31 January 2025
At the end of 2021, my time at Rocket Mortgage came to an (amicable) end; the things they had asked me to do were done (more or less--there was more work to be done, but others could pick it up and run with it), and the next things I thought worth doing at Rocket were not things they were interested in. So, we parted ways, and I set back off into the wild blue yonder to find my next role. What followed was what I call my "involuntary sabbatical"--three years of job hunting and interviewing, a bizarre mix of freedom and frustration, and more than a few "false starts" that felt solid yet evaporated. It's been quite possibly the strangest time of my career thus far.
Now, as I prepare to re-enter the full-time workforce, I find myself thinking and feeling and reflecting on the last three years, and I thought I'd share because I live in the perpetual belief that somebody on the Internet might find this useful. (Or, perhaps, you just want a deeper insight into the maelstrom of crazy that is me.)
Rather than try to string a narrative out of this, I think it a little easier to just post ad-hoc blurbs and admissions.
This was not fun, but it wasn't terrible, and it might've been necessary. I think I got infected with the "I'm in tech, I can get a job anytime I want" fever that I've seen infect so many of us, and it was probably a good wake-up call. The tech sector isn't the same as it was--which is good, we were in a huge bubble, and arguably still are--and that means that everyone in it has to adjust their expectations for how long a job search at a senior executive level is going to take. (And I'm nowhere near the top of the "executive level" to boot.) I probably still have one or two more of these in my future before official (voluntary!) retirement kicks in, but even if I spend the rest of my career at Capital One, I think it's important to realize that we aren't in "Oh, I'll just interview tomorrow and get a job" mode anymore.
Having alternative income streams is really helpful. For the last three years (actually the past ten, but the last three are what's relevant here), I've been teaching part-time at UW-Seattle, and that helped a great deal with expenses. Having that part-time gig helped extend the runway a lot. (Plus, it was nicely distracting and gave me something to be doing instead of climbing the walls and driving everyone around me crazy.)
Three years is simultaneously forever and not that long. In some ways, it feels like just yesterday that I was saying farewell to my teams at Rocket; in other ways, it feels like that was a lifetime ago. I can't tell if that's a factor of my age, the length of time between gigs, or what.
Ageism: Did it have a role in your search? How did you deal with it? Oh, boy, this one. My wife and I are definitely split on this; she's convinced that it factored very heavily into comapanies' evaluation of me for a role, and I'm not as sure as she is. Sure, there's a fairly hefty amount of ageism in the industry, but most of that is in the "tech bro" sector, where the twenty-somethings who are bum-rushing the startup/VC/Y-Combinator scene are absolutely convinced that now that they are armed with {fill-in-the-blank-current-hot-thing} they have all the answers they need for any problem that beckons. Frankly, I have zero interest in working with those folks anyway, so if they're discriminating against me, it's probably pre-emptive (I'd be discriminating against them in turn, in case that wasn't already obvious), reflexive (it's mutual discrimination), and convenient (saves us both some time).
What I do think is happening, though, is more economic in nature. Let's be honest, with 30+ years of software experience under my belt, if I've made any progress at all in my career I'm not cheap. If the job calls for somebody who's a mid-level manager and I apply for it (either deliberately or by mistake), I'm very possibly overqualified--which in itself may not be a problem--and overcompensated--which is very definitely going to be a problem. Is that an ageist thing? No, except in that "very senior" will generally only be a label applicable to people who've been around longer, and are therefore older.
I'm not saying ageism doesn't exist, and I'm not saying that I haven't been on the receiving end of it--I can think of a few jobs where it might have played a factor. But I can't tell for sure, and obviously no company on the planet is going to admit that out loud.
