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  • Writer's pictureJohn Lim

MF 372 : Writing series: Don O'Connor ("Failing Spectacularly")

Updated: Jun 16, 2022

On this new mini-series, I speak with authors and writers, covering a wide range of genres. Today, Don O'Connor joins us to talk about his book "Failing Spectacularly" and why you should know your why before writing. More at

Moving Forward is also available on Apple Podcasts, Stitcher Radio, Google Podcasts, Spotify, and Amazon Music.

Don O'Connor

Don is an author based out of Ottawa, Canada and a self-professed "Boomer" who doesn't feel or act it. Don and I connected on Twitter and as a fellow early riser, his tweets are among the first I see when I hop on at around 5 am. As I learned in this conversation, Don has had a prolific career, over 40 years working in hospitality, retail, both in management and executive positions.

Writing journey

Don has always wanted to be a writer since his high school days where his favorite subject was English, and his early aspirations were to be a journalist. Don wrote short stories all through school, a practice that would continue well into his career. While Don didn't become a journalist by trade, he amassed over 25 years of stories from his professional and personal life; documenting them into a binder. He also started a company newsletter while working at an inbound call center. Don became a one-man publication, writing, editing and delivering his newsletter. This grit and determination led to other opportunities, including an invitation to present a proposal to the company leadership for employee success and retention. Later, Don's wife encouraged him to share his stories at family gatherings. Don found his inner raconteur, reading many of the entries from his binder.

A toast to a big step forward

After a positive response from his familial audience, Don decided to take a big step forward as a speaker. He joined Toastmasters, an international non-profit organization whose goal is to help its member improve their public speaking skills. It was here that Don found his voice, literally and figuratively. Don also became a leader, becoming club president of his local chapter.

Failing spectacularly

Don was also an aspiring stand-up comedian. Don was a natural story and joke teller at work, regularly eliciting laughs and positive feedback from his co-workers. Don decided to take his comedic act to the next level. He went to a local comedy club and secured a three-minute gig. To prepare, Don spent time rehearsing, honing his material, and getting feedback from his peers. On his debut, Don not only killed it but was told that his set was the "best three minutes of my life." He did so well that he was asked to stay after all the other acts were finished and got to speak for another 25 minutes!

Riding this wave of initial success, Don asked the club owner for a second shot and got his wish. However, as Don shares, at this time his professional and personal life took a turn for the worse. As a result, he didn't spend time developing new material or preparing the way he did the first time. The night Don got up on stage for the second time was in a word "horrible." He describes it as the "longest" three-minutes of his life. Worse, he was told by the general manager that he was banned from the club for life.

Don eventually got his groove back. He joined Toastmasters, where he not only shared this story on stage but many others.

From "spectacular failure" to inspiration for a book

Don didn't avoid this "failing spectacularly" episode by hiding it deep inside a mental drawer. In speaking with Don, it's clear that he isn't shy about sharing his stories, both good and bad. He took what many would deem a massive "failure" and extracted lessons, learnings, and humor, which he shared on stage and eventually on the page. Don's goal is to teach others that failure isn't something to shy away from, that "bad things are gonna happen." What's important is how we respond to it, how we pick ourselves up and move forward. Don also reminds us that laughter is a powerful antidote to whatever momentary pain or embarrassment you may experience from a setback or failure. Moreover, by sharing this painful episode, Don won the encouragement of others, including his wife and fellow Toastmaster members to put his stories into a book. Don's spectacular failure became an inspirational book called "Failing Spectacularly."

Writing tip

Don's biggest challenge was listening to editors and feedback. Don is a headstrong storyteller and writer. He learned to respect and consider the opinions of others, all in the service of making his book better. Don's advice is to know when to listen, even when your natural inclination is to talk.

For those who are beginning their writing journey, Don advises knowing the "what" and "how" are great but more importantly, you must have a strong "why." To that end, Don recommends a book called Start with Why by Simon Sinek. Finally, Don shares that if you pursue the self-publishing route, it's a huge learning curve with a lot of technical aspects to master. For his second book, Don worked with experts for those technical aspects so he could focus solely on the creative. He recommends that rather than do it all yourself, "go get help" with the backend management when it comes to self-publishing.

Don's announcement about book 2

Connect with Don:

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