Solo diaries

Of all the lessons Harriet Rubin has learned after two years on her own, the most important may be this: the very same things that make soloing rewarding are exactly what make it hard

In July 1997 I left a big company to work for myself, vowing never to manage or lead another creature, not even a dog on a leash. I went solo. No more stupid bosses and stifling politics. I would do the work I wanted to do. Soloing would turn me into an adult, no longer dependent on Ma & Pa Organization. I would, in Marshall McLuhan's memorable phrase, not just earn a living but learn a living. Every day would be new.

Two years later I altered my course. I joined the Internet company iVillage to help it start a new Web channel. Once again, I'm managing and leading in the world of earning a living.

Why? Why go back to an organization after achieving freedom? Had Solzhenitsyn come to miss those hard crusts served in the Siberian gulag? Had a high school graduate ever begged, "Oh, let me repeat the 12th grade?"

The tunnel at the end of my light came in the form of an offer I couldn't refuse. The people at iVillage invited me to create content on women, work, and identity. They're giving me a free hand to try to restyle content on the Web. And they're giving me something soloing never could: the tools of scale. Their Web site reaches more than 7 million people a month. Those are Star Wars numbers. How could I say no to emissaries of the Force? To a hungry person, everything looks like food. To a soloist, everything you dream of but don't have can be defined by one word: scale.

And to some extent, I am still a soloist: I don't have a desk (except at home), and my hours are not completely full-time (though I work 12-hour days and more, as does everyone in the Internet world). In short, iVillage has become my major client.

Still, it's not soloing at its purest. I'd worked hard to go solo, to make the transition from big corporate editing and publishing to little-me writing and consulting. The first months were a nightmare. I was drawing on my savings. Jobs were slow to come in. I worked harder than I ever had. I stopped seeing friends, afraid to spend time or money on anything other than surviving. That's the point at which I began writing a journal for Inc. Eighteen months later, when I posted my last journal entry, I was a thriving soloist -- thriving in financial and practical terms, at least. But I signed up with iVillage anyway.

Because for all I'd loved about and learned from soloing, I needed a vacation from it. I was worn down by having to invent myself every day. When a client needed a consultant, I became a consultant. When consulting jobs ran dry, I sold myself as a speaker. At iVillage I don't invent myself repeatedly. Every day I am "director of the new work channel." I don't live from job to job or feel the need to have a dozen possibilities circling overhead to remind myself I'm needed, like an air-traffic controller at O'Hare. One of the causes of solo fatigue is the need to create a strong "brand called you." You can't solo well without it. But this brand called you demands constant feeding. A brand is an external state: the perception of you in the eyes of your customers. Every day that you're not out in the marketplace reminding people you exist, you disappear.

Soloing is particularly hard on single people like me. There is no other salary to fall back on, no secondary source of benefits. Solo, you also become your own parent: you pay yourself, tax yourself, administrate yourself.

Don't get me started on the money. Businesses can deduct 100% of the cost of health-care benefits from taxes. Individuals can't deduct anywhere near that amount. Although I was paying nearly $10,000 a year for insurance, I still had to fight with Cigna for months to get a medical ID card -- a flimsy paper card whose edges curled as soon as I held it in my hand during a doctor's office visit. Now the safety-net part of the struggle is over for me. The company pays my benefits. I got a Cigna card in a week. It's made of sweat- resistant plastic.

Still, there isn't a day when I don't miss what I had. If soloing means having to become your own parent, going back to a job is like moving in with your parents. iVillage is a pioneering company. Yet I wasn't prepared for the feeling of being back on the inside.

The first days of meetings hit me like the flu. The watercooler gossip, the small talk, the "Have a great weekend!" and "Did you have a great weekend?" left me dazed and sick. I'd been spared niceness rituals for two years, and now I felt as if I were in a hospital where people acted as if they couldn't say what was really on their minds. I could see why people with jobs get so little done, and why soloists get so much done. Meetings are too long; conversational calories are horrendous. The time wasting made me lethargic. Cut the organizational sweet and fat from your day, and the energy you gain is stupendous. People in organizations are smiling themselves into an early grave!

