5 Reasons You SHOULD NOT Job Stack
You Must have the Right Stuff
As the Captain of the Tortuga Society it’s my job to teach all you landlubbers how to maximize your income and obtain the life you’ve always dreamed of through the asymmetric strategy we call job stacking.
Being a seasoned Job Stacker, it’s also incumbent upon me to dispel any notion that job stacking is an entirely easy enterprise. In fact, today, job stacking has become one of the more difficult employment strategies to pull-off effectively (assuming you’re even of the caliber to land two remote positions).
What ensues are five reasons you SHOULD NOT Job Stack. If you want the solutions to these problems — you’ll have to pay me or become a fully fledged Tortuga Member.
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The Reasons You SHOULD NOT Job Stack Are:
The Bullshit Jobs Era is Over
You Can’t Handle the Cognitive Load
You Don’t Have Thick Skin
You Don’t Have Grand Ambitions (Business / Art / Exit Plan)
You Have No True Männerbund
1. The Bullshit Jobs Era is Over
It’s the year 2021 and the market is flush with fully remote juicy sinecure positions. The hiring process is fast-paced, managers are eager to create new positions, and having a STEM or adjacent degree has never been better. Covid stimmies are flowing and the market is booming — our beloved corporations are looking to maximize profits for their shareholders. In this funny money environment — the easiest way to do so is to market just how much your vaporware nonsense enterprise specializing in extracting an additional 2 seconds of screen time from dopamine laden teens’ eyeballs is growing.
So they went on a hiring spree…
Now did they actually need 90% of these new positions? Not at all. But for the intelligent among us, this was an incredible opportunity: a surplus of high-paying remote jobs that asked little of us sans an occasional Tableau report or ad-hoc SQL query. The true glory days of job stacking…
The first reason you shouldn’t job stack is that this halcyon era of yore has long since ended. There are many reasons for this: the Fed’s raising of interest rates, the rise of AI, and deeper policy decisions rearing their ugly heads.1
Remote jobs are increasingly rare and there’s more competition than ever for the few that remain.
These trends on their own are bad enough but the situation get’s much worse when you realize these few remote full-time positions are far from “bullshit”. Even if you’re able to beat the odds and land two of them they will be a far cry from the sinecure’s of 2021.
Over the past three years in particular, layoffs have been massive and the positions that remain are increasingly asked to do more with less staff. In 2021 your particular data analysis department may have had 11 team members to split the work requests that came in. In 2026, that department likely now consists of only four team members to take care of that same workload.
Take it from me; I’ve had my two fully remote positions for over two years now and they keep me busy the entire eight hour day (and occasionally some weekend time as well). Now let me be clear — this is an amazing setup and I make well over $300k now. My wife doesn’t have to work, I was able to help my parents retire, will be able to purchase a nice house with 60% down soon and I’ve gone on some amazing trips — all thanks to job stacking.
So if you aren’t a particularly agentic intelligent guy — job stacking is most likely out of the realm of possibility for you. It ain’t 2021 anymore bucko.
2. You Can’t Handle the Cognitive Load
Here’s the thing: Job Stacking is more about juggling identities than it is about juggling tasks. A simple way to understand this is by thinking about your current role. What would it look like if you doubled the work load? Obviously, it would be a straightforward 2x increase. This isn’t the case with job stacking — it’s more like a 2.5x increase in work load.
Why?
Because we aren’t just doubling the work that needs to be performed; we’re also doubling the identities we’ll need to slip in and out of. Job A will have its own set of team members, applications/software, exigencies, meeting schedules, etc… as will Job B.
You will need to context switch multiple times every day. You will need to manage priorities among the two jobs every day. You will be held accountable by two different bosses every day.
You will need to persistently manage your calendars and block time off to avoid the dreaded double meeting and sometimes this will fail. The true mark of a pro job stacker is how many double meetings he’s survived… the left headphone attached to a meeting in Job A, the right to a meeting for Job B — engaging in the terrifying dance of remaining muted for each as long as possible and listening assiduously for your name to be called. Better make sure when you unmute for Job B you remain muted for Job A… there are many horror stories of stackers getting caught this way. 4
Best of luck to you if one or god forbid both meetings require cameras on (you best be quick on your feet for some improvisational excuses).
3. You Don’t Have Thick Skin
Invariably, if you have 2+ remote jobs you’ll encounter a time or two where you’re unable to deliver on all your workload for one reason or another. This is where you must have thick-skin and be able to stand your ground.
Concerning the matter of getting scolded by your manager(s) this will happen. If you’re going to job stack you must be able to roll with the punches. This can be especially difficult to handle if you’re a highly conscientious person. Should this occur, you’ll need to be a man about it and take responsibility for the mistake (best to have some excuse but suggest you could’ve avoided said excuse and will next time).
Beyond getting scolded there’s the larger importance of being able to stand your ground. In order to job stack effectively you need to protect your time as much as possible. When you block out time on your calendar and a higher-up schedules over it you need to be able to (professionally & politely) stand your ground that, that time is off limits. The moment you budge is the moment your superiors and team members lose any respect for your time. 5
Seriously, don’t be a pussy — you must protect your time.
See point number 2 again for the consequences of the damnable double meeting.
4. You Don’t Have Grand Ambitions (Business / Art / Exit Plan)
For many here at Tortuga we call Job Stacking “The Final Boss” of their professional ambitions. They start as lowly barnacles, work their way through the bootcamp, land their first hybrid tech position, accumulate some skills & connections through their work and Tortuga’s network, then land their first remote position with our staffing firm, finally securing their second and joining the rank of Captain.
Here’s the thing though…