Single and Fearless.

After four months of a wonderful relationship gone horribly awry, I’m back where I started: Single.

Of course I’m laughing at myself.
“Really, Sherilynn?” My inner hater laughs. “Again?”

But it’s not so bad.

As I open up more about the things I’m doing (expressing myself through music, singing dumb little ditties about boys I meet in bars, trying new things, etc), more people open up to me. Being yourself forms new bridges of understanding between the world and you.

For example, only now, after revealing my vulnerabilities, have I realized that this phenomenon (phenomena?) of breaking up and meeting new people is not so much a phenomenon (there’s that word again), but rather, an unspoken way of living that a majority of the world’s population happens to trudge through. … Not that I have any actual statistics on hand, but a larger percentage of my immediate conversations center on this topic, and one can only surmise, yes?

Being single is kind of amazing.

I’ve always wanted to be single. I’ve just never had the opportunity before. I don’t think I’ve gone 6 months without a boyfriend. … Make that three.

… WTF?!

This makes me realize I need to grab life by the balls while I’m still single and do everything I’ve ever wanted to do as soon as possible. I’m a grown woman. I’m 27 years old. I’m in my late twenties, for Christ’s sake. I should be enjoying myself!

So, knowing me, and knowing I’m statistically likely to fall hopelessly in love with some new and charming stranger soon (save me!), I’m doing everything I’ve ever wanted to do right now.

What I’m currently doing with my life:

Playing my ukulele every day, riding my motorcycle everywhere, very purposely kicking ass at work and relishing the “pats on the head” for a job well done, enjoying napping, breathing through yoga, stretching a lot, just talking to people, opening myself up to the world, embracing the pieces of me that I like and have always liked, loving myself, loving the people I am lucky to have in my life, writing more (digitally and in a diary/journal), drawing more (people ask me to draw for them sometimes, so I do these little 5 minute doodles, and their reactions are always really sweet), enjoying making the people around me smile, enjoying making people laugh, enjoying pushing myself by joining conversations and situations that make me uncomfortable, collaborating, and just loving life.

And that’s just to begin 2015.

Tonight, I realized that for the first time in my life, I’m single. Really single. And if this is what I’ve been able to accomplish in such a short period of time, can you imagine what else is out there waiting for me?

I’m so excited to get started!
So excited that I wrote a song about it for my ukulele and recorded myself singing it.


YouTube Preview Image



I’m gonna’ be alright.
That’s what I told ’em.
It doesn’t matter what they say.
You don’t have to worry.
Because I’m so strong, and I’m working on mmm-me.

And once upon a time,
I was so weak I needed you by my side.
But that story’s gotta’ change,
And so I’m cruisin’, yeah, I’m movin’ on to me.

Cuz I feel high
Taking the world by storm, got that look in my eyes, like
I feel great
Stealing the show, gotta’ go. I don’t wanna’ be late.
Sights to see, places to be–
There’s always somewhere for me
New horizons, open roads–
I’ll probably even move to a new zip code!
It’s so excitin’.
I’m getting ready
To be me.

This morning when I woke up,
I put my clothes on, skipped the makeup, sprayed perfume.
Stepped outside, the sun was shining (baby).
The birds were singin’, and the roses were in bloom.

I said “hey there” to a stranger.
He said I heard you singing love songs, humming tunes.
I invited him to listen.
I sang so sweetly, kinda flirty, made him swoon.

(Repeat Chorus)

Ahhhh ah-ahhh
Ahhhh ah-ahhh
La, la-la-lah, la-la-lah, la-la-laaa

Ooooo oo-oooo
Ooooo oo-oooo
Doot, do-do-doot, do-do-doot-do-doo-dooot

I’m so excited
I’m gettin’ ready
To be me.

After playing and singing my song about a million times and in a million different ways, the lyrics have become a kind of mantra for me. I feel like because of this song, every decision I make lately is filled with excitement, and every hello to a stranger is a possibility waiting to happen. I live like I’ve got somewhere to go. I’m happy. I’m not being afraid to say what I want to say or do what I want to do.

