My friend and colleague, Erin, had a market bag that boldly said: “Stop Telling Women to Smile.” Like many other women, I’d heard this statement before, but seeing that bag every morning ingrained it. It is so important when we point to a simple nuance that seems like a small offense, but its’ offense over time is so much more.

Of course, we (ladies) have all been told to smile. It’s a pickup line from some uncreative, thoughtless, gross man while passing us on the sidewalk. “Come on sweetheart, give me a smile.” Let’s just disregard the street harrassment for the moment because there are 19 million horrible pickup lines from men who add little to our society. We know they are dumb and many women are putting beautiful words into this movement.

But what about when you’re told to smile in a professional setting? Or from someone you love?  From someone you respect — man or a woman?

I was in a meeting discussing high level strategy with a well-regarded male mentor. We had huge decisions on the horizon; we were crunching numbers in our heads working through variables and options. The whiteboard looked like graffiti, our plans scribbled in different directions. The mentor kept pushing us to think bigger and to be honest, I respected and adored this man —  everyone did. He was accomplished, cool and funny. The situation was also intimidating. I was working double to calculate every word I said for fear of saying the wrong thing. I didn’t want to over-complicate something or let something silly slip out.   After all,  I was intimated by this successful man. Then the mentor looked at me and said, ‘You should smile more. You always look so stern,’ crossing his arms to mimic how I was sitting and flashed a mock sad face.

I wasn’t offended. I was hurt.

How could he think I don’t smile? I am very pleasant! Upbeat! Positive! I even get a good punchline in from time to time! I am kind;  I smile at strangers as they pass on the street;  I put my cellphone down when ordering at a counter and always make small talk with my Uber driver.

It took me months to realize how deep this comment cut. After he said it, I’d try to be as “bubbly” as possible around him, but then I realized why this comment hurt — It was wrong.

Not only did I actually NOT need to smile, he was making an attempt to alter my appearance. Or more precisely, what basis did he have to give me that kind of feedback? Was I making him uncomfortable with my perceived scowl? Was I supposed to be doing a little jig as we discuss the future of my company? My face is not here for your pleasure; you are not entitled to it. It is not my job to make you feel more comfortable.

And then comes the age-old question, Would he have said this to me if I was a man?

Think of it like this: Someone tells a joke and they tell you that you should have laughed harder because your reaction made them uncomfortable. You are discussing politics on a deeply personal issues and someone tells you to shimmy your shoulders because you take things too seriously. You are told to wear lipstick because it makes you stand out.

Are you skeptical that this happens in a professional setting? Or perhaps you believe these little, innocent remarks don’t make a big difference in the long run. I recently heard about this badass former-first lady, former senator, former Secretary of State that ran a meticulous campaign for president. Kicking ass, taking numbers, and breaking ceilings as they say. So she’s on track to win the nomination of her party and, yep you guessed it — she’s told to smile.

Um, why would she have to do that? Can’t you tell her to, learn her facts or focus on the issues or something perhaps relevant to the campaign? Nope, smile. Why should any woman alter her face, body in someway to make anyone, especially men, feel more comfortable, more validated?

Of course, you don’t need me to tally up the number of times this was said to Hillary as compared to the number of times it was said to other presidential hopefuls.

We hear this on the news and feel a pang of outrage and it feels like there are so many battles.  Is this the battle we should fight? But as every woman knows, it is different when these comments are directed toward your face from a superior, someone you respect, someone in power. It muddies the waters and does exactly what’s so insidious and outrageous. It makes you question yourself. It takes your confidence down a notch, even for a second. It makes you wonder in the dark of night if you are less than.  Am I not already doing enough? DO I have to smile more? Is that really true?

Unfortunately, we females have become numb to comments like this. If it weren’t for seeing Erin’s bag every day, maybe I’d never be writing this. But as I started to ask my male friends and colleagues, “Have you ever been asked to smile more?” they all usually had the same reaction, “What? Why the weird question?” Ladies, on the other hand, never batted an eye-lash — it was a unanimous ‘yes.’

I do not believe this comment that was made to me on this day had any valid context. To be fair, this is a different comment in the context of, I believe this piece of feedback will help you succeed. As in:

• You should listen more in order to achieve X result.
• You should do more team outings in order to achieve close relationships.
• You should smile more in the office so you seem approachable resulting in team coordination.

Yet in the context of “just because” this is where the damage lies.  Be aware of the language you use to females, particularly on their appearance. What are you actually implying? Have you provided males the same feedback? And let me be clear, I am not just talking to men here. Women fall subject to the harmful appearance control too, myself included.

Personally, I think women throughout history have worked pretty hard to make men feel more comfortable in this world, more validated. I think it’s time to work towards the opposite. What if men in the workplace worked to make women feel more comfortable. What would that type of workplace would that look like?

NO SERIOUSLY, WHAT WOULD THAT LOOK LIKE? Would women stop being pressured to grab beers with the boys and men be forced to sit in nail salons after work? Imagine an office where men pushed for flexible, wfh hours and were the ones that left meetings early because the sitter called in sick…

Let’s get there. We can start by stop telling women to smile.

