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?

Goodbye and thank you, Automattic

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.

YOLO

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.

Continue reading "Goodbye and thank you, Automattic"

When I grow up, I want to be a generalist

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?

Was it time to really grow up?

How to Be Everything Book CoverThen I encountered Emilie Wapnick's book, How to Be Everything: A Guide for Those Who (Still) Don't Know What They Want to Be When They Grow Up (affiliate link).

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.