Consulting: Did you consider going back to (individual) consulting? Well, in one sense, I absolutely did, because a few roles (including the one at Capital One) started with a contract relationship, sometimes deliberately as a let's-try-before-we-buy. I also did some spot consulting for companies that had no interest in me long-term (and vice versa, to be honest). But in general? Nah, I'm not interested in trying to build out my consulting practice--frankly, I did it, I got the T-shirt, and I'm very happy with the idea of working for somebody else, so long as I professionally respect that manager. That's what I've discovered about me: Regardless of what the company does (with a few exceptions) or who runs it (with a few exceptions), I don't really care about the company. I care much more about the people around me in the company--who am I working for, who is working for me, who am I working with, and am I having some kind of impact there.
That last point, by the way, I've found to be way more important than I would've guessed of myself ten or twenty years ago. It matters to me that I'm making a difference inside the company, much more than what that actual difference is. I don't need to be saving the whales, but I do need to be making somebody else's life better somehow.
LinkedIN is a terrible platform for finding a job. Although this will come as no surprise to many people, I have determined that the social media platform that was ostensibly designed for professionals to engage with one another is now quite terrible at it. I can honestly say that in the three-year timeframe, after clicking the "EasyApply" button hundreds of times--choosing both to share my LinkedIN profile and fill in their online application form--I got exactly one interview out of it. (And that was to a game company early in 2022, which ironically was something of a 'why not' kind of apply.) Even the "new model approach" to LinkedIN, where you not only click the EasyApply but message the CEO/CTO/hiring manager/recruiting manager/anybody-and-everybody–you-know-at-that-company, doesn't work. Maybe it's all the ghost job postings, maybe it's the fact that it's too easy for anybody to click the button, but whatever it is, LinkedIN as a vector to getting an interview and a job is pretty much entirely obsolete and probably should be shut down for many candidates. (Ironically, LinkedIN making it easier for people to apply did exactly that--made it easier for people to apply--and as a result now recruiters are swamped beyond any reasonable human capacity. Which means that LinkedIN didn't make it easier to apply, it just means that now the gates are further back.)
Networking remains king. Almost all the roles I got a chance to interview for came from my connections/network. Many of those connections came from staying in touch with people on LinkedIN, so I can't say that the platform is worthless, and it does help with a professional focus, so it's more effective to connect with other professional-type folks on LinkedIN than say BlueSky or Mastodon, so there's that. And to all of you who said, "Hey, I bet my company could use a little Ted in their life," thank you! From the bottom of my heart, yours were the only real leads I ever got.
AI doesn't help. Seriously. Resumes written with AI are awful, entirely too easy to spot (from the recruiter's perspective), and don't catch anyone's eye (in terms of standing out from the crowd). Using AI as your interview buddy is also not a great tool--it takes too long to type in prompts, and trying to make the responses sound like natural spoken language is just... bad.
(Full disclosure: I've never actually done the 'cheat with ChatGPT' in a real interview, but I did try it as a 'practice' attempt--as in, I sat in my office when no one was around, and I played both sides of the interview. I asked myself a question, then typed it into ChatGPT and tried to read--aloud--the response in a way that didn't sound forced or awkward. Ironically, part of the problem is the fact that ChatGPT actually uses full sentences, which is the first clue that somebody's reading something out loud. Almost nobody does that in an impromptu spoken conversation. Seriously, listen to any interview on TV. We swtich thoughts in the middle of a sentence all the time, and rarely can we hear the punctuation in the response. It's why AI transcription services get so many things wrong--humans are nondeterministic!)
Be prepared for an emotional rollercoaster. It wasn't the first time I'd been without a gig, so the first six to nine months were pretty chill--like most tech professionals, I sort of assumed that "something will come along". (I mean, I didn't just sit back and wait for the offers to pour in, I'm not that arrogant.) But when it got to twelve months and nothing had worked out yet, I started getting a little nervous, and by about the eighteen-month mark, I got depressed. I knew, intellectually, that it wasn't just me--the market's been a mess since the pandemic started--but even then, and with amazingly supportive spouse, family, and friends, it was still hard to not listen to those dark voices that said, "You're done, you're all washed up, you're worthless, nobody will ever hire you again, go pick out your spot under the freeway, you failed everyone you ever loved." (Seriously, that's what my internal dark voice was saying.) It helped that I could give voice to that and have people around me react to that.
