THE NYC POST: A Long @$$ Recap of My Fun, Fearless Adventure

**Warning: this post is a lot longer than 600 words, which is the statistic average number of words people read on a blog post before tuning out. I don’t usually write this much, but every so often a topic leaves me no choice. So here, have a story from my life, and just know that the first 600 words isn’t really the good stuff. If you just want fashion, I’ll do a clothes recap at a later date. You people go home for now.**

THE NYC POST: A Long @$$ Recap of My Fun, Fearless Adventure

When I was an angsty child, I was sure that NYC wouldn’t win my heart over like every other person on the planet. I could live without an “I heart NY” shirt. I thought I’d seen enough pictures of Times Square. Taking a stinky underground train sounded kind of complicated and, well, stinky. The first time I finally visited I even thought it was nice, but just not for me.

Well somebody slap me, hand me a piece of pizza, and call me Lady Liberty because, dammit, I’m in love!

For those of you just joining, this past weekend I attended Cosmopolitan Magazine’s Fun Fearless Life Weekend. The event was a two day production of speakers, panels, and networking events for self-proclaimed Cosmo Girls to go and get some insight from women (and a few men) who are at the top of their careers and living truly engaging lives. It was designed to be just like reading Cosmopolitan Magazine, except IRL (that is girl talk for “in real life”).  The weekend was packed with celebrity guests working in a handful of different industries talking about how they stayed motivated to get to the top, what was going through their minds in their early 20’s, and valuable lessons they employed along the way. Throughout the weekend, attendees got to mingle with each other and enjoy makeovers by Maybelline, shopping experiences by Express, and fun photo ops from Cosmo, such as getting one’s picture taken as if you were on a real Cosmo cover.  One of the other exciting bonuses was the cocktail party Saturday night that took place in the Hearst building (home of Cosmo offices) where we sipped and surveyed the skyline as the celebrity speakers and guests got to have a chance to meet, take selfies, etc..  Overall, the event was a whirlwind of girl power, shaking hands, and hypnotizing speakers.

You know that saying “light a fire under your ass?” Yeah, I feel like I am sitting on the 4th of July. 

*breekeerrreeekerrreee* lemme BREAK IT DOWN.


Serendipity put me on the same flight to NYC as one of my dear friends, who picked me up at 5:30 a.m. Thursday morning. We laughed through the tiredness all the way across the country. I was nearly hesitant to get off the plane. After ten days of experimenting with a video countdown, I was just then realizing how much time had passed while I was busy in my internet world. It gave me butterflies.

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Classic PDX carpet pic. Had to.

Once in town and checked into my hotel, I met up with Robin and her boyfriend Chris. Robin and I competed at Miss America together in 2012, and became instant friends. She came in from Rhode Island to spend a day with me. Whenever we get together it is as if time never passes, and those are my favorite kinds of friends to have. We grabbed dinner and a drink with one of her college friends on the Lower East Side and then parted ways for the night.

On my way home I felt invincible. I was on my second or third wind. I was riding the trains like I had been doing it for years. I wore strappy heels for 16 hours and I didn’t want to die. Somewhere in the bustle, my butterflies subsided and I had an electric current running through my veins. I was finally in NYC. This was not a drill.

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No filter, just magic.


Robin, Chris, and I met in the late morning at the American Museum of Natural History. If you haven’t been, go. This is the closest thing I have ever experienced to a children’s picture book library being brought to life size. Wild animals posed in their natural habitat, dinosaur bones, space exhibits, Earth exhibits, historical exhibits,  artifacts from the centuries, and even butterflies! These butterflies weren’t in my stomach, they were swirling around my head in a climate-controlled room.  It was enchanting.

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Lunch was at John’s Brick Oven Pizza on Bleecker. It had come to me as a recommendation from a native New Yorker I had been at a dinner party with the week before. The sauce had that signature tang that makes NYC pizza the stuff of the gods. It was perfect, and we said our goodbyes with smiling bellies.

