Womanpreneur Wednesday – Rachel Sobel

Meet Rachel Sobel, the mastermind behind Whine and Chees(its) – a super funny outlet for this sassy mom of 2.

Rachel and I first met at a blogger event a while back.  She was pregnant with her second daughter and for some reason, I love chatting with pregnant people.  I love them!

We chatted for a bit before the event began, and her humor and candidness made me like her even more! (Oh, and she’s from Long Island too…)

Her articles and social media posts are about real life mom-ness.  Some are straightforward, where you catch yourself nodding your head in agreement; some are snarky/hysterical and you are still nodding your head in agreement.

Well on to the good stuff…I hope you enjoy this interview as much as I did.  She cracks me up!

When you were little what did you want to be when you grew up?

A cocktail waitress but specifically at Bobby Rubino’s, because I like the lace bloomers that stuck out under their obscenely short skirts.

How did you come up with the idea to start Whine and Cheez(its)?

I’ve always written professionally but it was very business and product- focused. I have a technology PR background and loved it for more than two decades. Then while I was working for a software company and hating life, I started hatching my exit strategy. I hated their culture of mean girls breeding mean girls. I hated missing things at my kid’s school because there were only so many sick and personal days. My heart was not invested. I started a blog focusing on stories about my family, getting divorced with a toddler, dating as a single mom, remarrying and blending a family, and everything in between. I started getting messages and emails from other women thanking me for being so real and honest. Every one of those messages fueled me even more. My audience grew. My writing was accepted on big sites like ScaryMommy, Today Parents and HuffPo and I was even invited to be a regular contributor to PopSugar. I realized that even though there is certainly a lot of noise amongst those writing about motherhood and the accompanying territory, every voice is different and there is someone out there who will relate to what you are saying and take something away.

What is the biggest struggle you’ve encountered as an entrepreneur and how did you solve it?

The time management and balance are by far the hardest. But I stopped trying to find it because it doesn’t exist. My life is chaotic and there are never enough hours, but that can’t always be an excuse. I stopped trying to fit into the box of what I thought working for myself and from home should look like. I don’t work 9-5 and sometimes I don’t do any work during the day because of kid schedules and still having a toddler home with me. Instead, there are days I get down to business when the kids are asleep and on the weekends when my husband is home and can occupy the kids. I take deadlines seriously and have never missed one, but I do it all on my terms and it takes some time to get used to that mindset when you have spent your career working for others.

What do you think are the pros and cons of being a womanpreneur?

The best part is that you are creating something with your own hands and are driven by a very real passion. There’s nothing more fulfilling than that and the fact that I have two little girls watching me do it is EVERYTHING. However, the overwhelming majority of the time, everything falls on you. It’s your name, your livelihood and nobody you hire will ever be as invested in it as you are.

Do you have any mentors or coaches that you work with?

Not officially. But my writing has introduced me to a community of badass women who do the same thing and we lean on each other a lot. We speak daily and are constantly sharing ideas, our work to get a gut check and even collaborating. They have become my biggest support system professionally.

What advice would you give to someone reading this that has the entrepreneurial “itch”?

Do it but be somewhat calculated. Don’t just quit your job and a give up a paycheck to pursue that dream. Because being able to pay your mortgage is awesome. If you are married or sharing a household, have those very honest conversations about money before you make a move so that when you do decide to jump ship and start something from scratch, everyone is on the same page. It’s much easier to be an entrepreneur when your partner is behind you one hundred percent.

What is the secret to achieving work-life balance for you?

There is no secret because it’s impossible. I just do the best I can every day. Some days I nail it and some days I am crying in the shower at bedtime because all day I have been cleaning up toy explosions, chasing my toddler while she’s aggressively emptying an entire box of tampons all over my house, getting eye rolls from my tween and nobody wants to eat the dinner I’ve cooked.

How do you find inspiration?

From everyday things. Writing is such a subjective and personal process. Sometimes I will come across a picture on my phone and it spurs a story idea. Or something will happen with one of my kids at school. There’s also tons of material that inherently comes from being married. For me and the type of writing I do, it’s all about that relatability factor and the willingness to be vulnerable. So, when I experience things in motherhood or marriage, I know there are others out there having parallel experiences who will hopefully nod along as they read.

What is your favorite book?

I can’t tell you the last time I actually read a book other than The Very Hungry Caterpillar and Good Night Moon. But when I can actually get to it, I love autobiographies and especially ones from strong, funny women who push boundaries.

What is your favorite quote?

So many! Coming in at a whopping 5’1″, I’ve always loved Shakespeare’s, “Though she be but little she is fierce!”

What do you do to decompress?

Veg out in front of the TV with a glass of wine and Vanderpump Rules, The Bachelor, Real Housewives or anything steeped in crazy drama.

I Know You Just Bookmarked Her Site…

Rachel’s real, through and through.  She brings up topics that we all think about but may not verbalize.  (You can thank her in the comments!)

Aside from Whine and Cheez(its), Rachel is part of The Real Housewives of Instagram – a cheeky parody about bloggers.  Definitely worth a watch!

Please connect with Rachel via her website, Instagram, and Facebook.

Check out the previous Womanpreneur Wednesday spotlights:

Fatima Torres

Carli Brinkman

If you know of a womanpreneur that you would like to see showcased on my Womanpreneur Wednesday series, please comment below!