Tag: work

Joining a Giant Company: Three Concerns

I started working for The Walt Disney Company in August of 2021 – it has 190,000 employees. The Walt Disney Company’s employee base is roughly the same size as the biggest city I’ve ever lived in.

(that’s Providence, RI, by the way)

As a younger man I did work for larger organizations – The Federal Government (roughly 2 million employees) and Starbucks (in the neighborhood of 350,000 employees) – but that was in some ways a different professional landscape. I was an AmeriCorps community organizer, I was a part time barista, whereas at Disney I’m a Proper Professional, I have a letter/number designation

(P4! Senior Product Manager II!)

I have to navigate the workings of the organization to accomplish my goals in a way that is different from those other jobs.

Since becoming a tech professional, I’ve worked at two organizations prior to Disney – Automattic, the parent company of WordPress.com and Tumblr, where I was employee number 130-something, and dbt Labs, where I was employee number 42. While these were both undoubtedly tech companies, in the same broad industrial space as Disney’s tech arm, I did have my concerns about shifting my professional context from the startup space to the established enterprise space.

(even just considered by itself, Disney Streaming Services, the arm where I work, is larger than dbt Labs and Automattic combined)

That’s what this post is about – what those concerns were, and how they’ve played out so far. Note that I’m just about seven months in, and I still have a lot to learn, and some of the following may turn out to be inaccurate, or maybe overly optimistic!

Concern: A big company won’t be as flexible or as energetic as a startup.

This concern, I’d say, is partially correct. I think maybe what I’ve found to be more important is, figuring out what I really value at work. That is to say, there is some part of working at a startup, of always having nine hats and a dozen projects to juggle, the constant uncertainty and balancing act of this vs that, of some weeks where you feel like you’ll never get to grab a breath – there is a part of me that really is temperamentally inclined toward that way of working, and the intensity of the relationships you develop in that environment.

What I’m coming to see now, though, is that I am not sure that I particularly like that part of myself; to be in a constant state of reaction and forward momentum at all costs can be thrilling, but it isn’t necessarily good for you, or your marriage, or your mental health. It might not even be particularly good for your career – more on that later.

The flexibility piece, I think I have been surprised by: I am able to operate in some ways more flexibly at a larger organization, because, and this may be especially notable for a Product Manager, who has to work across departments and functions quite a lot to get basic things done, you have so many more degrees of freedom. When you’re at an organization of 48 people, there are very few decision makers, very few paths to success for any given proposal or suggestion – when you have dozens of departments and directors to chat with, the opportunities for creative solutioning open up in ways that I had not ever expected.

Concern: I will be stifled and stymied by suffocating adherence to The Process.

Another sort-of-true, sort-of-not concern here. There are times when I do feel some pining for the faster cycles and lower organizational overhead of my earlier startup jobs – but I also think that the trade off makes sense, as an organization gets larger, and the pieces become more complex to place correctly, and the timelines and dependencies multiply exponentially, of course you need more scaffolding and structure to keep everyone rowing in the same direction.

There are also times though, especially on a Thursday afternoon, when the week’s Zoom Fatigue is really settling in, that getting a checklist of super clear action items from someone that outline exactly how to move my project forward, can be a balm on this PM’s decision-blasted brain. Sometimes it can be nice to not have to generate generational change in an explosive way at will, and instead, write the doc, and set up the meeting, have the simple satisfaction of a mildly productive day.

Concern: Working at a giant organization won’t allow for the kind of rapid career advancement that a startup can offer.

This one I feel may be right, depending on how you think about career advancement.

Part of it has to do with titles vs toolboxes (and there’s probably a longer post in here that I can loop back to later) – there’s also something here wrapped up in the book Peak (by Anders Ericsson, I had to search my own site to find, shockingly, that I haven’t written about this book already!)

That is to say, joining an early stage startup can represent a huge title gain – you can jump to a level that possibly wouldn’t be accessible to you otherwise. This can be amazing for your career, especially if you’re trying to make a lateral or business-area kind of shift (see my own move from data org to product org, in fact!)

But what it doesn’t afford you, the high stress, high energy, mostly-reactive world of a growth stage startup, is much space for reflection and repetition – since you’re doing, nearly by definition, new things all the time, and learning just-enough on the fly to move onto the next brand new thing it can be really challenging to build meaningful mental models around how to do the work itself, in a way that is sustainable and excellent – what I’m calling here the toolbox.

Whereas working at a larger org, with lots of folks in similar roles, with semi overlapping experience, can offer the kind of community of practice that you’ll struggle to find at a smaller org – notably in Product, where there tend to be few professionals, and they don’t typically have built-in opportunities to peer mentor or skillshare.