Recently, I was asked to speak at my alma mater. It was an honor and a privilege, and of course, my parents were were so proud. My mom begged to invite all her friends. In fact, I had been given an award, Alumni Entrepreneur of the Year.

It was Homecoming Weekend and the campus was buzzing with excitement. After much deliberation in a Nordstrom’s dressing room, I had decided to wear a tight white power dress. I felt a bit overdressed and formal compared to my normal style, but the second I zipped that thing up, my mother swooned and I knew I had to wear it – for her sake.

I’ll mention that I went to a fairly conservative college, but that really doesn’t alter the story because it could have happened anywhere. This is a place that taught me that I have a voice and gave me the strongest girl tribe I could fathom — heck, they asked me to come and speak on female entrepreneurship. Again, to be clear, this story isn’t meant to take away from the amazing values and tenacity of the institution. It really could have happened on any stage, at any place.

My speech was focused on a couple things that I’d learned from my story as a female entrepreneur:

1. There needs to be more of us.
2. The trials, slights, adversity that women face in this space occur daily.
3. More women need to be on stage, giving speeches.

Well, I arrived an hour early like any good speaker and a young technician approached me to get me set up. He looked me over and said,  “That’s what you’re wearing? Does the dress have pockets? There’s nothing to clip the microphone to…you’ll have to change or wear a belt.”

Without giving me a moment to respond, he had ran off to find me a belt. A belt!

I don’t know what I would have said if he hadn’t run off. I was speechless.

In my head I’m thinking, “Has he never mic’d someone in a dress before? Does a microphone not clip to a dress? If one can mic up a Kardashian, how in the world is MY dress a problem?”

While he was gone, the gravity of what was happening sunk in. Excuse me, did he just outfit-shame me? Did he just make me feel like it was inappropriate to wear a dress on stage? Was I the first person in a dress he had ever mic’d up? There’s no way.

I turned to a young woman standing next to me, she could see the confusion and rage that was crossing my face. “Don’t worry,” she said, “He is just scared to touch your bra.  I’ll help you get hooked up. I am the only woman that works here in the tech department — this stuff happens all the time.

Another moment of women helping women. Thank you, sister.

Then Mr. Scared-of-Bras returns, thrusting a black belt from some raincoat in my direction. “Here, wear this”, he said.

“There’s no way I am wearing that,” I snorted.

He threw up his hands and gave me that all too familiar look. The one that says without saying, ““Whoa, this chick is getting huffy.” The one that reminds you that when a man says ‘No,’ he is being assertive, yet when a woman says ‘No,” she is being difficult.

“C’mon, we can figure this out”, I said, “Let’s see this mic…it’s gotta have a clip or something.” Within moments I had the dumb mic clipped to the top of my dress and we were good to go.

My blood was boiling.

Is this how all women feel when they are about to walk on stage? Is this why I don’t see enough of us in front of an audience, standing tall, speaking our message? Because we’re told  we look different, like we’ve done something wrong?

My girlfriend and college roommate was the one coordinating the event. She happened to walk by backstage and I quickly shared the story, joking that I should incorporate it into my speech. I mean it was so fitting.

“Are there any female engineers or designers in the room?”, I would say. “Great, can someone design a microphone that fits a dress?” I felt like it would get a good laugh.

Her response was immediate. “This happens all the time around here. Please say something.”

Unfortunately, my speech was so committed to memory that I forgot to mention the story on stage. Not that I wanted to call the guy out — I wouldn’t do that —  but I wanted to prove the point about how daily this struggle is. If more women were in leadership positions, this wouldn’t happen, but the truth of it is:

• Female entrepreneurs only make up 7% of venture-backed companies
• Only 10% of Fortune 500 companies have female leadership
• And 20% of Congress is female

After laying out these sobering facts, I shared about the times my business model was called ‘cute’, or how I was often only introduced to investors that “invest in female companies” as if we are a special sub- species. I talked about how the  #metoo movement impacted my office and Silicon Valley, well before the movement hit Hollywood.

I challenged women in the audience not to take a backseat. Please don’t. Yes, we have made progress, and yes, things are changing but we sure aren’t there yet. I talked about my love for that campus, for what it and its people had given me. I’d love to come back again someday and speak again, but I do not want to come back to  to share the same message. I want the daughters of tomorrow to to say, “Equal pay, Kaitlyn? What’s that?”

Ladies, we are close.. Let’s keep going. Let’s grab hands and cross the finish line of this race.  Let’s do it for our daughters so they’re never outfit-shamed for wearing a fabulous white dress.

My mother is 62. She is beautiful, funny and has quick wit. She rides horses. And when she rides,  it is the most fascinating, bold, courageous sight to see.