Keep in mind your friends want to help. I admit it, sometimes my friends were more interested in being sympathetic when I wanted them to tell me how to fix it, and sometimes they tried to tell me how to fix it when I just wanted validation. It happens. It's not their fault, either. I'm certain if I'd said, "Hey, just validate me on this, eh?" they'd have done so, or if I'd asked, "How would you fix this?" they would make suggestions. Heck, once or twice I did ask for suggestions, and they did, or sometimes admitted they had no quick fixes for me. Key thing is, they were always trying to help, even if sometimes it wasn't what I wanted. (And, to be fair, sometimes I didn't realize what I'd wanted until later in the conversation!) There were still times I got frustrated when they didn't give me what I was looking for, though, and it took a moment for me to remember that they couldn't know what to give me because I didn't ask.
More to the point, friends show up. More than anything else, though, what I've figured out (I think) is that the real meaning of a friendship is that they just show up. They don't have to know what to say or do or how to fix things. They just have to show up. Most of the time, there really was nothing they could say or do. But having them show up, even if it was to just shoot the breeze or talk about their lives for a while, it was way more important than I'd thought it would be.
I should've been more focused in my search. I can do a lot of different things: architect/"thought leader" IC, VP Engineering, VP Developer Relations, CTO, and/or lead a practical R&D effort. (I've done all of those things, though the titles varied from company to company, in keeping with their salary bands.) I initially thought that would be helpful, allowing me to shape myself to whatever-sized "hole" a company needed filling. NOPE. It actually became a hindrance, as I found recruiter after recruiter who simply couldn't figure out what kind of role I was interviewing for. It got even worse when recruiters would ask, "What's your ideal role? What's the kind of things that make you get up in the morning?" (In other words, "What's your passion, so we can make sure this job has it so we don't have to worry about motivating you ever again?") No matter how I answer that question, I was in trouble:
Honestly, as in, "I have all these different interests and thinigs I like to pursue." Recruiter: "Wow, there's no way this role can give you all that. You're probably not a good fit. Thanks, and good bye."
Clinically, as in, "Look, I'm not trying to find a passion job, because I'm seasoned enough of a veteran to know that no job is perfect, and I bring my 'A' game no matter what the job has me doing." Recruiter: "You're dodging my passion question, so you must not be super-pumped for this role. You're probably not a good fit. Thanks, and good bye."
Dishonestly, as in, "I have always longed to be working in a role just like this one." Recruiter: "You sound 'off', like you're not being truthful or honest with me. Bringing your 'whole self' to work is important to us. You're probably not a good fit. Thanks, and good bye."
I eventually got to a point where I would just go through this little diatribe with the recruiter, and leave it at that. Which itself presented problems because now my answer doesn't fit on their scoring rubric and artificially marks my candidacy as less-appealing.
What I probably should've done is created six different forms of resume, one for each of the different kinds of things I was interested in doing, "tuned" to that particular role. Not job-specific, mind you, but a generalized "VP of Engineering resume", a "CTO resume", a "VP of DevRel resume", and so on, taking a particular slant on the things I've done and how my experience set me up well for that particular role.
It really surprised me, discovering this, because I'd always assumed that being multifaceted would be viewed as an asset to the company, but instead, it really played off as more of a liability. Despite the rhetoric, it really seems like companies are more interested in single-dimensional people than they are people with a variety of skills.
Speaking of interviewing, lots of companies do it really, really badly. I had a few conversations with recruiters who were genuinely amazed at my resume, portfolio, books, and GitHub repositories... and then still insisted I needed to go do their LeetCode coding test. Seriously?
