Tough Love From a Self-Help Writer

self help writer
Lisa Cleary, Photo: Desiree Ortman Photography

For many of us, it’s safe to say that just thinking about our most embarrassing moments or worst meltdowns can put our stomach in knots and make us wish that the memory eraser from “Men in Black” actually existed. But as a tough love self-help writer, Lisa Cleary’s entire job is based on recounting those memories that others would rather lock up.

“My work is inspired by anything challenging in my life, I actually work best when I’m sad,” she says.

As she’s gotten older, she’s taken on the more difficult moments in her life that made her feel alone and isolated. “I write on situations that resonate with people so they can say ‘Oh her too, I’m not alone.’”

Cleary, a Baltimore native who’s written for NBC, TODAY, HuffPost, Women’s Health, and The Financial Diet, gravitated towards self-help after writing health pieces for NBC in 2011.

“I found that people always want to improve themselves, and it applies to pretty much every area of someone’s life,” she explains. “For me, I really enjoy writing about people and how to improve our interactions with one another.”

Read: From Gowns to Masks

“Tough Love”

self help writer
Photo: Desiree Ortman Photography

As she began reading more about self-help, Cleary found areas where she wanted to fill the holes and improve on what had or had not been said. To her, the industry had a tinge of toxic positivity about it.

“I see a lot of entitlement these days, and it’s really bothersome to me because we can manifest what we deserve. But we also have to process our emotions and ourselves and put in that hard work,” she says.

Many writers seemed to only want to talk about the goal of self-improvement instead of how to actually reach it. Goals can easily be set. But Cleary points out that without the necessary steps put in place, it’s difficult to accomplish them.

“I write about my meltdowns and my awkward moments to show the more realistic side of self-improvement, and that’s where the ‘tough love’ comes into my writing. No one wants to talk about the low points or where you have to start, but everyone has conflict and sadness and self-loathing, and that’s natural,” Cleary says.

What counts as self-care? Read: How We Get Self-Care Wrong

Turning a Breakdown into a Book

Accepting yourself and your imperfections is exactly what she hopes will resonate with people in her new book, How to Survive a Breakup: When all of your friends are birthing their second child. This debut work follows Cleary’s real-life meltdown at 31 after an intense breakup, a massive layoff, and two unanticipated moves.

“I went through my own rock bottom,” says Cleary. “I was single, unemployed, homeless, had a good amount of debt, and the funniest part was that I was a self-help writer

She felt like she was moving backwards as compared to her friends who were married and having kids, and because of that she felt incredibly alone. “People sympathized but couldn’t necessarily understand,” she explains. “I needed a sounding board but didn’t have someone to talk to.”

self help writer
Photo: Provided by Lisa Cleary

That’s why she decided to write her book, to give people in her situation the kind of support they might not have. Because the book was written while Cleary was going through everything, it captures the in-the-moment raw emotion that comes with disaster and breakdowns, and follows her from the first steps she took to building herself back up.

The Toxic Milestone Mentality

Though she thinks anyone could get something out of her book, Cleary is generally marketing it to women because of what she calls the “toxic milestone mentality,” or basing one’s happiness on goals to tick off a checklist.

“There’s a lot of pressure on women to have a home, career, family and balance it all,” Cleary says. “It hangs over our heads no matter where we are in life, and if we stick with this mentality we’ll never have enough because we’ll always want the next best thing.”

She hopes to show women that getting laid off or not having a partner in your 30s doesn’t mean you’ve failed. Though Cleary wants marriage and kids, she now wants it when the time is right for her.

“I want to encourage people to know that happiness shouldn’t be sacrificed for what they think they should have,” she says. “Being single isn’t the worst thing life can hand you. My greatest fear used to be being single, now it’s to experience life and its transitions, and complain about it the entire time. Why would you want to hate your life along the way?”

“How to Survive a Breakup: When all of your friends are birthing their second child” is now available in print, and the Kindle version will be released on Aug. 22. To learn more about Cleary and read her work, visit her website at and follow her on Instagram @lisacleary3.

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