I’ve never been particularly good at handling grief. I suppose no one really is. As a child, I can remember the feelings I experienced when my Grandma passed away. And Bubba, my paternal grandfather. Although to this day, I don’t know that I could articulate those feelings.

As I grew into my teen years and saw friends pass away, I went from “not good” to “absolutely bad” at handling grief. I numbed my emotions with copious amounts of gut-rot liquor. When my friend Jay died, many nights for a long time after would end with a drunken and clumsy fist fight with a friend, poorly masked tears, or both. Through my later teen years and into my twenties, as other friends and family would pass, the cycle repeated itself.

After moving across the country, I remember being torn that I couldn’t be there when my Nana and my Uncle Jon passed. But through it all, one of the few constants in my life, my grandfather was there, a rock of a stability in the often turbulent seas of my adolescence and early adulthood.

He was recently admitted to the hospital. He’s comfortable. But at 94, it may be his time to go. My mom tells me that when he was regaining his speech, his frustration manifested in a clear, “this is bullshit.” Grampy is nothing if not independent. Perhaps occasionally to the point of being stubborn. I wonder where I get it from…

Now, at 32, sober and exposed to the raw emotions that accompany grief, I find myself as I often do in introspection. Grampy has lived 94 full years. He taught me how to fish. He taught me how to whistle with a blade of grass. Although I never managed to quite get that down…

Even at 94, he was independent. While his garden this year paled in comparison to the vegetable gardens I remember from my youth, he still not only took care of himself but found fulfillment in helping things grow. And his orchid flowered this year.

Memories keep surfacing, as I’m sure will be the case for days to come. I remember the picture of him at my parents’ house, leaning against his motorcycle. I remember Joe the Crow and the other injured animals he saved and nursed back to health. I remember spending hot summer days under the shade of the screenhouse he built, at his house on South Longyard.

As I wait at Gate 15 for my flight to see him, I find myself sad yet grateful. Sad that it may be time to say goodbye. But grateful for having him in my life. And grateful that I have a rare opportunity in that I get to say goodbye to someone I love before they go. I don’t know what I will say. But I’m grateful for the opportunity.

Meet Jetpack: Ryan

Jetpack — Essential Security & Performance for WordPress

Our dedicated team of Happiness Engineers is one of the best reasons to jump into Jetpack. With direct access to a global team of WordPress experts, our customers know that they’ll always have the help they need to get things up and running smoothly.

These folks are smart — really smart. Any chance to pick their brains about all things related to WordPress and Jetpack is a great opportunity to learn something new! We recently caught up with Ryan, a longtime team member and passionate WordPress enthusiast, who has some interesting advice for the millions of folks building their online presence with WordPress.

It’s no secret that you know a lot about WordPress. How did you first get involved with the software?

I’ve been using WordPress since 2008 or so. Back then, I was working at a small company building websites for local businesses. As website requests got more complex…

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Catching Up

It’s been awhile since I’ve written on my blog. I’ve started to write a few things. But I can’t seem to click that damn “Publish” button. And the longer I put it off, the more difficult it seems. Funny how that works…

As I dig through pages of rough ideas, semi-finished posts, and random notes, I thought we could start by catching up. This past year has been one hell of a ride. With 31 on the horizon, I can’t help but reflect on 30. So let’s see where we’re at…

On the Road


Alanna, Sammy, and I spent the majority of last year on the road. After living in Los Angeles County for the better part of a decade, we picked up and decided to visit my childhood home and bounce around the East Coast for a few months. We left California in June and drove ~3,300 miles to Massachusetts.

As mentioned in previous posts, it was a rollercoaster of a trip. I hit some low points and was forced to face some demons that I thought I had left far behind. While in Massachusetts, my anxiety plagued me every waking moment some days. I was forced to go back to the basics. But by the end of our stay, I feel I finally made my peace with my childhood home. We hit the road once again and landed back in California in November.

Where’s Ryan: Road Trip

The Desert


Once back on the Left Coast, we decided to move somewhere a bit quieter. After contemplating the move for awhile we landed in Joshua Tree, which is a small town two hours east of Los Angeles. We signed a lease back in December for a spot about 10 minutes from Joshua Tree National Park. Seven months later, we’re still digging it. It’s quiet. The skies are beautiful. There are lots of places to explore. There’s no LA traffic. So far, so good.