I don’t mean to say that this is a pure binary – it’s probably a sliding scale, and I’m sure there are some orgs that offer access to both title and toolbox. I also don’t mean to imply that one is better than the other – they’re both growth, but certainly different kinds of growth, and choosing one or the other (like many things!) is an exercise in trade-offs.

Fatigue: Emotional and Intellectual

I know not everyone follows my LinkedIn profile with rapt attention. That’s OK – I don’t follow your LinkedIn profile very closely, either.

So, you might not know; I’ve moved into a different-but-not-so-different role at Automattic (the folks behind WordPress.com, Woo Commerce, Jetpack, and a heap of other great stuff)

I was previously leading a support team, and have since moved into a role that we call a Data Analyst, on the Marketing team.

If you’re familiar at all with Automattic’s naming policies, both for jobs and teams, yes, this is an outlier in the direction of the mundane in both cases. I went from being a Happiness Engineer on Team Athens (and also technically on Team Redwood) to being a Data Analyst on Customer Activation.

100% consistent with Automattic standard, though, are the many and varied hats that come with this role: at other companies my day to day work could be described as Marketing, Growth Engineering, SEO, SEM, Pay Per Click, Customer Success, Data Science, even a little bit of database architecture. It’s a lot!

(As a sidebar, I think the job duties and title change may make it seem like I’m making a career change or otherwise sort of changing direction – let me assure you, my focus continues to be on building explosive value for our customers. I’m expanding my tool set – not changing my approach.)

Today, was a cognitively demanding day. Working remotely means taking on a lot of responsibility for structure and organization of one’s work – I’m still figuring out how to do that the best way I can, in this new role. It also means being disciplined to push back distractions which are constantly at the ready in any browser window.

Spending hours looking at databases, considering queries, performance, outputs, accuracy – this is work, it’s real work, and it builds fatigue. A day of work, focused, attentive work, can certainly leave me in need of a deep breath and a long walk.

(I personally find it especially hard to think critically and well about SQL, statistics, databases, and so forth, near the end of my work day. It’s like I’m running out of gas.)

What struck me today was how different this kind of fatigue feels, especially compared to the kind of fatigue I’d feel after a tough day leading a team of Happiness Engineers. I’ve reduced them into two distinct types for the title – Emotional and Intellectual – but I’m sure there is some overlap, maybe some days more than others.

Maybe the difference is, in the lead role, the fatigue comes from trying to serve others, trying to hold them and their full personhood in your mind, whereas in this analyst role the fatigue comes from the intensely individual and personal kind of focus it takes to do it well, to take it seriously.

It does feel different to say to my wife, “I had a hard day – I couldn’t get the data types to reconcile the way I wanted,” rather than “I had a hard day – I think I really let some people down.”

Maybe they’re not different. Maybe I’m different.




Working Remotely and Getting Weird

Boiled down, the Big Idea of this Post is this: working remotely is awesome because it lets you be much weirder than if you were working in an office, and this makes you happier and more productive.

I’ve spoken before about how working remotely means you lack certain social signals in your day – however, working remotely also means that you don’t have to worry so much about what folks around you think of your behavior – since there are likely only folks around you when you choose to have them around, be it in a cafe or a coworking space or whatever.

Something I have come to deeply appreciate in the remote work environment is the opportunity to run experiments on myself and the way that I work, to become happier, more productive, and a bigger impact agent within Automattic.

I don’t think of myself as a particularly anxious person, but I do think that I’d struggle to pull off some of the things I’ve tried in a more traditional office setting.

When I was working with the Terms of Service team, each day was a bit of a roller coaster – you never knew what you’d run into (but lots of golden cucumber derived medications, oddly), but it wasn’t always the sort of thing that weighed lightly on the conscience. I would often take 2-3 breaks during the day to lay quietly on the floor in Shavasana to still my mind and listen to my own breathing.

When I was first working with a live chat team, I tried working a number of different hourly and daily configurations – four long days, three long days and a few hours here and there the other four days, six shorter days, etc.

Working remotely also allows you to see how other activities can impact your day – for a long time I’d take a break in the middle of my day to go to the gym. I eventually found that my day before the gym tended to be less focused, less productive, so now I get to my local Y at 5AM on gym days – that way I’m home before Mango or the Doc wake up, and I usually get some quiet work done in that post-gym, pre-breakfast window.

