Be Careful Whose Advice You Buy

Photo of a bottle of sunscreen from Baz Luhrman's Everybody Free video

It was late September, 1999, and the Phoenix heat pressed against my skin as I slid into my Jeep Cherokee, which had recently lost its AC. Every commute to downtown felt like a slow roast. As I wiped sweat from my brow, I found myself wondering, for the hundredth time, if I made the right … Read more

How The Blizzard of ’99 Changed Everything

Matt Cavallo moving to Arizona in 1999 filing up his jeep

It was February 1999, and I had just returned to Hingham, Massachusetts, from Phoenix, where my uncle Matt, my namesake, had gotten married. The sun-drenched desert felt like another world. While I had spent the past few days basking in 80 degree temperatures, Massachusetts had other plans. A late-season snowstorm loomed, and I was back … Read more

Rejection, Walt Disney’s Swamp, and My Own Crossroads

Walt Disney pointing at a map of Florida.

I woke up to another rejection email today. It was polite, almost too polite: Thank you for responding to us. We appreciate your platform and mission. However, after delving a bit more into the market, we could see this project isn’t quite a fit for us. We decline with the greatest respect and deepest regret. … Read more

Footprints in the Sand

Sunrise over Gun Rock Beach in Hull

It was July 15, 1982, my sixth birthday. The year before had been busy for our family. My dad had just finished building our new house in Hingham, and my sister had been born on my dad’s own birthday. Life had shifted in more ways than a five-year-old could track. But that summer, my mom … Read more

Bill and Ted’s Excellent Lesson in Collaboration

A picture of older Bill and Ted in the phone booth.

On a flight home from Boston, I found myself watching Bill & Ted Face the Music. It was Thanksgiving, and Jocelyn and I had just spent the holiday with my family, catching up with old friends and reminiscing about the past. As I settled into my seat and let the movie play, something about Bill … Read more

There’s No Such Thing as Good Writing Only Good Editing

The conference room buzzed with tension. We were three days into a company summit in Sacramento, five round tables filled with team members hunched over laptops and printed documentation, hashing out our customer onboarding process. Papers rustled, pens tapped against notepads, and someone let out an audible sigh of frustration. What was supposed to be … Read more

Monster in a Box: Taming the Digital Dilemma of Unfinished Work

Gerard and I were back at our usual lunch spot, sandwiches from Al’s, the window open to the noise of State Street, when he set his phone down on the desk between us and hit play on a grainy clip of a man in a red and blue checkered shirt sitting alone at a table … Read more

A Turn-of-the-Century Immigration Story

A picture of colonial home on 67 lake street in Weymouth MA.

The nurse handed me a cane. A standard-issue black cane with a soft Styrofoam grip. As soon as it touched my palm, something inside me shifted. The hospital room, the nurse’s voice, the weight of my diagnosis, they all faded. Because I had seen this cane before. Not this exact one, but one just like … Read more