It wasn’t planned, but we adopted a rabbit named Bruno. Alanna’s dad got Bruno at the swap meet last Summer. Bruno came to our new house in January for a sleepover… and he never left. While I never planned on having a rabbit, he chewed right through our security deposit and into our hearts. He grew on me and has since become part of the family.

Mental Health


One of the first things I did when I got back to California was see my doctor and my therapist to get a handle on my insomnia and anxiety. In addition to General Anxiety Disorder, I was diagnosed as having Obsessive Compulsive Disorder.

Prior to the diagnosis, I didn’t know much about OCD. Like many, I assumed OCD was essentially germophobia, excessive hand washing, and being overly organized. It turns out there are many subtypes. The more I researched it, the more certain aspects resonated with me. My OCD manifests as Pure OCD and Somatic OCD.

The following excerpt from explains it well:

Every person is different. Relationships, hobbies, careers, talents and lifestyles vary from person to person. Obsessive Compulsive Disorder does too. OCD is a complex mental illness that affects every sufferer differently. Contrary to what many people believe, it is not all about handwashing and organization. While there are similarities across cases, individual manifestations tend to mirror specific anxieties based on a person’s unique life experience.

It may sound a bit odd, but the diagnosis was a bit of a relief. By knowing what I was dealing with, I could figure out how to manage it. And if I keep adding acronyms to my name, maybe people will think I’m someone of prestige, like a doctor. Ryan Cowles GAD, OCD.

I started a low dose of an SSRI and have been back in regular therapy to learn how to manage my OCD when it spikes. It’s hard to say if it’s regaining stability, the medication, or the therapy that’s helped the most. But I feel much better than I did just a few months ago. My sleep is getting back on track. I’m making steady progress and it feels good.

270 Days


I’ve gone 270 days without any alcohol. In the past, I always considered myself a social drinker. I’d have drinks when we’d go out with friends. I’d have drinks on the weekend. But the last year has me re-evaluating things and trying to figure out how to better take care of myself. I wasn’t drinking every day. I was functioning in day-to-day life. But I was leaning on alcohol as a crutch.

It got to a point last Summer where I turned to drinking to help with my insomnia. I knew it wasn’t healthy. And it took me to some dark places. But at the time, it seemed to be the only thing that worked. So I was drinking to fall asleep. Taking a step back, I realized it was contributing to the cycle of anxiety and depression. So when I got back to California, I decided to take a break from alcohol.

The first few weeks were tough. I was forced to face my anxiety without the safety net that drinking provided. It felt very raw. But as time went on, it got easier. I gained some clarity. I discovered this thing called “Saturday morning”. And it feels good to not be hungover every weekend.

I still haven’t committed to never drinking again. I have enough trouble committing to plans for next weekend. But for the time being I’m taking a break. I still enjoy going out to bars, shooting pool, and being social. The only difference is I’ve swapped the PBR tallboy for a Ginger Beer.



The company I work for, Automattic, offers a fully-paid three-month sabbatical when you reach five years of tenure. I started my sabbatical on May 28th. While some coworkers have traveled, taken time to learn a new skill, or done something incredible, I’ve taken a more low-key approach. I needed time to disconnect and recharge. I set no lofty ambitions for myself and instead have been learning to take care of myself.

I’ve spent time with family. We’ve gone on some short trips. I’ve been playing video games with my brother-in-law and my nephews. And I’ve spent time laying in the hammock in our backyard.

With a little less than a month of sabbatical remaining, I’m working on building a routine for myself. And I’d like to work on a few small projects. I want to write. I want to paint. I want to draw. But I’m not pushing myself too hard. Slowly, I’m starting to reconnect with those passions.

Where’s Ryan: Sabbatical

Figuring it Out


I’ll be 31 next week. As I put the pieces together, I’ve realized there’s no one-size-fits-all guidebook to this “life” shit. But being forced to go back to the basics has given me a chance to reflect on what truly is important to me. Some days are better than others. The good days are easy to share, while the difficult days are often hidden. We’re quick to share our highlight reel, but hesitant to talk openly about our struggles.