Let me back up for a moment, my mother is Mexican. My mother’s step-father was a horse trainer. Growing up they lived in a trailer on a rich lady’s property; they were the hired help. They were poor. Yet on that farm, in the trailer, helping her step-dad, it is there my mother fell in love with riding horses. She rode the rich lady’s horse with dreams of one day owning her own horse and always took the little white-girls’ hand me downs. She claims her love for horses is what kept her out trouble and especially provided her a dream to pursue college and get out of her hometown.

She went to college as an Equestrian studies major and when her roommate showed up in a pink cadillac and a matching pink cadillac horse trailer, she realized one simple fact when it came to owning a horse; you have to be rich. So therefore the dream faded away and she got married, raised kids and it got tucked away as one of those things that kids just dream about.

Until she turned 55 years old. And my brother took her horse back riding for Mother’s Day. She hadn’t been on a horse in 30 years. And she cried. And realized, it’s time to get back on the horse again. And so she did.

Not only did she get back on the horse. She rode every day and saved up every penny and eventually bought a horse. A gorgeous show horse. An expensive horse. She earned it.

One Christmas I bought my mother a brand spanking new bridle (it was $100) and she got a weepy looking at it. And she said, you know I never thought I deserved new things. Even after all these years, I never thought I was worthy of owning brand new things.

I look at my mother and think; you can achieve your dreams. You can get back on the horse again no matter what your age.

And you know what? I have never seen her more happy, her hair more shiny or her smile quite as white as when she is on that horse.

The only time I’d ever flown first class was on my honeymoon. It was glorious and extravagant, and part of me wanted to reserve that experience solely for my honeymoon. Silly young-girl-in-love thoughts.  

That was until the day my business partner suggested (c’mon she really insisted) we fly first-class because we had just raised a pretty big Series A round of funding. This wasn’t to London or Paris or anything, just a hop down to LAX from SFO, but she wasn’t taking ‘no’ for an answer. This is just the way she rolls and I respect her for that.

Ever since, I have this little practice. When I walk through first class toward coach, I look closely at who’s already been seated. I look for a powerful business woman sitting alone.

And sadly, very sadly, I hardly ever see her.

Maybe you’ve noticed this too. When I look, I see mostly men. Sometimes I see a woman, but she usually looks like she’s sitting next to her partner. I rarely see that badass woman, sitting tall and alone. I want to see her. I want to see her not wearing a big diamond, but wearing fabulous shoes. Yeah, girl, I see you. And you look good. No man bought you those shoes, you bought those shoes. You worked for those shoes. You sit in first class, watching us filing back to our tiny seats in coach, knowing that you worked hard for that seat. Ms Fabulous could have booked a coach seat, but no she sits there sipping her complimentary champagne and I hope it tastes delicious.

Ladies book first class. Just do it.

If men deserve it, you deserve it.

Work your ass off and demand to fly first class. We deserve a seat at the table and we have EARNED first class. When I see you sitting there, know that I’ll high-five you as I walk by, or maybe listen to my own advice and sit down next to you.

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Oh hey loyal fans. Welcome back.

Why do I want to start a blog? (again)

Well, it has been on the to-do list for a long time now.  I had one when I lived in Haiti and I really miss the ritual of getting thoughts out into the world. Remember Kaiti in Haiti? Ah yes, a classic. Apparently I love a good rhyming blog name.

A few things have been happening lately that make me want to write. Well, more than a few. I’ll get into those more once I start click clacking away…

Some of my inspiration comes from what I’ve been reading lately: Love Warrior by Glennon Melton Doyle. OMG I saw her at the airport the other day and was  too nervous to do anything other than stalk her around the terminal. Mission accomplished. I mean, her book is life changing, shattering and beautiful. It made me want to be as self-aware and human-aware as Glennon is.

I’m also inspired to write because of my life coach, Dushka. More on her later because she is freaking amazeballs and helped me realize that I’m amazeballs too. I have a lot to say! I have a lot to share! I have thoughts that are worth reading and most of all, I need to organize my thoughts. Wrestle with them, grapple with them and own them.

Why is writing different than talking or thinking? I guess thoughts somehow become more concrete, more solid, more eloquent on paper. Glennon put it well (of course) in an interview she gave where she said writing is like being a detective. All day long you have no idea how you feel or why you feel, you are clueless! And then when you get the chance to write it all down, you start seeing the clues and patterns. All of a sudden, things start making sense.

And finally, I want to write because, for a long time I have felt not myself  (whatever that means). I think back to the 23-year old Kaitlyn, and think, “I like her. People liked her.”

Yet, I wonder if when I am 40 I will look back and long for my 30-year old self. Goodness, I hope not. I think writing might help me prevent that from happening. Maybe it sounds cliche, but I am writing  to my find myself.

So there’s all these reasons for me to write. And if that wasn’t enough, the universe seems to keep at it. At dinner the other night, a friend said that in your 30’s you know just enough to be fearful. And later, someone asked what would you do if you could do anything for a career. My response — become a blogger, and in my head I thought, so I can overcome that fear of my 30s.

So, here I go…