Let’s face it; I don’t have the kind of career that plants me at the same desk for forty years and rewards me with a gold watch at the end. To someone not familiar with the past twenty years of digital media, it would seem like I can’t sit still with any one company. That’s not a bad thing. Particularly if you’re considered a pioneer, an innovator, a game-changer. A cork on the tempestuous waters of change. Let me explain.

My resume is two pages long at present. I could make it even longer, but decided to trim it at the 20 year mark. Stuff that hit the cutting room floor includes work on the very first in-home VOD trial, a bunch of work on early Avid technology and time as a VFX Supervisor on stuff like the X-Files and Snoop Dogg videos.

It scares recruiters when they see a lot of hopping around on a resume. In a typical profession, this might imply that I’m flighty or disloyal; ready to jump ship after a year or two. This fails to take into account the highly volatile nature of companies that are on the bleeding edge. They fold all the time, get bought out, run out of capital, reorganize or pivot out of the space. As it turns out – of the eleven(!!) companies listed on my resume, I’ve only left a company voluntarily to pursue another opportunity three times in my career. In 1999, 2004 and 2010. I’d say that’s pretty darn conservative.

“But wait,” you say. “My buddy Fred has been with [Digital Company X] for seven years.” This isn’t to say that some digital jobs can’t be long-term. I have friends with “Webmaster” as a job title. Nothing wrong with that, but I would wager that they aren’t leading the way in terms of pushing the envelope or exploring what’s next. That’s what I do. Getting laid off every other year sucks, but it affords the opportunity to ditch legacy baggage and explore something new. Managing an e-commerce site for a decade, you might get to explore QR-codes or implementing OpenID, maybe even make the site “responsive” for smartphones and tablets, but that’s about it.

I explained to one interviewer that it would be nearly impossible to rack up as many “First to Market” innovations as I have by staying with only one company. The only way I could likely pull that off is to work for Google or Apple. Rarely do you find a company with enough budget to poach from them. If it helps to make a case for some thread of continuity, I have worked with about five key people repeatedly throughout my career. Companies come and go, but relationships and reputation outlive them all.

To the hiring managers and recruiters who’ve winced at the quantity and duration of positions I’ve held over the years, I would encourage you to instead consider my substantial and well-documented track record of producing groundbreaking products and services representing billions of dollars in revenue.

Will your company be around in a couple years?

Will your company be around in a couple years? It is now my standard practice to inquire if a company has the operating capital to last five years. If not, then there’s really no basis for throwing shade on my work history.

For those playing the home game, here’s the score card. You can check out my resume here.

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So what is the ROI on failure? The answer is wisdom. Wisdom is expensive in terms of material and emotional cost. It comes from taking risks, jumping without a net, going for it. Not many companies have the stomach for failure. Not many survive it. Smart companies seek out those who have gained wisdom on someone else’s dime. They have a saying with motorcycles, “There’s two kinds of riders, those who’ve laid down their bike and those that haven’t yet.”

Staff your company accordingly.