Life Lessons Inspired by Anne of Green Gables

I Recently finished watching Anne with an E, and I must admit that the story left me rather reflective than simply entertained. It tells the story of an orphan girl who is blessed to find a home at Green Gables. Her character becomes almost a lens, through which we consider courage, imagination and integrity.

Anne’s story takes place more than a century ago yet her perspective feels surprisingly relevant, and I am writing this piece while my own reflective thoughts and emotions are still lingering.

Anne Shirley has a remarkable way with words, but more importantly, she has a remarkable way of perceiving the world. Set in the late 1800s long before modern society even existed, Anne still manages to inspire and embody change.

She has the courage to be herself and to speak her mind. She believes in her dreams with disarming sincerity. Intuition guides her in every action, rather than fear of rejection. Although, like many of us, she experiences, moments of vulnerability and doubt along the way.

Watching her made me reflect on how we navigate our own ambitions today. Because in many ways, entrepreneurship, and life itself, is not so different from Anne’s journey. It all begins with imagination.

The Courage to Imagine Something Different

Anne’s greatest strength is her imagination. She refuses to accept the world exactly as it is presented to her.

If Anne were mentoring a founder, I imagine she might say something like:

“One must always allow a little room for imagination. Otherwise the world becomes terribly small.”

Innovation begins in exactly the same place. Every business, brand, concept, or idea begins as a quiet thought that most people dismiss as unrealistic. Yet imagination is often the foundation of progress. Without it, nothing new would ever be created.

Authenticity as a Compass

Anne rarely adjusts herself to fit expectations. Sometimes it leads to success. Other times it leads to growth. But she never abandons who she is. In life, and in business, we often feel the pressure to follow formulas, strategies, or trends. Anne would likely disagree.

“It seems to me that the most wonderful thing as a person can do is simply be themselves — especially when the world expects otherwise.”

Authenticity is not just a personal virtue; it is also a strategic advantage. The most memorable brand, ideas, and leaders are rarely those who imitate others. They are the ones who reveal something true.

Photo Lummi.ai

The Invisible Work Behind Beautiful Things

Anne’s life is full of romantic imagination, but it is also full of effort, learning, and resilience. There are failures, misunderstanding, and moments when the world seems determined to test her optimism.

Entrepreneurship can look very similar from the inside. “Lovely things rarely happen all at once,” Anne might remind us. “They grow slowly, like gardens, if one has patience enough to tend them.”

The most meaningful work often happens quietly behind the scenes, long before anyone notices.

Believing Before Proof Exists

Anne has an extraordinary ability to believe in possibilities before they are visible. In the world of business, this may be one of the most valuable qualities a person can have.

Before a brand is recognized, before a product is launched, before the audience appears. Someone must believe in the vision first. “It is not foolish to believe in something wonderful,” Anne might say. “It is the beginning of making it real.”

Following what Feels Right

Perhaps the most powerful lesson Anne offers is her relationship with intuition. She does not make decisions purely based on logic or approval. Instead, she moves toward what feels right in her heart, even when it is inconvenient or misunderstood.

That lesson feels particularly relevant today. In a world filled with strategies, metrics, and constant comparison, intuition is often the first thing people silence. Yet it is frequently the most reliable guide.

I’m not underlining the importance of strategy. Strategy matters. But strategy also needs to feel aligned, and Anne reminds us of something fundamental.

Imagination matters.

Authenticity matters.

Belief matters.

And sometimes the most powerful thing we can do, whether in life or in business, is simply to trust the voice that is quietly speaking to us.

Perhaps we could all benefit from being a little more like Anne.