Lisa Loeb was in uncharted waters when, in 1994, “Stay (I Missed You)” rose to the top spot of the Billboard 100 chart. Loeb became the first artist without a record label to accomplish that feat. Looking back, she said she never imagined the music industry veering in a direction where many artists prefer to make and release music themselves.

“It always it resonated with me that you should always have an independent streak, for sure,” she said in a call from Los Angeles last week. “You should always have a relationship with your fans; you should get their information so you can let them know what you’re doing. You should always make music that you believe in and not get conned to make music that you don’t want to because it’s the corporate thing to do.

“So I’ve always felt strongly about that. But I never imagined that we could sell music directly to fans, even without having actual physical copies of the music that we were making. I mean, that’s shocking. It’s really amazing to me. The problem with it is, it’s hard to monetize and it’s important for musicians to be able to make a living. But aside from that, it’s pretty amazing that you can have so many different relationships with your fans, make music and share it so easily.”

Lisa Loeb was able to turn the success of “Stay (I Missed You)” into a successful 25-year career in the music industry and on Feb. 28, she’ll release her 15th album, A Simple Trick To Happiness, on her own label, Furious Rose. In that time she’s also become successful writing children’s books and music (winning a Grammy in 2018), helped compose the songbook for New York musical production “Camp Kappawanna,” started a charitable organization that sends kids to summer camp, runs her own fashion eyewear line, acted on TV and is married with two children of her own.

A Simple Trick To Happiness is the 51-year-old’s attempt to write less cryptically while keeping the songs as personal and poetic as ever.

“I went through a phase where I saw some other songwriters writing songs that were personal but sounded like they were literally dumped from their journals,” she said. “I didn’t feel they were crafted. So I had this sort of feeling that I was against people who write things that are too personal. But then I realized there was a way to get the best of all worlds, and that’s my goal.”

The songs present relatable challenges alongside affirmational and empowering messages and reminders to help each other and ourselves. Moody single “Skeleton” is about repairing broken friendships. “Tell your new friends where we’ve been/ That we’re not just a skeleton,” Loeb softly sings.

Piano ballad “Another Day” takes on inevitable and bittersweet change—”But everybody knows that life can change like the weather/ And everybody wants the things they know to stay the same/ But we’re not gonna last forever.”

There’s a rollicking rocker about deciding to prioritize the good over the bad in life, “This Is My Life,” and a meditative acoustic-guitar-tinged tune, “For the Birch,” about not letting life wear you down by taking it one step at a time through hardships.

One of the highlights is the exuberant “Sing Out,” which Loeb specifically wrote to perform at a Nashville gay pride event. The song, which she wrote with L.A. singer-songwriter Eric Lumiere, was inspired by inspirational sing-alongs like “I’d Like to Teach the World to Sing (In Perfect Harmony).”

“I’ve written in so many different ways, in so many different songs, about being yourself,” she said. “I just think it’s so important for people to be themselves to be proud of who they are. And in in the LGBTQ community, especially, it’s so important for people to feel comfortable to be themselves. There’s been so many places, and there are so many places, where they’re not allowed to be themselves.”

Loeb said she plays at many political events, fundraisers and charity events for causes in which she’s invested.

“I show up and they want me to play my music and so I’m up there playing ‘Stay’ and a lot of love songs, and it just doesn’t feel right,” she said. “I don’t get to be in the moment of how I’m feeling. … I realized I need to start writing songs that feel right for some of these occasions where I get to be up there in front of a community … and sing something that really feels right for the occasion.”

The only type of song Loeb said she hasn’t figured out how to write—yet—is a political one about what’s going on in the U.S. right now.

“I do feel passionately about what’s going on in the country and that I would love for there to be some big changes in our government,” she said. “And I think that we have a president right now who is not very smart or kind or strategic or diplomatic. He’s sort of against everything that that my family stands for and that my values stand for. To be able to craft a song like that is complicated, so I try to do other things to make a change at the moment.”

The album opens with “Doesn’t It Feel Good,” with Michelle Branch singing backing, about a broken relationship. It’s representative of the album as a whole with an empowering message about being strong and willing to make changes in one’s life.

“It’s a song about taking your own life into your own control—with respect,” Loeb said. “Some people forget that they can make a change in their life.”

Then there’s “I Wanna Go First,” which Loeb said she wrote in a sardonic mood. She and producer and co-writer Rich Jacques had been joking about writing a bunch of “depressing love songs,” and this bit of dark humor came out about wanting to die before your significant other. “Eaten by zombies or swallowed by sharks/ If there’s anything left, they can use my good parts,” Loeb sings with an earnest delivery. The music is mournful while the lyrics would fit the likes of Fall Out Boy.

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As Loeb prepares to release A Simple Trick To Happiness, her first “adult” record in seven years, she’s still active in her other musical pursuit: writing children’s songs. In fact, she called shortly after finishing a studio session for Amazon Prime show “If You Give a Mouse a Cookie,” which is based on the children’s book. She and a partner write the songs sung by the characters, as well as the soundtrack versions available online. She just finished work on the show’s third season.

She began writing children’s music long before she and music industry exec husband Roey Hershkovitz had children of their own. The original inspiration was her nostalgia from kids’ programming from when she was a child.

The style and genre allow her the freedom to pursue writing about different subjects, such as first day of school experiences, which carry a lot of emotions for younger listeners.

“There was a sense of humor and heart and storytelling,” she said. “Then I had kids, and I started making stuff that was a little bit more like kids music. I realized kids also want to hear the ABCs.”

Her latest children’s album, Feel What U Feel, won the 2018 Grammy Award for Best Children’s Album, which means a lot to Loeb, herself a voting member of the Recording Academy. Artists in the field take their jobs—to craft songs of the highest quality as well as wholesome and educational—very seriously.

That’s important to Loeb as a parent, as well. Her children, who are 7 and 10, are exposed to a lot of music by her, her husband and by their peers. But Loeb has mixed feelings.

“They listen to things that might be explicit or where people are expressing themselves in a way that I normally wouldn’t [want them to hear],” she said. “I’m kind of strict about words that they are using. I know words are just words, but still I feel like they can find better ways to express themselves.

“There’s certain subject matters that that I think [are] a little too early to have kids being involved listening to,” she said. “We also try to be fairly open with our kids when it comes to art, but it’s like a fine line. You have to make sure your kids are mature enough to listen to things.”

Follow editor Roman Gokhman at Twitter.com/RomiTheWriter.