HE LIVED A LIFE OF “YES.” YES TO HELPING. YES TO ADVENTURES. YES TO BEING THE FIRST ONE IN AND THE LAST ONE STANDING.
If you’re holding this magazine, chances are you already know Paul Or maybe you felt like you did even if you only met him once That was his magic Paul didn’t just enter a room, he owned it Not in a loud, look-at-me kind of way but with warmth, humor, and a magnetism that made you feel like you were the most important person in the world If you needed help, he was already there If you were down, he had a story, a hug, or a harmonica solo ready And if there was music playing, well, chances are he was halfway through a blues riff before you realized he brought the band with him
Born on June 17, 1976 in Ware, Massachusetts, Paul the proud son of Bruce and Jeanne Holloway filled his 49 years with more energy, laughter, and connection than most people do in a century He lived a life of “yes ” Yes to helping Yes to adventures Yes to being the first one in and the last one standing Whether you called him son, brother, husband, teacher, coach, co-worker, or friend, you knew: Paul was one of one
He was a proud graduate of Quabbin Regional High School (Class of ‘94), earned his bachelor’s degree from Fitchburg State in ‘98, and later a master’s from Bay Path University But ask anyone what Paul really mastered in life, and they’ll tell you: connection Kindness Service And making every moment matter
For 14 years, Paul taught at Palmer High School as a special education teacher He spearheaded the launch of Unified Sports programs like Basketball and Track & Field, along with a cooking class that brought students together in the most nourishing way possible His goal was simple but powerful: make sure every student had a place to belong and feel valued He brought special education and general education students together in ways that transformed the school culture creating teams, classrooms, and friendships that transcended any label
And it didn’t stop when the school bell rang Paul was always working behind the scenes organizing fundraisers, seeking out resources, doing whatever it took to give his students the extras they deserved Field trips, gear, experiences they weren’t just nice-to-haves To Paul, they were musts, because his students mattered And he made sure they knew it
When Paul wasn’t in the classroom, he was building something figuratively and literally A 25-year veteran of the Holloway Painting Company, he brightened homes and businesses with his skill and unmatched work ethic And starting in 2022, he proudly served as a volunteer firefighter with the Holland Fire Department, answering the call when his community needed him
THAT FIRST DATE LASTED SEVEN HOURS.
By Kristina Dobiecki Holloway
I remember the first time I saw Paul
It was the start of a new school year at Palmer High All staff had returned for meetings I was heading to the auditorium, rounding a corner in the lobby and there he was Talking and laughing, completely unaware that he’d just changed the course of my life.
I stopped in my tracks, turned to a colleague and whispered, “Who’s that?” She replied, “That’s Paul Holloway. He’s new. I think he’s dating someone here.” So I smiled, nodded, and tucked that moment away.
What none of us knew then was that Paul’s new classroom, room 317, had the perfect view of my office window. And taped to my window, still hanging from the year before, was a sign that read: HELLO ROOM 317
Paul thought it was a welcome note just for him
On his lunch break one day, he called to say hello and thanks for the sign Confused at first, I then remembered the old sign and awkwardly explained that it was from last year He probably turned bright red but it was the first of many laughs between us
We were friendly colleagues for eight years Timing never quite aligned We were both navigating life and other relationships And then, at an end-of-year pool party in 2019, somewhere between floating in the water and a round of yard games, Paul asked me out.
My mind screamed “ohmygod, ohmygod, ohmygod!” and then I casually replied “Yeah! That’d be fun.”
That first date lasted seven hours.
We connected instantly and authentically. He was kind, funny, open, and made me feel so comfortable around him. On the third date, at the beach, Paul declared that he wasn’t interested in seeing other people I agreed, and we made it official
We filled the next few years with concerts, beach days, road trips, meeting & loving each other’s family and friends, and lots and lots of laughter When Covid hit, and the world shut down, Paul and I decided to stick together Those types of together 24/7 situations can often make or break a relationship We were thrilled that it made ours stronger We cooked corned beef, planted hot pepper seeds, tried to learn Heart of Gold and What’s Up on the guitar, and went on a hike everyday to a new spot
And then, one summer day off the coast of Hyannis, in the middle of the ocean, Paul asked me to marry him With his Grandma Alice’s ring Right there in the waves, one hour into our week-long vacation He said he couldn’t wait It was bold (a little risky), and completely perfect I said yes before he could drop the ring in the water.
