he needed to address. Andy was instrumental in getting Sun Micro blog-enabled (I will expand on Andy’s story in the future, when I post the chapter I wrote on blogging and the growing demand for corporate authenticity for the More Space Project).

In his “ample” spare time Andy speaks internationally about the impact blogging is having on corporate communications, he consults, and he sails. He asked me for recommendations on neighborhoods closer to the water, as he and his wife are looking for a new house, hopefully before their first child arrives in April.

“You better figure out how you’re going to find the time to be a Dad,” I joked.

“No worries,” Andy said, in his worry-free Kiwi lilt.

Andy fascinates me on a number of levels. Sure, he’s started 15 companies, has held high-level corporate positions, and is finishing a book. But no ONE accomplishment defines the man. When I left my full-time job it felt like a physical leap from land to a dinky little rowboat; I’d braced for the rocky ride from “corporate” persona to Bohemian and prayed the little vessel would take me to stable ground. I’d even bought new casual clothes so that I would more convincingly play the part of a self-employed person.

The Workaholic's Choice

So I guess I got my comeuppance for working like an idiot. I’m sick. Really sick. I woke up Sunday thinking I had to barf. The last time this happened I’d had too much to drink. The last time this happened without any alcohol involved I was 10; so you can imagine my surprise when, after taking the evening off and going to bed early for the first time in a week, I wake up feeling so lousy.

Funny how the body does that—it says “screw you” only after you are nice to it again. While you are in the trenches it fights tooth and nail to get you through. I didn’t consume anything Sunday except green tea and two pieces of toast; today I managed some Malt-O-Meal. I remember, when I was in the seventh grade, one of my friends got mononucleosis, and the rest of us wished we could get it too because she missed a month of school and came back looking really skinny. But in adulthood illness has lost its allure; it’s now a big time-suck.

Despite feeling like I had to vomit constantly, I insisted on getting work done. Of course this is stupid because your brain runs at 20 percent capacity, so work take five times as long to complete. After hours of struggling I said, “enough” and watched something completely brainless, Napoleon Dynamite.

Before you judge my obsessive attitude toward work, consider George Stalk, Boston Consulting Group’s strategy wizard, who was profiled in this month’s Fast Company.

Job Wanted: Corporate Mother, Has Experience

My mother called me on Monday to “check in.” She does that when we haven’t spoken in at least 48 hours. When this happens she knows that there are two likely scenarios: 1) I’m incredibly busy and buried in projects or 2) I’m dead. Not one to jump to conclusions, she called to make sure that I was Option #1.

Normally I love talking to my Mom. Something about her voice has comforted me since I was a child. I could have a million things to do, but if I really need to calm down I’ll call her and chat/gripe for five minutes, and then I’m fine.

This time, however, I was beyond busy. I had a colleague working with me trying to troubleshoot a computer issue; one of my clients was on the other line and needed quelling over a missed publishing deadline; I was starting to smell myself.

“Hey,” she said. “How’s it going?”

“Woman I can’t talk now; I’ve got crap coming out of my eyeballs.” I get dramatic when I get stressed out, and maybe a bit self-important.

An aside: I’ve called my mother “Woman” since high school, when a friend’s mother came over to gripe about something I’d done, and she kept calling me “Lady,” (“Just what did you think you were doing, Lady!”, she kept saying) My mother waited patiently for this woman to leave before rolling her eyeballs and saying, half-laughing, “That’s right, Lady! You got that, Lady!”

I was 16 at the time and responded, “Don’t call me Lady! Call me Woman.”

“No, I’m Woman,” Mom responded. You are Woman-ette.” For some unknown reason, the names stuck.

“Oh well then I won’t bother you,” Mom said. “You get right back to what you are doing. Talk to you later—”

“Wait a minute, Mom, is everything OK?”

“Just fine, Babe. I got laid off today, but I’m fine. Talk to you later. M’bye.” She even managed to blow me the obligatory kiss that she did at the end of every phone conversation.