Couldn’t face the world today, so I ordered pizza and binge-watched Jersey Shore. #blessed

I’m sometimes hesitant to write so much publicly for fear of oversharing. But fuck it. I am nothing if not honest (I believe “real AF” is the proper nomenclature). And I find writing to be therapeutic.

As for my current day-to-day, the good days are starting to outnumber the difficult ones. And coming up on 31, I’m finally learning how to take care of myself. Now that I can put some of this anxiety and depression bullshit behind me, perhaps I can get back to writing about other topics as well. We’ll see…

Cheers to 2018!

The Blog

Some years go by slowly — not because they’re busier, but maybe there’s just more out there in the world to stop and notice. We hope the and Jetpack community offered you some of those moments this year.

Maybe it was a helpful chat with someone on our Happiness team, or maybe you discovered a cool new feature that made business or blogging even easier. Perhaps you read something on that inspired you. We just want to say thanks for being here, and we’re excited to see what you all accomplish in 2018 and beyond.

Below are some highlights from the year in — and make sure you check out Discover to see more favorite moments from 2017. Happy New Year!

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Road Trippin’

Alanna, Sammy, and I are back in California. We covered about 3,200 miles (5,150 km for you, Richard) over the course of eight days. We stopped at some cool spots along the way, had a couple quick visits with friends and family, and stayed at our fair share of La Quinta Inn & Suites (“La Quinta” is Spanish for “Next to Denny’s”).

I still have pictures to go through of our trip to Massachusetts, so it’ll be a little while before I am caught up with editing photos. In the meantime, here’s a video of our trip back to the Left Coast that I created using Google Photos Assistant. You can also find a few more flicks under the Road Trip tag on my Where’s Ryan Blog.

And here’s a before and after photo for good measure. Or I suppose, an after and before picture. The difference a week can make…


Making my Peace

Alanna, Sammy, and I have been in Massachusetts since June. When people ask how the trip has been, I’m not sure how to reply. It’s been a rollercoaster. Lots of ups, its share of downs. Now, with just a few days left in Massachusetts, I find myself reflecting back and putting it all together.

This is the longest I’ve stayed in Massachusetts since moving to California at 23. I’ve visited a number of times, but never for this long. As you may have read in an earlier post, this trip has forced me to go back to the basics. A lot of old wounds, that I thought had healed up long ago, re-opened. And without the same support system and tools I have available at home in California, I’ve had to adapt and figure it out.

Not only is this the first time I haven’t had “my own place” since being an adult, but I’m revisiting a lot of things that I thought I left behind. I’ve been back in my childhood home. That in itself carries a lot of weight. I drive by places that bring back memories. Some good. Some not so good. Some days it seems that I everywhere I turn, I’m confronted with the memory of a friend that has passed away, or a traumatic time in my life. But there’s a lot of good, too. And for years, I’ve felt guilty about appreciating that good.

Driving past Southwick High School in early Fall reminds me of how much I hated school. But just up the road, I can stop at Provin Mountain, and hike along Metacomet Ridge to one of my favorite spots.

Driving through Westfield, past our first apartment, I’m reminded of the time we got jumped, beat up, and harassed by cops on the street corner. I’m trying to let go of that, and instead remember the times I rode my bike along the old NYNH&H rail line in Westfield.

Driving through Springfield, I pass by neighborhood where I played basketball, hopped fences, and learned important skills, like how to roll a blunt. But instead of scaling fire escapes, I found myself visiting several of the museums and historical places. Turns out, Springfield has a deep and rich history… Who would’ve thought?

I found myself trackside with friends. I took several trips down Memory Lane. We swam. A lot. And we explored places that I never visited when I lived here. We checked off the “leaf peeper” badge with a visit to The Berkshires. We went up to Vermont. A few times. And I’ve started to appreciate the beauty that’s been right down the road from my parents’ house.

I had deep conversations with both of my parents, that were probably years overdue. Looking back, I was still a kid when I left. With 3000 miles between myself and my parents, our relationship never fully matured. But I feel I’ve got that now, and I’m glad.

I wrote letters to my some of my friends that have passed away. It was surprisingly therapeutic. It’s helped me let go of the fact that they are no longer here, and instead of focusing only on the bad, I can remember the good times we had together. It still hurts, and that will never go away completely. But I’m letting go of some of that guilt, that has stuck with me for well over a decade in some cases.

