
20 finalists.
20 stories of bold, beautiful transition.
Thousands of votes.
One winner.
Let’s high five, group hug, and toast the wonderful Skyler McCurine who was won bragging rights, tons of love, and the $500 cash prize for being the winner of the Stratejoy Essay Contest!
Wanna know a little bit more about Skyler? So did we. We had a little meeting on the interwebz and asked her a few juicy questions that helped us get to know more details about our lovely winner.
How long have you been a member of the Stratejoy Tribe?
The past few months, I have good friends that have met Molly and have been encouraging me to form a strategic alliance. A few weeks before the contest started I had a rally of colleagues cheering “Skyler, Skyler, Skyler!!! Do it!”
What’s your favorite post that you’ve read on Stratejoy?
I actually wrote a commentary piece about the 10 Ways to Date Yourself. As a single woman venturing through the world and the sometimes terrible men in it (lol), it’s important to have cojones. You have to fall madly in love with yourself, date yourself, treat yourself the way a sincere gentlemen would. Also there was an article about comparing yourself to people on the internet (I can’t find the title of it) but I found it literally five minutes after I was crying comparing my life to my Facebook friends, feeling behind, single, and a little overweight. That article was so true, we create a virtual facade about how happy we are and only share the beauty and hide the fear, insecurities, and sadness. Meaning, the people I was legally stalking aren’t perfect.
What will you be spending your $500 prize on?
I am a gutsy woman in transition, how fitting that Stratejoy and I found each other. This money is going to my Better Business Bureau Membership and the rest in savings!
What’s your favorite Molly-ism? (That’s the name we give to the little quotes and sayings that are Molly originals that she has. )
I repeatedly peruse the Quarter Life Crisis page and send it to all of my hot mess 20 something friends. (LOL). People often joke about the QLC, but it is real, and hard, and no one prepares you for it. I always found solace and comfort in the recognition that I’m not alone and that what I was feeling was very real. Sooo, my favorite Molly-ism is:
Quarter Life Crisis, The term might be silly, but the process of growth is anything but.
If you could give your pre-transitional self 2 sentences of advice, what would it be?
You will do it but you must be patient and when you have accomplished your heart’s deepest desires, your tumultuous journey, heartaches, and rough times will show the world that you are credible. Remember, Oprah Winfrey didn’t get an Emmy over night. Also, don’t go to Jack in Box as much (haha).
What little morsel of advice would you give ANY woman in ANY kind of transition right now?
I was working on a proposal that was slowly drowning me, I was so overwhelmed with everything I had to do and worrying how in the hell I would pull it off. My colleague came over to me and asked “how do you eat an elephant”. I threw my hands up and said “I don’t know how” (expecting a silly popsicle stick joke) and she lovingly said “one bite at a time”. Your life, your transition, your dreams, goals, whatever they may be will come to fruition but it happens in little bits, small nibbles. Be patient with life and yourself. In retrospect it all fits together, that clarity is so hard to find betwixt the turmoil but trust that fate has you where you are meant to be.
Congratulations again to Skyler, our finalists, and everyone who entered the Stratejoy Essay Contest. We heart you all!
Just in case you missed it, here is Skyler’s winning essay:

“Introducing the class of 2008!” I marched proudly across the graduation stage, eagerly aware of my reflection being broadcast via jumbo-tron to the thousands of proud parents in the audience, including my own. As I shook the dean’s hand and got hold
of the diploma that I had worked so hard for, I could literally feel a change and shift from my pilgrimage across the stage. I pictured my life as a full blown bad-mamma jamma with her dream job of 60k a year and a wooden floored loft with bay windows and sky lights was waiting for me on the other side of that platform. Little did I know that as I crossed the stage, it was more like walking the plank. I was transitioning from naive
college bliss where my biggest worry was what I would wear to Friday night’s theme party into reality. I crossed the stage stepping into the daunting unfamiliar, aka the quarter life crisis.
The evolution from college student to working adult is like a transition from theory to practice, dream to fruition, and of course tax-free to paying citizen. I feared what this grand shift would mean. I wondered “How will I be a contributing member of society?”, “Will I ever have autonomy?”, and graduating in the worst economy since the roaring 20s, “Will I even find a job?” Jiminy Cricket, what the hell did I get myself into? Finally understanding why my brothers took years to graduate, the super senior methodology became more appealing at the rising of each sun.
Shortly before graduation I fell madly in love with an inanimate object: a red balloon. I once watched my favorite television character prance across the Brooklyn bridge with a dozen red balloons, her strut oozing sensuality, confidence, pride and a strong sense of self. That image stuck with me. Little did I know that a red balloon would be the answer to my quarter life hysteria. I started receiving red balloons as gifts at parties and birthdays. Pretty soon they took on a life of their own. I started seeing them all the time, serendipitously, when I needed them the most. Then one day, my fate was sealed and the ticket out of my awkward transition was sent first class via a sign from above. I was having a minor freak out in my beat up car, a case of the “mean reds” (as Holly Golightly refers to in Breakfast At Tiffany’s), a panic wondering what my calling was. Betwixt the fall of the first stinging tear, a little girl in the car in front of me let go of one red balloon. It was that very moment, right there that defined the next few years of my life.
I reflected back to my stint in retail providing (too honest) customer service at a major department store. I was talked down to for sending customers elsewhere for better deals and a better fit. I HATED the sales aspect but loved those intimate moments when I was able to help women feel utterly beautiful. We have all experienced the defeat that comes from the dressing room. We have all seen women walk in hopeful and walk out as if they have witnessed a tragedy (it’s just their own cellulite, saddle bags, and muffin top looking back in the mirror). I loved being able to wipe the blur and occasional tear from my clienteles’ eyes to remind them that they were, indeed, BE-YOU-tiful and that you can be fabulous at any age and in any body frame. It was why I started Le Red Balloon, a comprehensive styling service that coaches through kindness and compassion.
The tumultuous past few years, years of transition, emotional stretching and challenges has given me the drive to continue Le Red Balloon (LeRedBalloon.com). My business is the manifestation and extension of my true self; it’s an extension of all the love I have within. I revitalize my client’s sense of self through their wardrobe. I have finagled the ability to fuse my love of red balloons and encouraging others into a business.
The transition from graduation and dreamer to Corporate America and realist revealed what my true passion is: making women feel beautiful. I have learned what I’m really made of: sugar, spice, style, tenacity and a dollop of gumption. I have learned that I can handle much more than I thought I could and when I was cursing the high heavens, in retrospect, I realize that transition was the catalyst lighting the fire underneath me to continue, to thrive, and to share red balloons with the world.
You see, Le Red Balloon is the embodiment of my most authentic self.
Life is a string of transitions, revealing the spice, cojones, and in some cases, red balloons in us all. So, three snaps dahling. Remember you are utterly fabulous and when a rough transition stares you cold in the face, give it a kiss on the cheek and say thank you; it might just show you what you’re made of.
You can find Skyler on Twitter @leredballoon