A few folks have asked what I've been working on since leaving full-time employment at the end of 2019. Here's an update:
Graduate studies
I've continued my graduate studies in journalism, and I'm currently planning to graduate next year with a master's degree focused on reporting and storytelling. My classes thus far have included:
Studies in Journalism and Communication Theory
Social and Cross-Media Storytelling
Journalistic Judgments
Data Journalism
Emerging Technologies
Diversity & Media
Coming up this fall I'm diving into "Intro to Statistical Methods" and "Media Audiences and Content Strategy."
Overall the program at Ball State University has been good for me. I'm learning a lot and the material is interesting and relevant. It's pretty focused on building a skillset in research, news reporting and media production, and given that I've done a lot of those kinds of things professionally and for personal projects, there have been times where my impatience to apply my skills and knowledge has made me wonder if I needed to finish the degree program at all. But most of the time I just appreciate that I'm getting to take my interests and knowledge to a new level in a new context, and that I'm honing in on what I might (and might not) be able to contribute to the world of journalism.
Growing my SaaS application
About a year ago I launched a software-as-a-service tool called WP Lookout, aimed at helping WordPress professionals keep track of things happening with the themes and plugins they depend on in their work. I've continued to add new features and get a few paying subscribers, and it was fun to have it featured in some industry press coverage (WP Tavern, Post Status). This summer I've been working with a contractor on marketing and strategy for increasing user signups.
Overall this project continues to be one that mostly scratches some personal itches (solving a technical problem I had for myself, learning the Laravel framework, getting practice launching a modern SaaS offering), and the fact that it might be useful to other people is a bonus on top of that. There are plenty of other features I'd like to add to it, but I'm also trying to make sure my time invested is proportionate to the value it brings me and other people, especially since there are other (unrelated) SaaS tools I'm working toward building and launching, along with various open source software projects I contribute to.
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.
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?
After more than 5.5 years at Automattic, I recently decided that I am ready for something different, and today is my last day at the company.
The things about Automattic that excited and impressed me when I first joined in 2014 still excite and impress me today. The mission to democratize publishing and help people to better tell their stories. The pioneering of a distributed model for hundreds of people to work well together. The way even small improvements in a few lines of code could affect millions of websites. The focus on transparency and excellence in communication. Working with kind people from all over the world in a constant flurry of collaboration and creativity.
I'm proud of the contributions I made in that time, and I know that I got to work on some of the most interesting projects of my professional life so far.
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.
Like many other kids, early in life I was confronted with questions about what I would be when I grew up. What one single area of study, profession and career would I build my life around? I gave the question all the weight it seemed to deserve because I didn't really know another option.
When it was time to pick a focus in college, I considered a lot of different paths; minister, writer, diplomat, teacher, political activist and computer scientist were among them. But I thought I needed to pick one. Technology was the area where I had most consistently thrived in what I did, so I made my choice.
For the almost twenty years that followed I thought I had my thing I would be when I grew up. I was a tech guy running a tech business. I did a lot of different things as a part of that role, but there was a strong overarching theme I could easily explain in answer to, "what do you do?"
When I started working for someone else, I was sheepish about it at times. I liked the work itself but I was slow to adjust to the public identity of "tech employee," worrying that it was a step backward from "tech entrepreneur." And because employees are ultimately carrying out someone else's vision (no matter how much they share in it), I wondered if I had lost access to my own driving, anchoring passion for what I was doing with my life.
It didn't help that the popular narrative about how to be GREAT is to pick one thing and devote your life to it. One day when I was feeling particularly disoriented about what I wanted to be when I grew up, I encountered something along the lines of this tweet, presumably written in response to the question "how can I be amazing?"
You pick something you want to get good at and you devote every day of your life to it. That’s it. No secrets.
Oh dear. I had many things in life to be thankful for and happy about, but did I have the one thing I wanted to devote every day of my life to, professionally speaking?
It was neat that I'd run for political office, performed as a magician, taught college classes, organized conferences, hosted a podcast, learned to fly an airplane and run a company, but was enough enough? Was it time to stop messing around with side projects, passing interests and skill-building that was tangential to my "one thing," whatever it was?
And thank goodness I did! As I read Emilie's words, I came to identify strongly as the type of person she calls a "multipotentialite," sometimes also referred to as a polymath, renaissance person, jack-of-all-trades, generalist, scanner, or a puttylike person.