For years, I’ve felt guilty about enjoying and appreciating the good things that my childhood home has. Perhaps it’s a bit of survivors guilt. It’s been hard to see through the negative and focus on the positive. But I’m getting to a point of appreciation. And I’m getting closure on things, so I can finally fully embrace who I am and where I’m from.

So… while it’s been hard to be here at times, it’s been really nice, too. I’m going to miss eating pizza in Pine Hill Cemetery with Alanna. I’m going to miss walking around Stanley Park with Sammy. I’m even going to miss the shitty dive bars. But it’s all only a plane ticket away, and we’ll visit again soon.

On the other side of that, I’m excited for what’s next. For starters, I’m excited to see my doctor and my therapist, to see if I can get my sleep and anxiety back under control. But more than that, I’m excited to look for our next place to live back in California. While 18 year old Ryan could sleep on couches and floors, 30 year old Ryan needs some stability. And a couch. And WiFi. And Netflix.

So yeah, it’s been a good trip.


Automattic Grand Meetup 2017

I spent last week in Whistler, British Columbia for Automattic‘s annual Grand Meetup. If you aren’t familiar with Automattic, (and let’s be honest, the only people reading this are my parents and other a12s, so you should already know) we’re the company that builds and supports things like, Jetpack, WooCommerce and several other products on the web.

One thing that makes Automattic unique from most traditional companies, is that our company of 600+ employees is scattered across the globe. We have no central office, and we all work remotely. Our day-to-day communication is done using Slack (RIP IRC), internal blogs called P2s, as well as voice and video chats. Except for one week out of the year… That one week, everyone in the company gets together to work, socialize, and spend time together.

Throughout the week, some folks work on projects, some take or teach classes, and others hold down the fort by doing their regular job. The time outside of those work hours is filled with socializing, a Town Hall Q&A with our CEO, 1:1s with teammates, group discussions, team building, Alpine Bar, and… exhaustion. It’s a busy week.

This was our second year in Whistler. Last year, aside from a hike to Whistler’s Train Wreck, I didn’t get outside of the hotel conference rooms too much. I tried to change that this year. I once again hiked to the Train Wreck with Karen and Erica. I went for a long walk around Lost Lake to talk about Q4 with my fellow leads Kraft and Anne. I walked around Whistler village while talking with teammates. Although it’s an exhausting week, it felt good to get outside a bit more this year.

Keeping with my personal theme of late, I also had a chance to reflect. This year’s Grand Meetup was my fifth. At my first Grand Meetup, Automattic was a company of about 150 people. We could all fit in one (large) room. I remember being daunted by that number. I remember talking with employees who had been here for 4 or 5 years, and it seemed like such a long time. Today, according to an internal stat, I find myself closing in on that 5 year mark myself:

You started on 2013-05-28. Of the 610 other a12s, 128 (21.0%) started before you, 2 (0.3%) started on the same day, and 480 (78.7%) started after you.

By some rough math, that means that I’ve been with Automattic longer than four out of five folks I awkwardly stumbled into on elevator rides last week. It seems bizarre to me, because I so often still feel like the “new kid” at school. Maybe it’s Impostor Syndrome, maybe it’s social anxiety, or maybe it’s just a byproduct of our growing company. Whatever it is, it’s been interesting to reflect on. And while the GM can be exhausting, challenging, and long, I find it a good opportunity for me to grow as a teammate, as a lead, and as a person.

It’s almost been a week since I’ve returned to Massachusetts, but I find myself still decompressing from the Grand Meetup. It’s been a rollercoaster of a week. I’m glad to be home with Alanna and Sammy. But I miss my friends and coworkers, most of whom I won’t see for another year. It’s hard to go from 0 to 100 with structure and socialization, and then back down to 0 again, within eight days. I suppose that’s just part of transition…

In the coming weeks, things will return to “business-as-usual” – whatever that means. And come next year, I’ll worry about the structure and long days of socializing in the days leading up to the GM. But I’m already excited for it, and several more to come.


Back to the Basics

As mentioned in my previous post, Alanna, Sammy, and I recently road tripped from Southern California to Western Massachusetts. The journey itself had its ups and downs, but overall it was a blast. We arrived in Massachusetts the second week of June for a friends’ wedding, and we’ll be here through September, for another wedding.

