Chris Wiegman

Looking Back on a Decade of Progress With an Eye to the Future

One of the highlights of the last decade was giving the keynote talk at WordCamp Utrecht 2018

It’s been a wild ride this year, both personally and professionally. If you had asked me on 1 January where I thought I would be as I write this I can definitely say it wouldn’t be where I am today. Some of that is a very good thing and, some of it probably not so much. Going back even further, as one decade turns into another, and my life at the start of 2010 would be unrecognizable to me today in so many ways. I’ve learned so much, done so much and reinvented myself to a degree I never would have thought possible. If the past is any indication of the future, the next decade will, hopefully, be just as amazing.

A Decade of Change

At the start of 2010 I was still flying on occasion for my role at Southern Illinois University. We had just bought our first house and I was working on a Masters degree in Computer Science. I hadn’t, yet, opened a WordPress.org account or started any work on the projects that would come to define me professionally over the rest of the decade.

From IT and Drupal to Engineering and WordPress

The biggest change for me over the previous decade was a migration from an IT role where I was managing all aspect of IT for the Aviation programs at Southern Illinois University while building their website in Drupal to being a full-time engineer working on the technologies and services behind WordPress. If I’m honest with myself, this transition does make some sense. I hated the support functions of IT, and WordPress, as we all know, far surpassed Drupal over the coming years in terms of professional and economic opportunity. That said, when I started full-time back at SIU in 2007 I had a five-year plan but didn’t expect it to come to fruition. It was more of a hopeful guideline of where things could go.

Our original goal had been to stay in Carbondale for 5 years while I worked on a degree and then move on. The catch was, especially after buying a house, we didn’t think that would actually happen. In January of 2012, five years to the day after arriving back in Carbondale, we drove away to Austin, TX where I would start a new job for significantly more than double the pay and only a fraction of the responsibility I had at SIU all with my Master’s Degree in hand.

Transitioning to Engineering

The first few jobs after leaving SIU could best be termed as development rather than engineering. I wasn’t solving anyone’s problems, instead I was implementing code and tools that had already been decided on. It was fun, but it was missing something.

I’ve tended to view the two roles as, first, a developer is really someone who implements with code, usually without solving any complex problems other than that which would come simply with the implementation dictated by someone else. In contrast, an engineering role is something in which one is presented a problem to which code is just one possible solution. The latter requires more original thinking and the ability to manipulate multiple possible outcomes to best meet the needs of all stakeholders in a sustainable fashion. The latter, I quickly realized, was my goal but the former was what paid the bills for a newly minted computer science graduate. It was time to start working on leveling up.

Ironically, or perhaps not so much so, the project that would help me transition from one role to another was something I started as a student to both build my portfolio and to help make my life easier in my IT role at SIU. Better WP Security was a WordPress plugin I had considered a possible resume item at best. As a student I wanted something I could show off later and had a problem I needed to solve to manage a small WordPress instance for the university. In other words, it let me solve real problems and wound up scratching an itch that I had and, apparently, so did many others.

While Better WP Security wasn’t exactly what I wanted to do for the next 35 years, it was the first project where I truly served as an engineer rather than a developer. I sold the plugin to iThemes at the end of 2013 where it lives on as iThemes Security. It didn’t make me rich and it wasn’t a what I would consider a full-time job but it did elevate my name in the WordPress community and help set me up for numerous jobs, projects and other opportunities in the years to come.

WordCamp San Francisco 2013

If there is one conference I can say defined the decade for me, even more-so than Better WP Security, it was WordCamp San Francisco 2013 where I first learned about Vagrant in a talk by Mark Jaquith. From that talk I started a series of projects that would carry me through today. From Primary Vagrant to Ouroboros to DevKit and Local it turned out one problem I’ve really wanted to solve was just how bad the local development environments were for WordPress. Security was fun, but helping people get the tools they need to do real engineering was where my heart has been. I was hooked.

Six months after WordCamp San Francisco 2013 I knew it was time to send Better WP Security on its way and get started on something new. I sold the plugin, and all the other plugins I had at the time, to iThemes and spend the next few years looking for the perfect gig.

On to Sunnier Pastures

At the end of 2014, with Better WP Security sort of behind me (I worked on it for 14 months for iThemes although my heart really wasn’t in it anymore) it was time to move on from Texas as well. I still love the people I met in Austin but it was never home. What we found was a great opportunity in Sarasota, FL where we could have a home in a walking neighborhood that would check off nearly all our “want” items in what could actually be a home for us. We bought it sight-unseen thanks to an excellent Realtor who happened to be transitioning to real-estate from WordPress and, in Jan 2015, packed up our stuff and moved to Florida. We had found home.

On to “The Dream Job” and Making a Home

Almost five years later we’re still in the house in Sarasota where, other than the summer weather, we’ve been quite happy. I’ll admit I’ve got the urge to move again and try something new, particularly outside of the US, but even if we do move I don’t see us selling the house. The location is just too perfect. We can walk to pretty much everything and now only need a car for very few things. That has been wonderful.

In the time we’ve been in Florida, though, it’s taken a while to find a workplace I could call home. I went from iThemes to 10up to the University of Florida and, in 2018, I finally found the right fit in WP Engine where I was hired to build developer tools for their biggest hosting customers.

The WP Engine job was perfect. Not only did it allow me to finally build developer tools as I had always dreamed but it opened me up to a host of new technologies and techniques that I just hadn’t come across in WordPress. When I took the job I figured it would be written in NodeJS as, well, it seemed as a WordPress development the only two technologies than anything were built in anymore were JavaScript or PHP. I knew I already hated working in JavaScipt but it seemed a descent trade-off, particularly in a company that really seemed to do their engineering right.

