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Some Whine with Those Cheez-Its: Q&A with Writer Rachel Sobel

Are your kids complaining about the grave injustice that is not being able to have a third lollipop today? Ask them if they want some cheese with that whine.

Ba dum tssss. Parenting joke!

Want more parenting jokes with a dash of sass, some hip hop beats, a bathtub full of Cheez-Its, and a sippy cup of wine? That’s where Rachel Sobel comes in. But believe me when I say you’ll come for the jokes, but stay for her heart and her smarts.

Meet the Very Funny Rachel Sobel

Rachel Sobel is a former PR maven turned full-time writer living with her husband and two daughters in Florida. And, as the kids would say, this lady keeps it 100. As real as they come, through the good, the bad, and the ugly. I met Rachel by way of a meme crush and then turned that crush into a full blown love fest when I learned more about her past, her present, and the community she has built to support and entertain moms. She’s the real deal.

Come get to know Rachel, the brains behind Whine & Cheez(Its) in this Q&A. And then get to following her on all the internet things, because you’re going to want more of her in your life.

Who’s That Lady?

Becca: For those who aren’t familiar (yet!) can you give a rundown of Whine & Cheez(Its), how it got started, and how you have seen it grow and evolve? 

Rachel: It has been a journey, I’ll tell you that!

I have always been a writer by trade, spending my entire career in public relations and communications. When I moved back to Florida, got divorced, experienced single mom life, dating as a single mom, and eventually meeting someone (whom I am now married to), I felt like I had A LOT to say. I started the blog mostly as an outlet for myself to get my feelings out.

In the beginning, I told funny stories about my family and personal experiences. When I realized I was truly building a community of supportive women looking to laugh, cry, vent and commiserate, I started to dig a little deeper and push myself out of my comfort zone, which had become funny anecdotes laced with comedic delivery. I knew I wasn’t alone in any of the things I was experiencing but I wanted to foster real dialogue and unbridled conversations about motherhood in the trenches.

What has been the most exciting moment for you over the past few years as you have grown your following on Whine & Cheez(Its) and reached a huge audience with your blog, social media, and writing for other publications?

It never gets old seeing my bylines on sites like PopSugar and Today Parents. But what gets me every time are the messages I get from women all over the world either thanking me for putting what they are feeling into words, or even sharing personal stories about similar topics I have shared.

I’m humbled and excited every time someone takes to time to reach out and have a conversation, or be vulnerable with me because they know it’s a safe space. 

Life’s a Stage

Let’s talk your weekly Facebook/Instagram live video session, Live from My Closet! What do you love about producing video? Was it terrifying at first? This is a completely selfish question because to me video is the scariest and I want you to tell me I don’t need to do it, or that it’s no big deal and I need to get over myself.

Live streams are interesting. I’ll admit that I’ve always been on some sort of stage my whole life so it doesn’t freak me out. But, it’s a really weird dynamic to talk into a mic while looking at yourself on the screen without knowing if anyone will show up or even comment. That’s the part that gives me a little anxiety every time.

I love video, but particularly lives, because its a huge opportunity to connect with an audience and have a real back and forth. I try not to take it too seriously and just have fun. And there are times that I have a hard time being “on” if I’ve had a bad day or my mood is blah. But I committed to those Monday nights and I love the conversations that happen in that little closet so much.

There’s not a ton of interaction on a static Instagram post aside from likes and comments. So, the ability to mix things up and have a chat in real time with other moms is like therapy.

Some Very Real Talk

You’ve been so open about the hard stuff in motherhood. Single parenting, miscarriage, postpartum anxiety, the mental load. That kind of openness and honesty is so refreshing and helpful to other moms. What motivates you to break down barriers in this way?

We have to break down the barriers because if we don’t there are so many women suffering silently.

People are afraid to share the ugly stuff. They think they will be judged as a mother. But the ugliness is a very real part of motherhood. We all have struggles and the minute you open up and become vulnerable is when the healing starts. You find common points with others. You find your people. You even find people you never thought you’d have anything in common with, but end up bonding over a specific part of mom life you see as a challenge.

Motherhood is amazing but it can also be polarizing and scary. We don’t have to pretend we always have it together. There is nothing to prove and no contest to win. Admitting you are having a hard time does not make you a bad mother, it makes you an honest one. My heart hurts for mothers who don’t think they can open up and I hope that as we share more of the tough stuff there will be a shift in that mindset.

Rachel’s Swivel Story

You’ve made a swivel in your career from PR into the world of writing and social media, and you’re crushing it! Any advice for those making a career change, particularly from employee to solopreneur? 

Sometimes I feel like it’s crushing me! I am working harder than I ever have in my entire life and it’s not easy.

But I tell my girls all the time that they are so lucky because the whole workforce has changed. You used to go to college and then pick from a bunch of existing professions that all fit neatly into college curriculum – lawyers, doctors, accountants, etc. But now, I truly believe that if you have a passion for something there’s usually a way to monetize it.

I guess my advice would be to be equal parts strategic/calculated and willing to take major chances. You also have to manage your expectations because it’s not easy and it doesn’t happen over night. It took me years to get something accepted into the online publications on my bucket list, to grow my social media audiences, and to gain traction in general.

So many people around me are constantly checking analytics and digging into the nitty gritty of when they are posting and why and living by those numbers. But that goes against every reason I started this business. Sure, I check those numbers because at the end of the day this is my livelihood, but I also know that when I write or post something authentic and from my heart, I can’t go wrong.

I also think one of the best things I ever did was to surround myself with people who lift me up, support me, and believe in my work. Moral of the story: Be a realistic dreamer.

The Career Sweet Spot

How have you found your career sweet spot (the overlap between your strengths, passions, and value to others) as a writer and influencer?

I think finding that sweet spot is an ever-changing thing because your priorities shift. I don’t feel like I have balance among those things, I feel like I have chaos, but the chaos works for me.

In the beginning I felt pressure to write about things people expected me to write about or to employ similar tactics to what others were doing on social because it worked for them. I’m human and therefore suffer from serious self-doubt and other insecurities. I would get caught up in negative comments, rejections from submitted articles, and brands not wanting to work with me because I wasn’t “big enough”. The minute I stopped caring and trusted my gut is when everything changed.

My virtual village was a game changer too. I have dozens of women, a small subset of those that I speak to on a daily basis, who have become my people, my web work wives, my sounding board. It can be lonely as a soloprenuer, but when you find the people who completely get you, it feels like you have an entire team standing with you every step of the way.

All of that helped me let my guard down even more and add additional layers of honesty and authenticity to my writing. That’s when the brands started to come in droves, too. People like real and can smell canned and fake a mile away. I think real always wins.

It’s Okay to Play Favorites

What’s your favorite piece you’ve ever written and why?

I never thought my favorite piece would be a darker one, but my article about my miscarriage for PopSugar is it for sure.

I was completely destroyed when I lost that baby. I couldn’t be around people; I was sad and hopeless and felt like my body gave me a big screw you. Eventually I became pregnant again, was hospitalized twice and spent the end on bedrest. But I delivered a healthy rainbow baby.

Because of the miscarriage, I was so scarred that I was terrified throughout my whole pregnancy. I wasn’t sure I wanted to talk about any of it publicly and then I felt like a fraud. My life for the most part had become an open book and now I was hiding something that completely changed me as a woman and mother.

I wrote and re-wrote that article for several months after my second daughter was born and cried every time I opened it. I still do when it pops up. But that article impacted me personally and professionally. I couldn’t even keep up with the emails and private messages I got from other women detailing their own heartbreak and showing appreciation that they felt less alone. It’s a sisterhood you never want to be part of, but it’s filled with so much compassion and understanding.

That’s also the piece that taught me that I didn’t always have to be funny. A little balance is good. It was gut wrenching to write but also cathartic. 

How about your favorite meme?

My favorite meme is a bit harder to pick, but I think it’s the one that says, “If you like a toddler staring you square in the vagina as you change your tampon, then motherhood is right up your alley.”

The minute that went live the comments started rolling in and I was crying from laughing so hard. Even at the ones from the sanctimommies who preached about how children should never have to see those things and mothers could have privacy for those moments. I don’t even know what privacy is and I think I speak for 99.9% of mothers who feel the same. But congrats to that .1% who figured it out.

The Laugh Factory

Speaking of memes, they are awesome. And yours are especially awesome. What role does humor play in your life as a mom, wife, friend, and professional?


We have to laugh. As mothers and as humans. It’s a release. It’s healthy and it feels good.

Too many people take themselves so seriously and walk around with a dark cloud hanging above them as if they are impervious to humor and that in itself is sad. There are so many ridiculous things we experience as mothers and when you can laugh at them with other mothers, there is nothing better.

My older daughter already has wit and sarcasm that I don’t think I achieved until my 30s and she’s only 10. My husband and I built our relationship with humor as a major pillar. Funny is one of the best compliments to receive and one of the best characteristics to have. I also come from a line of funny people and our family gatherings are far from buttoned up.

Life can get heavy. The news is tough to watch. Kids suck the life out of you. Laughter is the best thing to make all of it more palatable.

We Heart the 90s

Can’t let you go without talking about the 90’s. So your 90’s favorites in rapid style – musician, TV show, overly processed food, fashion trend!

Musician: Notorious BIG (no joke – I had a 90s hip hop baby shower with my second, complete with custom Biggie & Tupac cookies)

TV show: Toss up between 90210 and Sex and the City.

Overly processed food: Any of the chips with Olestra that basically ended up mimicking a colon cleanse.

Fashion Trend: Black “going out pants”, tube tops and all the body glitter. All of it.

Parenting Advice from Rachel Sobel

Last question! Any piece of parental wisdom you’d like to drop on us? I always like to share that my go-to piece of advice is “none of us know what we’re doing” so the bar is quite low on this.

Make motherhood your own.

There are no experts. YOU are the only expert when it comes to YOUR children, so do your thing and don’t let others get in your head. You’re killing it even on the days when you feel like it’s killing you.

She’s awesome right? I’m so thankful for the chance to interview Rachel Sobel because it gave me a good reason to be super nosy about her life while also sharing with you some serious gems of wisdom. Pure career/motherhood/life gold.

Do any of us have it totally figured out? Of course not. But if we can laugh every day, find a good support system, take chances on ourselves, and stick with it… well, good things are going to happen. Of that Rachel and I are pretty darn sure.

Find Rachel Sobel on Instagram, Facebook, Twitter, and her blog Whine & Cheez(Its)!

Read More Q&A From Funny Ladies

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