Warning: This post isn’t a fun road-trip story. It’s probably not a feel-good read and touches on some potentially triggering things. If you prefer to pass over this one, that’s fine. I’ll post the rest of the pictures from the road trip soon.

I have mixed feelings about Massachusetts. I was born in Springfield, and I spent the first 23 years of my life in Western Massachusetts. I take pride in where I’m from. But it wasn’t always the easiest place to grow up. And some of those years were tough. I had friends pass away. I had issues at school. I had issues with anxiety. I had issues coping.

At 23, I moved about 2,800 miles away, and thought I left much of that behind. I made a life. My beautiful and incredibly supportive girlfriend became my fiancee, and then my wife. We adopted our dog Sammy, who quickly became a part of our family. Through therapy, patience, and persistence, I worked through a lot of my anxiety and past-traumas. I learned how to cope. I learned how to be happy. I got my shit together.

Fast forward a few years to June 2017, when we rolled into Massachusetts. Everything that I thought I left behind punched me right in the face. And for the first time since being 23, I was in MA, and I had no plane ticket home to LAX. The first few days were okay. A lot of catching up with old friends and family. A lot of processing. And not a lot of sleeping.

When I was younger, my anxiety would manifest itself in insomnia. Over the years, I learned how to deal with it. And I hadn’t had a bad bout of insomnia for quite some time. I knew MA would be tough at times. But I didn’t realize just how triggering it could be. And I forgot how shitty insomnia can be. It’s been a few weeks, and I still find myself struggling to get a decent night’s sleep. Sunrises are beautiful, but not when they signify another failed attempt at sleep.

Beyond that, I found myself without access to some of the tools that I use at home to deal with insomnia. I found high-CBD marijuana to be a huge help with sleep issues. But my medical marijuana card doesn’t work in MA. I found a good therapist who helped me work through insomnia and anxiety, who is now 2,800 miles away. I have a good primary care doctor, who can’t prescribe medications across state borders. I felt like I tried all of the right things, and hit a wall every time.

But I have Alanna. I have Sammy. I have my support network. I do have tools. And I’m not that same scared kid that couldn’t figure his shit out. 19 year old Ryan would’ve gone off the deep-end. 29 year old Ryan is figuring it out. So, with the support of Alanna, Sammy, and my friends and family, I’ve been working at it. And I will figure it out.

My mom always says, “Every cloud has a silver-lining.” Which I think is complete bullshit (sorry Mom). But lately, I can see it. I’ve gotten my anxiety in check. The insomnia is still there, but sometimes you need to take a step back in order to move forward. And it’s led to a lot of self-reflection.

I wouldn’t recommend insomnia to a friend. But I’m figuring out what’s really important to me. I’ve been getting out of the house. I’ve been taking walks and going for hikes. I’ve been revisiting nature. I’ve been walking train yards, taking pictures for my next zine. It’s nice to disconnect and reconnect (insert XML-RPC joke here). I’m figuring it out.

I still don’t believe that everything happens for a reason, nor does every cloud have a silver lining (what does that even mean?). But this has all forced me to make peace with parts of my past. And I’ve realized that when we head back to CA, I am indeed ready to settle down. And with facing some parts of my past, I can take the good parts with me back to CA, and make peace with the rest.


Alanna, Sammy, and I just road-tripped from Southern California to Western Massachusetts. I posted a few photos along the way from my phone using the WordPress mobile app to my Where’s Ryan? blog. And I took just over a thousand pictures on my camera, which I’ve been going through since… I have the first batch ready here.

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Bottle Tree Ranch

From Rock-A-Hoola, we made our way to Bottle Tree Ranch in Oro Grande, CA. Right off of historic Route 66, Bottle Tree Ranch is the creation of Elmer Long. Over the past few decades, he’s created hundreds of bottle trees and pieces of folk art which make up this unique forest.

We pulled up to the entrance in the late-afternoon. The property is free to enter, with a box near the front gate for tips. There didn’t seem to be anyone else there when we got there. Walking through the rows of bottle trees, hearing nothing but wind chimes and cow-bells, was a little eerie – which added to the experience.

The late-afternoon lighting was beautiful. I found myself walking in circles, snapping photos, noticing things that I’d previously walked right by. It’s a hard place to capture in pictures, but I tried…