I highlighted so many passages while reading How to Be Everything, but here are a few worth excerpting (page numbers from the HarperCollins Kindle Edition):
that the key to thriving in an uncertain economy is having “a mind-set that embraces instability, that tolerates—and even enjoys—recalibrating careers, business models and assumptions.” In the postrecession era, adaptability is not merely an asset; it’s a necessity. (pp. 26-27)
[On studying the components of a happy multipotentialite:] They had all designed lives that provided them with three common elements: money, meaning, and variety—in the amounts that were right for them. (pp. 34-35)
For multipotentialites, productivity is about more than just getting things done. We need to make sure that we’re working on the right things, that our schedule is conducive to getting things done, and that we understand when it is time to abandon a project and move on to the next. (p. 147).
The principle goes like this: the majority of our activities can be divided into three categories: creating, connecting, and consuming. Creating involves bringing something new into existence. Connecting involves reaching out to others and can include activities such as responding to e-mails or posting on social media. Consuming is any activity that involves research or learning. It can consist of reading books or articles, watching movies, listening to podcasts, and so on. All three categories of activities are important. But to get the most out of them, you should respect the combining rule: Connecting and Consuming activities can be combined, but should never be combined with Creating. (pp. 171-172).
One of the most common concerns for multipotentialites is that we won’t measure up to specialists who have been working in a field for decades...Being effective matters more than being the best...Your work should be about delivering, not about reaching the top of your field. (pp. 185-186).
What does it mean to lead with your multipotentiality? It isn’t just about accepting and embracing your inner wiring. That’s only the beginning. To lead with your multipotentiality is to build a sustainable life around your plurality. It means figuring out, in practical terms, how to get the money, meaning, and variety you require so that you can flourish. (pp. 201-202).
These were just some of the passages that had me nodding along vigorously, feeling understood and spoken to in ways that rarely happen when reading a "professional development" book. I am a multipotentialite! And I'm really happy about it.
In the struggles I mentioned above, I had been trying to find my new "one thing." The book helped me see both that my past approach to life and work was not as single-minded and focused as I thought it was, and that what I actually want professionally and personally is the freedom to explore a wide variety of interests, practices and experiences.
When I was running my website development business, I wasn't just a tech guy running a tech business. I was a software developer, graphic designer, project manager, accountant, lawyer, sales person, marketing person, manager, personal coach, and so much more. I also managed to find time to be a community volunteer, non-profit board member, and even candidate for elected office.
As Wapnick says, "The easiest way to work for a boss who lets you wear many hats at work is to be your own boss. There are few careers more multifaceted than entrepreneurship." This was so true for me; co-founding and running my own business was one of the best things I could have done for embracing my multipotentialite nature.
Fortunately, my current job also allows me a lot of potential to live out my best multipotentialite self. Working for a distributed company that values "what you deliver" over many other things, and in a field that's at an intersection of so many of my current interests (software engineering, journalism, writing, the open web, democratizing publishing) is amazing. I don't have to hide my long lists of things I'd like to try. I can pursue my passions so much more easily than if I were commuting every day to a single location with a narrowly defined role whose success was measured by how many hours I appeared to spend on it at my desk.
Wapnick calls this the Einstein 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." It's one of four different models for living a multipotentialite life that she describes, the others being Group Hug ("having one multifaceted job or business that allows you to wear many hats and shift between several domains at work."), Slash ("having two or more part-time jobs and/or businesses that you flit between on a regular basis."), and Phoenix ("working in a single industry for several months or years and then shifting gears and starting a new career in a new industry").
The book did a great job of laying out some strategies and tactics for thriving within each of these models. I am always in danger of distraction, feeling bad that I don't have enough time for all my interests, or wrestling with what to say when people ask what I'm up to these days. Having advice on how to manage all of that while making sure I give the things that are important to me my best energy was really great. (The related article on 9 Ways to Explain Your Multipotentiality to Non-Mulitpotentialites was also really helpful - it's what resulted in the "Deep Generalist" label I'm now using for myself on social media and elsewhere.)
If any of what I've said about being a multipotentialite resonates with you, even a little bit, I can't recommend How To Be Everything enough. I'm planning on reading it again soon, if only to work through some of the exercises and questions that accompany each chapter in a little more depth. And if you're REALLY interested, Wapnick also started The Puttytribe, a community of multipotentialites looking for conversation and support.
