The scarlet letter of entrepreneurship

See if this scenario fits.

You spend years working in the corporate world, learn a few things and one day you decide you've had  enough and strike out on your own.  Perhaps you're tired of being passed over for promotion or you just know you're capable of more than the middling opportunities that come your way.

Maybe you're motivated by one too many late night infomercials but whatever the reason you finally make the commitment and say goodbye forever to your cubicle.

Or so you thought...

Striking out on your own rarely affords instant gratification and tests your resolve on a daily basis.  You have your freedom but the list of things you don't have sometimes make you wish you would have stayed in your nice warm cubicle. 

As time goes on there's one of two things that will happen.  You'll be a success and never look back or you won't and you'll be looking to get back to that cubicle.  Thing is the latter may not be an option for you.

In today's job market with employers demanding more from their employees than ever before a candidate with an entrepreneurial background has an uphill battle.   Why?  Well, in case it hasn't jumped out at you yet, an ex-employee turned lone wolf offers a management challenge few supervisors want to tackle.

A free thinking self-motivated rebel may be the ideal employee for Google or Facebook (or at least it used to be) but ABC corp. doesn't want the hassle.  They just want their employees to follow the rules, not take too long on their breaks and get those TPS reports in on time.

Sadly, more often than not Interviews can be more of a test of wills than a friendly conversation.  A lifelong corporate type will be naturally suspicious of a candidate who once threw off the reigns.  After all if it wasn't good enough for you before why would it be now?

That will be the only question on their mind by the way.  Some may even vocalize it.

Conversely, an interviewer that secretly harbors a wish to flee his own corporate prison may see the candidate's abandonment of their own cherished dream as a personal failure.  From there it goes downhill since no matter what skills are professed, the failure to capitalize on them invalidates all your grandiose assertions to the contrary.   

If the interview is with a potential employer in the same line of business as the candidates former solo effort, chances are the interview is less about the job and more about getting the goods on the "competition." 

Interviewing someone viewed as a competitor (and that's how they see you) brings all the baggage of the standard interview plus the perceived risk that you'll somehow steal all their customers and strike out on your own if they hired you. 

From a business standpoint it's a safety play.  After all, how likely is it that Steve Jobs would have hired Bill Gates? 

You're not being interviewed, you're being pumped for information.  Once they get it they're done with you.  I've often felt like I should send an invoice at the end of one of those.

In these days of drug testing, background screening and credit checks just to get to the interview table how can anyone possibly overcome the stigma of a being a risky candidate?

I wish it were simple but the only way to overcome the objection is to minimize the experience.  It's a rage-filled, sucker punch to the gut but it's often the only way. 

It's maddening to have to undervalue your accomplishments but I'd put better odds on a winning lottery ticket than getting in front of a potential employer that sees your solo efforts in the same light you do.

You have two choices at this point. Suck it up as they say, swallow your pride and pad your resume with "regular" jobs that show you're a good member of the corporate denizen.  A regular job can be contract work, temporary jobs or anything BUT working for yourself.

Your other choice?  Sell the extra car, take out a few loans and keep trying to make it on your own. 

You'll either finally figure out how to be successful or go broke and be out of work so long that you won't have a work history anyone will care hearing about anymore.  Perfect for when you go for that sweet gig at the convenience store or fast food joint.

I'm not trying to be flippant, this is reality 101 in the job market now.  Threats to the status quo can come from as little as showing up to the interview with too loud a tie to the "wrong" work history. 

Fair is a relative term when you're looking for work.  Employers are demanding guarantees from candidates that they would never subject themselves to.   Your solo accomplishments exist in a context far less certain than your cubicle dwelling competition.  A fact most hiring managers are unable or unwilling to accept. 

Forewarned is forearmed.  You'll waste a lot less time and aggravation if you know the score going in.