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.

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