2021 Job Search Retrospective

The last time I was job-seeking, I described what I was looking for on this very blog. The post was descriptive and even a bit demanding, and then the role I found was so utterly ridiculously perfect for me, I can only call it a success. I think there’s a bit of psychology to a “here’s what I want in a job & here’s what I DON’T want” blog post, no matter what your level or newness to a given industry. Describing characteristics of a job you want lights up a “hey that’s me/my company!” affirmation in a brain, and describing characteristics you do NOT want lights up a whole other defensive part of a brain, I think, that says “well we don’t do exactly that, and here’s how we’re actually really good about this even though it might seem to share this characteristic,” that serves to engage and make folks want what you are. Also, I think displaying some “taste” and preference paints a more whole picture of you as a human being, which helps you stand out. These are all my opinions and just what worked for me, and I may even be laying my cards out too much since it does kinda feel like a “trick.” At any rate it’s all a bit moot since I haven’t done this since 2016, and the job landscape for newcomers to tech is so different than it was five years ago.

I was looking for a new job privately this time. The reasons for this are not complicated or dramatic; I wanted something very different to broaden my perspective, I wanted to be paid better, and I wanted to get onto a track where I could get a senior title by the time I’m 40 (about five years from now). I’m a late-comer to tech & I worry about the perception people might have of me, being in my 40s and being given junior level responsibilities, alongside the double whammy of sexism and ageism, which is not here yet but is certainly on its way – anyway, a lot of anxiety as you can see. However, I only had my applications, network, and cover letters to express these things, rather than a more inbound request with the above mentioned blog post, because despite truly loving my job and trusting my team at work, I did not want to tip my hand. The power imbalance is just too great to feel comfortable doing that – I have a mortgage to pay and an uninsulated house to heat!

The Process

So first off, I put a few feelers out, and made a Trello board. I made a Trello board for myself the last time I was job-seeking, and it served to organize my efforts extremely well. Everything in job seeking is phases, so each job, represented by a card, would travel along each phase, sometimes skipping a lot of them straight to the Rejected column, and sometimes seemingly languishing in a pre-interview state for months (for good reasons).

Surprisingly, most of the cold jobs I applied for were via LinkedIn. Their interface has gotten better for this in recent years, though I don’t think that the “instant apply” feature is very useful – if no one makes any effort to personalize or customize your first touch, then without STANDOUT credentials, I don’t think it will usually result in anyone reaching out. The best ones I found were those that said “apply on website,” and while that’s definitely harder and there were many that asked what felt like short-form essay questions, I had good luck with those – I like writing, haha.

But is writing the job, when looking for Operations/SRE/Devops/Infra (all of these are search terms that more or less apply to what I was looking for)? I do think good communication is an undersung part of working with others, however I’m no better an engineer than someone who didn’t have the education and focus on writing that I had in my early life, and yet I’m preferenced because I can express myself clearly and enthusiastically. So, while it advantages me, I think it’s ultimately an odd additional hoop that will make it harder for people with various learning disabilities, ADHD, anxiety, and others, to apply. I don’t know a solution to this – more phone screens? That is hard to do. Probably the answer is “spend more time/money” than a technical solution.

So, the breakdown. I applied for fourteen jobs over the course of about a month, received one offer, was rejected by eight, and I told a further five that I was no longer interested. Fourteen in a month might not seem like a lot, and indeed if I had not been employed that number would be at least double that, but it was really very nearly too much for me while continuing to work at my current job, which again, I like very much and respect my coworkers hugely.

My strategy for each “job card” in Trello was to add it first to the first column, To Apply. In that, I would put a URL to the job posting. When I came back to apply to the job, I moved the card to the Applied column, copy-pasted the entirety of the job posting into the Description of the card, and attached the resume and CL (if applicable) to the card itself. This makes each card pretty heavy honestly, and I’m happy I was able to do this all on a free Trello plan, because they’re hosting a lot of very similar resumes/cover letters for me now!! And I referred back to the job postings, often removed before they’ve even hired for it, constantly, in trying to find the right things to say during screens and interviews. And with each new job, I tweaked the resume a bit, and wrote entirely new cover letters each time.

quick cover letter sidebar:

Quick sidebar, let me tell you my strategy for cover letters! “Hi, thanks for receiving my application, I’m excited to work with you because a, b, and c from the job posting, and I know I’ll be a great fit because x, y, and z alignment. My experience suits this role particularly well because REASON. Thank you for your time!” The attitude needs to be “I’m a professional, so are you, let’s work together as mutually respectable humans!” No supplication here, and no more than a paragraph, SOMETIMES two! At the end I could post all of my cover letters, I think that could be useful. No names though obviously.

Anyway, back to the process. So after I sent things off, preferably to their own career page portal, it was usually a few days before people got back to me. Sometimes it was the next day, sometimes it was a couple weeks. This felt pretty fast to me, because I’m fortunate enough to be in a specialty that is in high demand. That will change someday, so uh, I’m gonna try to put some money away for that inevitability.

I also talked with a couple recruiters. Local recruiters often have access to jobs you wouldn’t otherwise know about, and are always worth chatting with – everybody makes money if it works out, and it’s in their best interest to help it really work out! If you end up leaving a job which you have been recruited into, their fee is often reduced, and the trust relationship between the recruiter and the company is harmed. In my experience, they did not have access to many larger organizations, but to lots of good local companies, which may be what you are looking for.

The Nos (From Me)

So let’s talk about some of the ones I turned down. A lot of the smaller local companies ended up being supporting Software-as-a-Service (SaaS) applications – a few cloud servers and the networking behind it, and all the other bits and bobs to make that run smoothly. No small task, but that’s what I’m doing at my current role, and I want to see what else is out there. Another really common trait I found in many of these jobs was that they were ready to hire their FIRST ops person. They’d gotten by with some setups in the cloud, and now wanted to hire someone dedicated to the task, to save money & grow. I don’t want to be anyone’s first ops hire, I was at my current role, and while I know more than I did then, the pressure is too much – possibly BECAUSE I know more now, I know more of how it can go wrong!

  • A friend of a friend reached out, we’ve talked about jobs before, wanting their first ops person as described, and I did turn him down (no interviews yet, so who knows if I’d have even made it to the point of an offer) and suggested that instead of one ops person, they hire two. A hard sell, I know, but which would create a collaborative working environment, scale for much longer than just one person, and ease the inevitable crispiness of the lone ops engineer.
  • Another place made a device and app that monitored and controlled kids’ internet and computer usage. Fuck your surveillance software, I will never take a paycheck for that. That kind of shit KILLS QUEER KIDS.
  • Another place did dynamic ad insertion on all-“free” tv. No thanks, that’s another shade of data gathering/selling (who’s paying for all this bandwidth??) and who knows, maybe/probably more insidious shit.
  • Another company’s hiring had seemed good, if corporate, until I talked with my technical interviewer, who wasn’t on the team but who had been serving in the role I was interviewing for on an interim basis. This person was very stretched thin, I am guessing, but hadn’t prepared for my interview, which really is not acceptable. He had no prepared questions, and instead seemed to pick out pieces of my resume to quiz me on edge cases as he thought of them. I did ok generally, he asked me detailed questions about nginx configuration and I didn’t do well and he said so, and yo, those docs are rough and imo, benefits from collaborative pairing because it’s tricky AND critical to get right. I was actually counting down the minutes til the interview was over. Toward the end I’m like, “so would we be working closely together” and he said “oh yes, oh yes, very closely,” and I made my decision to withdraw at that moment. Pretty sure I would have been condescended to there! So I had a bit of (perfectly professional) back and forth with the recruiter who asked me to reconsider, but man, I can’t work with that dude.
  • Finally, the last place I withdrew from, I’m actually a bit torn on. Had a recruiter screen where I made it super clear that my coding is no better than Fine and has never really been production (though I do have a hair of python in production at my current job), and from there the experience was quite good – initial chat, engineering manager chat, and then a technical challenge which was my favorite of any I did (some places had take-homes, some didn’t), where I submitted a chonky bash script and a Dockerfile to modernize & automate a manual process that a hypothetical team needed. It was all via Github. Because it was over the holidays, it took a bit to get back to me (this is a good thing), and by the time they got back to me, there were a number of comments on my PR. This was also the week of the actual fucking attempted coup in the United States. I was feeling frayed. I didn’t know if I was proceeding with any of the jobs because of a bit of silence (again – this was a good thing, because it means people were taking actual time off!) and a lot of fear on my part. I didn’t really enjoy what seemed like deliberately obtuse questions, but I responded, and then he asked MORE questions, and it just, I was really tired. I’d been applying & interviewing for jobs non stop for nearly 3mo by that point, while going to my day job. So I withdrew, after learning that this person was on the team – it just seemed like he was communicating very indirectly, where it could have been a collaboration. I know that evaluating PRs for candidates is difficult. I also wish there had been expectations set around the number of back-and-forths on the PR – I do that all day at work and it’s critical to be able to do that well and with kindness – but I didn’t know that we’d be doing that with this PR, and I was honestly out of juice by that point. At the end of the day, I think I’d have been able to handle this if it had not been such a civically stressful week.
  • Neck in neck with the job I took was one at a… platform as a service company I can’t really describe without giving them away. I was pretty intimidated by this entire process, they said they really wanted Ruby and/or Rust, and I just don’t have either of those (“some python?”), so I made that really clear and they still wanted to go forward with me. I thought I would be out after an initial set of technical questions, I wasn’t, I thought I’d be out after the technical interview, I wasn’t, and then I made it to the final round of interviews, but by that point I had an offer in hand from where I ended up accepting, so withdrew. I would totally apply here again, despite a high technical bar everyone was very kind.