The best part of working remotely for a company that understands the import of results over butts-in-seats is you’re able to fit your work to your own ebbs and flows, rather than trying to fit yourself into someone else’s understanding of what The Work should be or look like.

My current schedule would absolutely get me in trouble in most traditional workplaces – a lot of the work that I do doesn’t look like work – it looks like going for walks or staring at a whiteboard or reading a book. It also doesn’t look like a regular work schedule – can you imagine pitching this during a job interview?

Well, I’ll put in an hour, maybe 45 minutes on Mondays, Wednesdays and Fridays between 6AM and 730AM. Tuesdays and Thursdays it’ll be a little more. I break for breakfast and picture books every day for about two hours.

I’ll be around-ish for most of the day until maybe 4:30, 5PM, although I won’t be at my computer or even really available for some unpredictable amounts of time.

I’ll also work on the weekends sometimes, but not always. But sometimes.

It would be a hard sell! But, this setup isn’t random or the result of whim; it’s the result of literally years of experimenting on the way I work, the times I work, when and how I approach each part of my day and each of my responsibilities.

Whether you work remotely or in a more traditional workspace, give some experimentation a try – you never know what might help you make a leap forward 🙂


Working Remotely Means Making Your Own Signals

My first job out of college was with AmeriCorps – I was a community organizer in Binghamton, NY, working on something called the Binghamton Neighborhood Assemblies Project.

The Neighborhood Assemblies were a series of small direct democracy experiments, based in each of the cities voting districts. It was a fulfilling way to spend time, and was exactly what I needed to dive into after giving graduate school a try.

The community organizer gig didn’t have what you’d call much of a set schedule – our office was based out of City Hall, and we came to get to know the signals of the rest of the building.

When we heard the planners head out to get lunch, it was around noon. When we could hear the local alternative radio station, playing through tinny boombox speakers, it meant folks were gone for the day, and the janitor was doing his job. When the hallway lights went out, it meant we were the last ones in the building, and probably time to start thinking about heading home.

It’s been the same for all of my jobs – small signals that indicate where you are, how your day is going, what time it is. In cafes there were early morning customers and late-day duties – you didn’t mop the floor until an hour before closing. Signals.

Working remotely, especially if you work mostly from home, lacks these signals. There aren’t other folks around who present regular patterns of behavior and expectation that you can build your own day around. There isn’t an entire building’s ebb and flow that you can float along with.

There are pros and cons to this – it allows you as an individual to find your own best way, your own ideal schedule and timing, in a way that being mandated to a particular place at a particular time would preclude. It allows for a lot of this kind of experimentation, in fact.

Having no signals can also allow for, or in some way legitimize, the inclination for a lot of tech workers to put in just one more – one more ticket, one more pull request. This is how you end up working far into the night, really letting your work overflow the bucket you had set out for it.

This is a con – a lack of exterior signals, of social signals, may lead us to overwork, to burnout, to unreasonable expectations of ourselves.

It leads us to the question so common among remote workers – “How do I know when I’m done?”

The answer is, naturally, whenever you decide you’re done. It’s the deciding that’s tricky.

So, the remote worker has to create these signals for herself: through experimentation and weighing of options, to create signals to indicate the end of the work day.

You could construct signals to indicate the beginning of your day, when to take lunch, etc – but I think most important for your mental health is finding a way to put a punctuation at the end.

I’m lucky insofar as The Doctor and Mango tend to get home around the same time every day, so I have a nice bookend to my work. I know about when they’ll be home, and I don’t pile anything time-sensitive or must-do in that calendar slot. When I hear the car in the driveway, I quit Slack, I close my laptop, and that’s it.

It’s very freeing. If you’re working remotely and have not yet built yourself some type of end-of-day signal or ritual, I totally recommend it.

It could take any format – maybe you have your computer set to play a particular song at a particular time. Maybe you have a certain last task every day, and you follow it up with a walk around the neighborhood. Maybe you use IFTTT to flash your office lights at 5PM.

Signals are important. When we work remotely we are lucky enough to build our own.


Feasting and Flexible Work

Feasting and Flexible Work

Something you all may or may not know about me is that I am a big fan of Mexican food. Well, I say that but I suspect what I’m really a fan of is American Mexican food, which is probably a different thing.

Growing up we had your standard Family Taco Night fairly regularly – hard shelled tacos, ground beef, the quintessential starter taco.

I’m not ashamed to admit that Taco Bell introduced me to soft tacos. I had to learn about them somewhere, and I think at the end of the day Taco Bell as a gateway drug into new taco horizons is an acceptable origin story.

Continue reading “Feasting and Flexible Work”