My Stints in the Chocolate Factory: A journey of worker well-being
It seemed like the perfect job. So why can't I sleep?
Years ago, I worked at a large media company that specialized in technology trade shows. A dear friend who worked there helped me get the role, which I took after months of unemployment–many of us who were working in San Francisco startups in the early 2000s know this time as Downturn 1.0.
In the first all-hands meeting I attended, conducted via teleconference on a Polygon device, the Los Angeles-based CEO launched the call and in short order started screaming at employees both in the room and listening remotely. I don’t remember what he was so upset about, I was in such a state of shock. I looked over at my friend, who shrugged and threw up his hands as if to say, “What are you going to do?” This ridiculous display was apparently standard operating procedure at the company, and, well, at least we all had jobs, right?
Months into the role, I became used to screaming matches in meetings, at events, even at a team dinner. I hung out with a woman on another team who faced a similar dynamic. She would sneak upstairs to my office and hang out when her nose started bleeding–a telltale sign, she said, of extreme stress. Another manager had to leave the company due to abdominal distress. I was starting to see a pattern and tried to transfer to another team but was caught trying by the group GM, who told me he would never provide the needed approval for me to join a new group, cementing my decision to just leave. The economy had picked up, and I didn’t need that kind of toxicity in my life anymore.
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Fast forward many, many years later. I’ve accomplished my share of successes as an entrepreneur, and taken a leadership role at a large tech company in what seemed a natural extension of my work scaling a startup. It was my experience as an entrepreneur that got me the role, serving the startups segment. Now I would get to manage a team in an intrapreneurial division of a Fortune 100 company.
To go into the details of it all would be impossible, and possibly NDA-breaking. Suffice it to say, familiar feelings started on Day 1 of being unsafe. I walked into a situation with a team in flux. My new boss left involuntarily; and my new, new boss would leave shortly thereafter. Each time my team was folded into another team with different expectations, politics and resentments. I received personally insulting emails from people I had never met before, admonishments and warnings from teams I had only just started working with. One manager introduced himself to me by sharing that he would not work with a member on my team – I would have to figure out how to run events without the benefit of his events team.
Similar to my earlier job, this role was untenable, but this time I took it much more personally. I was a senior leader now, an experienced professional who prided herself on executing and getting along with internal and external partners. I needed to be an example to my team. I had turned down a counter offer from my previous employer for this opportunity: How would it look if I couldn’t even last in this new role for six months? If I couldn’t even get my teammates to get along? If I couldn’t bring my global peers together in a big kumbaya?
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So I started doubling down on things I could control, hoping to succeed in the areas I couldn’t. I worked nights, weekends, pulled all nighters, plowing through a team strategy, dozens of required courses, meeting stakeholders in other global regions, and getting as close to inbox zero as possible – something one of my GMs said was essential to succeeding at the company. I hit my KPIs and even added to them to show I was serious.
I got sick. Really, really sick at the company’s annual conference, but I stuck it out, pretending I didn’t have a 102-degree fever and strep throat, thinking, if I screw this up my management will never trust me to execute. The company had an intense work ethic and accountability culture, and actively weeded out weak links. I never wanted to be a weak link. When COVID hit and all flights out of San Francisco were grounded, I attended a partner team offsite in London, virtually, for two days, from 1a to 9a; then attended my regularly scheduled meetings from 9 to 6p PT.
The company was also known for its productivity and solutions-focused environment. There were automations for everything – from approving your direct-reports’ expense reports to compliance checks. If any of my reports had so much as an expense on an expense report undocumented, I would get a notification, and if I didn’t respond to the notification my manager received a notification. An inordinate amount of my time was spent playing notification whackamole and hounding my team to complete open tasks and tracking down the sources for notifications that were likely meant for previous employees, but had to be addressed to avoid warnings from my own manager.
Ironically, among the hundreds of daily emails I received was a weekly management tip, as part of a mandatory management course I was auto-enrolled in, that read: Cancel meetings that are not necessary. Set boundaries. Protect your time.
The thought of doing that and keeping my job was inconceivable to me.
Nearly a year in I got a prescription for anxiety meds. Despite working now 15-18-hour days and nights, I couldn’t sleep. And I was starting to question my mental capabilities around anything other than work. I started losing things and forgetting any commitment I made outside of work. I stopped talking to friends and family–there was simply no time to do so, but I also forgot to call people back, or respond to their emails. I picked up the meds but didn't take them, worried about being reliant on medications to get through the day.
Despite my efforts and even some wins, none of it was acknowledged. I was swept over by a tide of new management. I left the company unceremoniously, mentally, physically, and emotionally numb.
There is no redemption story here. I simply hit rock bottom and slowly thawed my way out of it. Close friends suggested I take a few months to get my bearings again. One said to me, with love, “Promise me you won’t talk to any companies until you sound like yourself again.” I found simple joys in such things as doing laundry, washing dishes, grocery shopping, taking care of my family, activities I had previously outsourced because I was too busy. I reconnected with my kids–needless to say they did not get the best of me that year.
I felt both grateful and troubled; I had been well-paid and could afford to get well again, but so many people don’t have the option of taking yoga classes and waiting it out as I did until they find something better. They have had to endure mental and physical exhaustion and assaults on their health and dignity because they need a paycheck.
And being well-paid is not justification for being treated poorly. The cost to our well-being is too great.
In that space of constant toxicity I lost the thread of agency, of optimism – perhaps the greatest asset I could bring to a role. I lost my personal power, pride in my work, my well-being. I think of myself, times many millions of others for whom this is just a typical day at work, and see it as potential wasted.
But still, being an optimist, I’ve noticed a personal evolution from that time. I’ve become a better manager. I trust my gut implicitly. I don’t sweat others’ mistakes, or hold mistakes against others if I see they are learning from them. If I see someone struggling I ask them, how can I help? If something you did troubles me, I don’t presume you are an awful person; I ask to talk it out. I ask you how you are doing before jumping into the litany of tasks we need to do. I notice if there are too many tasks to logically do and reprioritize if needed. I try to be flexible if I’m needed when I’m “off,” but generally hold my ground around no meetings during school drop-off and pickup. I don’t schedule calls when I’m in the car, when I’m sick, or when I’m with other people to “optimize the time.” And I don’t believe that saying I’ve had enough is a weakness.
That ain’t nothing.
You made it! A tough journey, but you found the way
This was so powerful and honest to read. I loved it!