I'm grateful to have found a framework that gives new meaning and structure to my past and present pursuits, and that makes me even more excited to think about the future.
Starting next week, I'll be shifting my focus at Automattic and joining our "WordPress Concierge" team.
It's a small group of talented folks who build custom WordPress sites for influential people and organizations across a bunch of different industries. I'll be creating and supporting the sites we work on while also helping to help the team scale up its internal tools and processes. I'm excited to flex a different mix of skills and ship some new kinds of things.
It's hard to believe that it's already been more than three years since I joined Automattic and began working with the VIP team, where I'm wrapping up my time this week. That role has been full of its own interesting and rewarding adventures that have taken me deep into the heart of the systems and tools that power the modern open web.
After years of various roles in which I've been solely or jointly responsible for hiring people into businesses and organizations, I offer some thoughts on what I think works.
Hiring is ultimately about entering into a new relationship with someone. Actions and words that truly honor the joys, anxieties, vulnerabilities and interdependencies of that process will tend to make it more successful. Things that treat it as a cold, harsh, impersonal transaction will tend to make it (and your organization) less successful.
A successful process, by the way, could mean that someone is not hired just as much as it could mean they are. Clarity about the long-term fit is more important than short-term harmony and avoiding disappointment.
If you create an application, screening, interview and hiring process where people can check off a bunch of boxes that culminate in their employment, they will tend to optimize for that. It doesn't mean they are disingenuous or won't be good employees, but it may not be what you want as you build a team. Asking people to follow specific instructions is fine - it can be a good way to screen out bulk applications and clarify someone's interest. But lean more toward creating an interesting dance between equal partners, and then seeing how everyone feels when the music stops.
Keep candidates updated as much as possible at every step of the process. Let them know you've received their inquiry and when they should expect to hear a next response. If there are delays on your end in evaluating their application, say so. Try to respond to every candidate who follows your basic instructions about how to apply, no matter how far they make it in your process. Don't play mind games, you are not running Fight Club.
Résumés are useful as a summary of someone's professional identity, but should only be a starting point for understanding what they would bring to your organization. Putting together a flawless résumé (and possibly a cover letter) should be a baseline for understanding someone's attention to detail and ability to communicate clearly. A résumé with typos, lots of fluff or other problems can probably be discarded early on.
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."
One of the questions I get most since joining Automattic is about what it's like to go from working with a company where we were mostly collaborating in one office space in Indiana, to working with a fully distributed company, where everyone works from home, coffee shops, co-working spaces or similar spots around the world.
(The other main question I get is about what it's like to go from being "the boss" to working for someone else - a post for another time.)
The short answer: I'm appreciating and enjoying it, and I think it is the future of many kinds of work.
The longer answer follows.
The question of a distributed versus in-person setup for a team or company is discussed often in tech circles, perhaps even more so right now as tech companies face hiring challenges and considerrelated immigration policy issues. I feel like I've experienced both sides in some form now, having built and managed a web development firm for close to 17 years with a strong focus on working together in the same physical space (experimenting with remote workers along the way) and now having worked almost 8 months in a fully distributed configuration.
Going in to my new job, I was initially skeptical that I would find a distributed setup to be better than what I'd experienced working with my team in an office together. I thought it would be exciting, interesting and different, and despite all of the enthusiasm I'd built up for it (especially after reading The Year Without Pants: WordPress.com and the Future of Work) at some gut level I still suspected it would be a kind of nominally acceptable, second-best alternative to working with people in person. Continue reading "Distributed vs. In-Person Teams"→
One of the main reasons I get excited about Internet technologies is that they amplify the power of the written word and other kinds of creative publishing. Modern online tools enable bloggers, software developers, poets, journalists, novelists, chefs, filmmakers, marketers, photographers, artists, scientists, organizers and many other kinds of people to bring their creations to the world, at a constantly decreasing cost. And even through all of the cultural transformations we've seen spurred on by the Internet, the power of the written word remains - publishing can still change minds, start movements, spark connections, capture beauty, reshape lives.
Next week I'm joining Automattic, Inc., the company that makes WordPress, runs WordPress.com, and provides a bunch of other publishing-related tools and services. I'm joining the WordPress.com VIP team as a full-time VIP Wrangler, where I'll be helping to provide support, hosting, training, and other services to some of the biggest and best WordPress sites on the web (NY Times, TED, CNN, Time and more).
There are many reasons I'm excited about this, including:
