Failures

I like the idea of tackling shame head-on by simply putting the responsible stimuli on display. This post may later get hidden, depending on whether these details are wise to be associated so closely with my consulting business, but for now: caution to the wind!

As mentioned previously, I installed Ubuntu 25.04 because I carried out a long overdue wipe and reinstall of my personal development laptop. Mainly, I was hoping to get rid of a bug that is causing a crash randomly as a result of some interaction with the touchpad.

As I dug in, though, it also proved an opportunity to exhume some startup and project carcasses. There were a few things that I didn’t even recognize (sorry Thane, I’m sure I cared about vnide whatever it was) but mainly just a lot of painful projects.

I guess on some level I hadn’t really processed the loss of some of those dreams until I stared at the folder names in the terminal while the cursor patiently blinked and blinked and blinked.

It’s not so much that I felt attached to the code. Code changes all of the time and the less there is of it, the better. But the ideas those projects represented, the problems they tried to solve, the warm impressions of late nights with a coworker and memories of cold, late nights alone, all erasable with the swift injection of an rm -rf.

That hurts like a resonant whack of your knee cap on cement – a nice shudder that vibrates up your femur and gasps just long enough for you to anticipate the hurt but not long enough to numb it out.

So rather than wait until the next surprising club to the head the next time I’m rustling around in the closet, here is a list of my professional failures of the last decade or so:

  • 2014: I spent the summer in Los Angeles floundering as I tried to learn how to translate rudimentary coding skills into actual application development, on top of that I encountered my first sour business deal: an internship with a flakey early stage startup that never paid me
  • 2015: I unceremoniously quit the startup upon which I had pinned all of my post-secondary-education dreams and settled for a job at a dev shop
  • 2016: I took a two year hiatus, in the meantime several of the clients that I had worked on at that dev shop ended up taking off, without me
  • 2017: I returned to web development to find that angular.js had all but vanished and everyone was doing Angular or react now
  • 2018: of the four companies that offered me a job upon my return, I picked the one that now no longer exists in any meaningful way, worked for several months with no pay, and didn’t get that equity agreement in writing
  • 2019: no overt failures that I can think of this year. I did spend a lot of time distracted with personal stuff, so I hardly remember what I even worked on
  • 2020: yeah this was an extra crazy year, covid plus additional personal life drama
  • 2021: this should have been the year of our acquisition, instead our competitor got acquired. I took up the CTO mantle and made the wrong hires and failed to push forward the most meaningful projects
  • 2022: I quit the company after having to lay off most of the team as a result of the company burning through a huge portion of funding that was supposed to last years
  • 2023: I went all in on a new startup as the technical co-founder, again no pay and again failed to get an adequate equity agreement in writing, a tenuous arrangement that lasted less than 6 months, then jumped onboard another startup, this time simply as a senior dev
  • 2024: that startup predictably failed to grow as much as they predicted and had to cut their most expensive head (me). So I joined one of the companies that I had worked with in 2015, and got to witness first hand the long term consequences of both technical architecture decisions and culture degradation as a result of an unsuccessful acquisition/merge (the acquisition had happened, the desired result had not)
  • 2025: I attempted yet another go at a startup – this one had already passed through the hands of three technical teams in its short existence. The tech stack problems were fixable, unfortunately the culture was not. Did I get paid cash this time? No. Did I get my equity agreement? No, I did not. I have I learned my lesson? Apparently not.

I should probably follow this up with a wins post (learned optimism is an incredibly powerful mindset) but I’d also like to revisit some of these situations for generalizable lessons, too.