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.

Create a story, join a story, tell a story?

As I have been thinking about and working on "what's next" for me professionally, a theme has emerged around storytelling. Despite the fairly technical nature of my work to date, storytelling is a concept and a practice that has consistently been woven into the challenges and projects I take on. And as I ponder the future, it's been useful to see how each possibility fits (or doesn't fit) with that theme too.

Here are some of the general possibilities I'm considering through that lens:

Create a new story. Found a company. Make something new. Write actual stories or books.

Tell other people's stories. Journalism. Publishing. Podcasting. Interviews. Investigations.

Be a part of someone else's story. For a while, anyway. Get another job at an organization I believe in. Help lead an organization or team through a time of transformation. Give my time and talents to a cause I am excited about.

Work on story-telling tools used by others. Launch a product or service. Build or contribute to software. Do consulting or freelance work.

Learn from the stories already out there. Read books and articles, listen to podcasts. Catch up with friends and colleagues. Browse the aisles of the library. Wander in the woods. Explore new places.

I'm early in my own process of discernment, but I'm settling on one point of clarity: I may be retiring from doing "just one thing." Recalling the different modes of living out my multipotentialite self, I think it's time to shift away from the Group Hug approach ("having one full-time job or business that fully supports you, while leaving you with enough time and energy to pursue your other passions on the side") and instead shift to the Group Hug ("having one multifaceted job or business that allows you to wear many hats and shift between several domains at work"). Embracing my multiple passions and a skillset that spans many different kinds of roles and industries will, I think, mean honoring the time and focus each one deserves, instead of largely relegating everything except a narrowly focused job or project to what I can get done in my spare time. Easier said than done.

I've also had a hard time describing this time of transition to others in any kind of concise or confident way. As one person said, I'm not conforming to normative standards for professional/life changes. It's great to acknowledge that, but still makes for awkward light conversation.

Helpfully, I recently encountered Scott Berkun's article, Changing your life is not a (mid-life) crisis, and it's full of good stuff, including:

I imagine for myself a lifetime of changes initiated by me. I know I’m too curious, and life is too short, to follow the conventional footsteps that everyone is quick to defend despite how miserable they seem in the following. We use the phrase “life long learner” but it’s corny and shallow, suggesting people who quietly take courses or read books after college as if the essence of life were merely a hobby. We need a term for life long growers, people who continue to examine and explore their own potentials and passions, making new and bigger bets as they change throughout life.

A hard thing about this time is resisting the temptation to make safe bets that I know I can win. I've been there and done that, and even when I've taken risks or tried new things that others were uncertain about, I've had an almost embarrassingly good run of professional success as a result. So now I'd like to take some risks make some bold moves and step further outside my comfort zone along the way. I want to create, or tell, or be a part of a story that has some good twists and turns.

Let's see where this dimly lit path (that may not be a path at all) goes, shall we?

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:

Continue reading "Building momentum for your distributed work day"

Power in a distributed org

It's striking to see the differences in where power gathers in a distributed organization, compared to where that happens in a more traditional office setting.

When people come together in a physical space there is a lot of time and energy spent on appearance. The work isn't just about "what are we doing" but also "how do we look and how do people perceive us while we're doing what we do."

When people come together to work in a virtual/online space, the focus shifts.

In an office setting, I see power and influence gather around...

  • The person with the newest, coolest and/or most expensive clothing
  • The person with the larger corner office
  • The person with the most assistants
  • The person with the most impressive sounding title
  • The person with the closest parking space
  • The oldest, richest, whitest males
  • The person who's allowed to create or interrupt meetings
  • The person with the most impressive social and public-speaking skills
  • The person who uses their power to get what they want

In a distributed organization, I see power and influence gather around...

Continue reading "Power in a distributed org"

Working for someone else

This week marks two full years of my employment at Automattic. I was fortunate to celebrate in person with a number of my colleagues as we hosted a workshop for our clients and partners in beautiful Napa, California.

People who know that I co-founded and built my own tech business before joining Automattic often ask me what it's like to work for someone else. My short answer is usually:

  • I miss some of the joys and challenges that go with being ultimately responsible for the success of a business venture...
  • ...but Automattic is a place where I am trusted with a level of autonomy that I'd be hard pressed to find in many other employment situations, and
  • I am mostly just enjoying discovering new ways of doing things and being a part of a bigger team with greater resources available for innovation.

This post is my longer answer. While working at another company it has been useful and interesting to notice what it's like to have a change in my professional identity, not be "the boss," enthusiastically support something I didn't create, and try to balance the joys of "employment" with the inner itch to again be a "founder."

Continue reading "Working for someone else"

Startup

startup-podcast-coverI've just finished raising $1.5 million in investor dollars, building an office and growing a staff to start a new media company focused on narrative podcasts.

Okay, not really.

But I HAVE just finished listening to the first season of Alex Blumberg's podcast Startup, which documents his process of envisioning and then creating exactly that new company, Gimlet Media, from the very beginning. The show is so well done that I felt in on some of the best and worst moments in starting the business, and I learned a lot along the way.

Continue reading "Startup"

Zero to One

I thoroughly enjoyed Peter Thiel's Zero to One: Notes on Startups, or How to Build the Future.

It's one of the few "business books" I've read recently that incorporates anything resembling a coherent global ethic into thinking about what it means to create and grow a business. Beyond that, he gets into some great reflections on human creativity, optimism and pessimism about the future, and investing.

I didn't always agree with Thiel's views or counsel, but I found his thinking to be clear and his insights helpful, especially on what it takes to build something that makes a substantial and/or lasting difference in the world. Read through the lens of my past experience creating a startup tech business and my current thinking about what I can do for the world in the future, there were some lovely and/or cringe-worthy "ah-ha" moments.

I highlighted many passages as I read, here are a few that stand out:

Continue reading "Zero to One"