Ode to the backup plan

The idea that someone will stay at one company for a whole career went out the window more than a decade ago. Now most people will have more than eight jobs between the time they're 18 and 32 years old. To Baby Boomers, this is a shift in thinking, but for those of us who came after them, it's business as usual.

In keeping with my fellow Gen-Xers, I changed jobs ten times in the ten years just after college. And I adapted well to the Internet economy where star players switched jobs every year or so to gain those (now incredible) 25% raises. But at this point, I have to confess that I feel a little worn out.

At first, the free-agent no-one-owns-me attitude seemed great with all that flexibility, room to move up, the brand of you rah-rah. But the reality of a free-agent nation is hard. Friendships made at work are generally short term because the jobs are short term. Frequent insurance changes mean frequent changes in doctors. And there are too many times when the gaps between full-time jobs for free agent hunters are too big for a savings account to bear.

At this point, the free agent nation feels alienating, unstable, and financially risky. I long for a company that I can stay at for the next fifteen or twenty years even though I know the odds of that happening are slim.

It won't happen because most companies that have jobs that last forever take forever to make any other changes also: Slow and boring. Gen-Xers and Ys expect more from careers than any workforce in history. Fun, flexible jobs with new challenges around each bend are the typical goal, and like my peers, I am prepared to give up stability in exchange for that.

But I feel like maybe things need to be more calibrated. I have lived through layoffs, dot-com bankruptcies, and terrible economies. And I have lost jobs because of my own stupidity, too; pushing too hard on a good boss for more flexibility than was reasonable. All these situations have added up to constant, low-grade worry that I have no idea where I'll be five years from now.

I spend a lot of time figuring out how to keep this worry from overpowering me.

I have a five-year and ten-year plan for my personal life and my career. That helps a little because even though my career is not predictable, I have a steady vision for where I'm aiming to be, so I can adjust my tactics to accommodate both unexpected opportunities and unexpected setbacks.

But the thing that really has helped me succeed in the free agent universe is that I am always working on two or three ways to reach my career goals. I have found that putting all my eggs in one basket is too much pressure — I become too scared to take action on anything, because I start feeling like every phone call, every meeting, means so much.

Keeping a few eggs in my basket is like job insurance. I am never sure what will work out, but something always seems to go well when I have a few options. For example, when I was running my own software company I wrote articles on the side. And I also taught college courses. I didn't know what would come of any of that. As it turns out, the teaching never amounted to much. But the writing took off after 9/11 when my software market fell apart.

Now most of my income comes from a book contract. But I continue with lots of freelance projects because I never know what avenue I'll end up taking to get to my long-term goals. I admit that I also peruse help wanted ads. I don't think I'd take a corporate job now, but in a free agent nation, I wouldn't rule anything out.

Having a long-term vision for my career gets me excited about the possibilities in my life, but having a backup plan keeps me from going nuts over the lack of stability in the workforce of the new millennium.