08/22/2011 12:40 pm ET | Updated Oct 22, 2011

The Day I Wore Lipstick to Wall Street

I'll tell you ladies, a few decades on Wall Street, and there's not much left for the imagination. Can't tell you how many times I thought, perfect training ground for stamina, espionage, covert operations....

Who needs Langley!

We've come a long way (more to do) from the way it used to be. Though the recipe for success then still applies now.

Let's travel back a few decades.

Freshly minted out of a hoitsy toitsy New York investment banking sales and trading program (back in the 1980s), I had an encounter of the first kind. The memorable day I wore red lipstick to the office.

I had just come back from a super-shrunk maternity leave, more like a vacation, although it wasn't that exactly. Having a baby (plus another youngster) didn't figure into the workplace equation. I was in the trenches with the Big Boys. To have an expectation for an understanding of feelings that mothers go through integrating career and family, would have been unrealistic back then.

In the 1980s, there was an "understood" dress code too (especially in a Midwest regional office, New York was a bit different). Largely dark suits (or muted light colors for spring/summer) with skirts to the mid-calf. Demure dresses just started to work. Forget about cleavage or bright colors. Cleavage would have rendered one a "floozy," back then. The one bright spot -- nothing about the kind of make-up one could or could not wear.

This whole concept of having multiple wardrobes -- one for work, one that "felt like me" -- silly really. It strained my budget too, one that included child care for my two young sons. Over time, I kept a style in synch with my personality (more organic, fluid), where I didn't need to rethink the process. I was mindful that I was a professional -- like I needed a reminder? Hey, talent comes from the brain, soul, personality... not the outfit, and certainly not the lipstick.

Within the first few months on the job as a rookie (in a regional office), I got to thinking. Need progress here -- a bit more spunk and fashion in this "understood" world. It was lonely. In a trading room with four long railroaded trading desks, the bulk of the female population (a handful) resided on one -- money markets/short-term fixed income.

OK -- so I woke one morning and said,

"I feel like red lipstick and a dress today!"

Now keep in mind, I just had my second son. Albeit thrilled to be a mom, I couldn't wait to get back into shape, to feel feminine. This, but one, of the many sides of femininity, and even then, it takes different forms for each of us. Finally, my favorite silk dress fit again. Not tight or anything like that, but you know how silk is -- it's not cotton.

After the New York training program, I had not yet worn red lipstick in a regional office. Red lipstick eventually became my signature -- Lancome's matte red, discontinued over the years, much to my chagrin. Wouldn't you know, once in love with a color, it's invariably replaced with something new. Buying a backup when you find a color you like isn't a bad idea.

Well, the red lipstick/dress combo caused a little volatility that day, not the market kind. Our trading desk was right outside the glassed-in executive office.

First, one of the lights lit up on the trading phone switchboard. Then, my mentor and his boss bee-lined into that glass office, frenetically pacing back and forth, talking. My mentor looked perturbed.

The morning trading rush subsides. I'm called into a conference room (my mentor refused to participate), so his boss was the messenger. Once sitting down, in an awkward manner, he mutters,

"It's about... it's about your... it's about your lips...."

Couldn't believe it at first! I could see where this was going. I figured I'd spare him the anguish.

"Let me take a guess, it's my lipstick and somehow I look like a lady of the night?" I was being polite. Mind you, I wasn't even wearing any other make-up.

In a relieved tone, he proceeds apologetically,

"Yes, yes... ahhhh, no, that's not what I mean and it's not me. I like it, I mean it's OK, but it's coming from... from...."

I say, "the higher ups?"

Once again, he sighs with relief, "yes, yes," -- then, quickly and quietly, sneaks in "don't wear that dress again."

I guess the message was lose the lipstick at that point (not the dress, thank goodness), with the box of tissue conveniently located on the conference room table. Afterwards, my mentor pulled me aside, relayed obvious displeasure over the rendezvous, in his customary manner of expletives.

I just went back to my desk and resumed work. When I was done with work, I reflected.

Now, I had a choice here -- let it get to me or what's to be learned. Don't get distracted, never lose sight of your destination -- let your inner core, the "I know I can do this" guide you. The external noise doesn't much matter then.

Red lips did shake Wall Street that day, but not me.

Obviously, career paths are riddled with obstacles and opportunities. How do we play the "deck of cards" (be it fair or unfair) that's dealt us at critical points, that collectively form our careers?

I looked at the encounter as an experience in readiness. To survive and succeed on Wall Street, provisions were to be made -- load up on humor, focus, Teflon; outlearn, outwork. Pick your battles. Granted, some situations can be worked through, others not -- better to know sooner than later.

While the Big Boys were distracted by red lips, I focused on "knocking the cover off the ball."

Red Lips went on...on to Shake Wall Street!

One, of many, Wall Street Tales.