Goodbye, Cubicle. Hello, Startup!

Author Michelle Goodman offers women irreverent yet practical advice on making the leap from corporate job to independent venture

Author Michelle Goodman, a self-described former "wage slave," left her cubicle in 1992 to work for herself, and never looked back. But the transition wasn't easy for her. Indeed, although women make up one of the fastest growing segments of entrepreneurship, Goodman discovered that most find it difficult to make the leap (see BW Online, 1/31/07, "The Face of Entrepreneurship in 2017").

So Goodman culled the lessons from her own trials and errors along the way to solvent self-employment and compiled them in her practical and irreverent guidebook, The Anti 9 to 5 Guide: Practical Career Advice for Women Who Think Outside of the Cube (Seal Press, 2007). BusinessWeek staff writer Stacy Perman recently spoke with Goodman about getting out of the cube and on your own. Edited excerpts of their conversation follow.

You called yourself a wage slave. Why?

When I had a full-time nine-to-five job as a publicist for a book publisher, I wasn't enjoying it. It wasn't so much the job, but the construct of working for the man. I'm the kind of person who wants to work for myself at home, picking my own hours, colleagues, and projects. It's the opposite of what I thought was a wage slave.

What impelled you to go out on your own?

A rebellious streak at age 24. Perhaps I had trouble with authority figures, but I wasn't the poster child of how to be successful. For example, [had I known at the time] I would have saved money in the bank first, gathered more than one client before I left, stuck it out a bit longer in the cube, and collected more contacts and skills that would have come in handy when working on my own. I was only in the work force for three years after college.

What generally keeps women from going out on their own?

Fear. I think what's different for women than for men is they feel like the decision has to be 100% right. But it's never going to be a 100% sure bet—but being 80% sure just might be good enough.

In general, men are more brash and confident. Women overall have a harder time asking for money, which is what you have to do over and over again when you're self-employed. Also, women tend to have a harder time marketing themselves. They think it's bragging and uncouth, but marketing is a huge part of being self-employed.

What were some of the biggest lessons you learned during the "groping in the dark phase," as you call it?

Get a little bit more educated about what it means to run a business before diving in. I learned what makes a good contract by signing a lot of bad ones. I could have saved a lot of heartache and financial strain. There are so many great resources out there related to self-employment, like SCORE (score.org).

Another thing that I wished that I'd done was not to have leapt into [self-employment] without a better financial plan. [I wish I'd] asked myself questions like: What's my backup plan? How long before I say that I haven't made enough to live on and it's time to go back to the cube or a temp job?

Marketing [myself] was another learning curve—it was almost a personality thing. I was incredibly shy and loathe to go meet other people, but there's no other way to get clients. Back then [in 1992], you couldn't hide behind e-mail and the Web.

What are the most difficult transitions to make from leaving the office/cube to self-employment?

For a lot of people, it's discipline and managing your own schedule. You're used to going to work in an office for eight to 10 hours. The tendency, when working for yourself at home, is to think "I have got all day. I can do my shopping or meet someone for lunch." And it doesn't work out very well.

In the book, I talk about easing into it slowly, even working at it on the side. It allows you to test out a new business and see if the market is taking to it. Only get what you need, and don't go overboard. I went overboard.