We had the good fortune of connecting with Rachel Sobel and we’ve shared our conversation below.

Hi Rachel, what do you attribute your success to?
Vulnerability. If you are going to venture into sharing your life very publicly as one of the biggest parts of your livelihood, being vulnerable and authentic are key. Social media is swirling with what I like to call fauxthentic content. People share embellished stories and filtered photos to show the world what they WANT you to perceive. I never wanted my social profiles to look super curated. Instead, I leaned into gritty truths, chaos, messiness and challenges in addition to all of the “fun stuff”. When you share real parts of your life, you will attract people who truly relate to you and it creates community and camaraderie. I feel most successful when people are able to form connection and engage in dialogue because of the truths I share.

Let’s talk shop? Tell us more about your career, what can you share with our community?

I am a storyteller to my core. Even early in my career, I worked in public relations and telling compelling stories was the crux of my job. As my life and priorities changed, I took big professional risks by relying on my ability to tell stories. I started writing short, humorous stories about my life and family. The overwhelming response from strangers fueled my fire and ability to peel back my layers even more. The more work I published; The more my social presence grew; The more speaking engagements I booked; The more brand partnerships I landed; The more comfortable I became with clearly communicating my truths. Like many writers, I use humor as levity but I am not afraid of baring my soul.

I struggle with the pressure to always be creating to remain relevant. I battled (and still do) with impostor syndrome. I have a hard time with rejection or if something I have poured myself into, doesn’t come to fruition.

Then I remind myself how lucky I am to be doing something I love and cultivating something I am proud of. I always thought working for myself would be easier than the high demands from my time in corporate America. It’s so much harder. If I don’t create, I don’t make money. I’m a one woman show doing everything by myself – the writing, the social media, the pitching, the IT support, the website content. I don’t clock out at 5pm. I’m doing all of it in between shuttling my kids around, cooking 752 different meals a day, and navigating offensive amounts of laundry.

I am my brand and it feels overwhelming a lot of the time and the lines between my personal and professional lives are blurred. I have such a profound appreciation for the people who have joined me on this unconventional journey and even take the time to engage with me sharing their own stories.


If you had a friend visiting you, what are some of the local spots you’d want to take them around to?

I will always choose to eat every chance I get. So, aside from the obligatory beach visits (because that’s what everyone who visits Florida wants to do), I would pack our time with crazy amounts of delicious food.

I have places I love in Dade, Broward and Palm Beach counties and I dream about many of the dishes they serve.
In Miami, we would hit Prince Street Pizza and Miss Crispy Rice for more casual bites during the day. Then we’d kick it up a notch at Stubborn Seed because pretty much everything Chef Jeremy Ford puts on a plate is magical. In Fort Lauderdale we’d need two dinner seatings. The first at Heritage and starting with the Black Mushroom Arancini. The second at Takato for some of the best sushi I have ever had. Might even splurge and do the Omakase. In Palm Beach County, we’d wander around Mizner Park and grab dinner at Kapow followed by the late night cookie bar at Mo & Ma Bakery. The next night we would go to the always fantastic Buccan in Palm beach or Akira Back in the Rey Hotel, a new favorite spot of mine with creative and delicious sushi and other asian-inspired dishes. We’d seal the deal with another round of cookies from Blueprint Cookies.

That’s just the shortlist 🙂


Who else deserves some credit and recognition?
It all started with my mother. She’s made of moxie, wit and the best heart I know. She’s loyal, honest, and as real as it gets. My mom taught me to embrace everything about myself. It just took me until my 40s to truly understand what that meant. She’s magnetic and hilarious and has always shown me unwavering support. I am the mother and woman I am because of her and every bit of feistiness she instilled in me from day one. All of that spilled into my career as she cheers me on every single day. I am able to be real and raw because of the path she paved and I will be grateful for the rest of my life.

Website: www.whineandcheezits.com

Instagram: www.instagram.com/whineandcheezits

Linkedin: https://www.linkedin.com/in/rachel-sobel-88a1102

Twitter: www.twitter.com/whinecheezits

Facebook: www.facebook.com/whineandcheezits

Other: Tik Tok @Rachel.Sobel.Writes

Image Credits
Katharine Defalco Skolnick, Defalco Design

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