Silicon Insider: Working at Home

June 7, 2007 — -- OK, enough with the fantasies, let's talk turkey about what it's really like to work at home. I've done it now for a quarter of a century.

In 1981, I quit my job as a business reporter at the San Jose Mercury-News. I was young, cocky and frustrated with writing too many quarterly financial stories and not enough creative features. Oddly, the paper punished my temerity by giving me a promotion — and I spent the next glorious year as an investigative reporter, coming and going as I pleased, chasing down the really big stories.

Unfortunately, there are only so many big scandals floating under the surface of a place like Silicon Valley at any one time. And so, after a year, I found myself sitting in my 1969 VW bug in the Merc parking lot, holding a cardboard box filled with all of my office possessions.

I was 27 years old, I had $200 in the world, and zero job prospects. Both my friends and my professional peers thought I was completely out of my mind -- and I didn't necessarily disagree.

Yet, I somehow survived. Indeed, over the last 25 years, I've only had a real job -- as editor of Forbes ASAP magazine -- for a total of three years. For the rest of the time I have worked at home as a freelancer.

During those years my wife (she's a painter, so she hasn't had a steady job either) and I have lived in a converted chicken coop, bought gas with quarters, and I have driven as much as 75 miles just to pick up a check instead of waiting for it to get mailed.

But we've also been comparatively wealthy, bought houses and property, driven fancy new cars, and traveled the world. And though I've done some really humiliating scut writing jobs -- press releases, annual reports, brochure copy, ghostwriting, etc. -- I've also been free to do the kind of writing I've always dreamed of: books, newspaper columns, magazine essays, even a television miniseries.

I've given speeches around the world, been on the scene at the birth of some of the world's most famous companies, hosted three TV series, and won a number of writing awards.

Had I stayed a daily newspaper reporter at a mid-sized daily, I likely would have never known any of these experiences. On the contrary, I'm now at the age of those folks I saw in the newsroom when I was a cub reporter, the men and women who had once worked on the big stories but were now reduced to night police radio, obituaries and school district meetings.

But most important, despite all of those warnings I got from my peers (not to mention the little voice inside my head) saying that the life of a freelancer was too volatile, and too unpredictable, to make a permanent career, the truth is that I have managed to continuously earn a living during all of those intervening years. Meanwhile, the people who warned me about my fate have, to a person, been laid off from at least two jobs. And now many of them are fighting to survive in that ever-shrinking world of daily newspapers.

So what have I learned from all of those years working at home? Well, a lot of things you probably aren't going to read in any other article on the subject. Call it the real-life rules of working at home, whether you are a freelancer, contractor, or merely a corporate telecommuter.