Getting ‘Scary’ turned out to be fortuitous for Jill Smokler.

Jill Smokler, a New York Times bestselling author, entrepreneur and social influencer, always knew she wanted to be her own boss.

What she didn’t know was that her once-small mommy blog would become her golden ticket. As the founder of Scary Mommy, one of the country’s most influential parenting websites, Smokler spent a decade sharing with the world the highs and lows of parenting.

“When I started writing the blog, people weren’t entirely honest about how difficult motherhood could be,” says Smokler, 41, of Pikesville. “In general, parenting is difficult and we want to have a village of people we can feel support from. People were hungry for someone to be real about what it was like, and I filled that void.”

While Scary Mommy ultimately became a website with a following of millions of parents, Smokler started the blog in 2008 when her youngest son was just 3 months old as a way to chronicle her days as a stay-at-home mother and post photos for her family and friends.

“I began the blog as a hobby,” says Smokler, whose three children are now 15, 13 and 11. “It was before Facebook and Instagram, so it was a place for me to post cute pictures of my daughter and two sons. I started the blog not really understanding what blogging was or that anyone not related to me would be interested in it, but within the first year I realized I could really expand.”

A graphic designer by trade but an entrepreneur at heart, Smokler quickly created herself a website, brought on contributors to write about experiences foreign to her, and with the help of her middle son, coined the name Scary Mommy.

“I didn’t come up with the name in a calculated way,” says Smokler, who graduated from Washington University with a degree in graphic design. “At the time, my middle son who was 2 was scared of a Disney movie and started referring to everything around him as scary — including me — who he called ‘Scary Mommy.’”

Shortly after Scary Mommy took off, Smokler partnered with Target for an online makeover project and was asked by a literary agent to write a book.

“I don’t consider myself a writer, so I initially said no. But the agent told me writing a book was like writing blog posts on paper, so we put together a proposal,” says Smokler, of her bestseller, “Confessions of a Scary Mommy,” which was published by Simon and Schuster in 2012. “That first book was such a high. I got to do talk shows, interviews and a book tour. It was an exciting and magical time.”

It was also around that time that Smokler started a nonprofit, which helped families afford meals for Thanksgiving and birthday parties for kids.

“Someone had confessed on the site they couldn’t afford Thanksgiving dinner,” Smokler says. “The community rallied together in what I thought would be sponsoring a handful of meals, but we ended up sponsoring more than 150 meals. It was magical to see people come together and do nice things for others.

In 2015, Smokler, who has since written two other books, sold Scary Mommy to Some Spider Studio, where she worked as chief content officer until 2018. Now, she’s looking towards the future as her professional and personal life shift gears.

“I have an interesting story on how my career evolved,” says Smokler, who was named by Forbes magazine in 2017 as one of the top-10 parenting influencers. “There are things I would do over and things I would change. That, coinciding with my husband coming out of the closet and the ramifications of that, mean the last few years of my life have been a bit of a whirlwind. It’s entertaining and could make for a good memoir or pilot. I also plan to start a podcast in the next few months.”

Smokler says she has a lot of ideas for what’s next and will be just as passionate about her new venture as she was about Scary Mommy.

“What I built was something I loved, benefited from and really used as a consumer,” says Smokler. “You have to make sure you attach yourself to a business you really love and are committed to because it’s a lot of work. For me, Scary Mommy was my sanity when my kids were little. It’s where I went if something funny happened or I needed to vent. It was my lifeline.”

Aliza Friedlander is a Baltimore-based freelance writer.

Join Jmore for our 2nd annual celebration of Baltimore’s Jewish Entrepreneurs — JBiz Entrepreneur — on June 4 at the Maryland Historical Society.