Tom Ashbrook is the author of The Leap, a first person account of a drastic career/life change. Ashbrook had the kind of job that would send other journalists into fits of envy. He covered the biggest stories, traveled the world and wrote for one of America’s great old newspapers, the Boston Globe. He had his pick of assignments, a good salary and a secretary. Still, there was something gnawing at him: He was missing out on what he viewed as the biggest event in his lifetime -- the Internet's transformation of the world and economy in which he lived.

In 1996 Ashbrook made a move that even he considered to be borderline outrageous: He quit his job and started an Internet company with an old college friend. At the time he had a wife, three children, a mortgage and no promise of funding for his business. It was, in short, not exactly what his wife had wished for.

His company, Home Portfolio, is an Internet destination site for people in search of home design products. The site presents a selection of top-of-the-line and hard-to-find products and directs users to retailers. Ashbrook has spent the past five years frantically building this company.

Home Portfolio now has more than 100 employees and recently received its latest round of venture funding -- $70 million. His wife, incidentally, has forgiven him.

Ashbrook recently spoke with Monster.com about career/life transitions, the New Economy, and the Free Agent economy. Here are some excerpts from our conversation:

"It was a gig to die for. I can't deny it. I had a great gig but there comes a time when you have to look to the frontier. When the frontier is so exciting, so revolutionary, you see that what you thought was a great gig suddenly doesn't have the same profound impact as it used to. I could travel the world and report from anywhere I wanted to. I had a secretary and a beautiful office and all those kinds of old economy trappings. And with all of that, I felt that the work I was doing was not having the same impact that this New Economy was going to have. The center of dynamism in the world had moved away from my industry, at least for a while. Clinton was right when he said, ‘It's the economy stupid.’ In the last decade, it has been economic change that has really beaten the drum, and has really set the tempo. I wanted firsthand experience with it."

"I've always been a bit of a heat-seeker. When the Alaska oil boom was on, I spent a couple long stints working there. When Asia was having its enormous boom in the 80s, I spent 10 years in the region. When the Berlin Wall was coming down and foreign news was all the rage, I was foreign editor at the Boston Globe. But by the early/mid 90s, I was sitting in Globe strategy meetings and people were telling us, ‘Ten years from now, the Boston Globe will be abandoned; the presses will be quiet; no one will bother to read the paper; and there will be tumble weeds blowing throughout the newsroom.’ I thought, ‘Oh my God, I don't want to be part of that. I want to be where things are going, and that pushed me right out the door.’ Now, in fact, that industry is still around and it's been making a ton of money, a lot of it from dotcoms. But it was an issue of being where the real happening edge is. That is what took me to journalism and in a way, it's what edged me out. But I'm still very attached to my lifelong commitment to being an observer and a writer. And they say that in this New Economy, we'll all have a half-dozen careers in a lifetime and if that's true, I don't see why we shouldn't have at least two at once."

"I was sitting in an old economy industry in the early 90s and feeling the first tremors of the world really starting to change around me. I began to go absolutely nuts sitting on the old side of the fence. I felt I had to get out to the frontier. I think in the late 90s we went through a period that, when we look back at American history, it will be remembered very much like the California Gold Rush or the Klondike but with much greater long-term impact. You could see this wave of change coming that was so profound and so huge and I wanted to be in it. I didn't want to be crushed under it. I wanted to be part of the change; not a victim of the change."

"I was turning 40 and I thought, ‘I'm never going to have a better combination of energy and insight than I have right now.’ I may have more insight later but I won't have more energy. If I'm ever going to take the leap, this is the time to do it. And there was that big, blue Hawaiian wave coming; it was impossible to resist."

"I have always loved beautiful homes and had a strong interest in design, but I never pursued it. I was looking for a foothold in this new world, but I had no B-school background; I had no money; I had no technical background; I didn't understand circuit boards or widgets. This wasn't about learning C++; this was about envisioning how this new technology could impact a $250 billion industry and could effect people right where they live -- right in their homes. That was appealing. In a funny way, it had a special appeal after all my years of covering wars and famines and great affairs of state. The idea of having an impact in people's homes -- in that intimate setting, helping people create personal living environments that were magical to them individually -- had a kind of gritty reality, an intimate impact, and that was appealing to me. It was smaller scale; it was touching people right where they live. There was something about the change of scale in that that I liked. Of course, I like that intimacy being paired with a gigantic market."

"You'd be surprised at how the skills you build for one career might have incredible value in an entirely different career. I couldn't fully appreciate it, but my journalism background was great training for this wild world of Internet entrepreneurship. Journalists are constantly thrown into positions of complete flux and uncertainty. And they have to be confident that at the end of the day, they're going to come out of it with the story, or the product. Journalists start every day having no idea where they're going to be before the day is over. That certainly has been the situation with most people in the Internet in the last few years. Journalists work under impossible deadlines but they learn to do that with the confidence that they will deliver on that deadline, even when it seems impossible. Journalists are always trying to contact new people and establish a rapport with them quickly and gain their confidence in order to move ahead. It's the same with entrepreneurs. So I have a whole skill set that I developed in one career that turned out to be incredibly valuable in a second career. But I didn't know that going in. It's very empowering once you learn that. I think the take away is that you need to take a step back every once in a while and think about the skills you're developing. Don't think of them just in terms of how they apply to the current job but how they apply to other fields. There are tremendous opportunities and talents that we all carry around that have amazing applications in new fields."

"The drumbeat in the 90s was ‘Employers no longer have an obligation to their employees. We’re all free agents; we’re all on our own. The companies will do what they have to in order to survive.’ In that environment, it is very empowering to be aware of how your talents can be applied in a new field, in a new career. It gives you the courage you need to operate in this much more fluid economy."

"The Free Agent economy can be a cruel world. But it’s also a reality and I thought it was liberating to stop clutching my old job and that security blanket and start focusing on the talents I had right in my back pocket. That actually empowered me in many ways. When my perspective changed in that way, this new economy became less frightening and more exciting. What could have been depressing became thrilling. What I had seen as a kind of scary wilderness suddenly looked like this big area of freedom. It really changed my outlook on work and opportunity. It got me out of the paranoid, defensive crouch that I was in and got me standing up and realizing my own talents -- and we all have them -- and acting on them in a way that made me feel liberated instead of frightened.