Also, I suck at interviewing. I'm not going to blame the companies entirely here; over the course of many of them, I've come to realize that I am nowhere near as good at the skill as I'd assumed. Had I to do it over again, if it were a job I really, really, really wanted, I'd practice it with somebody else. (Literally, write out the STAR-like interview questions, have somebody ask them, deliver the response, and then together workshop the result and try again if necessary.) For the record, I've never practiced interviewing before--and I probably lost a few jobs because of it.
Also, let me make it very clear to everybody out there doing interviews: If the candidate can offer you credible evidence that they are, in fact, capable of writing code (GitHub projects that aren't forks, blog posts they've written with code in it, publicly-recorded user group talks, whatever), just do yourself a favor and believe them. The amount of effort it would take to "fake it" at a public level, when coupled with the trivial effort required to poke through the falsehood, vastly exceeds the payoff. I honestly think the concern at some (most?) companies isn't "We don't want to hire somebody who isn't technical" as much as it is "I don't want to be the one fooled by some shyster who pretended to know code because then it reflects badly on my ability to judge technical skills and that could hurt my career in some undefinable way and at the very least means I will have to endure the mockery of my peers". But don't take my word for it--try it! Try to fake your way through an interview on a subject on which you know absolutely nothing and have no experience. It's way, way harder than you might think.
Recruiters, stop trying to insist you're not transactional. Of course you are. Over three years, I had dozens and dozens of conversations with (company-employed or -retained) recruiters who insisted that they wanted to stay in touch after the interview cycle fell apart, and the exact number of those recruiters who actually did? Zero. Nada. Big Goose Egg. I won't judge you for it, but in return, just stop pretending.
Executive headhunters (where they work on behalf of the candidate, not the company) are extremely rare. I found exactly one that wasn't an agency (or an outright scam), and just as I was about to work with them, my circumstances changed for the happier. (In truth, I want to bring them something just to try and keep the connection warm; sort of keep them on speed-dial, just in case.)
I wish I could've come away from this timeframe with something to show for it. I mean, three years of quality time with my spouse and family is great, but for so long I've had this running mental thread that keeps whispering, "I could totally do interesting side project idea if only I had the time to do it." Well, I had the time, three years' worth, and I got so few of those side projects done. I suppose I could chalk it up to, "Looking for a job is emotionally draining, and I needed to keep my mental health charged," but part of it is, I spent way more time playing StarCraft II and Heroes of the Storm than I'd like to admit. (On the other hand, I did spend a lot of time tending my research garden and then later working on the DevRel book, so it's not like I was just twiddling my thumbs the whole time. Still... would've been nice to finish up a language or write that game or... something. Even just getting into a gym habit would've been nice.)
I'm finding that I'm kinda looking forward to retirement now. If retirement is essentially the last three years minus the worry about financial future (aka, we know that we're covered for the monthly expenses), then yeah, retirement's going to be pretty cool. I was always worried that I'd go a little stir-crazy with nothing concrete handed to me to do. I still might, but I have a better idea of how I want to approach it and what I want to do during it. Next time around, I'm definitely looking for ways to do it differently, but that's because I now understand just what the weight of "Eh, I don't have to be up early today, I'm going back to bed (and sleeping 'til noon)" every day feels like.
Redmond, WA, really needs a 24-hour Coke joint. All the Denny's in town shut down years ago, and nobody has stepped up to take over that slice of existence. It's where I wrote most of my MSDN and developerWorks articles back in the day, and while yeah, pandemic shook a bunch of things up, I'm surprised that we haven't seen a 24-hour diner joint fill in the Denny's-shaped hole here in Eastside Seattle. (BTW, it has to be a Coke joint--Pepsi is dirty garbage water that any day now will be reclassified as toxic waste.)
I don't know if any of those help anyone, or if they just trigger an automatic "WTF are you talking about?" or what. This post was more for me than for anybody else anyway, so if you made all the way through to the end here, well, thanks for reading.
(NOTE: Edited again on 1 Feb 2025 to address a few questions Adam messaged me over LinkedIN that I realized I wanted to add here, and correct a few typos Ron was kind enough to point out.)