5 Lessons I’ve Learned From One Year at Automattic

As of a few days ago, I’ve now been working for Automattic, makers of WordPress.com, for just over a year. It’s hard to believe that just a short time ago, I was ending my trial and starting full-time on a product that I both love and believe in.

I’ve written quite a bit about the trial process and what a day in the life of a Happiness Engineer looks like. But, I haven’t written much about insights working for a distributed company or how I now view customer support. In other words, what I’ve learned over the past year working at Automattic. In no particular order, here are the top five items.

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Where to Find Ideas

Lately, I’ve been on an idea tear with more ideas hitting my head than I could ever put into action. Admittedly, not all of these ideas are great, but I hit a bit of a slump over the last few months so I’m just happy to have the idea machine going again.

Ideas have been coming from anywhere and everywhere, but I’ve found a few specific places that I look frequently. I thought I’d share the outlets where I’ve had the most success. I’d love to hear suggestions from you though, particularly on podcasts and book recommendations.

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Mental Pictures

It’s been just over a month since my wife and I stepped onto the altar in Chicago, Illinois for a day that we’ll remember forever. Well, at least I hope we can remember all of the amazing details forever.

I proposed to Charlotte on February 17, 2013 amidst a slew of cacti on the top of a mountain in Golden, CO. We wanted to wait until fall so we could celebrate the cool weather, changing leaves, and great seasonal beer. Since we didn’t want to throw together a wedding in just a few months, we decided to push the event until the fall of 2014.

At that point in time, it seemed like the date would never come, but as with all eagerly anticipated events, it did indeed come. And, then it flew by.

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Yes, I Work in Customer Support

I often have a hard time communicating exactly what I do on a daily basis when someone inevitably asks. It might be that they’re not familiar with WordPress.com (although that’s becoming rarer!), or they’re just not very interested in tech at all. In the beginning, there was also a bigger issue that I hated to admit. The role of customer support also just felt, oh I don’t know, a little embarrassing.

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NFL and the American Cancer Society

In fact, the NFL’s claim of 100 percent proceeds from auction and 100 percent proceeds from retail has translated to an average of just $1.1 million every year since they partnered with ACS six years ago. That’s less than .01 percent of the approximately $10 billion the league made in revenue last year.

Really interesting/eye-opening article on Vice about the NFL pink campaign meant to raise awareness for breast cancer.

(H/T Next Draft which I discovered through Matt)

Cat’s Cradle

Cats CradleAuthor: Kurt Vonnegut
Title: Cat’s Cradle
Published: Sep. 8, 1998

After hearing Tim Ferriss recommend Cat’s Cradle multiple times on his podcast, I had to give this a try. I’m a big believer in reading fiction every once in awhile although my natural tendency is to read nonfiction. Vonnegut’s writing style is completely unorthodox and at times, a bit unusual. The satirical writing and hilarious character set will leave you laughing. If you’re looking to take a break from nonfiction, I’d recommend giving this a shot.

Buy Experiences, Not Things

Essentially, when you can’t live in a moment, they say, it’s best to live in anticipation of an experience. Experiential purchases like trips, concerts, movies, et cetera, tend to trump material purchases because the utility of buying anything really starts accruing before you buy it.

Fantastic piece on the Atlantic regarding spending money and happiness. Meshes well with some of my thoughts on spending money.

(H/T Diego)

A Day in the Life of a Happiness Engineer

This week, many of us at Automattic are documenting our day to give everyone an idea of what it’s like to work for an entirely distributed company. If you’re interested in reading more you can follow the tag #a8cday at WordPress.com and on Twitter. Here’s my day as a Happiness Engineer.

Whenever I tell someone I’m a Happiness Engineer, I normally get a blank stare followed by one of two reactions:

  1. The person pretends like they know what that means and no further questions are asked.
  2. A short chuckle ensues with the follow-up question, “So, what does that mean?”

I definitely understand. Before working at Automattic, I had no real idea what a Happiness Engineer might do.

So, what does a Happiness Engineer actually do on a daily basis? The short answer: we do whatever it takes to make the user experience as great as possible at WordPress.com. For those that want more, here’s my complete schedule from October 6th, 2014 to give you an idea of what it’s like to work for a company that is 100% distributed.

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Start Something That Matters

Author: Blake Mycoskie
Title: Start Something That Matters
Published: Sep. 6, 2011

I knew relatively little about TOMS before I started on this book. I really enjoyed reading Blake’s story and the lessons he continues to learn throughout the journey. What started as a unique idea to help put shoes on the feet of impoverished children has blossomed into a worldwide brand that continues to do great things for less fortunate individuals.

I found this read particularly inspiring. Blake describes how he started TOMS with very little, working out of his apartment in California. In some instances, they had so little money in the bank they couldn’t afford to pay the bills. What ultimately matters is that they continued to work to make things happen. This was perhaps my favorite quote:

‘Someday’ is a disease that will take your dreams to the grave with you.… If it’s important to you and you want to do it ‘eventually,’ just do it and correct course along the way.

I also really enjoyed his take on telling a story. It reminded me a lot of Simon Sinek in his now-famous TED talk, How Great Leaders Inspire Action. Sinek outlined that great leaders start with the “why” not with the “what”. By portraying your overall vision, people buy into your mission. Mycoskie had a tremendous quote on the topic:

When you have a memorable story about who you are and what your mission is, your success no longer depends on how experienced you are or how many degrees you have or who you know. A good story transcends boundaries, breaks barriers, and opens doors. It is a key not only to starting a business but also to clarifying your own personal identity and choices.

If you like reading inspiring stories of companies and individuals changing the way the world works, I would highly recommend giving Start Something That Matters a read.

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Einstein on Reading Fiction

If you want your children to be intelligent, read them fairy tales. If you want them to be more intelligent, read them more fairy tales.

– Albert Einstein

The Daily Mail isn’t normally my most trusted source for scientific literature, but they highlighted some research last year that seems to back up Einstein’s quote. Notably:

Furthermore, while reading, the reader can simulate the thinking styles even of people he or she might personally dislike. One can think along and even feel along with Humbert Humbert in Lolita, no matter how offensive one finds this character. This double release — of thinking through events without concerns for urgency and permanence, and thinking in ways that are different than one’s own — may produce effects of opening the mind.

The researchers suggest that reading then, is a way of becoming more open-minded. ‘Exposure to literature may offer a [way for people] to become more likely to open their minds.’