A new venture, WP Lookout

A few months ago I had an idea for a new tool and service that I thought could be useful to WordPress developers and agencies who manage lots of WordPress sites, but who can't or don't want to go all in on automatic updates. After spending some time thinking through the details and researching what was already out there, I decided to go ahead and build it.

I started writing code and building features on July 1. A month later in early August I launched the first version to a production environment, and now I'm starting to tell people about it.

Please, allow me to introduce WP Lookout.

I've already written about why I think this service fills in some important gaps in the WordPress ecosystem so I won't say a lot more about that here. If you're someone who has worked with keeping multiple WordPress sites up to date and secure, hopefully you see the potential benefit. And there are a lot more features I'm excited to be working on.

Even if you don't travel in those circles, perhaps you'll identify with this sentiment: we have all of these things in our lives running software that someone else has written (routers, computers, apps on our phones, the navigation systems in our cars, the firmware on our TVs), and we're supposed to keep them up to date with the latest versions, usually in the name of speed and security. But often that turns into a part time job of logging in to those devices, finding the settings screen where updates are displayed, and trying to understand what's changed and how much it matters. Automatic background updates are helping in some cases. But wouldn't it be nice if these devices and tools could come to us and tell us when they're ready for an update, and what exactly has changed? So, WP Lookout is set to do that for at least one small corner of the Internet.

It's been a while since I've set out to launch and grow a new business from nothing. It's thrilling to again be thinking through architecture, strategy, business model, marketing, finances, legal paperwork, scaling, innovation and all the other pieces that go along with trying to make something thrive for the long term. It's also vulnerable to be putting something out into the world and wondering how it will be received, or if anyone will care.

I'm hopeful that good things are ahead. Regardless, I'm proud of what I've done so far. I've learned a lot along the way — about building a SaaS ("software as a service") business, about how awesome developing with Laravel is (I'll write more about that soon on my tech blog) and about what solutions people who manage multiple WordPress sites might or might not be looking for to make their lives easier.

After I'm a bit further along I'll share more details and updates. In the meantime, please check out WP Lookout.

Does your organization need help figuring out remote work?

If your business or organization has been struggling through the unexpected shift to emergency remote/distributed work, and now wants to step back and build a distributed work culture that actually thrives, I'd like to help.

How does accountability and management happen in a remote workplace? How do we avoid Zoom meeting burnout? What does a productive home office setup look like? What cultural shifts are needed? What collaboration tools and software might be most helpful? How do we make decisions quickly when we're not in the same place?

If your leadership is asking these or similar questions, I can help you find some answers.

There are now a ton of great articles, podcasts, interviews and other resources out there about the mechanics of remote work. For some organizational leaders, that might be enough to get you started. For others, you may benefit from a collaborative, customized process to look at your particular organizational culture and structure, and develop a plan for shifting into sustainable distributed/remote work.

So I'm beginning to offer just that as a paid consulting service. Through conversations, workshops, assessments and other forms of engagement, I'm helping organizations move past the emergency reaction phase and into a long-term distributed/remote work setup that works for everyone.

Visit Distributed.Coach To Learn More

I'm passionate about the benefits — to individuals, organizations and society as a whole — of the distributed work model. I also enjoy helping organizations think about and plan for change. I've built and led fully distributed teams, and I've also built and led organizations where everyone came in to the same office to work together. I’ve seen both models up close, and I know from experience what works and what doesn’t. Especially as the implications of COVID-19 have forced so many organizations to rethink their operations, but even prior to that, I have wanted to contribute to this global shift in how we work.

If you are a part of an organization that would benefit from my expertise, or know someone who is, learn more and get in touch at Distributed.Coach.

Why are you giving social media companies free marketing?

Pretend you are the Director of Marketing for a business or organization. A tech company approaches you and they ask if they can put their logo on all of your promotional materials. All they want is a little space in the corner of each brochure, billboard, business card, television spot and newspaper ad you pay to produce. Preferably in color. But they can’t pay you for it. They need you to do this for them as a favor, for free.

What would you say?

If you wouldn’t take that deal, why in the world would you give Facebook, Twitter, Instagram or any other social media company free advertising space on your real-world promotional efforts?

