Disclaimer: This article is for informational purposes only and does not constitute legal, financial, or employment advice. Consult with qualified professionals regarding your specific situation.
Somewhere right now, someone is sitting in two Zoom meetings simultaneously. They’re muted in one, nodding along in the other, and collecting two full-time paychecks for the same 40 hours of work.
They’re part of a 201,000-member underground community that’s rewriting the rules of employment in the remote work era. They call it “overemployment,” and they’ve built an entire playbook around a simple premise: if you can finish your job in 15 hours, why not take on two more?
The question everyone asks first: “Is that even legal?”
The answer is more complicated than you’d think.
Section 1: What Exactly Is Overemployment?
Define the terms:
- Overemployment (OE): Working multiple full-time jobs simultaneously, typically remote positions
- Dual employment: The formal HR term for holding two jobs
- Moonlighting: Traditionally a side gig, now often refers to secret second full-time jobs
- Polywork: A newer, more legitimate-sounding term for multiple income streams
The key distinction most people miss:
When someone says “I work two jobs,” you probably picture someone working 80+ hours a week—one job during the day, another at night. They’re exhausted but transparent about their schedule.
Overemployment is fundamentally different. These people work 40 hours total but get paid for 80-120 hours by working 2-3 jobs during the same time block. They’re not burning out from excessive hours. They’re gaming the system through efficiency and secrecy.
The r/overemployed community:
- 201,000+ members
- Founded May 2021 (peak remote work era)
- Tagline: “Work multiple jobs during the same 40 hours, reach financial freedom”
- Active playbook sharing, strategy guides, and success stories
- Members report earning $200K-$1M+ annually
Section 2: So… Is It Actually Legal?
Short answer: Yes, but…
There’s no law in the United States, Canada, or most developed countries that prevents you from holding multiple jobs. You can work at McDonald’s in the morning and Starbucks at night. You can be a full-time teacher and a weekend wedding photographer.
The catch: Your employment contract
What IS typically problematic is violating your employment agreement. Most full-time positions include clauses about:
Conflict of interest provisions:
- “Employee agrees not to engage in any activity that competes with the Company’s business”
- “Employee shall devote full business time and attention to the Company”
Moonlighting policies:
- Some require disclosure of ALL outside employment
- Many prohibit working for direct competitors
- Government jobs often ban dual employment entirely
Non-disclosure agreements (NDAs):
- Protect proprietary information
- Prevent sharing client lists, strategies, pricing
- Create liability if you work for a competitor
Non-compete clauses:
- Explicitly ban working for competitors (enforceability varies by state/province)
- Can extend beyond employment termination
Here’s what most OE practitioners know:
As one $1.1M/year data scientist on r/overemployed put it:
“I don’t want to get too much into details about whether it’s legal or not but I accepted the risk given the potential reward. Somewhere in your job contracts probably has a clause or two about moonlighting or related activities but the rule of thumb is don’t accept jobs that obviously cause conflicts of interest.”
The legal risk isn’t criminal—it’s contractual breach leading to:
- Immediate termination (for cause—no severance)
- Potential clawback of compensation
- Legal action for damages if conflicts harmed the company
- Blacklisting in your industry
Section 3: The Conflict of Interest Minefield
Why some dual employment scenarios are instant disqualifiers:
Imagine working full-time at Ad Agency A while simultaneously contracting with Ad Agency B. Both agencies pitch the same types of clients, use similar strategies, and compete for the same market share.
The problems are obvious:
- Both agencies likely pitch the same clients
- Access to both companies’ pricing strategies
- Knowledge of both companies’ client pain points
- You’re literally bidding against yourself on the same projects
The NDA nightmare:
- How do you NOT use Agency A’s strategies at Agency B?
- You absorb proprietary information daily—compartmentalizing is nearly impossible
- Even unintentional knowledge transfer violates NDAs
The reality check:
Would a plumbing company hire someone who’s simultaneously working for their competitor? Would Google hire a developer who’s also coding for Meta? Would a law firm hire an attorney who’s representing opposing clients?
The answer is always no—even with complete transparency.
