Burnout and Quitting

This has been sitting in my publishing queue for quite some time, and I've been internally debating if I should publish it or not. "Conventional" wisdom is that you should never say anything bad about a previous job or any previous manager because it shows disloyalty to anyone you might work for or with in the future or something like that.  

I'm not sure I think that's remotely true, and even if it is, would I want to work for someone who dislikes honest opinions and wouldn't hire me because I was willing to share a negative experience?  

It really feels more like another Boomerism from 1963 that I've internalized, but still: there is a risk in being open and honest, and if you do it in public, there is always the risk that an open and honest discussion will backfire on you.

I joined a C funding round startup in 2015, and it was a fantastic decision. There was a buzz in the air from the energy of my coworkers, and it was clear that they enjoyed what they were doing, who they were as a business, and that the future looked fantastic because growth was going nowhere but up, and fast.

I got in at probably the best time because of the opportunities that exist in such an environment for skill growth, and job growth, and yes, the money and benefits were amazing.  I learned more about Linux, networks, how to manage projects and teams, and the tooling required to do all of that at scale than I had learned in the previous decade doing similar work. My skill set and abilities grew immensely over the years, and it's something I'm going to be forever grateful for because it's opened so many doors that would never have been open otherwise.

I legitimately felt like I worked somewhere that mattered, was building something that mattered, and that the people I worked with genuinely cared about issues in my life and would be willing to work with me if something in my life happened that interfered with work.

As an example of what I'm talking about in terms of how everyone was treated was that when my mother died I was able to take several weeks off to be with her in hospice and deal with the aftermath and nobody said anything at all about the time I was out, and hell, my manager even sent flowers.

As with all things in life, however, all good things must end. (There's no good job under capitalism?)

The downward spiral started when the founding CEO was forced out because the board and outside investors wanted to go public and get their money back out.  Not unreasonable; that's why they invested in the first place.

There wasn't a lot of pressure internally to keep the founders, because a lot of the early employees felt the same way: they had large chunks of equity and a liquidity event would benefit everyone.

The replacement CEO that the board decided would be the right man to get us over the line and public was a horrible pick: 100% a total outsider who knew nothing at all about how the business runs, who the customers are, and what success and growth look like.  

Work was pure chaos for over a year as there was a whiplash-inducing focus change on products and market segments that made things utterly impossible to focus and work on projects to completion because there was nothing but TOP PRIORITY problems and no resources to fix any of them.

It was professionally turbulent but the core of the culture survived intact, and from a day-to-day perspective very little changed for the team I was on or any of the teams I worked closely with.

Notwithstanding that it still was a great place to work, I think it was pretty clear to everyone that this wasn't going to result in a stable and profitable public business, so out with the old (again) and in with the new (again).

Our next CEO came with a much better pedigree, but his almost first real interaction I had was him slagging the remote nature of the business.  This was incredibly concerning because I was a remote employee, and if your new CEO starts by saying 'Well, I don't know about all this remote employee stuff', the concern is the least of the reactions a sane person would have.

I got more concerned as we went through our first round of layoffs because it felt like me being remote in a business that no longer wanted to be remote and having layoffs was a major indicator I should expect a rug pull at any moment.

Ultimately it looked like as he onboarded he understood the value of remote work, and we then ran right smack into COVID, which made everyone a remote employee by force.

The only thing that kinda stunk to me during the rest of that year was that we were on a hiring spree, mostly to fill C-levels and directors, but we were busy doing it from the CEO's Rolodex. I get wanting to bring people you've worked with before into your new company, and in principle, I don't oppose the idea, but some of the hires were just bad.  We hired a lot of people who were just there for 'One more IPO before I retire', and didn't give half a crap about the company, the culture, or the employees.

We also hired several REALLY bad picks who demolished several pillars of the business, and several groups never really recovered from being pillaged and stomped on by people who didn't understand the value, why we worked the way we did, and that a lot of customers were unhappy with the destruction of things just so we could save a couple of bucks on the payroll.

Worse, I finally ran into something I had never experienced before: spending a year working on 'process'.

At first, it looked like it was a massive improvement: we had clearer guidelines on a lot of things which had always been a bit seat of the pants, and clarified our escalation paths and who owned what and who to talk to about things.