How is it that I’ve never lived like this before?!
And are there still people out there who have never tried this? Because they are missing out.

Being single is like living in a whole new world.
Suddenly, everything is an option.

Mumble: It’s a little overwhelming actually. I don’t really know what to do with myself with this many new choices, hahaha.

I mean, I could literally do anything I set my mind to, and I’ve already proved that to myself about a million times over. My life has been incredible. Really. It has.

… What should I do NEXT?!

You know how sometimes you look back at your life and reflect on your personal history like you’re critiquing a bottle of wine? “Oh, 24, yes, that was a good year.” Or, “My early twenties were shit.” Etc?

In year 27 of my life, I’ve embraced the feeling of being fearless. Fearless in my decisions, fearless in embracing who I am, and fearless in my acceptance of others.

It has been amazing.

Learning and Moving On

I am so grateful for my last relationship because it was filled with so many wonderful memories. In many ways, it helped me heal from the abuse I took from my previous relationships, taught me how to let someone in again, and I discovered what it was like to work very hard for someone out of love. I was grateful for it while it lasted because it gave me much-needed experience. The fact that it ended in a really awful way doesn’t take away from the fact that I cared about the person I was with while I was with him, and knowing this, embracing it, kind of blows my mind.

When I think about expending energy on being angry at someone or hurt by someone, it leaves this sour taste in my mouth. I have better things to do. Sights to see. Places to be. Like the song I wrote! I’ve got shit to do, people! Out of my way!

I’ve also learned that I’m not interested in badmouthing ex-boyfriends, and that it’s a useless exercise for me. What’s the point? What happened between us was between us, and it’s mine to learn and grow from, no one else’s. … Which makes it all the more baffling now when I discover that someone has been badmouthing meee, but then, I’m not responsible for anyone’s actions but my own. So I’m okay with that, too.

Because maturity.

Choosing To Be Happy

As I grow older, have amazing experiences, and hungrily chase after more, I realize more powerfully that all of my feelings and experiences are based on choices I make. Regardless of the circumstance, I hold the reins to my life, not anyone else.

So, I’m choosing very purposely how I want my life to go.

I choose to enjoy being single.
I choose to enjoy the unique things that make me, me.
I choose to hurl myself with excitement into new experiences.
I choose to look forward to being uncomfortable and pushing my limits.
I choose to be fearless.
And I choose to be proud of my accomplishments.

Breathe in.
Breathe out.

Damn, I feel good.

~ Sherilynn “Cheri” Macale


PS. Some parting wisdom from a friend just recently out of a relationship as well and with much more experience than myself: “Every decision you make from now on should either be ‘Fuck Yeah’ or ‘Not At All’. Imagine your life as a movie, and always make decisions based on whether it’s in the script.”

I’m down for that.

This year, I’m grateful for money. Kinda.

“What the hell are you eating?”
“Those frozen crab puff appetizer things from the freezer,” I reply, kicked back in my Nikes while tucked into a much-too-large SKULLY jacket. The team is gathered up in one of our conference rooms in preparation for a meeting, and I’m settling in before it begins by, as usual, stuffing my face with food.
“Aren’t those … Y’know …” My boss ends his sentence in a face that makes it look as if he’s just smelled something effluvious.
“Disgusting?” I finish for him.
“Yes. That.”
“Yup, they’re terrible,” I reply, smiling mischievously as I finish off the nasty treat, its texture akin to shredded, soggy cardboard, and its flavor comparable to what I imagine raw shrimp might taste like if chewed up and spit out by a mama bird. Mmm.
He laughs. “Why are you eating it?!” He gives me a baffled, but amused look.
“Because it’s free.”

Ah, yes. “Because it’s free” is pretty much my reason for doing anything in San Francisco. “If it’s not free, get it away from me,” I always say!
… Okay, I don’t actually say that, but man, San Francisco is expensive!