  • The first place I was rejected was for an SRE role at a monitoring company. This would have been awesome but I was probably underqualified, they really wanted someone with more coding. I wish that it didn’t feel like, at so many places, that they wanted someone who was good at EVERYTHING – back end production development AND advanced, modern operations and monitoring. That is how many of these roles felt, and as my job search and discussions proceeded, I started to make it very clear in the beginning stages that I really don’t have much of a coding background.
  • The next place I really wanted has a market that is very specific so I don’t think I can generalize it here. Ha, I can’t even really say one of the biggest reasons I wanted to work there! Anyway, the pre-conversations went really well, lovely chats with the recruiter and the EM, where they asked about ops stuff, how ya do. Then they sent me a challenge which was a pared down version of their known product, and gave me a test suite and skeleton vars, and said make the tests pass. And I BASICALLY did, for, I think, 7 out of 11. I made yet another pass, ish, I wrote a lot about another, didn’t super know how to tackle another, & had really NO idea how to make the last one pass. Honestly I felt good about it, which might sound wacky, but I think I demonstrated enough Python to show that I can be competent with reviewing and analyzing code while doing a terrific job with ops, but they felt differently. This was the one big bummer.
  • Another, a cloud services/tooling place, it seemed like they were looking for jesus christ zirself and after a few interviews they turned me down. No surprise there.
  • Another, a budgeting app (sorta), was a GREAT process up until the challenge. They asked me to write a lot for the initial application, which I’m always happy to, and then I had thoughtful, great conversations with folks. Then they gave me an ops challenge which I did really like the flavor of, as that’s the kind of thing I’m good at and can do, but it was basically (at least) twice as much as I think it should have been for a reasonable challenge. I spent about fifteen hours on it over a few days, doing nothing else and depending on my husband to do ALL the cooking and cleaning and errands and stuff, which we usually share pretty equitably. It would have made a good “let’s see how far we get” pairing interview over a couple hours. It also would have been good if they’d set a time limit or suggestion on the challenge, or told me when they’d want it back. I asked for some of those a couple times, and was just told “hey, however long it takes you, that’s fine,” but folks, it’s not fine! I have a job and endless other obligations. So, I did ok on that, I wrote a ton of server provisioning templating from scratch, got stuff installed, struggled a fair bit with nagios from-scratch setup, ended up entirely losing access to one of the four servers (lol), and sent them 5500 words on the process, describing backup plans, safeties, & what I’d do in the workplace if these kinds of things went wrong. I did not get that job, and I feel like that’s fine, and that it was a poorly scoped challenge, though the content was good. But I was sad about it, because I think I would have done well with a better-scoped challenge, and I really like the product.
  • Another, I was iffy on culture wise because it seemed like a bunch of dudes in a small, not-growing company, and they were looking also for a jesus christ-ian replacement for someone who’d departed for happier trails and no doubt, much better pay for his skillset. Also they had misrepresented some things to the recruiter – there were no real docs and there wasn’t any intention of moving entirely from metal to the cloud. So I wasn’t sure, and then found out they made an offer to someone else about an hour after I had the initial chat with the EM. So that was probably for the best.

And finally…

Finally, the place that hired me! I have long been intimidated by this company, and I literally would not have even looked, if not for a friend who pointed me to the listings. It said “Senior” so I almost turned away without reading it! But I read it and thought hmm, not only am I capable of doing these tasks as stated, I would LOVE to. So I sent off my things the week before Thanksgiving, and then there was another delay over Christmas and NYE. There was a recruiter conversation, then a conversation with the Engineering Manager I’d be reporting to, and then a technical conversation that was kind and even informal feeling, and THEN I had my final interview the first business day of 2021. I took that day off work (felt weird, I really want to be there for planning and for that lovely first day, potential energy feeling) and the interviews went great. Talked with a data center sourcing manager, a VP about the values of the organization, a communication & collaboration interview with someone who reminded me SO MUCH of a sweet friend of mine that I felt immediately at ease and did really well with that, and finally a technical background & project work interview with a person from a team who works in the data centers themselves.

I cannot tell you how honestly easy and lovely this entire process was. I had GREAT conversations with everyone, and was comfortable enough to come up with the right stories and data of my past experience that was needed, HOWEVER they were not casual conversations, and each person had a proscribed series of questions they needed to ask. I cannot TELL you how much I appreciate this kind of process and planning and effort. A week later, they asked for my references, and after each one I spoke with my reference, and they said that the EM was very excited about me! A few days after that, I received an offer, and I spent a day in a VERY CHALLENGING haze while I needed to wait for the offer to finalize before giving notice at work and having all of those hard conversations.

So! I am halfway through my two weeks’ notice at my current job, and looking forward to three weeks off between, and then starting the new job at the end of February. I will be working on provisioning software for bare metal servers as managed entirely by the company, and I am so excited and so just… relieved, and lucky, that it feels like I have really found a niche which fits me and my interests. Also, omg, no on-call rotation!! Whaaaaaat!!

I hope this was useful for anyone trying to get a scope on the tech job market! Hmu if you have any questions or thoughts. Thanks for reading!