I’m really glad to say I was dead wrong. Instead of resigning myself to a tech stack I hated dealing with, we built the project in GoLang and I was able to see all kinds of tech in action. I was excited about tech again. I learned GoLang, started learning some Rust and got to play with everything from Docker to PHP and just about everything else. It was amazing. By June of this year we launched DevKit, WP Engine’s local development environment, in an open beta and started polishing it for more. Unfortunately, though, all good things come to an end.

Coming Full Circle at Work

In June WP Engine announced they bought another host, Flywheel. While work continued on for most it really rocked my world. Flywheel’s most popular product, arguably, wasn’t hosting but Local by Flywheel, a local development environment. It took a few months to work out the kinks but in October our teams were merged and DevKit was effectively dropped. Now I was working on a NodeJS product designed for mass appeal rather than difficult engineering and I hated every minute of it.

Don’t get me wrong, the team was great. The rest of even my team really would have rather worked on NodeJS than GoLang (and had done so on their own side work) and here I was. Not only had I no experience in the tech but I really had no interest in learning it either yet I did what I could and the team was great about it. Even if it had been my dream project I couldn’t have kept up with the rest as all had some level of experience where I had only ever installed NodeJS on a computer for Grunt and it had been at least three years since I had used that. Yet I was able to contribute and did my best to do so yet I was no longer influencing anything but simply fixing bugs and implementing the ideas of others.

Thankfully our work on DevKit hadn’t gone unnoticed though and the opportunities to join a few other teams opened up. In the end, just this past week I elected to stay on the Local team but move to SaaS services around it starting with some Laravel work (a tech I’ve enjoyed in the past) with the promise of a number of projects in technologies that actually excite me in the future. The real key though was the team. The folks at Flywheel have been great. Where we seemed to hit constant roadblocks on WP Engine teams (it took us months to get a signing key for Apple or even a simple Windows laptop for testing), Flywheel offered the opportunity to start a new project without the roadblocks and with a product manager who really seems to understand what we’re building. I might not be building dev tools for now but I am building something with a demonstrable goal and a team that can get the project done. That goes a long way.

Looking Forward to 2020

As I sit her writing this on Christmas Day I find myself looking forward to 2020 both professionally and personally. Two weeks ago I wouldn’t have said that as I felt trapped in a project I hated working on. I now have a team I love and a project list that will make a difference along with tickets for WordCamp Europe in Portugal for next June where Joy and I will be able to get away and see a new country. It’s going to be a good year.

Work and Personal Tech Projects

For work I’ll be building a suite of SaaS tools to help Local reach it’s potential as an asset for both Flywheel and WP Engine. This will give me exposure to a lot of tech with the hope that I’ll be able to see areas that I haven’t been able to in the past. From billing systems to network routers we have a lot of plans and all of them will result in experiences I’ll be able to take with me to help teams be successful for years to come.

On a personal side, I’ve found excitement in tech again by moving away from big tech and focusing on self-hosting a number of projects. That’s not the only thing I have planned though. I’m looking at starting a life-logging WordPress plugin to provide a private way of keeping track of my own data from location to pictures and more. I think of it as something of a digital diary I’ll be able to self-host. With this I won’t be leaving developer tools either. I’m pulling some of my Docker work out of mothballs to give me a robust developer environment I’ll be able to use on WordPress and other projects going forward. This time, I’ve got a few new tools in my toolbox as well to help make it all better than I had ever been able to do in the past. The only catch with the dev tools, this time, is they’re for me. I want to build a base I can use for my own work. They won’t be shared as I had done with similar projects in the past.

Health and Family Goals

Towards the end of this year I’ve finally been able to mostly break my addition to soda (although I write this while drinking a Cherry Coke, no one is perfect). Before a stressful Fall I had even managed to get my weight down about 12 pounds and was generally feeling better in general. I want to get back to this. If I accomplish nothing else for my health in 2020 I want to get back to where I was in September of this year minus the soda. I want to look better, feel better and not be so embarrassed to be seen in public.

With a little luck, by the time June comes around I’ll be feeling better just in time for Joy and I to take a real vacation. Of course, any trip for us involves a WordCamp but, that I can live with. I’m hoping we can get a few days of downtime around it as well as take a few weekend or similar trips this year that don’t involve constantly running from place to place.

Highlights and Plans

Of course, any good review post like this needs a list of the highlights. I’ve had a lot to be proud of this past decade including:

  1. Obtaining a Master’s Degree in Computer Science
  2. Settling Florida in a neighborhood that is finally conductive to the lifestyle we want
  3. Made use of our passports with numerous trips to Europe and Canada as well as a few others
  4. Spoke at 62 conferences and Meetups in 13 states and 4 countries
  5. Gave the keynote address at two different WordCamps
  6. Built and sold Better WP Security
  7. Built Primary Vagrant, Ouroboros and other Dev tools
  8. Wrote over 200 blog posts

Looking ahead to the next decade I do have some goals as well. Here are some of the biggest of them

  1. Live outside of the US
  2. Publish a book
  3. Give a conference talk in German
  4. Walk the Camino De Santiago
  5. Find a side-project or hobby I can enjoy
  6. Get back to flying by flight-instructing part-time

In the end, it’s been a wild ride. Here’s to hoping the next 10 years can bring the same progress while also allowing me a little time for enjoyment.