What the OE community says:
The warnings appear constantly across r/overemployed:
- “Don’t work for competitors”
- “Avoid obvious conflicts of interest”
- “Government jobs are off-limits”
- “Secrecy is mandatory”
The entire 201K-member community operates on the principle that employers will never knowingly accept dual employment in competing roles. That’s why it’s underground.
Section 4: How Are People Actually Doing This?
The OE Playbook (from actual practitioners):
Step 1: Find low-supervision remote jobs
- Seek “boring” roles with 5-10 hours of actual work per week
- Senior positions with autonomy and minimal meetings
- Jobs with asynchronous communication cultures
- Companies with “output over hours” philosophies
One practitioner shared this regret:
“2 years ago I had the perfect OE job: only needed about 5-10 hours weekly to do my work and absolutely no supervision. I quit this job because it was too boring. If only I had realized what I could do with this spare time. The lesson is: don’t find a new job, find another one.”
Step 2: Avoid conflicts of interest
- Tech + finance (different industries) ✅
- Marketing Agency A + Marketing Agency B ❌
- Residential plumbing + commercial HVAC ✅
- Google + Meta ❌
- Data scientist for pharma + data scientist for retail ✅
- Software engineer for direct competitors ❌
Step 3: Operational Security (OPSEC)
A successful data scientist earning $1.1M from three jobs shared his methods:
- Freeze background check services (The Work Number, TrueWork)
- Create multiple resumes (one shows only J1, another shows only J2)
- Use separate devices (3 jobs = 3 laptops, 3 phones)
- Block calendars with “Focus time” to prevent meeting overlaps
- Color-code personal calendar to track which company is which
- Never sync work calendars with each other
- Freeze LinkedIn or use fake name/no photo
- Tell almost no one (spouse and maybe one trusted person)
“Freeze your LinkedIn, or if you insist on using it, don’t put up your profile pic and use a different name. Freeze TWN, TrueWork, etc. Also don’t go around and tell everyone you’re doing it… I only told my wife and another close friend who is also OEing.”
Step 4: Meeting management
When meetings overlap:
- Join both, mute one
- Prepare written standup notes to quickly report
- Reschedule non-critical meetings using priority system
- Claim “connectivity issues” when needed
- In extreme cases, “I have to step away for a package delivery”
Advanced meeting strategies:
One practitioner explained:
“I have 3 phones for 3Js and each J has a different slack sound notification. It helps me know which J is messaging.”
Another tip:
“Have your note ready. Write down exactly what you did last week, what are the blockers, what are next steps. Ask J1 to go first, then ask J2 to go last and just quickly go through your standup note and move on.”
Step 5: Performance management
The counterintuitive reality: You have to perform well at all jobs to avoid scrutiny.
“The most important thing is: do not give your employers a reason to look into you. I strongly believe that if you do your job and do it well, no one is going to try and fire you.”
Senior-level practitioners emphasize:
- Use AI tools extensively for code, documentation, brainstorming
- Delegate grunt work to junior team members
- Manage expectations by proposing your own timelines
- Communicate early and often with visible progress updates
- Convert work into checkpoints: “X is 70% done, data pulled, model trained and validated, next step is deploying”
Section 5: Industry-by-Industry Breakdown
Where OE thrives:
Software Engineering/Tech (Most Common)
- Remote-first culture
- Project-based work with natural downtime between sprints
- High salaries make 2-3 jobs extremely lucrative
- Emphasis on output over hours
- Reality: If you can finish J1’s sprint work in 15 hours, you have 25 hours for J2
- Typical setup: $120K + $90K = $210K total compensation
Data Science/Analytics
- Similar to software engineering
- Often contract-heavy (easier to stack)
- Less meeting-intensive at senior levels
- High-earner example: $1.1M across 3 positions (2 full-time, 1 contract)
Digital Marketing (Proceed with Caution)
- Possible if you avoid competing agencies
- E.g., B2B SaaS marketing + E-commerce marketing (different sectors)
- Two traditional marketing agencies = conflict of interest nightmare
- Freelance/contract work more acceptable with disclosure
Consulting (With Boundaries)
- Multiple clients already normalized
- But W2 consulting vs. 1099 changes everything
- Strategy consulting often has strict moonlighting policies
Where OE is nearly impossible:
Healthcare
- Licensing boards require employment disclosure
- Patient safety regulations
- Mandatory rest periods between shifts
- HIPAA compliance complexity
Finance/Banking
- Heavily regulated industries (SEC, FINRA oversight)
- Strict conflict of interest policies
- Regular audits and compliance checks
- Background investigations
- Client confidentiality requirements
Government
- Explicitly prohibited in most contracts
- Security clearances require full employment disclosure
- Zero tolerance policies
- Ethics regulations
- Public records requests can expose dual employment
Law
- Ethical obligations to clients
- Conflict of interest rules enforced by bar associations
- Duty of loyalty requirements
- Malpractice insurance complications
Trades (Plumbing, Electrical, Construction, etc.)
