Digital receipts for paperless living

In trying to live a relatively paperless lifestyle, I notice what options stores and restaurants offer for providing electronic receipts instead of paper ones.

My favorite kind is where you use a credit card or mobile payment method that some lower level of infrastructure already knows about and you automatically get an email receipt without further prompting. Square has a great implementation of this.

Slightly less awesome but still great is the version where you use a digital payment method and then have to enter your email address manually, even if you've used the same payment and receipt delivery method at the same location before (I'm looking at you, most American chain restaurants that have the little mini-computer waiting at the booth when people sit down). A bit annoying, but still paperless.

Then there's everywhere else where printing a receipt is probably the only option. Especially at the grocery store, where the receipt and personalized coupons are several miles long, requiring their own bag to carry out. And look, there I am a few days later, awkwardly holding a crumpled piece of paper up next to the networked super-computer on my desk, manually typing in some details that some other networked computer somewhere else already knows about.

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Star Trek values

A few weeks ago I had the pleasure of attending a panel at Silicon Valley Comic Con consisting of various members of the cast of the television show Star Trek: The Next Generation. Brent Spiner, Gates McFadden, Jonathan Frakes, Denise Crosby, Marina Sirtis and Robert O'Reilly were joined by original series cast member William Shatner to talk about the show, their lives as actors, and what the Star Trek universe has taught and can teach us about the real world.

For someone who watched every episode of the show when it originally aired and who has remained a fan since, it was an hour and a half of nearly pure joy. For one, I was just excited to be a part of a whole auditorium full of people reflecting on how much influence the stories, dialogue and creativity of the show had on our lives, the panelists included. Several audience members stood up to say just how strong that influence has been, informing the careers they chose, the people they've become, the kind of lives that they now lead, and I was right there with them.

In watching Star Trek as a young person I remember being invigorated by the complex problem-solving scenarios that the Enterprise crew faced week after week. I learned from the principles of collaboration, mutual respect and cross-species equity that were practiced. I saw strong women in leadership roles, and I saw non-Caucasian characters developed with an unusual (for mainstream TV, anyway) depth and texture. And I was inspired by a vision of the future that offered so many possibilities for exploration, discovery and growth. I'm sure that my real-world evolution as technologist and computer geek was propelled forward significantly by my immersion in that make-believe world of technological wonders.

The panel also highlighted a new angle of my appreciation for the Star Trek universe. I hadn't previously thought about Trek as having a political point of view, because I assumed that the vision of a world where humanity had figured out how to eliminate poverty and hunger, celebrated and built on our various differences, and employed innovation to protect and restore the environment was a vision that anyone would embrace and want to strive for, and not a particularly politically-charged one.

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WordCamp for Publishers Denver

I'm excited to be a part of the team that is organizing the first WordCamp for Publishers happening in Denver, Colorado this coming August 17th to 19th.

In my work on Automattic's VIP service offering I've been able to see some of the incredible things that journalists and publications of all types are doing with WordPress - really interesting stuff that pushes the software in new directions. So when I saw some of my colleagues discussing an event that would bring engineering, product and editorial teams together around all the things WordPress can do in the publishing world (for publications big and small), I wanted to be a part of making it happen.

We're looking for speakers and sponsors now. If you know someone who might want to be a part of this first-of-a-kind event, please point them in our direction. And if you're involved in publishing with WordPress at any scale, or just want to learn about how media organizations are using it to modernize their publishing  workflow, I hope you'll consider attending. Tickets ($40) will go on sale soon!

Creating a private website with WordPress

When we became parents in 2015, Kelly and I talked about where and how we wanted to share the initial photos and stories of that experience with a small group of our family and friends. In case you haven't noticed, I feel pretty strongly about the principle of owning our digital homes. So I felt resistance to throwing everything up on Facebook in hopes that we'd always be able to make their evolving privacy and sharing settings and policies work for us, while also trusting that every single Facebook friend would honor our wishes about re-sharing that information.

I took some time to explore tools available for creating a private website that would be relatively easy for our users to access, relatively easy to maintain, and still limited in how accessible the content would be to the wider world. (I tend to assume that all information connected to the Internet will eventually become public, so I try to avoid ever thinking in terms of absolute privacy when it comes to websites of any kind.)