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Then began the solo leg of the trip. I needed to soak in the moment, and I needed to warm up. I needed some tea, and technology led me to my temple, Bosie Tea Parlor. Over a small pot of green tea the color of rose gold and two macarons I’d have hung from my Christmas tree, I was reset.

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In my social media blitz in the days leading up, I was an active part of the Fun Fearless Life Facebook event, posting questions about what to wear and if there were other parties of one looking to connect. Friday night I met up with one, named Alyssa, for a glass of wine and to attend the Express pre-party shopping event.

We met at a wine bar on 52nd and Broadway. She was wearing a long pink coat and came in a flurry. I think one of the first words out of her mouth was cheese. I knew we would be friends.

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A jewelry designer and gemologist, Alyssa was looking for a recharge at Fun Fearless Life.  She hated the term “basic bitch”, she had moved to New York 3 times, and she once dated a straight tap dancer. She loved to laugh and we did a lot of it. After scoring some free oyster shooters and looking at the clock, I scurried uptown to turn back into a pumpkin.

A late-night-pizza-guzzling pumpkin, that is. After all, it is a good idea to carb up before a marathon, even if the marathon involves no running whatsoever…


I hopped in a cab at 9 o’clock wearing my red Topshop crop top (say that 10x fast), Bailey 44 tulle skirt, Ivanka Trump strappy plum heels, and my express pink feather necklace (not pictured). You might recognize it from the Countdown to Cosmo Day 7 video:

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While you were asleep at 9:30 a.m., I was at David Koch Theater as twenty male models strutted through the audience, through the rows of screaming ladies inhaling purple fog and onto the stage where they unzipped their grey hoodies, and revealed upwards of 120 abs. (Yes, that means at least a six pack per model.) I am still LMAO over this, and it definitely lessened the blow of my phone screen cracking 5 minutes before.

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I should note that I lost a lot of pictures because my phone ended up needing replaced from this clumsy mishap. I’ll do my best with what I sent to Instagram. In the mean time, you should place two fingers on your control pad and separate them. This will zoom in on the abdominals above. You’re welcome. —

And we’re off! Joanna Coles the editor-in-chief of Cosmo welcomed everyone as the weekend’s emcee.  She is a no-BS lady in leather pants with a short platinum hairdo and British accent. Audience = starstruck.

Then the speakers wasted no time getting to the good stuff: how Sarah Blakely became a billionaire from her invention of Spanx, Megan Kelly on being a powerful voice in news media, Amy Cuddy’s famous “power poses” TED Talk, and even an 18 year old who has made nearly a quarter of a million dollars starting a jewelry business after her parents said they wouldn’t buy her a car, amongst handfuls of others. Chrissy Teigan interviewed male dating experts. Tara Mohr took us on a visualization experiment to our futures. Grace Helbig weighed-in on staying true to yourself on camera. Nasty Gal creator Sophia Amoruso talked about the humble beginnings of her mega-success. I wish I had the time to scratch the surface of these hours of fabulosity in this blog, but I just can’t. What I can tell you is that the women on stage were exactly that: women. Did they have exceptionally tasteful outfits and glowing stage presence? Yes, but they made it clear to each pair of ears in the audience that it wasn’t always the case. There were many days that came and went before their “celebrity” status, and all of it revolved around authenticity, tenacity, and consistency.

During the day I did what I could to keep up with social media, which, I’ve found if you are only doing it for your own pet project, can be a complete pain. I am pretty sure obscure dudes I graduated high school with have no interest in 20 shirtless guys or my selfie vlogs where I talk about my outfits, but I didn’t let that stop me. I actually tweeted at one point that I literally could not tweet fast enough, and during one of the “social media shout-outs” the ladies with the mic read my tweet and name aloud. +1 for apparently not totally sucking at social media! Another cool social media deal that didn’t take any real effort was the “Cosmo Cuff”. This was a wristband with a code which was scanned whenever there was a good photo-op, and it was put on social media for me! That’s right. I didn’t even have to do any leg thumb work when they snapped my pic at the magazine photo booth!