Soloing, on the other hand, is the most romantic relationship I've ever had with work. Everything Juliet said about Romeo and Romeo about Juliet, I could say about soloing. A client who appreciates you appreciates you -- not the name Doubleday or Bertelsmann or Montague or Capulet. Like love, soloing makes for a precarious life, but you have at least half the control: you need cash, but you can turn down work you don't feel good about, so you're always bathing in the good-feeling aura. When you fall in love, you think you are fortune's favorite child. It's the same with soloing. Have the courage to turn down a job, and a better one comes along. Choose a small assignment, and the surprise at the end of the rainbow is finding a window onto some big opportunity.

Love makes you feel like a star on the stage of your own life, and so does soloing. Designer Don Norman left Hewlett-Packard to go solo, and the first thing he did was read books on how to grow a company. Then "a friend wised me up," Don says, "suggesting I instead read books about Hollywood. He said, 'When clients call, they'll want to work with you, not any company. You're not building a company. You're building you. You're the star."

There are two ways I think about my semideparture from soloing. One is that it's no big deal to temporarily retire your bunny slippers. People change jobs; they change careers; they do lots of different things in the course of their lives. The other way to think is that compromising your solo status is a very big deal.

It may even be handing my soul to the devil.

Before the ivillage opportunity, I was planning to go deeper into soloing. I was looking for a cheap apartment in Italy where I would go for a year to write a novel. In the past year, some of my friends and family have died; others have gotten reprieves from serious illness. What sage said, "Death is man's greatest invention; that's why we save it for last"? On my worst days back in the belly of the organizational beast, when I'm struggling with a political snake who tries to bring me down to her sick level, I ask myself: "Why am I working for anyone else, no matter what the opportunity? Who knows how much time any of us has? Can I afford to put off my dreams to work on someone else's?"

Haunting all lapsed soloists is the ghost of the great Henry David Thoreau, who wrote his own diary of soloing, Walden. Thoreau left for Walden Pond on July 4, 1845, when he walked out of a boring civil-service job to prove to himself and others that a person could live independently. He believed that his hometown, Concord, Mass., offered no opportunities for meaningful work. Rather than living a life of "quiet desperation," Thoreau insisted upon living "deliberately." He built a hut with his own two hands. He earned his bread by doing a little surveying, performing odd jobs, and tilling a few acres for the beans and potatoes he ate. He wrote of his experiences in a book that became an American classic. Two years later the path to his door became too well trod, and he decided it was time for a new challenge. So Thoreau left Walden and eventually went to work in his father's pencil factory. He never again achieved anything as great as he did when he was solo.

If Thoreau couldn't bring "solo mind" to the organization, how could I? In walking out of my own Walden-sized apartment in New York, would I be going backward into a pencil factory? If exiting Walden Pond and the solo life killed Thoreau's creativity, would it kill mine?

The unexpected turn in my journey is a chance for a new experiment: to see if it's possible to be soloist at work. Is it possible for me to resist corporate politics and compete against no limitations but my own? Can I make my own vision come alive in a group setting? When I was a corporado the first time around, I blamed the company when creative solutions went wrong. I believed that organizations bled a person of imagination and daring. But what if the failures of creativity were as much my fault as the company's? By changing your behavior, is it possible to bring the best of soloing to even the most hierarchical organization and see a difference?

If my experiment works, it would show that soloists can help make organizations places they escape to, not just places they escape from.

For the past two years, I've presented myself in the pages of Inc. as a canary in a coal mine: I went into soloing as an experiment. If I didn't fall over dead, I could offer hope to others who wanted to balance work and life by pursuing independence from jobs. Now, by going back inside an organization, I'm being exposed to an early tremor of the next big shift in the definition of work: the barrier that has long separated the organization from personal life is breaking down. It's getting harder and harder to define a "soloist" simply as someone who leaves a job. It's getting harder and harder to define an organization by its employees. Even Warren Buffett, who invests in companies that have a "moat" around them, suddenly finds his portfolio underperforming.

