Job Stacking Gone Wrong
Did the Triple Job Stacker Get Humbled?
Imagine this: you’re on your fourth Monster at 9 AM, bouncing between three Slack windows, dodging Zoom calls like Neo dodging bullets, when your micromanaging boss from Job 3 asks for the third draft revision on a meaningless document due by noon. This is the moment you realize: you fucked up.
Nearly a year ago, your humble author re-discovered Walt Bismarck through his Substack. His writing truly resonated, but I was ultimately galvanized upon encountering his essay on job-stacking. His arguments rang profoundly true — I immediately recognized both the capacity and necessity within myself to pursue this path. Reaching out to Walt that day changed both our lives profoundly for the better.
Fast forward to today: I'm now co-owner of our curated fraternal & professional space, The Tortuga Society, and am a triple job-stacker (four if we count Tortuga itself). One of the features of Tortuga among many others, is that we actively instruct our members on mastering the art of job stacking: identifying necessary skills, selecting optimal jobs, dodging unnecessary meetings, and strategically utilizing an ADHD diagnosis, among other tactics. We've previously touched briefly on roles to avoid, but haven't explored them in-depth.
That changes now.
Late last year, I secured my third job, which initially appeared promising. However, recent months have revealed it as an extraordinary drain on my ability to juggle multiple positions, lead Tortuga effectively, and continue my Substack writing at the standard I demand. Ergo, I've chosen to leave this burdensome role in two weeks. I briefly considered mentally checking out and passively waiting for termination…but alas, my conscientiousness simply wouldn’t permit it.
Having endured this terrible job-stacking scenario firsthand, I’m uniquely positioned to outline precisely why this job became untenable, and crucially, the subtle warning signs to watch for when adding your second or third position.
In the rest of this article, I dive deep into the exact red flags you must recognize early, the pitfalls that sabotage job-stackers, and how to strategically protect your time, sanity, and earning potential.
To ensure you don't make the same mistake I did, subscribe now and learn to identify what makes a bad job-stacking position before you accept it.
Below you will find:
Real-world anecdotes of micromanaging nightmares.
A proven checklist of questions to detect and avoid "meeting hell" companies.
Tips for quickly recognizing the itinerant task chaos that derails productivity.
Actionable strategies for gracefully exiting a job that turned toxic, without ruining your professional reputation (and job stacking endeavors).
How to deal with multiple bosses.
How to utilize Time Zone Arbitrage and Get more vacation days.
If you’re serious about maximizing your income and sanity through effective job stacking, consider this article your lifeline.
Subscribe now to learn exactly how to recognize and escape the job-stacking position from hell.