The Scariest Thing I Ever Did: Taking the Leap With Self-Employment

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Howley (right) in Vietnam. (Photo by Ann K. Howley)

The scariest thing I ever did was quit my job.

For more than 20 years, I worked at an accounting firm. It was a good job. As a young, divorced mom, it allowed me to pay the bills and take care of my two children. But I was not happy, even working in a stable, secure job. It was not what I wanted to do and the longer I stayed, the more anxious I became. A pit of dissatisfaction kept growing in my stomach.

I always wanted to be a writer, and for years, I had stories bouncing around in my head that felt like pinballs that were going to burst out of me.

So, I quit my job.

After being single for many years, I had recently remarried. For the first time in my life, I did not have to live hand to mouth. What a relief it was to know that my kids and I were going to be OK if I left my job. So, with my husband’s encouragement, I quit doing what I didn’t want to do and started doing what I always wanted to do. As terrifying as it was, I created a new me. It was the best thing I ever did.

After I quit, I wrote my first book, a humorous memoir, “Confessions of a Do-Gooder Gone Bad,” and started writing for Pittsburgh Parent magazine. I wrote my first young adult novel, “The Memory of Cotton,” which has won numerous awards. At present, I am close to finishing my second novel, a fun, speculative, middle-grade fiction book.

Over the past 10 years, I have learned a lot of unexpected things about myself. It surprised me when I received invitations to speak at various events and conferences, but the biggest surprise was that I loved doing it. I also started hosting writing seminars and teaching writing classes for the Community College of Allegheny County’s (CCAC’s) community education program. I am so proud when my students go on to successfully publish their books.

As I look back, my heart fills with gratitude because being self-employed has not only provided me with an opportunity to grow, but it has given me the freedom to do other things that bring me joy.

My husband and I stay very active. I have run 20 marathons. (My husband, Pat, has run 25.) We have ridden our bikes on the 335-mile Great Allegheny Passage and C&O Canal trails to or from Pittsburgh and Washington D.C. four times. In 2021, we bought an empty cargo van and built a campervan, which we named The Paddy Wagon, and in the last three years we have made three cross county trips and traveled more than 80,000 miles in the van with our two dogs. I currently teach two other enrichment classes at CCAC: Bicycling from Pittsburgh to D.C. and Vanlife: How to Build and Travel in a Campervan.

We have taken two transatlantic cruises and have traveled to Thailand, Korea, Vietnam, Italy, Spain, Mexico and Morocco, which is why I study five languages every morning (Chinese, Korean, Italian, Spanish and Thai), which I never would have had time to do if I were still working full time.

However, the greatest joy of my life is having the time to spend with my grandbabies. We have three granddaughters all under the age of 4, and our time with them is precious.
“Bonnie, do you want me to play with you?” my daughter-in-law asked her 3-year old.
“No. I only want to play with Nai Nai,” she replied, referring to ME.

Do you hear me making a squeeing sound?

The truth is that having the courage to reinvent myself and have a successful and fulfilling career as a writer, speaker and teacher has allowed me to enjoy being a wife, mother, stepmother and grandmother
even more.

So, the next time I contemplate doing something terrifying, I will remember that sometimes the best things in life come from scary places.

Ann K. Howley says that writing for Pittsburgh Parent magazine has been one of the greatest blessings in her life. Find out more about her books and activities at annkhowley.com.

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