One Big Holiday 7 – The Journey Begins

On April 1st, Nicole and I hit the road, heading south toward Santee, South Carolina — the first leg of our long-anticipated One Big Holiday 7 adventure. After a day on the road, we pulled into town just before evening and checked into our hotel, eager to stretch our legs and find a good place to eat.

As I often do when traveling, I turned to Tripadvisor to scope out the best local dining options. Turns out, the highest-rated spot in town was just across the street: a place called The Captain’s Quarters. That kind of convenience is hard to beat, so we got ready and walked over.

The restaurant was buzzing — full of people enjoying their meals, sharing stories, and soaking in the warm, nautical ambiance. The hostess greeted us with, “You’re in luck, we happen to have one table available,” and led us into the main dining room. We were seated at a white tablecloth-covered table near a fireplace, surrounded by eclectic décor and, of course, a classic schooner-at-sea painting — because of course there was.

I ordered the pineapple salmon dish, which turned out to be excellent. It hit the spot after a long day of driving and set the tone for the trip ahead.

After dinner, we made our way back to the hotel and called it a night — content, full, and ready for the journey that lay ahead.

A Big Step Forward

My First Managed Services Contract

On January 21st, 2025, I had a meeting in Seaford, DE that I won’t soon forget. I was meeting with an existing client to go over what would become the very first managed services contract for Chesapeake IT Services LLC.

To say I was nervous would be an understatement. Excited too — but definitely nervous. This wasn’t just another service call or routine tech consultation. This was a formal agreement, a commitment, and a real milestone in the growth of my business.

When I arrived, I sat down with the owner and their parts manager. I walked them through the contract I had written, outlining the services, expectations, and support they could count on. To my relief, they didn’t just agree with it — they signed on the spot. Just like that, my first managed services deal was done.

Strangely enough, after the meeting I felt physically ill. Whether it was something I ate or just the overwhelming rush of nerves finally catching up to me, I’ll never really know. But looking back, I think it was the weight of how important that moment truly was — the pressure, the anticipation, and the realization that this dream I’ve been building was starting to take root.

That day marked a turning point. And no matter how far this journey goes, I’ll always remember where it began — at that little shop in Seaford, with a handshake, a signature, and one very unsettled stomach.

Cancun 2025

A Quick but Memorable Getaway to Cancun

A couple of months ago, Nicole and I escaped the winter cold for a much-needed Cancun getaway in January. It all started when I got an offer from the Westin Resort & Spa in Cancun—a 4-night stay for just around $300. At that price, how could we say no?

We made the most of our short trip, soaking up the sun, swimming, and snorkeling in the crystal-clear waters. Whether we were lounging by the pool, walking along the beach, or just relaxing with a drink in hand, it was exactly the kind of break we needed.

I even planned a couples massage for us, thinking it would be a nice touch to our getaway. Well… let’s just say it wasn’t quite worth the money. It wasn’t terrible, but it definitely didn’t live up to expectations. Lesson learned!

One of the most memorable nights was dining right by the ocean. The setting was perfect—until a huge downpour hit. The restaurant had a thatched roof, but unfortunately, it wasn’t fully waterproof. So there we were, enjoying our meal, while water dripped all around us. Instead of letting it ruin the night, we just laughed and made the best of it. It’s moments like that that make a trip truly unforgettable.

Even though the trip was short, it was exactly what we needed—a chance to relax, recharge, and create new memories together. Cancun, we’ll definitely be back!

The Proposal

The Best Christmas Gift: A Proposal to Remember

Christmas has always been one of my favorite times of year, but Christmas Eve 2024 will forever stand out as one of the best nights of my life.

Nicole’s mom and brother were visiting for the holidays, and we were all gathered in the living room, opening gifts in front of the fire, soaking in the warmth of the season. I had also arranged for her nephews to be on FaceTime, wanting them to be part of what was about to happen.

Then, the moment arrived.

Just as I started to get up to kneel down, her mom—without hesitation—blurts out,
“What are you going to do, propose!?”

I froze for a split second, then turned to her with a smirk and said,
“Why yes, I AM!”

Everyone burst into laughter, including Nicole, but I didn’t let the moment slip away. I turned to her, knelt in front of her, and asked:
“Would you make me the happiest man in the world and marry me?”

Through tears of joy, she said YES!

Suddenly, we were both crying and laughing—crying because of the overwhelming happiness of the moment, and laughing because of her mom’s perfectly timed outburst that made the whole thing even more unforgettable.

It was the most amazing night, surrounded by family, love, and a little unexpected comedy. I couldn’t have asked for a more perfect moment or a more perfect person to spend my life with. Nicole, I can’t wait for forever with you. 💍❤️

Gypsy Rose

Welcome to the Family, Gypsy Rose

Life has a way of bringing the right things at the right time, even when you least expect it. This December, Nicole and I adopted a new family member—Gypsy Rose, a sweet and playful 1-year-old cat who has already stolen our hearts.

For a long time, I wasn’t sure if I wanted another pet. In 2019, while I was away on a trip, my last cat passed away. It was traumatizing, and the thought of going through that kind of loss again kept me from even considering another animal. But then, Gypsy Rose came along.

From the moment we brought her home, she fit right in. She’s affectionate, curious, and just a little mischievous—everything you could want in a cat. Whether she’s chasing after toys, curling up in a warm spot, or just following us around the house, she’s already made herself at home.

We couldn’t be happier to have her as part of our lives. Gypsy Rose has brought so much joy into our home, and I’m glad I finally opened my heart again.

Here’s to new beginnings and the unconditional love of a pet. 🐾💕