This Job Stacker 20x’ed His Salary: Here’s How to Get Started

Imagine making a whopping $3.8M in annual salary from TWENTY different employers. That’s what an anonymous poster on Hacker News revealed recently. He leverages the power of ChatGPT to allow him to work more efficiently.

He originally posted back in June of 2021 about working 10 engineering jobs remotely, for a modest salary of $1.5M back then. Now appears he has landed even more lucrative jobs and doubled the numbers of jobs.

How to Get Started Job Stacking?

Have I piqued your interest? According to LinkedIn CEO Ryan Roslandsky’s data, it’s certainly a trend that’s gaining popularity.

If this type of hack is up your alley, and you want to learn more, I would suggest subscribing to the Overemployed subreddit. It’s an underground society of people working or seeking multiple remote jobs.

They use codes like J1 and J2 often referring to their multiple jobs, and boast about the benefits like never having a gap in their resume even if they get fired from one job. Many are enjoying the benefits of additional income to pay down their mortgages quickly.

And some have upwards of J5 or even more.

The mood of the subreddit is typically more empathetic toward to the workers that lose their jobs after being a loyal employee for years. Therefore, flipping the table on the employers feels justified.

and others like this where people lose their job without warning…

Finding Job Stacking Opportunities

Major platforms specializing in flexible remote jobs include:

  • FlexJobs: This comprehensive platform covers numerous industries and offers tailored search filters for 100% remote positions.
  • Remote.co: This job board caters exclusively to companies that support remote work, simplifying the search process.
  • We Work Remotely: Another remote job-focused platform containing a diverse range of professional opportunities.
  • Wellfound (formerly AngelList Talent): Primarily aimed at startups, this platform offers a unique avenue for finding remote roles in burgeoning industries.

Discrete Interview Techniques

When juggling multiple job interviews, discretion is crucial. Here’s how to manage the process:

  • Schedule interviews during personal time, avoiding conflicts with current work hours.
  • Utilize a private email account and phone number, maintaining separation from your primary employer.
  • Steer clear of public job-seeking updates, particularly via social media profiles.

Inquiring about Remote Work

During interviews, it’s essential to gather the full details on remote job policies. Ask the following questions to ensure a clear understanding:

  • Inquire about the specifics of the company’s remote work policy.
  • Are there any limitations, such as geographical restrictions, on remote work flexibility?
  • Are in-person meetings or training sessions mandatory, or can they be attended remotely?
  • What strategies are implemented to maintain work-life balance for remote employees?

Navigating Job Stacking Discreetly

Successfully managing multiple remote roles without discovery requires a focused approach:

  • Transparency: Where possible, discuss job stacking with each employer, especially if contract’s terms do not prohibit multiple jobs, to avoid potential misunderstandings.
  • Time Management: Allocate designated days or hours to each organization, setting a clear schedule to maintain efficiency.
  • Boundaries: Communicate working hours, preventing overlapping meetings or conflicting work tasks.
  • Prioritization: Recognize high-priority tasks, paying attention to open communication with employers to manage expectations and maintain a professional relationship.

Risks For Job Stacking?

For one, you are actually working multiple jobs. So unless you find ways to automate your job or you are very efficient at your job, it will be a living hell working multiple jobs.

You generally have to be have the attitude of not giving a flying F* to pull this off. Getting fired is always a risk, many in the Overemployed subreddit are often stacking the next job.

Before embarking on a job-stacking career, ask these essential questions:

  • Are there any contractual clauses, such as non-compete agreements, that limit or prevent job stacking?
  • Can you maintain a healthy work-life balance amidst the workload of multiple positions?
  • How will you adapt if an employer unexpectedly changes or increases working hours?

Can Employer Sue For Job Stacking?

In some cases, an employer may sue an employee for job stacking if it is explicitly prohibited in employment contracts or company policies. The likelihood of this happening depends on several factors, including non-compete agreements, intellectual property rights, and conflict of interest concerns.

One of the most crucial documents in such situations is the employment contract. If it contains a non-compete clause or an exclusivity agreement, engaging in job stacking might be considered a breach of contract. Non-compete agreements are meant to prevent an employee from working in a competing business for a specified period, and engaging in job stacking particularly within the same industry could potentially violate such agreements.

Additionally, intellectual property rights come into play when an employee uses confidential information from one company to benefit another company. If your job stacking situation involves businesses in the same industry or competitors, using proprietary information in the second job can lead to legal consequences.

If job stacking results in a significant conflict of interest, the employer may have grounds to take legal action against an employee. A conflict of interest occurs if the employee’s job responsibilities or loyalties are compromised due to simultaneous employment, potentially harming the original employer.

One recent example is the case of Google vs. Anthony Levandowski. While this particular case does not involve classic job stacking, the legal dispute revolves around an employee working for a competing company, which eventually created conflicts between the two employers.

Levandowski worked for Google’s self-driving car project (now called Waymo) and later founded his own autonomous vehicle company, which was acquired by Uber. Google sued Uber and Levandowski, claiming theft of trade secrets and IP infringement, since the core technology used in Uber’s autonomous vehicles was allegedly derived from Google’s own project.

Although not a straightforward job stacking situation, the case demonstrates how legal issues may arise due to multiple engagements within the same industry.

Is Job Stacking Worth It?

Pros: Increased income potential, diverse skill development, autonomy, opportunities for networking, and job security through multiple income streams.

Cons: Potential legal issues, limited free time, difficulty managing workloads, higher stress levels, reduced focus on each job, burnout risk.


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