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I think a couple of my Facebook friends thought this was real. I may let them continue thinking that. 

In reflection, one of the most meaningful speakers to me on the first day was the author of one of my favorite books, Meg Jay, who spoke about why a person’s twenties matter. She wrote a book called “The Defining Decade”. I had read her book even before she gave her TED talk nearly two years ago, and it changed my life. I’ve recommended it to nearly all my twenty-something friends. I’m certain I wouldn’t have been sitting in that chair had I not read her work, and yet there I was.

While the East Coast was counting down the minutes until 5 o’clock, I walked away from Lincoln Center a little cross eyed. There were so many hours of words I wanted to cling to in my brain! So many people I had met throughout the day! So many questions about what the night at the cocktail party had in store!

I tried to shut my brain off at a corner café window on the first floor of the Hearst building in the short break between the day and the cocktail party. I ordered my magic elixir, mint tea, and a hot chicken tortilla soup. On one hand, I was refreshed, but on another hand I was still waiting for something to shake me up.  I loved the messages, of course, but already felt pretty good already about my fun fearless life. It may not yet be as lucrative as I would like it to be, but, as far as fearlessness is concerned, I had flown the length of the lower 48  by myself to one of the biggest cities in the world for the sole purpose of meeting strangers for two days, and I was even wearing a crop top in public for the first time!

And in that moment, despite the masses of hot liquids I had just ingested, I froze. I had been relishing quiet introspection  as I spotted the editor-in-chief, Joanna Coles, and another Cosmopolitan woman walking inches from my face in the window of the café. I had a fleeting thought of bolting like Roadrunner out the door, abandoning my mess of soup and crackers, and tripping over myself to launch a stack of business cards in their faces like an explosive piñata of  white card stock , but I refrained. That seemed a bit desperate. So I sipped my tea in the poetic moment, watching the woman with the dream job stride past.

Then the ladies made a pivot turn and entered the café.

I took a hot, minty gulp.

There is a strange phenomenon that as  performer I have encountered through the years: the confident shakes. It comes at a time when either you let things matter too much or you get cocky. Or both. A person may know the words to sing or the cadence of the story, but when looking the audience in the face, the body tunes out the rational mind and just quivers. (One of the more comical times I can remember was when it happened during a high school show choir performance. I hit the high note in the front row and my upper lip shook. My ballad partner made fun of me for months after having to look me in the eye with sincerity on stage as my face was spasming.) Needless to say, as I hovered near the register with a cool, confident agenda to shake the hand of a woman who ranks highly on my list of professional women I admire, I was a jitterbug.

I overheard the women order mint tea. That calmed me a little as I took a sip of my own and argued with my shaky kneecaps, trying to explain to my body that these women are just two humans with similar interests. They were just years beyond in success and experience, but really just the same! My knees insisted.

“Hi, my name is Caroline McGowan, and I’ve come from Oregon to be at your conference,” I said in more or less words. I shook both of the women’s hands. They were receptive, as most humans with similar interests are. I explained my gratitude for women’s events such as this. I mentioned my affiliation with the Miss America Organization and how inspiring women is something I am really passionate about. I professed my love of Cosmopolitan. I made sentences. They engaged.  All three of us smiled. They were even complimentary of my outfit, and liked the crop top! If I die tomorrow or never interact with another employee of a fashion magazine again, I will always have this small memory to chuckle at and retort to my children when they decide I’m an uncool mom.

They politely excused themselves to a meeting before the cocktail party, and asked if I would be in attendance. I said yes, and asked if I could give them my card. They said yes, and my humble self-designed business card organically made its way into the possession of the two hands I had flown all the way across the country for a chance to shake.

God bless America. 

