Featured Entrepreneur of the Spirit: Dorothy Day

Sometimes, we can idealize the saints and think it’s impossible to aspire to their level of holiness. But the call to holiness is universal—meaning that each person is created to become a saint. This goal is attainable with the help of God’s grace. 

Dorothy Day, who is now in the process of canonization, understood this universal call to holiness quite well. Despite her dark past and struggles, she held firm to her faith in Christ and allowed Him to use her in tremendous ways. A bold Entrepreneur of the Spirit, Day made a major impact on the Church and society. We want to share some of her founding story with you here…

Restless Beginnings

Dorothy Day’s early years can be characterized as a restless search for purpose and true fulfillment. She was born into an Episcopalian household in 1897, but lacked authentic formation in the Christian faith. Drawn to activism from a very early age, she had a deep desire to serve the poor and marginalized members of society. She became a successful journalist in New York City, where she was well-known and respected for her literary prestige. She eventually became an atheist, an outspoken proponent of communism, and embraced a wild and promiscuous lifestyle in the 1920s. She went through a very dark personal period where she had several affairs, drank frequently, had an abortion, and attempted suicide. Dorothy eventually entered into a common marriage with a man who was an atheist and anarchist, and she gave birth to her daughter, Tamar, in 1926. 

Radical Conversion 

The birth of her daughter served as a catalyst for Dorothy’s journey toward the Catholic faith. She became drawn to spiritual things, reading and learning all she could about the Faith. This led her to eventually be baptized in the Catholic Church alongside her daughter. 

Even after her conversion, Dorothy was still drawn to radical causes and wanted to find a way to integrate her radical desire to serve the poor with her Catholic identity. She began utilizing her literary skills for the Catholic Church, writing for Catholc magazines and newspapers. 

Catholic Worker Movement

In the early 1930s, at the height of the Great Depression, the Catholic Church struggled to develop a clear response to atheistic communism in a way that focused on human dignity and the plight of workers. With her familiarity with communism and her newfound Catholic identity, Dorothy was able to spark a movement that proclaimed the truth about the goodness of both communal life and the dignity of work. 

In 1933, in the midst of 25% unemployment in the US, with the help of a man named Peter Maurin, Dorothy founded the Catholic Worker newspaper as a means of communicating the truths of the Catholic faith to modern society. If there was ever a time NOT to start a scrappy newspaper, this was it. But she felt called to begin the work and so she did.

Here are some of the ingredients of how she did it:

  1. Spiritual Routine 

Dorothy Day had a regular and disciplined spiritual routine that kept her close to the Lord in prayer and nourished her to do the extremely hard work she took on. Here’s a snapshot of her spiritual gameplan:

  • Daily 
    • Early Rising
    • Prayer throughout the day: Liturgy of the Hours & personal prayers
    • Daily Mass
  • Weekly: Sacrament of Confession
  • Annual: Retreat
  1. Bootstrapping in the Great Depression

Peter Maurin, Day’s advisor and mentor told her once, “In the Catholic Church, money has never been necessary.” While not everyone would agree with this statement, Maurin was referring to the great movements of the Church — monasticism, the Franciscans, and others that started without investment capital, just an idea, holiness, and dependence on God. This phrase is similar to something that St. Teresa of Avila once said about herself as she founded monasteries across 16th Century Spain: “Teresa and three ducats can do everything.”  Three ducats today would be about $500, a paltry amount for any aspiring entrepreneur. Dorothy Day raised the money needed to print the first run of 2,500 issues of Catholic Worker paper — a few dollars here and there — and it grew from there.  

  1. “Just Start”

When Dorothy Day was considering starting the Catholic Worker paper and houses, she wanted to have it all figured out before diving in. Peter Maurin advised her by saying, “The important thing is just to start.” Mother Angelica, who founded the Catholic media group EWTN in 1981, said something very similar, “I have to start; if it’s not His will, it will either fall apart or something will happen to really hinder it.” Of course, this idea goes right back to the Gospel as well. In Acts, one of the Pharisees warns his fellow men about battling the early Christians too much: 

“I tell you, keep away from these men and let them alone; because if this plan or this undertaking is of human origin, it will fail; but if it is of God, you will not be able to overthrow them—in that case you may even be found fighting against God!” (Acts 5:38-39). 

Interestingly, you see a very similar approach to launching business endeavors among secular entrepreneurs today as well. There’s an emphasis on starting the enterprise, remaining close to the customer needs, and “iterating” to find “product market fit” or a “minimum viable product” that can be viable as a business venture without putting in too much money at the beginning. Thus, in starting a business enterprise today, the important thing is also just “to start.” It’s fascinating to think that Dorothy Day had this same entrepreneurial approach almost a century ago as did Mother Angelica almost 40 years ago. 

Discernment, prayer, a good plan are all important. But sometimes you just gotta start!

  1. Building Momentum 

The Catholic Worker started with 2,500 papers on May 1, 1933. By September of 1933, circulation was at 25,000. The next year it had grown to 100,000. The Catholic Worker houses, which are dedicated to promoting the dignity of human life, the goodness of work, and the service of the poor, also started popping up around the country during the 1930s, growing from the first house in 1933 to 30 houses in 1941 to over 200 houses around the world today. 

Takeaways

Dorothy Day serves as a prime example of someone who knew her world, saw the needs of her time, and conveyed the message of Christ in a way that the world could receive. Because of her life experiences and her understanding of the world and climate around her, Day was able to articulate a vision and share the truth of the Gospel with the people and culture of her time. Day was undoubtedly a great leader, but she summarized her philosophy on leadership when she said: “There is too much talk of raising up leaders, and too little of the raising up of servants.”

Today, we too have the opportunity to share our faith with the people of our time and contribute to renewal within the Church. Looking to the example of Dorothy Day, may we not be held back by our past, but choose to say “yes” to whatever needs that the Holy Spirit inspires us to address now. And by doing so, may we continue on this journey to become the saints that we are created to be.


Links/Resources for Dorothy Day

Watch a short clip on Dorothy’s life

Watch an interview with Dorothy Day