Later, when we told my dad the news, my dad got ch and said, “I don’t know if he’s the man of your dream the man of mine!” That’s how you knew you found a
When we stood together on our wedding day, hand remember thinking: This man- this loving, open, fun, man- is my future. We danced to the two truest lyric better when we’re together, and how wonderful life i you’re in the world
I didn’t just marry Paul I married my best friend
And even now, heartbroken in this unimaginable grie the fact that it was real, true love that we shared No image on social media (though we all know Paul love our adventures on Facebook!) It was a love that lived understanding, and connection And that just a week passed, Paul said “We’ve got a great life, don’t we? smiled and said “We do ”
Paul, thank you for loving me, for choosing me, and f a wonderful life. I am so grateful to be your wife. The best parts of you will live on, and I will carry them forward for both of us.
I love you forever.
Kristina
I DIDN’T JUST MARRY PAUL. I MARRIED MY BEST FRIEND.
“IDROVEAZAMBONIONCE”
A job interview A one-liner A lifelong friendship
Back in the early 2000s, Paul and his buddy Stuie found themselves in Scottsdale, Arizona, wandering into a nightclub they’d visited the night before this time, looking for a lost wallet. They didn’t find the wallet, but they found something else entirely.
They struck up a conversation with the club’s general manager, who’d just fired his entire staff the night before (as one does in nightclub management). The guy needed help fast. So he asked the two fresh-faced, heavy-accented Massachusetts boys a simple question: “Do you have any experience working in bars?”
Paul didn’t hesitate He looked the manager dead in the eye and said,
“No, but I drove a Zamboni once ”
THAT QUICK WIT AND FEARLESS CHARM? IT WASN’T JUST A FUNNY MOMENT—IT WAS PAUL IN A NUTSHELL
That was it No résumé No follow-up explanation Just Paul being Paul charming, bold, hilarious, and impossible not to like The GM burst out laughing Hired them both on the spot
That quick wit and fearless charm? It wasn’t just a funny moment it was Paul in a nutshell. He didn’t need credentials to make an impression. He showed up, took the pressure out of the room, and turned strangers into lifelong friends.
That Scottsdale job led to a 24-year friendship, countless memories, and of course many, many more stories. But it all started with a Zamboni. And if you knew Paul it somehow makes perfect sense.
Jeanne Holloway
Paul and his mom, Jeanne Holloway, were a team Through many hurdles as a child and every season after, he stood by her and championed her. They talked often honest, thoughtful conversations that showed how close they were. Their shared love and kindness towards others ran deep, and it shaped the way Paul cared for everyone around him.
“JUSTBEYOU”
How Mr. Holloway Helped Me Shine at Prom
As told by
Taelynne McCloskey
High school prom is supposed to be a magical night but for me, it didn’t feel that way at first. I didn’t want to wear a dress. It just wasn’t me I started thinking maybe I shouldn’t even go But then Mr Holloway stepped in
He always knew how to make people feel better He understood me not just as a student, but as a person He knew my family my two sisters included and how I was the quieter one He used to tease me and say, “Be more like your sisters!” and then quickly follow it up with a warm laugh and, “I’m just kidding, Taelynne. It’s okay to be yourself. You’re unique just like your name.”
Those words stuck with me. So when I told him I didn’t want to go to prom because I hated dresses, he didn’t try to talk me out of it Instead, he lit up and said: “Let’s wear matching Converse ” That changed everything
On prom night, I wore what felt right for me with my favorite Converse shoes So did he And I didn’t feel awkward or out of place. I felt proud. And then came the photo booth. That’s where one of my favorite memories happened.
Mr Holloway put on a giant Viking helmet, grabbed a huge rubber chicken, and struck a ridiculous pose I threw on oversized sunglasses and grinned from ear to ear We took the goofiest, happiest pictures and in that moment, I felt like the truest version of myself
Bruce Holloway
Paul learned a lot from his dad, Bruce Holloway He kept Bruce’s Veterans Day tradition alive at the school, organizing the program each year because it mattered to them both. Paul’s steady work ethic, easy charm, and love of music were things that made his dad proud and made Bruce’s influence clear in the way Paul lived and led.
MR. HOLLOWAY DIDN’T JUST HELP ME THROUGH SCHOOL—HE HELPED ME BELIEVE IN MYSELF.
He made it fun to be me.