- Physically impossible to be in two places at once
- Most work isn’t remote
- Union contracts often prohibit working for competitors
- Licensing may require disclosure
- Job sites have physical presence requirements
Education
- In-person or hybrid requirements
- Union contracts
- Credential verification
- Background checks cross-reference employment
Section 6: The Post-COVID Explosion
Why overemployment is a 2020s phenomenon:
Before COVID (Pre-2020):
- Remote work was rare privilege
- In-office presence = proof of productivity
- Physical impossibility of being in two offices simultaneously
- “Face time” culture rewarded visibility
- 9-to-5 physical presence expected
After COVID (2020-2022):
- Sudden, mass normalization of work-from-home
- “Camera off” culture became acceptable
- Companies measured output instead of hours
- Geographic barriers eliminated overnight
- Managers learned to trust async communication
- Peak remote job postings: 2021-2022
The perfect storm: r/overemployed was founded in May 2021, perfectly timed to catch:
- Companies desperately hiring remote workers
- Employees realizing their jobs took far less than 40 hours
- Zoom fatigue making camera-off standard
- “Great Resignation” leverage for workers
- Normalization of side hustles and multiple income streams
The data:
- 201,000+ members in r/overemployed alone (likely 10x more unreported)
- Countless blogs, Discord servers, private communities
- LinkedIn posts (anonymously) celebrating dual income
- Estimated participants: Unknown, but substantial enough to prompt employer backlash
The backlash (2023-2025):
- Return-to-office mandates specifically to combat OE
- “Productivity paranoia” and surveillance software
- Background check companies tightening verification processes
- Remote jobs becoming rarer and more competitive
- Employers adding specific anti-moonlighting clauses
- But the community persists and adapts
Section 7: Cultural and International Perspectives
United States:
- “Hustle culture” makes dual employment more philosophically acceptable
- At-will employment = easier to quit/hide/get fired
- Weak worker protections = contract violations are employer’s only recourse
- No federal maximum working hours
- OE seen as either “gaming the system” or “workers fighting wage stagnation”
- Individualist culture supports entrepreneurial thinking
Canada:
- Similar employment laws to US
- Slightly stronger labor protections in some provinces
- Same OE viability, particularly in tech hubs (Toronto, Vancouver)
- More social safety nets reduce desperation factor
European Union:
- Stronger labor laws across member states
- Mandatory work-life balance protections
- Some countries have maximum working hours (even across multiple jobs)
- Working Time Directive limits to 48 hours/week average
- Cultural emphasis on single employer loyalty
- But still possible in remote tech roles
- France’s “right to disconnect” complicates always-on availability
United Kingdom:
- Similar to EU (post-Brexit)
- Employment Rights Act protections
- More acceptance of “portfolio careers”
- Gig economy more normalized
Japan:
- Traditional lifetime employment culture (終身雇用)
- Side hustles historically discouraged
- Recent government push to normalize “副業” (fukugyō – side business)
- 2018 policy shift encouraging dual employment
- But simultaneous full-time jobs still culturally taboo
- Loyalty to employer remains strong cultural value
Australia:
- Strong “fair go” culture
- Robust employment protections via Fair Work Act
- Superannuation (retirement) tied to each job creates paper trail
- Tax implications more complex with multiple employers
- Casual employment culture makes part-time stacking common
Singapore:
- Highly regulated employment
- Work pass restrictions for foreigners
- Strong anti-moonlighting clauses common
- Efficiency culture makes OE theoretically appealing
- But small talent market increases detection risk
Section 8: The Ethical Debate
Arguments FOR overemployment:
“Companies exploit workers, why not reverse it?”