Forget those $30 concerts with $14 cocktails at the bar, or those $85 brew fest events you end up spending $200 in because the food booths are so pricey. And please, friends, it’s not that I don’t want to go to your magical birthday party in Napa, but I’d rather wallow in FOMO than pay for the $200 all-you-can-drink-party-bus ticket. And if my lack of attendance means we can’t be friends anymore, so be it. Because, well …

I’m cheap.

If there’s money piled up in my savings, I will tell you I’m broke. If I’m coming to your party, there better be a bowl of potato chips and an open bar. When I see a menu where most items cost upwards of $24 USD or more, you can bet I’m hoping we’ll split the bill. And if I have to choose between eating at a nice restaurant near my work, or toasting disgusting crab puffs from the office freezer, well, I’m gonna eat the f*cking crab puffs.

This isn’t to say that I only do things if they are free, but more often than not, I am the perfect model of Cheapskate McCheaperson.

“I’m bored. Come hang out with me.” I’m texting one of my coworkers, bugging him to join me after work (my team mates are basically my family at this point; long hours at the office inevitably creates those sort of bonds).
“We could go get motorcycle gear at Scuderia?” He texts back.
“Blaaaah. Come eat with me. It’s too cold to go to Scuderia.”
“Where are you thinking?”
“The mall.”
“… Cheri, you are a grown woman. You do not need to eat at the mall like a penniless 16-year-old. Go get real food.”

Psssh. Real food?! The mall does have real food! Have you even had the combination pork bowl from Ajisen Ramen?! Or the crispy chicken avocado salad from Buckhorn Grill?! You are robbing your tastebuds of the delight that is San Francisco mall food with your hoity-toity “I don’t eat at the mall” nonsense. It is tastebud thievery, I tell you! THIEVERY!

goku gobbling food

“You make more money than 90% of our friends, Cheri. You are not poor,” another buddy says to me over Facebook chat. He’s trying to convince me to come out for the night, attempting to battle my phobia of spending money.
“So? Everything is expensive as hell here!” I reply.
“Yeah, but you’re young. Don’t you want to have fun?”
“Sure, but I also want to save money for a rainy day. Or my future. Y’know, like for a home? Or for my one-day family?”
“So you’re just going to sit on your money forever?”

What’s wrong with not spending money?!

I like to read. I like to play video games. I like to draw. I like to work out. I like to write. And guess what? It’s all freeeeee! … Er, mostly free, anyway.

Sure, sometimes I spend money to go shopping, but when I look at my closet, I also see piles and piles and piles of clothes I don’t really need but have been too lazy to donate or sell on Ebay. When I open my shoe wardrobe, it takes me ages to sort through the heaps of high heels, boots, and sandals. And don’t even get me started on my purse wall! That’s right. My wall of purses.

I’m not “poor” by any means, but I’m not so foolish that I truly believe I might never be poor or broke ever again. So, when I do spend, I spend wisely. I spend on things I actually give a sh*t about. If I jumped on every opportunity to tromp around the city with friends and go to brunch every single weekend, I’d probably be broke. And y’know what?

Being broke sucks.

I’ve been broke before, and it is awful.

When I worked as a consultant, paychecks would, often times, arrive incredibly late. So late that I’d have to petition my landlord for extensions on my rent, or piteously reach out to Mom and Dad for small loans to get by. At one point, I was working three jobs at once on top of consulting just to pay my bills: waitressing at an upscale restaurant by the beach, bartending at a wine bar on Polk Street, and even barista-ing(?) with San Francisco’s famous Philz Coffee (thank da’ lord for my bubbly personality; I had zero service experience and was hired based on charm and trainability alone).

Many bowls of soup were spilled, several apologies made as hot coffee toppled from countertops onto nice blouses, and small tips gratefully pocketed after eight hours on my feet with no breaks hustling back and forth between chefs and tables to ensure my patrons had the best dining or drinking experiences possible. Then, it was off to my next job. Double shifts, and sometimes triples were not uncommon for me.