They exited. I cursed my knees and took a seat for a second to laugh at the comedy of the universe. Perhaps their stack of business cards after the weekend would be just the right height to even out a lopsided chair leg in the office, or perhaps they would need a piece of paper to kill an unwelcome spider later and they’d use mine. The aftermath didn’t matter as much as the rush of being assertive at a moment’s notice, and this story will end without knowing if there was one.

I went to the main entrance, found a restroom, and did my switcheroo from my red crop sweater to a metallic purple cropped tank I scored at a shopping event held by Express the night before for Fun Fearless Life attendees. This was a last minute impulse buy that turned out to trump nearly everything I had done in my montage. Sometimes the Fashion Gods work in mysterious ways. Rocking the same plum shoes with nails and lipstick to match, I swiped on a bit more eyeliner, pulled back a sleek ponytail and took the illuminated escalator to the bellman-operated elevators. Between the glitz of the outfit, the venue, and the promise of the night, I have never felt more like Carrie Bradshaw in my life. On my way up I met a bubbly girl from 20 minutes outside the city named Christine. We shared a love of being blonde.

Once inside, I opted for sparkling water in a champagne flute and began to make my rounds. I met new faces and reconnected with women I had met throughout the day. I even saw a former Miss USA, Nana Meriwether, who I instantly bonded with over our pageant past. Girls hovered around a make-your-own necklace table provided by the same 18 year old who struck it rich with her jewelry business. The walls were floor-to-ceiling windows, and the city lights acted as a glowing wallpaper. As the room became populated, I hung back as I watched girls swarming their favorite celebrities to take selfies and shake hands. I was more interested in watching the room move than fighting for Instagram likes. I wondered if I would regret my disengagement of social media, since I had pledged so vocally that I would capture each moment. I resolved that I was out of allotted f**ks to give that day.

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My interactions through the night felt successful. I had talked to more conference-goers than I could fathom and had made some new friends.  I thanked Meg Jay for “The Defining Decade”. I had a chance to speak for a few additional minutes with other woman I had just given my card in the café. I spited myself with a selfie with one of the stars from the show “Orange is the New Black”. The celebrities were somewhat novelties amongst the crowd, and I was happier to stay social than to wait in a huddle to pretend Kelly Osbourne was really smiling out of excitement to be in a photo with me, a stranger.

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The night dwindled and a group of us toyed with the idea of hitting the town, only to realize our deep fatigue by the time we hit the lobby. It was 9:30 again, though this time it was night and so much had happened. I headed to the train to go back to the Upper West Side. There, I stopped for a late night salad where I looked entirely out of place, but was entirely okay with it. My feet were giving out and my face was tired of smiling. I wrote a Dorky Chick Diary, and then I snored.


9:00 a.m. I played pretend New Yorker as I snarfed a bagel and cream cheese in my face and walked fast to the subway where I stayed stoic and avoided eye contact. I was asked for directions, which gave me a thrill. My outfit was a pleather BCBG top with zipper detailing, black slim-leg pants from Banana Republic with 6 in. zippers on the bottom of the side seams, my classic black leather ankle boots, a camel scarf I scored at H&M while freezing on Friday night, and the Origami Owl necklace I fashioned at the VIP party the night before.

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No shirtless men today, unfortunately, but what was almost better was the Fordham University cheerleaders who came and did a cheer in Express clothes. I have been saying for YEARS how my dream is to have my own personal cheerleading squad, and this was probably as close as I’ll ever get. Hilar. Amaze. 

The day began a bit more serenely with a few yoga stretches done, true to Cosmo form, in high heels. The zen was obliterated with entrance of Adam Rosante, who is the single most energized person I have ever seen in my life. We jogged in place as he jubilantly yelled something about attitude and activity. I hadn’t had caffeine yet, but wished I would have.

Sunday’s speakers focused a little less on the job workplace and a little more on the real workplace: ourselves. YouTube sensation Jason Silva spoke on creativity. Jillian Michaels, Kelly Osbourne, and Cosmopolitan’s medical expert talked about body image and health.  Joanna Coles gave insight to her professional journey, and several panels dished on the importance of women’s leadership, especially amongst one another. Gabrielle Union even came forth and discussed the reality of her recently leaked nude photos and how it was not her crime to pose nude, but the crime of the person who put them online. Each speaker made the audience lean a little closer.

