December 2015

Planning has never been one of my strongest skills, or rather, sticking to a plan never has.

I’m not immune to following a plan but I appreciate the ability to be able to deviate and improvise when necessary. For better or worse, the past 2 weeks have been a reminder of how important of a mindset that is.

I hardly know where to begin as I’ve put thousands of miles on my truck in only a short amount of time so I’ll start on November 22nd—Mile 0—back in Austin.

With Thanksgiving and Christmas coming up it was time for me to head up north to spend it with my family.

…yet if you asked me just a day before what I was doing for the next week, I would have told you I’d be scrambling to finish my newest product at.

Call it laser focus or blatant negligence but realizing Thanksgiving was only 2 days away I packed my truck up and booked it to Florida. Notably, I enjoyed one of the most refreshing sleeps I’ve ever had at a rest stop somewhere in Mississippi later that night.

Thanksgiving was everything I had hoped for: a delicious feast cooked by my dad, Black Friday people watching with Eric and Mary (even getting hit on by a desperate, middle-aged sunglasses sales-lady), and of course, some time locked up in that damn hotel room.

It wasn’t soon after Faith and Kevin arrived from Virginia that we were all in that damn hotel room together. Luckily we all know how to have a good time with each other and I’m glad it lasted for almost that full day.

In the back of our minds we were wondering where Uncle Jim was. He was supposed to meet with Faith and Kevin from New Jersey and drive down with them to Florida, but no one had heard from him. This was unusual, even for Jim.

It was later that night we found out that Jim had suddenly passed and that was one of those things you just don’t see coming from a guy like Jim. The funeral was going to be in his hometown in North Carolina and I had to quickly figure out how to incorporate that into my travel plans.

With my next stop being Philadelphia for WordCamp U.S., I decided I’d head straight back down to North Carolina when the event was over. It was going to be a lot of driving, but for my family, it was completely worth it.

WordCamp U.S. was an amazing event. In short, it was put together for the passionate people who develop for and use WordPress to run their websites.

Until you’re actually sitting in the same room as hundreds of other people talking about a single piece of software that powers over 25% of the internet you don’t really grasp just how monumental the community really is.

And the community is really what made it—from the dozens of informative talks to faces I recognized from Twitter, I had as much fun learning new things as I did meeting new people.

Nina made travel easy for me by letting me crash at her place and my business partner Chris made transportation from Media, PA to the Philadelphia Convention Center less stressful.

I’m grateful for the new friends I made in Ryan, Carl, Gifford, Pete, and Mike, and even grateful for that strong IPA I drank with a stank look on my face at the after party.

For all the great times that came from WordCamp U.S., I couldn’t help but leave angry at myself.

Why wasn’t I on stage speaking? Why didn’t I know more people at the event? Why didn’t I feel like I had more accomplishments in the industry I’ve spent nearly 10 years in? Why haven’t I given back more to this incredible community?

The moment where it all clicked for me was at a talk with pretty basic content (at no fault to the speaker), and all around me people were having “a-ha!” moments at knowledge I had learned years ago.

I don’t strive to become the next big company in the space or have any desire to run a giant team. I just want to create the best products I know I’m capable of and teach what I learn as I go.

If nothing else, WordCamp U.S. was a wakeup call to me that I haven’t been putting in enough to get more of what I want out of my own life. This gave me a lot to reflect on on my drive down to North Carolina for Jim’s funeral when death started creeping back into my thoughts.

It was only fitting to come from a place where I felt unaccomplished with my own life to go mourn for a life that had so abruptly ended. Call it a coincidence or see it as a sign, but death always has a way of getting in your head.

The viewing before the funeral is always surreal, to see a member of your family lying cold in a casket. Just like at my brother Jason’s funeral, I was waiting for Jim to pop up and yell “Surprise!” to the whole room, only to leave disappointed yet again.

Most of what I remember about Jim are only in flashes from when I was much younger, but there was a moment he and I had on my 21st birthday a summer ago that will always stick with me.

Though not a drinker, I wanted to take a shot of something to celebrate turning 21 and Jim was the one I wanted to take it with. Having heard some of his crazy drinking stories before, I knew we’d be in for a good time.

Vodka was the poison of his choice and he told me to drink beer right after because he knew I’d get sick if I didn’t drink a chaser after. We took the shots, sitting in that damn hotel room, and that chaser of Miller Lite may have saved it from becoming that damn stinky hotel room.

After talking and bullshitting for a while with Kevin and little Jimmy, we started talking about our family and how he wanted to see the kids make something of themselves in the way that he and other hadn’t.

He knew I had my own business and was proud of that. Whether it be success in business or a degree from college, he told me he knew I’d be the one who did something, if nobody else.

To hear that from someone I didn’t know very well but who had been paying attention to me meant a lot.

The idea that I could be someone who did something great in the name of my family was one of the first times in my adult life that I valued family as something more than just people who took care of each other; it made me think about legacy.

Jim’s legacy is with his son Jimmy and the rest of us who’s lives he impacted with his one-of-a-kind personality. I wish I had gotten to spend more time with him, but I will be grateful for the time I did get with him and the opportunity to say goodbye.

If you’re reading this and knew Jimmy, or just want to help, it would mean the world to our family if you could donate a little to help us pay for his transportation and funeral costs. Jim is now peacefully resting in Shallotte, North Carolina.

So maybe this trip for the holidays hasn’t gone exactly as planned and the circumstances that have made me appreciate the versatility of my lifestyle have been far from ideal.

In return I’ve gotten closer to forgotten family, revitalized a passion for my business, made new friends, and gazed upon beautiful scenery from the road I may have never seen otherwise.

I still have thousands of miles to go as I sit here in this coffee shop in Virginia Beach and who knows what will happen during those miles.

All I know is I have a lot to be thankful for, a lot to build, and more plans to break.