Counteracting Work Theater

Thank you to everyone who wrote or texted me after yesterday’s post. I know when I put “crisis” in a post title it might trigger some sense that my wellbeing is in question. I was riffing on Byung-Chul Han’s recent work which argues that the move to story-selling (rather than telling) is silencing common narratives that bring us meaning (eg religion, middle class). And when I say “meaning crisis” I’m referencing John Vervaeke’s work, which argues we are living through a time of mental illness and pervasive modern feeling of existential disconnection, nihilism, and lack of purpose. Maybe my contribution back will be a finer grained definition of the ambition crisis I hinted at, where we simultaneously derive meaning and status from work (thank you Protestant Work Ethic) and know on some level that our truer selves are the part of us we bring home to engage with the people and activities we choose in our free time.

This certainly isn’t just a me thing, shows like Severance are exploring similar themes. If you want a primer, read (2009!) “The Gervais Principle, Or The Office According to "The Office" by along with “Be Slightly Evil” for a Machiavellian guide to organizational life — essays on power, leverage, and strategic imperfection for those who live and work in institutions (and baby organizations aspiring to become one).

Now I want to pre-face this all with a declaration that I’m not anti-work in the lie flat movement sense or the quiet quitting sense, but also I’m a founder and when not a founder I tend to work at the perfect level of executive-ness (either in actuality or in mindset) where I have a lot of agency over what I do and when I do this. Basically I am saying I’m privileged, and this makes me a less reliable narrator to some folks when it comes to the problem of work theater. But the thing is, I wasn’t always privileged and after literally shoveling manure, working every station at McDonald’s, dropping out of community college to be an intern at a global logistics company, joining a chaotic disaster of a startup… I finally found my way to Twilio and everything came together in 3 years of exhausting exhilarating work to set the stage for privilege that would take another decade to materialize. In the meantime, my net worth hit an all time low of about negative $1M (thanks global financial crisis!)

So what I’m trying to say is I know how to work hard and struggle. Or I used to. The beginning of my loss of innocence came at the end of Twilio, where at 26 I was heading up marketing and was hired over. My ego didn’t like that much, even though it provided quite a bit of relief from the daily making it up on the fly-ness of that job and the flat org of ~18 people reporting to me that suddenly had structure. But I was baffled, and it took me a long time to separate this from being generally butt-hurt, but the person who was hired doing do little, understanding our customers not at all, and getting so much compensation, stock, and generally being the new bright shiny object for the board and CEO. They were so good at “being an executive” and I watched with a mix of disgust and awe as they got budget I’d been fighting for approved, got the hires they wanted made, and generally gave every sign of being able to get things done without ever building an app or talking to a customer. This was my first up-close encounter with work theater.

Long story but they didn’t last long, another similar hire was made, and I quit and started a startup and got into YC and went on to make new mistakes and discoveries. But I kept processing that experience, and yes it was (is?) a chip on my shoulder. I felt embarrassed at the time to have cared so much, to have cried in the bathroom so often, to have teared up constantly in meetings with my boss. I was embarrassed by my intensity. Now I see it was a gift, and as I take inventory to figure out what to do next I’m tracing backthe lineage of my distaste for work theater. I didn’t realize it at the time but the stage was already set for this loss of innocence around work, but in my naïveté I couldn’t see it til it ripped away the one job that felt like a vocation.

So the professional coach in me asks, “what would you say now to your younger self?” And after giving her a hug, reminding her life isn’t fair, and reassuring her that all this frustration will one day result in becoming financially independent one day, I’d tell her not to stop considering what happened. I’d tell her to pay attention to how taboo it feels to say anything negative about the choices made by the boss you deeply admire. To pay attention to how much silencing yourself, even in your own head, is costing you in terms of ability to make sense of the world. To give yourself credit for deeply and sincerely loving the customers, from a place of genuine joy in getting to be part of their creativity and energy. To savor the incredible team, because they’re not all like this, and it might take a long time to find a situation like this again.

The thing is, I need to dig into the details of this experience to see if I can find the product to build in here. The path to that is to ask how the world can be different, and to find the people like me (back then). Is this a software problem? A problem to be solved with coaching? With consulting? With joining a company and being a great manager? I’ve tried all of these and I’m still trying out new approaches to fighting back against work theater.

This post is already long, so in the next one I’m going to dig into what it is and how it works and how it’s evolved alongside SaaS and other productivity and collaboration innovations of the last 15-20 years.

Thanks to my husband Kevin Morrill for patiently reviewing drafts of this post.