Mr. Holloway didn’t just help me through school he helped me believe in myself I still think about his words when people compare me to others He reminded me that being different isn’t something to hide It’s something to celebrate
And just like my name, he made me feel one-of-a-kind
HEWOULD’VELAUGHEDATTHIS
We all know Paul wouldn’t want anyone sitting around feeling sorry for themselves. He’d crack a joke, roll his eyes at a mushy quote, and say, “Alright, that’s enough of that.”
In honor of the man who could get a laugh out of anyone even a smoke alarm going off mid-cooking class we present the tribute Paul probably would’ve written himself if he weren’t too busy planning his next big adventure
If Paul Wrote His Own Obituary
Paul Holloway, 49, made his final entrance by sliding into Heaven on a Zamboni, Viking helmet on, shrimp skewer in hand, headed straight for the grill He was greeted by his late father with a celestial blues jam and a cold beer ice still clinging to the rim
He leaves behind an entire community of people who will keep telling his stories each time a little louder, a little funnier, and a little more Paul than the last.
He kindly requests that in lieu of flowers, you:
Buy a non-working boat, a bike you’ll never fix, and a golf cart with questionable wiring
Skip the dress shoes life’s too short to be uncomfortable, especially if there’s dancing involved
Help your neighbor whether they like it or not
Tip the bartender Help the underdog Call your sibling
And for the love of God let’s spend the day at Hampton soon!
If you ever feel down, he’d remind you:
““Life is not measured by the number of breaths we take, but by the moments that take our breath away ” Maya Angelou”
His final words were likely:
“And that’s how it’s done”
Heaven’s been louder, brighter, and way more fun ever since
CARRYITFORWARD: PAUL’SLIVINGLEGACY
Paul Holloway lived with intention, humor, and an unmatched ability to make others feel valued Whether coaching a team, answering a fire call, mentoring a student, or showing up for a friend he made his corner of the world better
And now, we can do the same in his honor
The Paul Holloway Memorial Giving Fund
Created by his loving wife, Kristina Dobiecki Holloway, this fund was established to keep Paul’s spirit of generosity and community alive It will help support the kinds of programs and initiatives that reflect what Paul cared about most people
From helping students feel included and supported, to fueling joyful experiences and random acts of kindness, this fund will continue to uplift lives in meaningful ways.
To contribute or learn more about the Paul Holloway Memorial Giving Fund, scan the QR code to the right.
THAT’S HOW LEGACIES LIVE ON —WHEN WE CARRY THE BEST PARTS OF SOMEONE FORWARD INTO THE WORLD AROUND US.
The Paul Holloway Effect
We invite you to honor Paul not just with a memory but with action
Choose one or more of these in his name:
✅ Volunteer for something that matters
✅ Help a neighbor without being asked
✅ Learn something new just for fun
✅ Tell a joke that will make someone smile
✅ Show up for someone who needs you
Then say, “This one’s for Paul.”
Because that’s how legacies live on when we carry the best parts of someone forward into the world around us.
ALEGENDSIGNSOFF
He didn’t enter a room quietly.
He didn’t leave one unnoticed.
Paul had a way of filling space not with volume, but with presence. With purpose.
He remembered names.
He fixed things no one else noticed were broken.
He brought people together in ways that never felt forced.
And if you were lucky enough to be part of his circle, you didn’t stay on the edge for long—he’d pull you right into the center
He built fires, cracked jokes, coached teams, hauled gear, answered calls, and never waited to be asked.
He taught by doing. Led by showing up.
And somehow no matter how much he gave he always had more to offer.
The truth is, we thought we had time.
More projects, more parties, more track meets, more shrimp on the grill.
But time, it turns out, doesn’t consult us.
So we’re left with what he gave us:
A louder laugh.
A better playlist.
A deeper sense of what it means to belong.
And a reminder that the good ones never really leave.
They just stop knocking.
And start showing up in other ways.
A harmonica riff
A flash of LED light.
A smoke alarm during dinner.
We’ll catch ourselves smiling at nothing.
And we’ll know exactly who it was.
Because legends don’t end.
They echo.
“Life is not measured by the number of breaths we take, but by the moments that take our breath away ” Maya Angelou
— The Holloway Family
Dear Father in heaven, We give you thanks for blessing us with Paul’s life. Thank you for the time that we each had with him. Paul shared his love to any and all.
His kindness, generosity, ability to share joy and happiness is an example that will be in our hearts forever.
We know that Paul is giving You a big bear hug, along with a hearty laugh and that he is safe and loved… ...until we meet again.
