[This is a guest blog by Greg Jordan]

It was the fall of 2005 and I was vulnerable. Fall seems to be when everything important happens in my life.

Guest Author Greg Jordan left Yahoo as part of his career journey; in this picture from this week, Yahoo’s iconic billboard leaves Highway 80 near the Bay Bridge after 12 years. Source: Mercury News

Caught in a fragile moment, I was being recruited away from a decent job at Forrester Research to work at Yahoo!, a company still struggling to be second best.

I was up for the challenge and was encouraged by the opportunity to work with an energetic crew of fun-loving, smart people.

I had already been moonlightingfor a few years – building rudimentary Web sites and helping growing businesses with their digital marketing aspirations. But it was on the side, and after hours. I wasn’t ready to quit my day job.

Unbeknownst to me, I was embarking on one of the most defining gigs of my life: a road to entrepreneurship.

I was working at Forrester, an IT research and consulting firm. Forrester is situated at the fascinating intersection of technology and business. It’s a place where one gets to hear first hand about leading-edge technologies, the companies that are engineering them, and the enterprises that buy them.

The market research world also has gravity with the investment community, because they’re constantly trying to pick a winner. It’s all interesting stuff, and you get a front-row seat. You watch, but you don’t touch.

Forrester was good. But I needed to get closer to the action. I wanted to go to the front lines.

Yahoo! was recruiting me to be part of their top-level ad sales team. This would definitely be the front lines. I would get Carte Blanche to design advertising solutions for some of Yahoo!’s most valuable advertisers. Yahoo! was in the process of busting up some of the silos that existed: search, display, mobile, custom. I’d get to access to the whole tool box.

At the time, one of the big trends was digital advertising and marketing. Search marketing, in particular, was piping hot. And Yahoo! was poised to potentially give Google a serious run for its money. I wanted in on the action. Now I could roll up my sleeves and have some fun.

Simultaenously, my marriage was falling apart.

I was naïve. Nonetheless, I did realize that my wife was anxious to move to Southern California – to be closer to her sister and family, and “better” weather. Me, I felt like the San Francisco Bay Area was my home, forever.

But the Yahoo! opportunity was down in Southern California (Burbank/Santa Monica) and that would satisfy a couple of my wife’s objectives. One of her ulterior objectives was to ditch me. More on that later.

I accepted the job with Yahoo! and parachuted in to Burbank, California (I mean that figuratively, in case you’re wondering whether I’m a sky diver).

I worked at Yahoo! for two years. I had a great ride, made money, and met plenty of terrific people. After about two years, Yahoo! implemented a workforce reduction program (ahem, I was laid off).

My wife implemented a husband reduction program, never moved down to Southern California, and, yes, divorced me.  But it was time for new beginnings. It was fall.

My cell phone was blowing up. Recruiters were sniffing me. I was fresh meatYahoo! alum with plenty of digital advertising experience.

One of the companies courting me was a search engine marketing agency called Enquiro (now Mediative) in British Columbia. They had grand plans, which included expanding into the United States market with an in-region presence.

They hired me to head up their first U.S. office in the San Francisco Bay Area.

Things with Enquiro started out fine. We were building a solid pipeline of prospects and signed a new customer. But after less than six months they fired me.

I was confused. A few months later I understood why: they were acquired by the Canadian Yellow Pages as part of a deal of an undisclosed amount. I’m sure I wasn’t needed, and their whole U.S. expansion effort never materialized. I was just a pawn.

Now it was 2010. It was fall again. I was forty-something-years-old and tired of being kicked around.

I had a strong desire to:

  • Do what I love doing
  • Live in the San Francisco Bay Area
  • Not get laid off again
  • Manage my own schedule

After some soul-searching and plenty of photography, the answer gradually revealed itself: start a digital marketing agency. It was the right time. I had kick-ass experience, stellar contacts, and sales chops to build new business. Another company was born in the fall of 2010.

By bringing on multiple clients I would curb the risk of being “laid off.” If one client stopped a project I wouldn’t lose it all. I was diversifying my income stream. I would be doing what I love, living in the Bay Area, and definitely managing my own schedule.

Sold. I was now in business for myself.

Fast forward.

It’s been more than a year, and we’re heading into 2012. I’ve brought on ten clients, and business is going well. Managing my time is challenging. But I get to pick my clients, and I’m enjoying life.

This past fall was mellow compared with past five. October of 2011 was my company’s one-year anniversary (one-year anniversary with a new girlfriend, too) and life is good.

Becoming an entrepreneur was an evolutionary experience for me. Yes, I had aspirations of starting my own business, but I started by sticking my toe in the water on the side.

I got lots of experience “working for the man.” And I realized there are few great things you can do on your own. Strong partnerships are important in most aspects of both business, and personal life.

by in Companies, Entrepreneurship