Living Boldly with Emily Ley

By Kelly MacLeod Photos by Kate Treick Photography

Emily Ley, entrepreneur and author, is an example of what it means to live boldly. Known for her Simplified planner brand — creating planners and paper goods for busy women — Ley’s journey transcends business success. Her story is one of courage, values-driven leadership and finding voice in challenging times.

SIMPLICITY WITH INTENTION

Emily Ley’s Simplified brand is often described as a planner company, but as she explains, it’s much more.

“We make planners and paper goods for busy women,” she said, but the heart behind the brand includes a passionate team that allows her to focus on her first love: writing. Ley’s writing spans lighthearted topics like “finding the best most comfortable jeans” to weightier issues such as public policy and women’s rights.

This blend of simplicity and depth reflects Ley’s approach to life and business: Focus on what matters and don’t lose sight of your values even amid complexity. Simplified itself is expanding, reintroducing wholesale and retail partnerships and diversifying product offerings. Yet, Ley remains grounded in living boldly by prioritizing purpose over ease.

COURAGE IN ACTION

Ley’s boldness became nationally visible when she and her company challenged tariffs that had a heavy impact on Simplified. It was a move that invited intense media scrutiny, political assumptions and personal risk. But Ley tried to approach it with a steadfast resolve grounded in facts, not feelings.

“I just kept seeing so much misinformation on the internet; I was seeing a lot of misinformation, people not understanding what tariffs were, or who was paying them,” she said. “And so I decided to share the facts of here’s our experience owning a business and paying tariffs.”

Unexpectedly, that post on social media went viral. Ley said there were overwhelmingly positive responses and people truly wanted to understand the information. She was not being political; she was simply sharing the impact on her business and her team.

“This isn’t red or blue. This isn’t Democrat or Republican, this is about the Constitution,” Ley said. “There are so many American dreams that are going to be lost because of this.”

When a constitutional law nonprofit invited her to sue the administration pro bono, Ley explains the gravity of this decision: “If we do this, this is going to be a before and after moment … making a social media post is one thing, deciding to sue the President is another thing.”

Still, Ley leaned into the fear.

“I talked to my team, my husband, and everybody was really supportive, and then it was just kind of a no brainer — of course, yes.” Her children watching her, she said, added urgency and meaning. “You have this unbelievable opportunity to stand up for what’s right. Are you going to do it?”

The lawsuit — which is currently on hold since another similar case is already at the Supreme Court — has brought some national attention and some backlash, but overall, Ley said the response has been positive.

“This is because we believe in the Constitution, and we believe in the law, and the negatives have been few and far between. I’ve had so many people reach out in the most positive, encouraging way from both sides of the aisle.”

LIVING BOLDLY
AS A WHOLE PERSON

Ley does not hesitate to live “out loud,” embracing both the joyful and the difficult realities of life. She has written several books and is enjoying focusing more on writing.

“Getting older and having a little more experience and wisdom under my belt, it’s been really fun to explore that writing-wise,” she said.

Balancing a demanding business and family life is another area where Ley practices bold living with grace. She rejects the myth of perfect work-life balance — describing it instead like riding a bike: “You’re constantly shifting your weight from left to right … if you lean too far one way too long, you’ll crash and burn. So you keep doing that back and forth and you’ll be all right.”

LIVING BOLDLY AND OVERCOMING FEAR

One of the most popular contemporary authors who writes about bravery is Brené Brown. In her 2021 best-seller “Atlas of the Heart,” Brown explores how to live boldly despite fear and uncertainty. The book is a profound roadmap for understanding and navigating feelings, empowering readers to face vulnerability as the foundation of bravery.

Living boldly, Brown argued, is not the absence of fear but the willingness to move forward in spite of it.

“Vulnerability is not winning or losing; it’s having the courage to show up and be seen when we have no control over the outcome,” she wrote.

Brown’s extensive research highlights how fear often masquerades as safety, leading people to build walls that isolate rather than protect. To live boldly, she encourages developing emotional literacy — the ability to name and understand your feelings.

“Connection is why we’re here; it is what gives purpose and meaning to our lives,” she wrote. Risking vulnerability to form deep connections is a hallmark of living boldly.

Overcoming fear requires confronting discomfort head-on. Brown acknowledges that “leaning into the discomfort of vulnerability is where the magic happens.” It is through accepting imperfection and uncertainty that individuals discover strength, creativity and freedom.

The lessons in “Atlas of the Heart” resonate in today’s fast-paced, often disconnected world, reminding us that courage is a daily practice. By cultivating self-awareness, empathy and courage, readers can transform fear into fuel for meaningful action.

In essence, Brown offers this message: Living boldly isn’t about having no fear, but about showing up with an open heart and embracing vulnerability.

Emily Ley’s life and leadership offer a vivid example of what it means to live boldly: with clarity, courage and authenticity. Her journey is a reminder that bold living is both a choice and a practice, involving moments of fear, growth and resilience. As she continues to expand her work and her voice — whether through new product lines, writing or legal advocacy — Ley inspires boldly living with intention.

“I talked to my team, my husband, and everybody was really supportive, and then it was just kind of a no brainer — of course, yes. You have this unbelievable opportunity to stand up for what’s right. Are you going to do it?”