Singer/songwriter Lisa Loeb has an independent streak that has served her well ever since she graduated from Hockaday in 1986. She was the first pop musician to have a No. 1 single while not signed to a recording contract. She followed that hit song, “Stay (I Missed You)” from the film “Reality Bites” in 1994, with six albums, including two that were certified gold. Loeb also created five children’s albums. “Feel What U Feel” won the Grammy for Best Children’s Album in 2018. Her latest release, “A Simple Trick To Happiness,” releases Feb. 28. Known for her cat-eye glasses, the entrepreneurial musician parlayed that passion into Lisa Loeb Eyewear.

What are your memories of Hockaday and Preston Hollow?

I went to Hockaday for 11 years, so I have a lifetime of memories. I used to love performing in the school plays at St. Mark’s, singing in the spring performances in third grade with the class, eating the famous cornbread and the doughnut cakes for our birthdays. I loved going to Write Selection and picking out stickers, the Container Store to pick out supplies and different colored plastic boxes to personalize with dottie letters. I loved buying needlepoint at Stitches and Patches, spending summer days in the library on Walnut Hill near Preston and going to summer camp at St. Mark’s Day Camp and Hockaday tennis camp.

What accomplishment are you most proud of in your career?

I’m proud of writing so many songs and continuing to evolve as a storyteller. I am also proud of my amazing fan base. Knowing they are listening and feeling their support really energizes me.

What is the most challenging thing you’ve overcome?

The most challenging thing in my career is the changing music industry. All of the work that a record company used to do now falls to a small team of people and the musician who’s also creating, recording and performing the songs live. I enjoy looking at the creative and the business side of things, but it’s also time consuming and sometimes hard to focus on so many different things at once.

What misconceptions do people have about your industry?

People think that the music industry is always glamorous, and there is that element, but it’s also a grassroots, hands-on business environment in which you have to be very involved to succeed.

Besides work, what are you proud of?

I’m proud of my family — my husband and two wonderful children. They are so kind and interesting, curious, funny, smart and a bunch of other adjectives too. Being able to balance my family with my work is no small feat. It’s always evolving, but I’m proud of the place that we’ve been in for years.

What is the best advice you ever received?

When you’re trying to do something involving others that you really want, don’t let them say “no.” A “maybe” is OK, but don’t let them say “no.”

[youtube] What is the best gift you ever received?

A jewelry/music box that plays “Rainbow Connection.” My husband and daughter gave it to me on an anniversary.

Who is your greatest influence?

I love writing teacher Natalie Goldberg, author of “Writing Down the Bones.” Growing up, I did well in school, but I wasn’t always encouraged to find my own voice. She has helped me get out of my own way so that I can write without editing my thoughts before they have a chance to be. It’s important to be yourself when you’re creating, because that sets one artist apart from others.

What advice would you give to someone who wants to go into your field?

Do the thing you say you want to do. If you want to be a singer, then sing, or a writer, then write. Also, always keep learning to do what you do better.

Have you experienced gender discrimination?

I’ve experienced some gender discrimination when it comes to radio in the ’90s. Women musicians would often hear that a radio station didn’t want to play your song because they were already playing a song by another woman.

What apps or gadgets do you find to be essential at work?

I need my iPhone, ear plugs for sleeping when traveling, MacBook Pro and a pad of paper and fast writing pen. I love the voice recorder on my phone for music ideas, TwistedWave for voiceover auditions, and the New York Times app for reading.

How do you relax?

I like reading, doing crossword puzzles, watching TV shows with my husband, hanging out with my cat and reading with my kids.

Given $1 million, how would you spend it on our community?

I’d love to spend money on underserved kids and their education. I have a foundation called The Camp Lisa Foundation that sends kids to summer camp who can’t afford to go. Summer camp is a place where kids learn about themselves and how to be members of the community, take chances in a safe space and have fun. It impacts their entire life.

How would you like to be remembered?

Professionally, I’d like to be remembered as someone who helped people feel empowered to have their own voice, to have and express their feelings, and to tell their own stories and understand the value of their own experiences.

This interview has been edited for clarity and brevity.