It was f*cking tough. Being a server is really hard, you guys. My wrists and fingers ached constantly, my feet perpetually hurt, and I stopped caring if I had worn the same pair of jeans to the restaurant or coffee shop 2 weeks in a row — I was too tired to care, and at the end of the night, all that mattered was counting my tips and praying I had enough to make it to the next month.

I was depressed. Depressed because I knew I was smarter than that. Sad because I knew what I was capable of. Upset because being a server makes sense for some people, but it didn’t make sense for me. I was good at it, sure, but I knew my own potential, and not being able to see that potential realized absolutely killed me. It wasn’t just that I felt I was wasting my skills, but that I feared for my future, too. Who would want to date a waitress/bartender/barista? How could I ever support a family on this paycheck, working these hours? I felt worthless. All of my accomplishments, my stacked resume, my amazing achievements — all of it felt useless.

I spent a lot of nights crying, feeling like a total piece of sh*t.


And then I got a call from SKULLY.

It wasn’t a full-time position. Not at first. But it was something. It was a rainbow of an opportunity, and the pot of gold at the end was a full-time position with a company that had an amazing story driving it, and I wanted that gold.

I dropped all three serving jobs to pursue my SKULLY contract, and I kicked ass. I worked well over the amount I was paid for, driven by this mad intent to prove my worth, not just to SKULLY, but to myself.

And somewhere in the process, I fell in love with my team. Because it wasn’t just me who wanted to prove myself — we all did. Each of us was in love with what we were doing because each of us was hired to fill roles we absolutely excelled in, for a company we 100% believed in. Being surrounded by this sort of passion and brilliance every day is intoxicating, and I was (and am) hooked.

Following my month-long contract, I was rewarded with a full-time position. My friends congratulated me. My parents called to tell me they loved me. But through it all, I felt scared. Scared because it was such an amazing opportunity, and it frightened me to think that one day, I might lose it. You don’t go from working 3 serving gigs and several consulting positions to the land of stability just like that — there had to be a catch.

So, full-time position in hand, I worked even harder. You think you like me now?! I thought. Just wait and see what I can do! In my full-time role, I attacked new challenges head-on, blowing expectations out of the water and exceeding goals where I could. I worked longer. More efficiently. I stopped getting sleep (much to the concern of my superiors who advised me several times to take it easy and get some rest), but I was addicted to the hustle, and no way in hell was something as simple as sleeping going to get in my way. SKULLY’s success became my success, and I was determined to see the company succeed.

Three months later, I got a promotion. And that scared me even more. It meant that SKULLY believed in me. That, heck, they liked me, they wanted to keep me on board, and they wanted to see what else I could do.

Promote me, will you?! I thought. You want to see what I can do with more responsibility?! I’ll show you, and I’ll make it look easy, too!

So I did. And I am. And god damn it, I’m going to continue doing it, and I’m never going to stop, because that’s what happens when you’re finally doing something you love for a living. In times where I roll my eyes playfully when being given a task, or moments when I whine about how much work I have to do, it’s only because secretly, work is my crack, and it is the most rewarding feeling in the world to feel useful, and to feel like I’m making a difference by contributing in a way that no one else can.

So yes, I’m making money now. And yes, I’m blessed.
But …

At heart, I will always be a cheap-skate.

Just because I’m doing well financially now and am successful today doesn’t mean I’ll always be. I feel safer with a cushion to fall back on, especially knowing how hard it is to find a well-paying job in the first place. I know the value of money, and I know how hard it is to earn. And I definitely work hard. I come from a humble background, with humble roots, with parents who constantly have their noses to the grind. We don’t come from family money, and we’ve been broke more often than we’ve been rich.

Thus, I am cheap.

