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Confessions of a Job Hopper

Written By Unknown on August 21, 2013 | 8/21/2013

I get exhausted when I look at my LinkedIn resume: Way too many jobs to keep up with, including the latest new gig at TheStreet, which is really little more than a return to the second-longest stop along the way.
But still, with eight full-time jobs in 40 years, plus two from very early in my career that for some reason are not even showing up on on LinkedIn — not to mention a bunch of side gigs — mine appears (optically, at least) to be the resume of an obsessive job-hopper.
My longest job ever, at the San Francisco Chronicle, lasted for 10 years. My shortest, at a Wall Street risk arbitrage firm, had me headed back to the newspaper biz after a little more than a year. The 1987 stock market crash didn’t help, but I was ready to leap — and the real-world experience of that job has helped me in every job since.
From that point on, starting with my job as a daily columnist in San Francisco, I changed how I viewed working. Building and running the column was like starting a business. It launched my brand and firmly established who I am professionally. Since then, I’ve always approached all my jobs as businesses. Salaries equal income. My name is Herb and I’m an Intrapreneur.
And I have this rule — and I tell this to my kids and anybody else who asks: A job, if you’re lucky enough to have one, is not a prison. If you’re bored, feeling underpaid, underappreciated, want to live in another part of the country or world (my reason for this move: to get back to San Diego) or you’re just too ambitious for your own good it’s okay to change jobs*. (*Just make sure you have the new one before you leave the old one! And never, ever burn bridges.)
I also advise: If you’re going to make a change, put yourself out of your comfort zone. Doing so forces you to challenge yourself. It doesn’t always work, but even my stumbles have been stepping stones to something better. Several times I even veered away from journalism — once to the arbitrage job; I was woefully out my league. But I always refer to as my sabbatical. Another time I joined a friend to start an investment research firm. It lasted two years. It was successful. It was also, at times, extraordinarily stressful —in a way only partnerships can be. (We parted and have remained good friends.) And I value the experience.
Don’t get me wrong, job-hopping has its downsides, especially if you have a family. Starting over is never easy. Leaving friends is harder. And the older you get, the more a move to a new region makes you feel like you’re crashing a party.
Then there’s the issue of loyalty, or lack thereof. Many employers simply don’t like or trust job hoppers. It has never been my intention to leave a job. I always start as if it will be long-term, which is why we have always bought a house, rather than rent, when we change cities for a job. But you also have to look out for yourself, especially in an era when companies across-the-board (notably in my industry) have shown an increased lack of loyalty to employees.
As one friend reminded me the other day, “Change is good; it reminds you you’re alive.”
No atrophy here.
P.S.: We’re on our fifth and last cross-country move back to the city we call home. Truth be told: Moving gets old, very old. (Watch for a future piece from me here on the logistics of long-distance moving; we’ve become pros at it.)

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