An Entrepreneur and Her Jeans Story: What Not to Wear to a Sales Meeting

by Jill Foster on July 2, 2009


Guest post by Amanda Steinberg, founder of DailyWorth.com. DailyWorth is a free daily personal finance email for women – delivering practical tips, empowering ideas and the occasional kick in the pants.

For more on Amanda’s insight (and wit!) visit her blog or sign up here for DailyWorth’s email.

Drool worthy
Recently I scored a drool-worthy sales meeting for my Web consulting company. Winning this contract would add a blue-chip client to our roster and serious inflation to our bank account.

The night before the meeting, I was anxious. What should I wear? To sales meetings, I usually wear nice slacks, an elegant shirt and heels. This prospect, of dot-com fame, was more likely to be casual, so perhaps jeans would be better. I texted a trusted male colleague to get his opinion.

Me: What should I wear? Tight jeans, hipster shirt + flipflops? Or dressy pants, fem shirt, heels?

Male colleague: Tight jeans.

That’s it. Two words. “Tight Jeans.”

OK, I get it. Point taken. My butt sells.
Five years ago, that wouldn’t have been the case (see my earlier post on weight loss). I remember being harassed at a night club on 14th street in New York City for having a very large butt, and we’re not talking J Lo butt. I was depressed about it for weeks. I’m currently and have been for about four years, quite slender, but the psyche of “fat girl” still follows me around.

High-dollar deals and feeding families
So my web consultancy means a lot to me, and its income feeds many families in the U.S. and abroad. I enjoy selling large, high-dollar deals that allow me to pay myself and my deserving team of hard-working web producers well. So, if wearing tight jeans helps sell deals, why shouldn’t I? I’m sure my mother read me feminist rants as bedtime stories, but I love putting on my size 6 jeans. And if that helps me beat out the competition, I’d really prefer to suppress my inner Gloria Steinem, thank you.

Twisted but honest
What struck me even more than my colleague’s curt reply was the willingness and ease with which I climbed into my skinny jeans the following day. I strutted my little tush past my husband, looking for a compliment, which he willingly bestowed. See, my thinness is definitely a source of pride, revenge on that jerk who called me “fat” in a bar oh so many moons ago, and something I work hard to maintain. It does give me power, I feel worthy of more attention (as twisted as that is), and I get it.

Brooks Brothers and reflections
In the end, my prospective client showed up in a classic Brooks Brothers suit and I sorely regretted my choice of clothing. I still don’t know if I won this particular contract. Regardless, I think my brain power overall was the selling point, not my clothing, and I don’t think I’ll be wearing jeans to a meeting like this again.

(Thanks Amanda for sharing this post from DailyWorth)

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