As it continued, though, it started showing that it wasn't really about improving workflows, it was about making paper trails for someone to follow later.  In my defense, I have never worked a large corporate job, so I have no basis for knowing if every company is this fucked, or if this was a special kind of disaster.

Ultimately, the problem was that the new meetings required by 'policy' were not ever productive. They were always prime examples of bikeshedding and resulted in situations where you'd have weeks or months' worth of meetings with tens of people to make simple decisions that, previously, would have taken one meeting and maybe an hour to determine sanity.

This destroyed my motivation: if I found a problem, we used to just figure out who owned it, maybe file a JIRA if the fix required more input from us, and then it would show up fixed in a couple of days (or even faster if we could convince the engineer who could fix it it was a serious flaw) to a workflow where you'd have a meeting about it, then a 2nd, the managers would have a meeting, then you'd have another meeting, and then you'd file a work item to have a meeting with the team required to fix it to do it, and maybe you'd fix an issue week to months later.

The underlying reason why this bikeshedding was especially toxic - even more so than you'd normally expect - was that my work was in the much faster-paced abuse and fraud world, that the timelines we were getting action on and fixes back to resolve issues were nonsense: we never got actual fixes shipped in a timeframe that mattered, because everything we got fixed was always fixing the problems we had 3 months ago, and did nothing at all to remediate the current crop of issues.

You'd be tail chasing for everything, and the workload never improved or even changed, because we have gotten utterly inflexible and prone to 2nd and 3rd, and 4th guessing ourselves rather than taking steps to resolve problems.

It demotivated me to the point where I would show up to meetings, and outline problems, but rarely push them to completion because there was no reason to invest that much time in meetings only to have it result in a fix that never fixes anything.

Worse, some of the feedback that would come back from engineering teams was that there was frustration that we kept asking for similar fixes for the same problem repeatedly because, yes,  nothing was being fixed for their time investment either.

The problem is, ultimately, at some point that's not nearly enough to keep you wanting to get up in the morning and I spent most of my last year of employment with a raging internal discussion on if I should just quit and move on.  It's a lot harder to leave when you're well compensated, because what kind of fool would willingly give up great big piles of money because they're just uninterested in the day-to-day work?

In the meantime, things degenerated further into having to be quantified by metrics, which means only work you can quantify was considered worth doing, so I went from pushing solutions and expanding what I know to be a ticket pusher: customer tickets, internal requests for action on abuse, and the occasional outside report which went through an internal escalation.

This was not remotely what the job was, what I wanted to do, or sustainable: doing tickets, frankly, SUCKS when dealing with a customer base that can't fix anything and you not being in a position to invest the time needed to work out fixes for them and, even in the case where you do, it gets stuck in committee so long that there wasn't any reason to invest the time you spent anyways.

The final straw that pushed me over was in an all-hands meeting where the CEO announced the removal of a large amount company-wide vacation days, the dramatic degrading of our health insurance offering, and his response to the very understandable and reasonable dislike of these changes was that we should all just stop talking and listen to him, which I think is something that nobody had ever really explicitly heard ANY senior manager say about anything - I certainly never had in the last 7 years.

There is merit in the 'you need money to eat' argument which, well, I can't argue, but if the trade-off for it is that you're mentally dead, physically exhausted, and an absolute raging asshole to everyone around you because you hate what you spend 8-10 hours a day (or more, if there's an on-call issue) doing, is it worth it?

Eventually, I decided it wasn't, and the right choice was to pack up my bags and move along.  I'm lucky in that we DID go public, and I did have early ISOs which isn't quite fuck-you money but it's enough of a runway for me to take a year or two sabbatical, figure out what I want to be involved with next, and relaunch.

The biggest thing I regret was not leaving two years earlier when I started feeling burned out and dragging myself through two years of frustration, exhaustion, and work that was ultimately pointless and not even slightly fulfilling.  

I know it's all nice to think you'll end up in a job you find satisfying and at some point, settling is the right way to go and I don't disagree: but you shouldn't settle for something that's so far from your interests and skills and just keep chugging along because inertia is a real and hard thing to overcome.

Edit: And shortly after writing this, they laid off half of the company to outsource the jobs to non-US workers, so I guess I really did bail at a reasonable time.