- Real wages stagnated for decades despite productivity gains
- Mass layoffs despite record corporate profits
- “Do more with less” = code for unpaid overtime
- No loyalty from employers = no loyalty owed
- Workers finally have leverage
“I’m delivering the work, who cares how long it takes?”
- Salary = payment for output, not hours
- If you finish in 15 hours what they budgeted 40 hours for, that’s efficiency
- Knowledge work isn’t factory work—time ≠ value
- Companies benefit when workers are inefficient (justifies headcount)
“Financial desperation is real”
- Healthcare costs, student loans, housing crisis
- Single income often insufficient for basic security
- Retirement concerns (pension extinction, 401k inadequacy)
- FIRE (Financial Independence, Retire Early) movement
- Paying off debt to escape wage slavery
“The system is already broken”
- Full-time employment doesn’t guarantee stability
- Companies use contractors to avoid benefits
- Gig economy normalized employer non-commitment
- Why should workers commit more than employers?
Arguments AGAINST overemployment:
“It’s fundamentally dishonest”
- Lying by omission on every background check
- Violating contracts you voluntarily signed
- Deception ≠ negotiation leverage
- Erodes trust in employment relationships
“It creates actual harm”
- Colleagues pick up slack when you’re unavailable
- Quality inevitably suffers when attention is divided
- Clients/customers deserve undivided professional focus
- Teams suffer when you can’t attend critical meetings
- Junior employees lose mentorship opportunities
“It’s unsustainable and risky”
- Burnout is real, even at 40 hours across multiple jobs
- Mental health consequences of constant deception
- One discovery = lose ALL jobs simultaneously
- Reputation damage across entire industry
- Potential legal consequences
“It perpetuates inequality”
- Only accessible to privileged remote knowledge workers
- Nurses, teachers, service workers can’t OE
- Widens income gap between white-collar and everyone else
- Creates two-tier system within already privileged class
The OE community’s own warning:
Even practitioners acknowledge the limitations:
“No matter what you do, OE is just not very sustainable long-term. Please have a goal in mind (a FIRE number, paying off mortgage/car loans, etc.) Once you hit that goal, consider quitting OE.”
“Exercise, get enough sleep, drink plenty, take time off/vacations and have a hobby so you can prevent burnt out. This is very very important to sustain being OE.”
The community openly admits this isn’t a lifestyle—it’s a sprint to a financial goal.
Section 9: The Tax and Benefits Minefield
Tax implications most people miss:
1. Higher tax bracket shock
The scenario:
- J1 withholds taxes assuming $100K income
- J2 withholds taxes assuming $100K income
- Your actual income: $200K (significantly higher tax bracket)
- Result: $15,000-$30,000 tax bill in April
From Reddit discussions:
“Make sure both jobs are taking off enough income tax or you’ll end up owing BIG at tax time.”
The solution: Request additional withholding on TD1 (Canada) or W-4 (US) forms
One practitioner explained:
“Figure out total amount of taxes that will be deducted at each job. Then run it again as if it was one job at the combined salary. Subtract the difference and divide by number of pay periods. Put that number on each TD1 for each employer.”
