Lessons from My Messy Shirts

“I have a stain on every shirt I own.”

After years of meeting incompatible life partners through online dating, I rewrote my profile and led with “I have a stain on every shirt I own." Was I trying to discourage every woman from responding? Just most of them, actually, and here's why.

We're taught that none of us are perfect, but we're also taught to put our best foot forward and present an image that is as close to perfect as we can. By doing so, one -- either innocently or intentionally -- presents a false picture. And those who respond to those “perfect matches” eventually feel as though they've been lied to. More often the case, one or both parties recognize that it wasn't a “good match.” As anyone who has ever been on an online dating site will attest, if you're looking for someone, you'll find plenty. If you're looking for “the one,” your choices will be few.

So by leading with that less-than-ideal factoid, my new headline accomplished several things. Those looking for perfection surely never read past that first line. Others who got a chuckle out of it, or appreciated the honesty, or had their curiosity piqued on what I might say next, continued reading. Granted, I'm certainly not the neatest person in the world, but I went on to explain that the main reason my shirt was stained was because I love to cook. But just stating that as one of the many “checklist” items so prevalent in dating profiles, I felt it would lose its effectiveness. I was no longer one of thousands claiming to be perfect. I was one of a few embracing his shortcomings and inviting those interested to do the same. So what I brought to the table came from the table so to speak.

As a director of advertising, I've learned that branding a company's product and services is not dissimilar to common efforts of promoting yourself. Prospects who engage with your website, social posts, and ads deserve transparency. Presenting any inherent deficiencies upfront avoids disgruntled customers down the line, while at the same time establishes your company as a transparent vendor.

Just look to Volkswagen which is credited with pioneering “turning-negatives-into-positives” advertising with its famously successful Lemon print ad.

I think this strategy should apply to jobseekers as well. Tell the recruiter if you've never used that app, for example, if you haven't. Tell the headhunter you don't know what that three-letter acronym stands for. And if the hiring manager asks you to name a weakness of yours, don't say you're a perfectionist. Instead, tell them you try to be but sometimes fall short.

Fortunately, one of those women found my honesty engaging and fell for this sometimes messy, always well-meaning man, all thanks to a messy shirt.