And y’know what? I don’t think being a cheap-skate is so bad. Being a cheap-skate has made me more grateful, more thankful for everything I have, and more appreciative of everything I’m given. Being a cheap-skate has made me more generous. Because I know how rough it can be, I consciously put effort into charity work, in donations, in attempting to brighten the lives of the people around me in simple ways, and in tipping the sh*t out of my baristas and servers. I make it rain on them hoes! … Hos? I’m not sure what the plural form of “ho” is.

dollar dollar bills y'all

So, I say let me enjoy my soggy frozen crab puffs. And please, don’t mind me while I slurp down my $7 mall ramen with gusto. If you want to treat me to something “better”, I will accept your generosity with overwhelming graciousness and thanks, but in the meanwhile, don’t cry for me for not living large — I am content with and grateful for what I have.

And I will never stop working hard to earn more.

~ Sherilynn

PS. Happy Thanksgiving, everyone. Thank you to my family for seeing me through the hardest two years of my life, for always being there for me, and for loving me unconditionally. Thank you to my friends for reaching out to me in times where I needed companionship the most, and being smart enough to recognize when I was too prideful to ask for love and affection. Thank you SKULLY for recognizing my potential, for giving me a chance, for scaring me in the best way possible, and for motivating me to learn, to grow, and to believe in myself. And thank you to my wonderful boyfriend who couldn’t care less if I was a waitress or a billionaire, and who appreciates me no matter what. Without all of you, I wouldn’t be where I am today. Thank you.

The boy who ran away from home with me.

JamesI took this picture of him nearly 10 years ago.

When I first met James, I thought he was so cool. He was the kind of cool that only a severely-sheltered girl of seventeen with zero worldly experience could imagine was cool. He had this sort of rebellious flair, this laid-back demeanor that made him stand out without having to say or do much at all. He had a presence, and when I first laid eyes on him, I immediately had a crush.

James was tall, fit, and had long legs. He had this mess of blonde, curly hair, and the other boys sort of flocked around him, naturally deferring to him in all matters requiring any sort of decision-making: where they sat, what they did after school, where they hung out during lunch — James was their leader. And when he spoke, it was always with purpose, always in that same deep rumble. He sounded like a man. He never seemed to vie for attention, and I suppose he never needed to, because everything he said made anyone within hearing distance stop to listen, and any small joke he made in passing cued belly-full laughter with ease.

From the first day he arrived at our little school, it became clear the other teenaged girls attending collectively believed that he was the guy to “get”. I remember seeing my female classmates walk by his desk during class to subtly pass him notes, letters he would unfold and read when the teacher wasn’t looking, then quietly smirk to. I remember seeing the school slut (yes, we had one of those) perch atop the edge of his desk and bunch her cleavage together between her arms while leaning toward him, striking up a conversation with him and laughing loudly at everything he said.

Though he was the object of many a girl’s affections, James remained cool. He never gave any one girl more attention than any of the others, and if anything, he ignored most of them to focus, instead, on his “boys”. They worshipped him for it.

For my part, I was never much of a flirt growing up. I was shy, incredibly well-behaved, nerdy, could barely dress myself, and a total tomboy. My idea of a good time was hanging out with my baby brother (still the coolest kid I know, by the way), playing video games, drawing, and writing in my diary. I didn’t exactly have much going on for me in the boobs department (and growing up, I actually believed breasts were everything), so when it became clear that what stood between me and James was a sea of young, hormone-driven teenaged girls all experienced in wooing and all eager to win him over, I gave up on the idea of us ever becoming an item and contented myself to merely fantasizing about what it might be like to date him.

Essentially, he had no idea I existed, and I was much too meek to assert myself and let him know I was alive.

Then one day, he talked to me.
He actually talked to me.
And us formally meeting completely changed my life.


We were in art class. My art teacher was a gentle sort of man, the type who quietly laughed off misbehaving students and very much wanted to be everyone’s friend. He never criticized our artwork even when it was truly terrible, but instead praised every chicken scratch doodle and encouraged us to keep practicing, raining down compliments on us at any sign of improvement. He was a major comic book nerd, and amidst the gaggle of delinquents surrounding me, I was his favorite student.

