Job jumping blues: '60 jobs later' and other tales

April 12, 2011: 10:17 AM ET

Whether you're itching for something better or you know time is running out at your current gig, negotiating a job change is a challenge. Here are three readers' stories from the front lines.

FORTUNE -- Whether they were jumping themselves or dealing with the assumption that they ought to jump, the following readers' stories speak to the immense challenge of determining what it is you want in a career and when it's best to take a risk and pursue another opportunity.

Weigh in with your own job jumping experiences. Leave a comment. And check out the next round's question below and share your story.

Hopping your way to the right gig

Between graduating from college and taking my current job, I had five jobs in the span of just under three years. Why did I move from job to job so frequently?

It was not until my current job that I realized that I preferred a job that actually used my skills and abilities, as opposed to the "cool" careers that I had previously pursued.

Although I did have five jobs, most were part-time. I had three main jobs, including my current position.

Job No. 1 was with a standardized test preparation company. I had worked for them for two summers during college, and worked for them again the summer after I graduated. I was offered a full-time position with them, but I turned it down to look for another job.

Each of the three summers I worked at the test prep company, I needed to introduce myself to an entirely new cast of colleagues. The low rate of employee retention struck me as a warning sign I saw no reason to disregard.

I had no idea what kind of career I wanted, so I decided to turn down a readily available position and pursue an unrealistic pipe dream instead. Having always been an avid baseball fan, I thought I'd see if I could work in major league baseball.

I quickly discovered that the supply of professional baseball jobs, like other entertainment industries, is far outstripped by the demand for such jobs. So, job No. 2 was not actually with a major league baseball team; it was with a minor league team.

In an attempt to wedge my foot in an exceedingly swift revolving door, and after six months of fruitlessly searching for something that was closer to my dream, I accepted an unpaid job. To supplement my meager – well, nonexistent -- income, I started working part-time jobs on the side.  For instance, I began teaching Sunday school at my local synagogue and helped out at my dad's law office.

Unlike the major league positions I was interested in, which involved determining which players to acquire and develop, jobs in the minor leagues revolve around two things: sponsorship sales and ticket sales.

Minor league teams are not in the business of winning baseball games; they are in the business of making money. They do this by putting people in seats, and then selling sponsorships and advertising based on game attendance. Sales, especially cold calling, has never been my strong suit.

I worked part-time for the team during my first season and moved into more of a full-time role the second season. With this increase in responsibility came an increase in pay, from zero dollars to $1,000/month.

As the season progressed, I realized that while I was working hard for many hours (especially on game days), I was being judged by the revenue I brought to the team, and in that sense, I was barely contributing anything at all.

In August of the second season, I proposed to my girlfriend of six years. As my personal life moved forward, I knew that I could not stick with the baseball life. Even if I had been successful, it would have meant making sacrifices to my personal life that I was not prepared to make.

The week I proposed happened to be a particularly hellish one on at work. Without going into too many details, it involved my car windshield being smashed and sleeping on the floor of the team trailer. It was time to look for something else.

My next job search took five months. I continued to work the part-time jobs I had started during my baseball days, while trying to find a job that better matched my skills. Five months may not seem long, but for me, it was miserable.

I now work for a non-profit educational company. While no employee is completely indispensable, I have learned from prior experience to make sure my work has an impact on the core business of the company.

Now that I'm in a more analytical position, I am better able to use my skills, which makes me feel happier and more productive. I've been at the company for five full years -- quite a change for this former job hopper.

--John, Norwalk, C.T.

Terminally unemployed? 60 jobs later

I've worked for some 60 employers in my life. In December 2009, I was fired from what apparently is proving to be my last full-time, "real" job. "Terminally unemployable" is how I prefer to describe how my life and relationships with employment and employers.

The first fatal mistake I made was never having an answer to the question we impose on all young people: "What do you want to be when you grow up?" Yes, I knew even as a teenager that the translation was "What career do you wish to pursue for the sake of earning money in order to buy stuff?"

