Path to Plunder - Week 1
Overcoming Resume Gaps, Outwitting HR, and Obviating DEI
Happy Friday, lads, and welcome to the inaugural installment of Path to Plunder—my new column on Tortuga Media, which you can expect in your inbox at the close of every work week going forward.
What is this?
Due to some fairly significant developments in my personal life I’ve recently decided to start job stacking again.
This time around I intend to be significantly more aggressive in the tactics I’m deploying than I ever was in 2023-2024, relying on both my own accumulated wisdom and the insights and advice of other accomplished job stackers within The Tortuga Society, such as
and .I’m going to be documenting THE ENTIRE PROCESS in this very column—from the initial job hunt, to interviewing and comp negotiation, to grooming my boss / coworkers during onboarding, to long-term office politics and expectations management, to ratfucking HR (should the need arise).
Along the way I’ll be dropping (anonymized) receipts—e.g. email exchanges, offer letters, pay stubs, etc. to offer the incredulous some proof this is all real, as well as KPIs against which Tortugans can compare their own performance.
At every step I’ll be entirely transparent about the various ways in which I’m cheating or leveraging Tortuga Society resources to seize an unfair advantage.
Anyone interested in staying competitive in the relatively hellish remote labor market of Summer 2025 should find this series intriguing and useful, so be sure to give us your subscription so you don’t miss any future installments:
Now onto the show!
Assessing the Situation
We’ll begin our analysis by itemizing my current strengths and weaknesses, starting with the latter so as to get the less pleasant part out of the way.
Weaknesses
- | Resume Gap—no work history since I burnt my ships last October
Believe it or not this one actually isn’t THAT big a problem all things considered… but you’ll have to keep reading to find out why.
-- | White Male
This one will be considerably more annoying, as basically anywhere I’m applying is sure to implicitly penalize me for it. But thankfully I have a plan to get around this one as well. Again—just keep reading.
-- | Technically Rusty
Most of the roles I’m applying for aren’t going to submit me to an especially rigorous technical evaluation. But such an evaluation needn’t be rigorous to be irksome, as I haven’t done anything technical AT ALL in approximately eight months and it will be a rather huge pain in my ass having to reactivate that part of my brain. I’ll likely need to spend a weekend or two brushing up on SQL and more niche Excel functionalities to ensure I can reliably handle such interviews.
Strengths
++ | 8 years of certifiable actuarial experience…
I literally didn’t learn anything “actuarial” in this span of time because after I left my first job I grew radically disenchanted with my career and stopped paying attention to the big picture trajectory of my deliverables. That said I absolutely have the verbal IQ to sell this experience as having entailed increasingly sophisticated responsibilities based purely on the titles I occupied, and that’s all that really matters at the end of the day.
+++ | …including 2 years in a prestigious Big Four consulting role
This is akin to having an elite university on your resume—it opens doors and acts as a tiebreaker in clutch situations (for instance, immediately after I resigned from said consulting role I was landing interviews for Director-level positions in industry firms despite only having made it to Manager in consulting because HR perceived this as a lateral). Anyway it’s been a few years so this distinction won’t be as powerful as it was several years ago, but I have a plan to milk it.
+ | Mischling-coded verbal acumen
In basically any STEM role I’m applying to I’m all but certain to be several clicks more articulate and conversationally adroit than any of the other neckbeards applying, let alone my cumin-scented competitors. That said it will take a bit of agency and elbow grease to ensure this advantage meaningfully works for me.
++++ | The Tortuga Society
The main advantage with Tortuga is the Brain Trust element—I can have guys who are applying to the same exact roles as me assess my resume and ensure it looks decent while helping me prep for interviews
I’ll also be heavily leveraging the resources we offer members, including:
Our guides to resume / LinkedIn optimization, penned by Sesped—a fella vastly more skilled at job hunting than poor Cap’n Walt. These lightweight and straightforward compendia will markedly reduce my cognitive load when attacking the most boring and onerous part of the entire job hunting process.
Our central repository of stackable job listings, updated each and every week by our intrepid Zoomette intern.
Our custom browser extension Queen Anne’s Revenge (QAR), a tool that rips listings from LinkedIn and automatically uploads your CV to each of them (and can even leverage AI to generate a custom resume for each position).
Our affiliate data analytics consultancy, for whom I’ve incidentally been working full time in a senior managerial capacity on a 1099 basis ever since I resigned from the aforementioned consulting gig.
:^)
Strategy
So what types of roles will I be shooting for?
Back in the day my stack was pretty much always structured as follows:
JOB A - Senior IC actuarial role at a large (ideally midwestern) insurer paying a little over $150k and mostly held for benefits / status (if someone knows what an actuary is—rare outside of insurance and former math majors—it’s considered far more impressive than being a generic data analyst). Usually would be a 10-20 hours per week deal but the workload would be distributed hyper-seasonally.
