The Anti-Loneliness Entrepreneur: Margaret Oliver’s Mission to Help Women Dream Again

Crowded rooms do not protect people from loneliness. Margaret Oliver learned that early, long before community theatre, financial education courses, or her bookstore became the extension of her larger mission to reconnect people with one another. Years spent rebuilding friendship through changing chapters of adulthood taught her that connection is something people must actively create, practice, and more importantly, protect.

“I went through my own loneliness experiences, and I realized pretty quickly that if I was going to have a social life, I had to go out of my way to be involved,” she says.

Raised as what she calls ‘a relative extrovert raised by introverts,’ Oliver highlights that she learned early that connection required participation. Her family valued privacy, and inviting friends home was rarely encouraged. That reality, she adds, pushed her toward extracurricular activities, sports, and community spaces where relationships could grow naturally through shared experiences. “You’re participating with people for something bigger than yourself. That’s how you build a connection,” she says.

Those lessons followed her into adulthood. Marriage brought relocation after relocation for her spouse’s career, forcing her to repeatedly rebuild social circles from scratch. Later came the realities many adults quietly carry: grief, distance, aging, and friendships altered by time. “People pass away. People move away,” she says. “How do you make sure you’re not isolated because of those circumstances? You reconnect. You find new ways to make friends as adults.”

It’s within this mindset that Oliver shapes nearly every part of her work. Through volunteer efforts with community theatre, educational initiatives, and her bookstore, Oliver has built an ecosystem rooted in storytelling and human connection. Community theater became one of the clearest examples of that mission in practice. Oliver notes that volunteering introduced her to people from every generation and reminded her that meaningful relationships are not limited by age.

“Sometimes, you have to make friends with people younger than you, or older than you,” she says. “Everyone’s at different stages of life, and they have so much to teach you.” She recalls meeting a widower at a local event who simply needed someone willing to listen after losing his wife. Their conversation eventually turned toward volunteer work and ways he could reconnect with others through creative collaboration.

She says, “This is one of the approaches I have toward dealing with loneliness. It’s one person at a time, one story at a time.”

Listening, she believes, has become a lost social skill.

“I would like to be an advocate for listening,” she says. “Deep listening with strangers really matters.”

Books became another pathway toward that mission. A lifelong reader, Oliver believes literature shaped her imagination and her understanding of people. Historical fiction, philosophy, cookbooks, mysteries, science fiction, and classic novels filled her shelves over the years, eventually turning into a personal archive she felt compelled to share.

That collection later evolved into TJ Oliver Books, a bookstore that encompasses educational and thought-provoking titles. According to Oliver, the name carries emotional significance. “Tomson Jane, that’s the name my parents intended to name their child before discovering they were expecting two daughters instead of one,” she says. “It was my way of bringing that name into the world somehow.”

The bookstore also reflects Oliver’s desire to support workers and local communities. Drawing from her experience as a union steward, she created discounts and community-centered incentives for union members while also exploring partnerships with independent authors seeking alternatives to larger publishing systems.

“It allows me to reach out potentially across the globe. Not just my own backyard,” she says.

Financial literacy forms another pillar of Oliver’s broader educational efforts. She highlights that her interest in the subject grew from watching capable, hardworking adults struggle because they lacked access to financial knowledge. “My parents were good people. But they really did not understand finances very well, and that caused a lot of grief,” she says.

As she educated herself over time, Oliver notes that she recognized similar struggles everywhere around her, particularly among women balancing caregiving responsibilities, careers, children, and aging parents simultaneously.

“I feel like the people who are the most squeezed are probably the people who need the information the soonest,” she says. Through courses hosted on her platform, Oliver focuses on practical financial education designed to help women make informed decisions about banking, retirement preparation, and long-term financial planning.

Her ulterior objective lies in offering tools for empowerment, facilitated by economic improvement. “I think a lot of women feel like they only have one structure available to them,” she says. “I want people to realize there are other ways to build a future.”

Oliver’s vision for the years ahead includes expanding educational programs, growing collaborative teams, supporting local writers, and building stronger community-based systems where people can share resources and opportunities together.

At the heart of all of it remains one belief Oliver returns to often: people become stronger together. She says, “Don’t let political climates make you feel helpless. You’re not helpless. And you’re less helpless the more you’re with people.”