My Exhausting Year of Job Stacking

Sometimes in life, certain windows of opportunity open up, only to eventually close. Recently, one of those unique moments in time emerged with COVID. For a few years, white-collar work underwent a dramatic shift to remote settings. Suddenly, an abundance of jobs could be done from home. I sensed this was a rare opportunity, I decided to capitalize on it by working multiple remote jobs simultaneously, an approach dubbed “job stacking.”

There’s a big reddit community about it, there’s even books written about it.

The concept is simple: As companies shipped employees laptops for at-home work, nothing prevented me from setting up two, three, or even more workstations on my desk. I would smoothly transition between laptops and meetings for different companies all day long. An entire online community and guides sprang up around this multi-job remote work lifestyle, proving I was not alone in riding this temporary wave.

@solesontech

This person is working two different remote jobs at the same time. What would you do in this situation? #remotejobs #careertips #remotewor... See more

For a short window amidst the chaos of a pandemic, the constraints that traditionally hemmed in 9-to-5 office life dissolved. Seizing upon the cloud-based, Zoom-enabled flexibility of the moment, white-collar laborers discovered they could labor on their own terms, writing their own employment rules. Of course, as virus fears ease and bosses beckon employees back into cubicles, the remote multi-job bonanza will likely fade. But for a brief period in time, the traditional paradigm of going to an office melted away, opening up an online Wild West of unbridled work adventures.

What is Work Mean?

This "job stacking" approach works because most office jobs don't actually fill up a full 8-hour day with intense, focused work. Employees are paid just to be available during business hours. Realistically, the core daily workload could be completed fairly efficiently within 4 hours or less for many white-collar roles.

However, Parkinson's Law dictates that work expands to fill the allotted time. Give someone 8 hours to complete a 90-minute task without tight deadlines, their nature is to stretch out the effort subconsciously to consume the total time available. For example, an end-of-day report due by 5 PM will generally get finished right at 5 PM, even if it could be wrapped up earlier. People tend to meander through workflow when extra time cushion allows.

But when you work 3 full-time cognitively demanding white collar jobs , you have so much actual work that you are actually deeply and fully working for 8-9 hours straight. It’s quite a difference experience. Rather than pockets of intermittent effort padding out a workday, you are locked into continuous intensity.

The experience became an daily endurance trial requiring detailed schedules, task checklists, activity simulators to keep multiple chat tools perennially "green" during gaps.

Why did I do this? For money. For really good money.

I also knew this era wouldn’t last long and managers would bring back workers to the office.

How To Make Good Money

Realistically, there are only a few viable paths to building substantial wealth in America: inheriting a fortune, launching a successful business, creating the next Harry Potter media empire, or climbing to an executive role at a major corporation. That's about it - the reliable options are limited for the average person.

Usually, ascending the corporate ladder is the main route accessible to regular working folks to making real money. But it's a tough climb, with the top spots fiercely contested by ruthless workaholics and political game players. America creates a rare version of the sociopathic work obsessed freak. Reaching executive suites requires immense sacrifice.

In investing, the rewards come through patience, strategy and occasional bursts of informed boldness. Job stacking flips the script - it's about endurance, time management maneuvers, wringing every drop of viable labor from your mental and physical bandwidth. Different approaches, yet both can yield financial stability. But while investing principles endure, job stacking arose only briefly thanks to a pandemic's distortions of traditional office work. For a short window, the brute force tactic delivered...until the strange times passed, and things returned to normal. But it does wear on you over the years.

In This Newsletter

Job Stacking for a year taught me a lot about myself, my limits and what I truly care about. I want to share with you my thoughts on this unique time when a regular white collar employee could make CEO money.

1) Four Lessons I learned Job Stacking For A Year

2) A Day in the Life: Job stacking as a remote worker, particularly in white-collar jobs, requires careful planning and management to ensure success and sustainability. You don’t have to be best employee but you have to be good enough not to get fired.

3) The Value of Leisure. For most of history, leisure was a sign of prestige. Today that idea has been turned on its head, and busyness is the new status symbol. Busy people are considered important and impressive, and employees are rewarded for showing how “hard” they’re working. Such thinking is not Lindy.

Lessons I Learned

1)The Fear is Gone.

The first lesson I learned job stacking is that the fear of losing your job is gone. The moment you lock in multiple income streams, fear evaporates. Losing any single job no longer induces panic when backup plans churn out paychecks.

This newfound boldness reshapes workplace dynamics. You stare down unreasonable demands from positions of strength, embracing the power to walk away at any time. Managers accustomed to compliance meet unexpected resistance. The cues signaling desperation—endless overtime, needles sucking up—get replaced by sober boundaries.

And here’s the twist: growing a spine earns respect, not resentment. Turns out people privately admire those exhibiting judicious backbone over spineless door mats. Suddenly, saying “no” becomes thinkable. The confidence of options speaks volumes.

@theoveremployedmarketer

With overemployment, you bo longer have to put up with 🐃💩 and company politics. #remotework #remotejobs #digitalmarketing

2) Be Suspicious of Promotions

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