The problem is I never wanted to be anything more than a relatively good man who, despite what I may or may not do in terms of employment, tried to leave the world a bit better than I found it.

I will turn 59 this August, which makes me one of those "baby boomers" about whom much has been written. What doesn't get written -- at least not often enough -- is this: There we were, all young and idealistic with those chants and slogans of "make love, not war," "down with the establishment," and so forth. And yet, once in positions of so-called power and authority ourselves, I think it's safe to say that no other generation proved itself to be more self-serving and greedy.

I can't remember a time when I didn't make distinctions regarding authority figures -- whether we're talking about government, business, or organized religion -- between simple and legitimate authority and those who confuse authority with superiority.

The fact that 18 of the 60 companies I worked for no longer exist lets me take the job losses a little less personally and makes me think that at least some circumstances were outside of my control.

And as foolish as I may have been at times in matters of jobs and careers, I was even more foolish in 2007 when I published a book that attempts to give depth to this very subject. That book, which is called "The Maniacal Laughter of the Damned," was as dead on arrival as my entry to the working world, armed only with ethical drive and vision rather than a college degree.

--Randy Vaughan, Vinton, V.A.

What companies ought to know about their "job jumping" staff

I was at a recent job interview and the manager conducting the interview said, "You're a young guy, and young guys like to jump around a lot. How do I know you will stay?"

I have encountered this assumption about how my generation even in my own family. My sister tells me if I stay anywhere for more than five years I am hurting myself, and my father gets visibly angry each time we tell him we are moving to a new job, complaining about our lack of loyalty.

There are a few points I would like every hiring manager to keep in mind before they assume the younger crowd is just flitting about with no sense.

We know you are not loyal to us. We have all seen everything from Enron to the more recent recession layoffs. Employers are not often thinking about their employees' loyalty when it comes down to who gets fired, they are thinking about what they can get from us employees going forward. No one should be surprised that employees look at companies the same way. We want to know what you can do for us in the future.

A fair raise isn't always a fair raise. I have seen this too many times to count. Joe gets hired right out of college, and his position pays $40,000. He works hard, improving his skills for two years. Every year, he gets a company standard raise of about 3%. Lets round that to $1,200 a year. Right when his pay hits $42,400, the company is growing and hires a new person right out of college for $45,000. Sooner or later, Joe finds out his two years of experience are getting him paid $2,600 less than the new guy. Not only is this not fair to Joe, but he can immediately turn around and find someone willing to pay at least $50,000 for those two years of experience. If you are not paying employees their market value, they will leave.

Fancy titles only fool a few. We have all heard of the 25 year old who was just made a VP. Some people even wonder how anyone could do it. Others know this person is VP of filing and have a little giggle. Yes, give out titles. They make people feel good, and they're free. Just don't think that we will pass up on that 10-20% pay jump because the other company won't put "vice president" on our cubicle.

Remember, we are a business too. We have, on some level, realized that we are marketing our skill set to employers. Since we only have one skill set, we sell to the highest bidder. This bid is made up of salary, benefits, and some factors you cannot control (like the commute). If you can't offer the highest bid, be gracious. The employee who leaves you today might come back to you tomorrow, or even recommend your company for a contract if you are in a related field. The point is, don't burn bridges. Every one of these employees who quits can be another connection in your network.

All of the above can be thrown out the window. Many people do not look at their jobs in a business fashion. Many people move around every five years because a magazine told them to. Many people feel they are worth a lot more than they actually are. You won't make everyone happy, but if you try to take your employees' point of view into account, you will be able to keep some people happy, which means keeping some talent in your department.

--Douglas Martin, Edison, N.J.

Editor's note: Fortune has verified the identities of all of the contributing authors. Some of the authors have requested to only use their first names or aliases to protect their identities.

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You Can't Fire Everyone: Working for no pay

Have you ever taken an unpaid internship or temp job to get your foot in the door? Have you managed any unpaid workers? How did it work out? Would you do it again? Tell us your stories and we'll highlight the most interesting and instructional ones. Email us at fired@fortune.com.

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