After more than two decades as a reporter and now as a sports columnist for The Wall Street Journal, Jason Gay has witnessed major victories: Super Bowl wins, Olympic gold medal ceremonies. He was at Citi Field a few weeks ago when the Kansas City Royals celebrated their World Series championship. As a young reporter at the Vineyard Gazette in 1992, he covered the high school football team’s state Super Bowl championship.

The wins he celebrates in his new book are more humble. “What makes people happy is not always the big, giant accomplishments: going to college, getting a cool job, marriage, family,” he said. His book celebrates “tiny little things, like being the last car in standby on the ferry. Or getting through Five Corners in the middle of July without having to wait 10 minutes . . . having just life’s little victories along the way.”

Little Victories: Perfect Rules for Imperfect Living was released last week. The author calls it “a rule book for people that don’t like following rules, an advice book for people that don’t like advice books.”

Mr. Gay calls the book a rule book for people that don't like following rules, and an advice book for people that don't like advice books.

The book stemmed from a popular 2011 column Mr. Gay wrote in the Journal, “The 32 Rules of Thanksgiving Touch Football.” (12. It’s okay to play with kids but don’t baby them. Just because your 7-year-old niece is playing quarterback doesn’t mean you can’t intercept her screen pass and run it back for a touchdown. She’s got to learn sometime not to throw into triple coverage.) He started to write more of the rules columns, and the idea emerged to compile them into a book.

But he decided he wanted to write something new, and landed on the little victories theme.

“So that was sort of the silly philosophy of it, then this thing happened in the middle,” he said by phone last week from Phoenix, a stop on his book tour. “My father became sick with pancreatic cancer.”

“So what began as this entirely humor book really took on new meaning, because my dad’s life really did become about little victories, about going for a walk or having a conversation or seeing his grandchildren. Those things that were sort of small in scope became the driving purpose of our family for the better part of a year.”

Short stories, many humorous and some embarrassing, from Mr. Gay’s childhood in Belmont, from his career as a journalist — an assignment to interview Rihanna on a private plane, where the star is asleep; going to Nigeria with a man who is meeting his birth parents — and from becoming a husband and father are interspersed with stories about his own successful battle with testicular cancer, his and his wife’s struggle with infertility, and his father’s illness and death.

“I think it injected the book with real personal experience, and I think it made it a different book, richer book,” he said. “It’s funny but also richer.”

Little Victories muses on clothing, friendship and being cool, modern technology and the workplace, and offers rules and thoughts on these topics and others. The reader comes away with helpful advice on the importance of choosing good wedding music and how to pack for a trip, but also meditations about finding those little victories and putting things in perspective. The difference, for example, between the actual stresses of being fired and your own or a loved one’s illness, and the little stresses, which shouldn’t be stress at all, of a boss not returning an email, Netflix buffering, and “anything to do with fantasy football.”

Mr. Gay, who lives in Brooklyn with his wife Bessie, young children Jesse and Josie, and a “passive-aggressive” cat named Baxter, said writing about his own life was challenging in a way. “You think, who the heck wants to read these things about my life,” he said.

“I think things that have happened to me are relatable,” he continued. “To me the trick is to be brutally honest . . . things that have happened to me that might be embarrassing or goofy or setbacks, tell the absolute truth . . . people respond to that.”

On the scene in Times Square. Mr. Gay's book is a humorous and poignant tribute to life's moments, big and small.

Mr. Gay’s first job out of college was selling advertising at the Gazette. “I wasn’t very good at it,” he said, adding that he was probably on the verge of being fired as a salesperson when he started doing some reporting. His first story, he recalled, was about the traveling Little League team.

He worked at the Gazette from 1992 until 1997, covering not just sports but town politics, the Steamship Authority and President Clinton’s visits.

“I needed a complete education in terms of how to be a reporter,” he said. “I had great editors, great bosses, great role models who taught me the ropes, and so it was like school for me.” He continued:

“There is something about being a reporter in a small community, especially a close knit community like Martha’s Vineyard is, especially in the off season, that teaches you the impact of what you write. You have to hear all sides and be responsible and spell everybody’s name right . . . it gave me a real respect for what stories mean and how they can impact people’s lives, even little stories.”

As a sports reporter at the Gazette, he covered Coach Don Herman and the football team’s run to the Super Bowl in 1992 — and their storied come-from-behind win against Nantucket in the Island Cup game that year.

Despite all he’s covered since, “nothing will ever be cooler than seeing them storm back,” he said.

His journalism career has been distinguished and varied. After leaving the Gazette and before landing at the Journal, he went on to work for the Boston Phoenix, The New York Observer, Rolling Stone and GQ.

And while he said he has always loved sports, he wasn’t always a sports writer.

“I love it as a subject matter because people care, for better or worse they care a lot,” he said. “It’s sort of the best of both words. People are passionate about it but you can have fun with it, you can have amazing things happen all the time at the highest levels and the smallest levels.”

In his book’s opening chapter, between advice about listening to more early Stevie Wonder and not serving soup at a dinner party, Mr. Gay tells his readers, no matter their profession: “Remember why you wanted to do something for the first time. How it made you feel. Why it made you happy.”

The author follows his own rules. More than 20 years after that first Vineyard Little League story, he said: “Believe it or not I still really love sitting down at a computer and typing out a story and trying to find a way to connect people to words. I really enjoy that as much as I enjoy anything in my life,” he said. “That’s never changed, that still makes me so happy.”

Little Victories, Perfect Rules for Imperfect Living (Doubleday, hardcover, 209 pages, $24.95) is on sale at the Bunch of Grapes bookstore in Vineyard Haven.