I thought about using WordPress.com, which offers the ability to quickly create a site that is private and viewable only by invited users while maintaining full ownership and control of the content. I passed on this idea in part because it didn't allow quite the level of feature customization that I wanted, and partly because it's a service of my employer, Automattic. While I fully trust my colleagues to be careful and sensitive to semi-private info stored there, it felt a little strange to think of creating something a bit vulnerable and intended for a small group of people within that context. I would still highly recommend the WordPress.com option for anyone looking for a simple, free/low-cost solution to get started.

Here are the WordPress tools I ended up using, with a few notes on my customizations:

Basic WordPress Configuration

For the basic WordPress installation and configuration, I made the following setup choices:

  • I put the site on a private, dedicated server so that I had control over the management and maintenance of the site software (as opposed to a shared server where my content, files or database may be accessible to others).
  • I used a Let's Encrypt SSL certificate and forced all traffic to the SSL version of the site, to ensure all communication and access would be encrypted.
  • I set up a child theme of a default WordPress theme so I could add a few customizations that would survive future parent theme updates.
  • I set "Membership" so that "Anyone can register" in the role of Subscriber (see more below on why this is okay).
  • For Search Engine Visibility I set "Discourage search engines from indexing this site".
  • For discussion I set "

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On training people

As a follow-up to my post on what I've learned over the years about hiring people, this is a similar list of what I've learned about training and onboarding people as you welcome them into your organization.

Many organizations reduce training to a pretty simple process ("here's the training manual, here's your trainer, go"), but I find it to be one of the most complicated and fascinating periods in someone's life with an organization. The initial days, weeks of someone's employment (or, in a not-for-profit context, someone's time volunteering or serving on a board) are highly influential in shaping the experience they're going to have in the long run, and the work they're going to do.

It's a time when they start to reconcile their "outsider" impressions of what you do and how you do it with what they see as a new "insider" with fresh perspective. It's where any idealism and over-simplification that happens during the hiring process runs up against the nuances of internal processes and the texture of individual co-worker personalities. Training can prompt many moments of truth about the new person's image of themselves as a part of your organization: "do I belong here?" "are they going to like me?" "can I live up to hopes/expectations?"

From the perspective of the people doing the training, then, I think successful training is a careful balance between providing enough structure to properly educate and acclimate the new person to your organization while also allowing enough freedom and flexibility to accommodate their learning style, pace, interests and questions - especially the "why are you doing it this way when you could do it this other way?" ones.

Whatever you do, don't figure out training on the fly. Don't let it be a 100% self-directed experience in some hope that throwing someone fully into the deep end is the best way they'll learn. And don't underestimate the return on investment you'll get from an intentional, comprehensive approach to training.

As the process gets started, minimize assumptions. Communicate clearly and directly with the trainee (a word that feels a bit demeaning but is useful here) about every detail of their first moments as a part of your organization: where they should be at what time (and in what time zone, if you're a distributed team), in what medium the training will be conducted (in person, text chat, audio chat, video chat, in groups or one-to-one), how long the sessions will be, what they need to bring, and anything they need to do in advance. Give your trainee every opportunity to get past nervousness and make a great first impression by removing unnecessary vagueness in these critical first days.

Communicate expectations and set clear training goals. "Over the next X hours/days/weeks we're going to walk through everything from this to that. Your main trainer/mentor/buddy will be this person and they are your main point of contact for the process, ask them whatever you want. Here's the format we'll use, here are the materials we're going to cover, and here's a list of all the things we're going to touch on. Here's how we'll track your progress through this training, and here's what we expect from you at the end of the process." And then make sure all of this information is known to the wider team and company. Continue reading On training people

Using Todoist to organize all the things

For just over two years now I've been using Todoist as my primary to-do list manager and personal organizer software. I pay for the upgraded Premium version at US$28.99/year. I really like it and it's helped me stay on top of all the things I want to get done in my professional life, personal life, local community and beyond.

(Before Todoist, I'd been using Taskpaper and loved the simplicity of its interface and file storage. The software hit a period of being unmaintained and I really needed something up to date, so I switched. Taskpaper has since seen new life as a project, it's worth checking it out again too.)

The Todoist website linked above already showcases many of its features so I won't bother repeating those, but here are a few of the things I especially appreciate:

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