If you get a few precious seconds of someone’s attention as they skim through your thing, why do you want them to spend part of that time thinking about someone else’s thing?

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Air travel and the carbon footprint of distributed work

In touting the benefits of distributed models of work, which I do often, there's a temptation to make the point that not having an office building and the energy-intensive practices that go with it (commuting, for example) must translate to a lower overall carbon footprint for distributed organizations.

While I think a lower carbon footprint is a possible benefit of distributed work, and one very much worth pursuing, it should not be taken as a given.

In fact, my experiences with distributed work (and in the tech world particularly) indicate that there are many, many energy-intensive practices to be considered, including:

  • The energy required to light, heat and cool residences with home offices that might otherwise go unoccupied during the day. I imagine temperature control in cavernous co-working spaces is also energy-intensive.
  • The computing power, equipment and energy usage at the growing number of data centers that support the many online services created and used by distributed workers (from collaborative office suites to audio/videoconferencing tools to Slack-bot cottage industry startups and more).
  • Any additional tendencies for distributed workers to have supplies and equipment shipped to them individually on a regular basis, compared to bulk buying or centralized shipping to an office. (Amazon next-day delivery is killing people.)
  • The materials, production processes and energy usage of laptops, phones and other devices that facilitate working from anywhere. Yes, there might be similar energy usage in an office environment, but whereas a physically central org might have an IT staff to repair/refurbish those items, with distributed that all mostly happens via shipping and may be less likely to facilitate re-using and recycling older devices.
  • Air travel and related energy usage to enable in-person meetups of distributed workers.

The last one feels important to dwell on for a moment.

Aircraft usage and flying account for a growing percentage of the climate change impact of human activity, some estimate 4 to 9 percent. "Take one round-trip flight between New York and California, and you’ve generated about 20 percent of the greenhouse gases that your car emits over an entire year," says the New York Times, citing the EPA.

So from an energy usage perspective, "I don't commute to an office anymore" starts to feel like a bit less to celebrate if at the same time one is flying around to meetups or conferences several times per year instead. More so if your office might have been a reasonable walk or bike ride away.

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Sabbatical cometh

In a few weeks I'll be starting a three-month long sabbatical from my work at Automattic.

As a benefit provided by the company, it's pretty amazing. After every five years of employment, Automatticians are eligible to take a two or three month paid sabbatical to have a break from work, refresh and recharge. Several people (mostly used to academic versions of sabbatical) have understandably asked what expectations are placed on us during that time: research, writing, professional development? Nope, it's all about having a break.

For me personally it's a really neat opportunity, and one I haven't had before in this particular way. I started my first company when I was 19 and have pretty much been working full time ever since. Automattic has a generous and flexible time off policy but to have such a significant amount of time to pursue hobbies, personal projects and time with family and friends is really quite an amazing gift.

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Building momentum for your distributed work day

Imagine that you are about to go on stage to perform some amazing thing that you know how to do. You're waiting in the wings for your moment to shine, and you want to bring your very best to the experience.

But then also imagine that you spent the last several hours or even days in isolation. You haven't really talked to anyone or had much human interaction at all. No one has given you encouraging words or expressed excitement about what you're going to perform.

And then you find out that the time of your performance has not really been set or advertised. There will be an audience but they will be coming and going from the auditorium where you're performing, and they may or may not be paying attention to you. When you do the thing you're best at, someone may or may not notice. Oh and the stage is actually going to be a small, dark closet.

Now go out there and be awesome? Umm....

It's a silly scenario, but for some people who work in a distributed environment, especially one where a lot of collaboration happens asynchronously across individual schedules and time zones, this is what the beginning of our work day can feel like: quiet, slow, isolated.

In a traditional office setting where workers tend to arrive, collaborate and leave on roughly the same schedule, the energy and pace of work can come from the environment itself. But for distributed workers, even when there is actually a lot going on in the organization we're working with, it can be a challenge to build momentum at the start of our days. Sometimes the work itself is enough to generate that energy, but sometimes we need help getting into the right mental space for high productivity.

So how can you build that momentum if it's not coming from your physical work environment? Here are a couple of things that I've seen work well:

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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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