Organizational boundaries are not what they used to be. Am I in an organization or out of it? Part of it but also apart from it? That distinction is important, because as the boundary erodes between organizations' demands and employees' personal and creative goals, then what is important is solo mind, not soloing. If you can act as a stubborn individualist inside the organization, soloists will have won. If you can come and go as you like, take on other clients, create your own job, work on a limited time horizon, and establish your own goals, then freedom for workers will finally be achieved. The Berlin Wall of organizations may be falling. The sledgehammer? Soloists!

To keep the lessons of soloing alive in a corporate setting, I drew up a list of the differences between company mind and solo mind. If I could figure out what made soloing work so well, maybe I could resist bad organizational habits.

I had come to love chaos over resources. A manager has budgets, minions, and a small amount of screwup room. A soloist has no budget, no minions, and a lot of screwup room. That is good. Could I preserve the experimental nature of soloing in an organization in which I had to account for myself and for others?

Also, as a soloist I had come to crave intimacy more than scale. You can't design big projects as a soloist, but you can design big ideas. Would the big-company hierarchy that makes scale possible also flatten my big ideas?

Next, I'd made a commitment to freedom over power. Sartre called freedom nausea. It takes getting used to the fact that no one is hovering over you. Now Ma & Pa Organization would be hovering. Could I learn to push back and not get sucked into the corporate culture? Could I say to the organization, "You can have this much of me and no more?"

Finally, solo, I appreciated the intensity of projects over the comfort of routine. Would routine dull my brain and make me compromise on the work itself?

The challenge is to keep chaos, intimacy, freedom, and intensity alive in my part of the organization. The way to succeed might be to resist conventional notions of what work is. For example:

Chaos thrives when you don't see failure as a big deal.

Playing it safe makes a person succumb to the worst of organizational life. If you don't care about your personal or career safety, you'll put the work first. If my iVillage project blows up, I can go back to soloing. I've proved I can take care of myself. Knowing that failure can't ruin me, I don't worry about it. It doesn't dictate or limit what I do.

Intimacy becomes impossible, but its opposite -- scale -- is not necessarily the villain.

My first time around in organizational life, scale meant bureaucracy. It was boss upon boss, each stupider than the last. Every decision required multiple sign-offs and lots of time-wasting politics. When I was solo, mine was the only sign-off required. But this time around at iVillage, scale looks delicious, not as an endless hierarchy but as a banquet of resources.

Freedom, once you have it, is not something you can lose. It becomes a personal sensibility, not casual Fridays or any amount of screw-you money.

I have a boss now. I have routines. But I feel they add to the possibilities of what can be created instead of limiting them. Writer Sue Bender once told me: "Going back inside an organization can help you become a better soloist. You'll breathe in deeper by breathing out. Working in a company is breathing out. You need to do both to maintain a balanced life."

We'll see. After the first few rocky days, when I thought I would die breathing recycled air or hypnotize myself nodding yes to colleagues, I began thinking that maybe organizations and soloists are not incompatible. I'm able to test my ideas in a bigger world and apply a wider palette of colors thanks to those same colleagues.

It's intoxicating. But most of all, it's humbling. I'm seeing how much colleagues can contribute to an idea. You need to have been working solo for two years to really appreciate that. Humbling -- I keep coming back to that word. Breathing out, you deflate. Individuality means more when you are part of something bigger than yourself.

I'm learning that a soloist can go home again, even when home is Ma & Pa Organization. Maybe the 12th grade would take me back. I still have a lot to learn.

Harriet Rubin is a "soloist in residence" at iVillage and the author of Soloing: Realizing Your Life's Ambition.