JOB B - Senior IC data analyst around $100k—think a SQL monkey informally supervising junior staff. This was ideally something where I could do all my hard responsibilities in 5-10 hrs / week and pawn off the rest to an Asian or fat chick.
JOBS C and D - Mid-to-Senior IC data / business analyst paying around $80-90k—this would be my Retard Role I could blow off if necessary and wouldn’t mind losing. Think a pure SQL / Excel monkey with a hard cap of 5 hours per week.
That said, for all of these tiers the primary thing I’d optimize around during my job search was paucity of meetings, as in practice meeting overlaps will virtually always be your most pressing limiting factor when job stacking.
This time around I’ll do something broadly similar, with a few important tweaks:
Probably no actuarial role
My credentials are expired for one thing, and I for sure don’t feel like going through the whole song and dance of getting them un-expired.
The actuarial world is way too small for someone controversial—it feels like practically everyone fucking knows each other, and even discounting my Substack infamy I burned quite a few bridges in that part of my life and don’t exactly feel like running into an old rival or some shit.
The extra $50k or so in salary isn’t even worth it because the actuarial role will absolutely impose at least 300% the aggregate cognitive load—likely better to just get two 110 IQ data analyst roles.
The additional prestige of actuarial vs. data analytics honestly isn’t worth the extra cognitive load or “professionalism” bullshit. Honestly if you’re not a physician or attorney (or maybe a professor) it’s kind of stupid caring about prestige even one iota. Also it seems like a lot of data analysts just call themselves “Data Scientist” and shamelessly steal the valor of that profession even if they’re doing nothing but rote midwit busywork in Tableau and it’s not like normgroids know the difference.
That said I’ll apply to a bunch of easy-looking remote actuarial roles on the off chance one of them is just an overpaid business analyst position, as I lucked out precisely like that in 2020 and it may very well happen again. I just need to get doubly lucky and have them not check my credentials.
Job A will be my easiest role this time.
The goal will be to find a Golden Goose—something that pays $80k+ but requires zero meaningful effort and I wouldn’t mind doing in perpetuity.
This will almost certainly be some kind of Data Analyst / Business Analyst role at a midwestern insurance company.
If I ever find something easier it will become the new Job A.
There’s a decent chance I’ll hand this one off to my girlfriend once I have the processes adequately systematized—essentially it will be a passive income where I just have to show up for meetings on occasion.
Job B will be something interesting I’m actually good at and enjoy.
I actually don’t expect to fill the Job B slot for a reasonably long time. But basically I’m going to apply for a shit ton of managerial and senior-level IC positions outside my typical wheelhouse, with the primary criteria being that they look interesting and would allow me to leverage my strategic and verbal acumen in a creative and fulfilling way.
This would probably something in AI or AI-adjacent.
Obviously I’d be playing for variance here rather than expected value, and it may even be more likely than not that I never find what I’m looking for.
Meanwhile I’ll have two or three Jobs C / D / E functionally identical to Job C in my prior schema and which I’ll largely treat as short-term piggy banks.
Now, ideally I’ll abandon some or all of the above once the labor market is shored up and our staffing firm has sufficient runway to start placing guys again.
And that actually informs the second prong of my strategy—namely, that once I’ve secured a position with decent benefits I’ll be attempting to land my additional roles as a 1099 worker so there aren’t any legal or administrative hurdles to using my new position within a company to directly place guys in roles with myself as the go-between a la Shylock in my Goy Story.
Anyway, the long and short of it is that my immediate goal is to secure two or three easy remote data analyst roles at glacial midwestern insurers, using my consulting experience, actuarial background, and verbal acumen to dominate the pajeets / lower order neckbeards / career changers I’m competing with.
The “Overqualified” Trap
The savvier among you are almost certainly wondering how I plan to deal with hiring managers curious why I’d give up a $150k-$200k career for a $80-120k one.
I had a whole procedure for dealing with this back in the day. Basically it all depends on their individual circumstances and personality.
A fairly large proportion of data analyst managers (especially in insurance) are actively taking actuarial exams hoping to move on up into the big leagues, or are themselves a former actuary who couldn’t be fucked to keep taking exams—if I get one of these chodes I’ll just say the exams were too much of an imposition on my work-life balance etc. and this will flatter them.
If I get a girlboss type or a super normie dude I’ll usually admit (always very bashfully, of course—the trick is to make THEM feel ashamed for asking you) that my imaginary fiancée comes from an affluent family and that this changed my personal calculus to value work-life balance more because the salary differential is no longer worth it etc.
With minorities and old people I like saying my mother has dementia and I’m looking for a role that will accommodate me taking care of her.