“Does anyone know who the X-Men are?” He asked us excitedly. There was a general but half-assed murmur of acknowledgement from the class, and I could see his shoulders slump a bit at the lack of energy.
“Yes,” I said, loud enough for him to hear over the mumbling and hoping to perk him up. He brightened at my response, continuing.
“Today, we’re going to invent our own superheroes! Does anyone have a favorite X-Man or superhero?”
“Sailor Moon!!” I squeaked enthusiastically, because Sailor Moon is the shit. Duh.
“WEENIE!!” Someone yelled at me from across the room. The class erupted in a fit of laughter.

Incensed, I swept the sea of giggling classmates for the source of this insult, surprised when I saw that it was him. James. His buddies were laughing and patting him on the shoulder, and he was looking at me with this triumphant smirk on his face, reclining back into his chair.

I couldn’t believe he just called me a “weenie”.
What the heck?!
Who even says “weenie”?!

… But it was such a harmless insult.
And he was just so cute.
And when I locked eyes with him, I couldn’t help my face getting hot.

I smiled nervously, then dropped my gaze to the pile of doodles on my desk, suddenly fascinated with the eraser on my mechanical pencil.


When class ended, I was far too eager to get out of there. Mortified at the idea that he had finally acknowledged my presence and faced with the potential opportunity to actually have a conversation with him, I did what any inexperienced and scared-shitless little girl with a crush would do: I stuffed my things into my backpack quickly, clutched my heavy three-ring binder to my nonexistent chest, and ran away! * To this day, I still suck at getting hit on. But just as I exited the door and had made it a few steps into the hallway, I heard him call for me.

“Hey! Hey, wait!” His voice was so recognizable. I knew it was him. When I hesitantly turned back toward art class, I saw him struggling to stuff his own papers into his backpack and hurrying in my direction. I quickly glanced around me, unsure if it was me he was speaking to.
“Uhm, me?” I asked shyly.
“Yeah, you,” he said, finally slinging his bag over his shoulder and standing next to me.

Oh god.
This was happening.
He was talking to me.
James was talking to me.
My brain short-circuited for a second, and I found myself staring. I had never seen him this closely before.

He had blue eyes. These really pretty, almond shaped eyes. And such long eyelashes. Wow.
And I mean, I know I’ve said it enough at this point, but man. He was so cute, and seventeen year old me was absolutely smitten.
I blurted the first thing that came to mind.

“What’s a weenie?”
He laughed, brushing his fingers through his mess of blonde curls before shoving his hand casually into the front pocket of his navy Dickeys, hiking his bag up higher on his shoulder. “You don’t know what a weenie is?”
“I mean, I know what a … Weenie is,” I said, sort of whispering the term in embarrassment, “but what did you mean?” I smiled shyly. I felt kinda sweaty. Man. Talking to cute boys is hard.
“Y’know. A weenie.” He glanced toward the ceiling and tipped his head from side to side, as if the movement would knock the definition out of his brain and onto his lips. “I don’t know how to explain it. It’s like, ‘dork’, or something.”
“Why did you call me that?” I asked, genuinely curious.
“Because you’re a weenie. You gave a weenie answer.” He was smiling.
“Okay… I guess.” I said, not really knowing what to say to that.
“It was just a joke. You don’t really seem like a weenie,” he said. And I was relieved, for some reason, even though I didn’t know what he meant by weenie, because y’know, he was cute, and I wanted him to think I was cool just like I thought he was cool, because that’s how the teenaged mind works, okay? “What’s your name?” He asked.
“Cheri,” I said, still in disbelief that we were actually speaking to each other. “What’s yours?”

I forget what we talked about after that.

And I guess it doesn’t really matter because the next thing I do remember doing with James was packing a bag and running away from home together, then going on one of the craziest adventures of my life living as a homeless teen for over seven months on the streets of Stockton, California, one of the most dangerous cities in the nation.

But y’know.
That’s a story for another time.

~ Sherilynn