My favorite quote from the day came from one of the panels. Nina Vaca, founder of the Pinnacle Group, said  “If you cannot see it, you cannot be it.” She was speaking about the importance of women as being mentors for one another, and that leadership cannot grow without leadership.

If you cannot see it, you cannot be it.

I repeated this to myself over again. The philosophy nerd inside of me says, “huh, well John Locke doesn’t think so!” but my simple heart feels it to be true. How can a person know what they can achieve if they aren’t watching other people who know what steps it takes to be there? These words, coming out of the mouth of a self-made powerhouse, paid homage to all of those before her and before them. These words made me grateful for the experience I have with the Miss Oregon Program, of course, and it also made me wonder just where I’d find the next set of leaders to teach me. I can only imagine the fabulous shoes they are out there wearing right now!

The day ended with a particularly charismatic speaker, Gabrielle Bernstein. At 25 she had a high-flying nightclub lifestyle that was fruitful on the outside, but siphoning her soul. She turned her life around and found her purpose to inspire others. Her message was to “be the light” or be the positive influence for others when there seems there is none because it will breed positivity into all you do. “Being the light” is the key, she said, to making fun-fearlessness infectious. The way she told the story was captivating, and a memorable way to conclude the weekend of powerhouses.

Elle King then brought out her guitar and belted a song about ex’s followed by her rendition of Aretha Franklin’s “Respect”. The striking Ms. Coles and her platinum hair thanked and bid adieu to the  the swarms of newly-inspired women, and they took off into the world they would change one day.


I didn’t leave Lincoln Center riding a unicorn of enlightenment towards rainbows of success. I didn’t feel weightless or any urge to run through the town listening to “Eye of the Tiger”. These were the feelings I had anticipated, but the sentiment was a bit more complicated.

I left feeling… ready.

“Ready” is a feeling I’ve been distracting myself from really well. Was Caroline who watched all of HBO Girls in 3 days “ready”? How about Caroline who took trapeze lessons with a Groupon? Or Caroline who stopped buying groceries and ordered takeout exclusively only to become Canned-Food Caroline? Or we can’t forget our favorite Serial-Dater Caroline…was she “ready”?

Hah, no. 

This readiness wasn’t like I morphed in a matter of seconds upon exiting the Koch Theater doors, but rather like the moment in childhood where you go to put on your favorite pair of pants and you find they are too short. “Hmm!” you might say, or “shit!” you might say if you are a grown-up with ill-fitting trousers.

As I write, I am experiencing a healthy combination of “hmm” and “shit”. Don’t take that the wrong way… Part of me was hoping for unicorns, and part of me is relieved my pants don’t fit. I’m looking realistically at my to-do list for the first time and it sucks, but knowing I’m ready to be clear about my goals to get to where I want to be in my career is so incredibly satisfying.

I have this weekend to thank. 

I took the train uptown to get my luggage, and for a moment it felt like it was mine. I was so city. There was one more stop I needed to make. The leaves were orange and the sun was soft through the clouds as I trundled with my roller carry-on through Central Park. It was a picture perfect Autumn afternoon, minus the fact that there were no suitcases anywhere near the middle of the park. Mine sounded like ten on the pavement, though, for whatever it’s worth. I was exhausted, sweating under my layers as I drug my luggage, and moving my legs like a machine. I couldn’t stop my feet; I needed to feel the flow of New York City one more intoxicating time.

I was ready. 




Thank you to all of you who read this memory. It is more for my records than anything, but I have yet to outgrow show-and-tell. I promised when I began DCL that this was designed to be a filter-free journal of accountability, and I think Past Me would be relieved to know the plan is going pretty well.

Cheers! To playing dress-up, and keeping it real.


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