The Recruiter Question
Generally in the past I’ve landed actuarial roles almost entirely through recruiters, but haven’t really used them for data analyst roles, which exist in a far higher volume and can be treated as more of a commodity. I’m going to take that same approach this time around and try to stay purely independent, but will hit up a data analyst recruiter in 2-3 weeks if I’m not getting any decent bites.
The LinkedIn Question
I’m going to begin my search without applying to any roles on LinkedIn.
Why?
Mostly a bunch of tedious and gay admin shit re: my old account you won’t particularly care about, but also because I utterly despise the site’s interface / aesthetic / culture and have never needed LinkedIn to get a role in the past.
Anyway, I’m going to discuss with my boys and assess what kind of bites I get without it, and will reactivate next week if it seems materially worth it.
Application Framework
I am not by disposition an especially organized person.
That said I turn into a veritable Nazi when starting a job hunt, for three reasons:
When going balls to the wall you’ll almost certainly be submitting hundreds of applications per week, and if you don’t systematize and scale such efforts the cognitive load will inevitably tank the quality of any individual application
With job stacking in particular you’ll for sure want to collect KPIs—think applications submitted, interview conversion rate, offer extension rate, etc.
After a certain point I’ll have the process sufficiently systematized that I’ll typically just pay some kid or girl to submit applications for me by the dozen, and the more airtight my organization the faster I’ll reach that point.
Resume Optimization
There are several important items to discuss here, but we’ll start this off with how I plan on bypassing that Resume Gap and discrimination against White Boys.
Outfoxing the Diversity Brigade
Yes, it’s 100% against the law for firms to discriminate based on race and gender.
Yes, they 100% do so anyway.
To give just one example—one time several years ago an actuarial recruiter accidentally sent me her master Excel file tracking the responses of client firms to her candidates, and it said clear as day in one of the entries that…
Well, take a look for yourself:
Yes, this is straightforwardly completely and utterly against the law, yet the firm is OVERTLY WORKING WITH THE RECRUITER to discriminate against men.
And if they’re going to engage in such rank deception then fuck it—so will I.
Going forward the given name on all my resumes shall be Juan, and I’ll also be fabricating an officer role in my alma mater’s Hispanic student association, just to drive the point home for any especially dense HR ladies.
Now, my birth certificate name will of course be listed on all of the official paperwork, but that’s entirely an HR matter—I very much doubt the hiring manager in any role will even notice the discrepancy, and if so I’ll have a canned story in my back pocket.
Bridging the Gap
The main thing normalfags don’t realize about “gaps in your work history” is there’s literally nothing stopping you from just making shit up.
Now, that’s a little harder if you have zero relevant institutional experience (which is to say institutional experience that can be plausibly sold as relevant) to speak of, but so long as you have SOME institutional credibility the HR lady can directly verify over the phone you have a boatload of options to choose from.
The classics include:
you’ve been working at a failed startup
you’ve been working for some dude you know who owns a business that could plausibly employ you to do something relevant
you were working for a firm that’s since gone out of business
you were working for an overseas firm (pick e.g. a French company that looks super professional but has zero English accessibility)
and far and away the best—you’ve been consulting on a 1099 basis through your own personal LLC, but are switching back to W2 work because your fiancée wants you to have a stable salaried paycheck and benefits
If you have a lot of hard verifiable experience and are a decent liar then the sky’s honestly the limit with this last one.
Now, if you take this route then HR could THEORETICALLY ask you to provide paystubs, but unless it’s the federal government or a major consultancy or something of that caliber the chances of that happening are honestly quite low. But either way, the worst case scenario is it happens and you need to ghost them.
The most reliable way to cover your tracks is to say you were a contract employee of a medium-sized consultancy that required your niche skillset to meet the needs of a particular client. Then you’ll want to describe 2-3 clients in broad strokes but anonymized (e.g. “a large health insurer”), with the subtext that it’s likely been ambiguated because you had to sign a comprehensive NDA… maybe you can imply one of the datasets is HIPAA protected, then suggest another is Lockheed or something… you get the picture. The goal is just to pass the HR lady sniff test.
As for the consultancy itself… well, I suppose this is where I’m insanely fortunate to have labored full time in a managerial capacity for the Tortuga Society’s affiliate data analytics firm over the past few years. Unfortunately this firm has a strict privacy policy when it comes to employee records due to the sensitive nature of its client data, and is unable to verify my own tenure there or anyone else’s, but if the firm has one saving grace it’s a level of professionalism and polish that by itself is sure to impress any HR sheila who comes knocking.
Anyway, when all is said is done the only hard and fast rule in this particular domain is to freeze your Equifax Work Number—MAKE SURE YOU DO THIS!!!!!
Other Concerns
And here’s where I’m dropping the Paywall.
Why?
Because dead men tell no tales…
…and broke niggas get no jobs.