2. Double CPP/EI (Canada) or Social Security/Medicare (US)
- Maximum contributions apply per person, not per job
- You’ll overpay into these programs during the year
- Get refund at tax time, but creates cash flow issue
- CPP/EI max ~$4,000-5,000 of overpayment annually
3. Multiple 401(k)/RRSP contributions
- Contribution limits are $22,500 (US 401k) or $31,560 (Canada RRSP) per person
- NOT per employer
- Easy to accidentally over-contribute = 6% penalty + income tax
- Must manually coordinate across employers
- Many OE practitioners max match at each job, then stop
Benefits complications:
Healthcare (US context):
- Two insurance plans = coordination of benefits complexity
- Primary vs. secondary coverage rules
- Potential for premium waste
- But maximum coverage for family
- Some OE people use both strategically
HSA/FSA:
- Contribution limits apply across all jobs
- HSA: $4,150 individual, $8,300 family (2024)
- FSA: $3,200 (2024)
- Easy to over-contribute
Stock options/RSUs (Restricted Stock Units):
- Tax implications multiply across employers
- AMT (Alternative Minimum Tax) concerns with ISOs
- Vesting schedules create complex tax situations
- Wash sale rules if trading in same securities
- Concentrated position risk
Retirement account complexity:
- Multiple 401(k)s need consolidation strategy
- Roth vs. Traditional across employers
- Mega backdoor Roth opportunities (if available)
- RMD (Required Minimum Distribution) planning
Section 10: Real Numbers – What People Are Actually Making
Case Study: The $1.1M Data Scientist
Posted publicly on r/overemployed with full expense breakdown:
Profile:
- 31M, 7-8 years experience
- 3 jobs: 2 full-time W2, 1 contract
- Master’s degree in Data Science
- All 3 companies are S&P 500
Income breakdown:
- J1: ~$400K (base salary + stock appreciation)
- J2: ~$300K (base + stock)
- J3: ~$400K (contract role)
- Total: $1,100,000
Time allocation:
- 40-45 hours/week total
- J1: 15-20 hours
- J2: 15-20 hours
- J3: 5 hours (contract, very predictable)
- Occasional weekend work “if a J decides to be a bitch”
Annual expenses (2025):
- Federal/State taxes: $360,000
- Savings/investments: $500,000
- Mortgage: $49,000
- Car payment: $40,000 (new luxury vehicle)
- Rent: $8,000 (renting while property is rental)
- Food/dining: $30,000
- Travel: $25,000
- Other: ~$88,000
His reflection:
“Compared to last year, I made more but ended up saving less mainly due to paying off a brand new car and traveling/eating out a lot. Lifestyle creep is real so stay focused, everyone!”
More realistic examples from the community:
Software Engineer (4 YOE):
- J1: $120K (fully remote, startup)
- J2: $90K (contract through agency)
- Total: $210K
- Hours: 45-50/week
- Strategy: J1 has slow sprints, J2 is maintenance work
Data Analyst (3 YOE):
- J1: $85K (corporate, boring)
- J2: $60K (contract, 20 hrs/week expectations)
- Total: $145K
- Hours: 35-40/week actual work
- Strategy: Automated most J1 reporting
Product Manager (6 YOE):
- J1: $140K (tech company)
- J2: $110K (different sector)
- Total: $250K
- Hours: 50-55/week
- Strategy: Strong delegation skills, async communication
Digital Marketing Specialist (5 YOE):
- J1: $75K (B2B SaaS)
- J2: $65K (E-commerce, different niche)
- Total: $140K
- Hours: 40-45/week
- Strategy: Different client bases, no overlap
The less successful stories (also real):
Failed after 2 months:
- Took on J2 in same industry as J1
- Client overlap discovered
- Terminated from both jobs
- Now has resume gap
Burnout case:
- Successfully ran 3 jobs for 18 months
- Made $380K total
- Developed anxiety disorder and insomnia
- Quit all 3, took 6 months off
- “Not worth it”
Caught via background check:
- Forgot to freeze The Work Number
- J3 background check pulled all employment
- Questions raised, investigation started
- Voluntarily resigned before termination
Section 11: The Detection Risk
How people get caught:
1. LinkedIn updates
- Someone sees profile showing new job
- Coworker from J1 notices you’re listed at J2
- Automated alerts when connections change jobs
- Recruiters see timeline inconsistencies
Solution from OE community:
“Freeze your LinkedIn, or if you insist on using it, don’t put up your profile pic and use a different name.”
2. The Work Number (TWN) / Employment Verification
- Automated employment verification service used by 70%+ of employers
- Background checks pull complete employment history
- Shows current and past employers, dates, sometimes salary
- Most people don’t know this exists
Solution:
“Freeze your TWN and TrueWork, etc. When you freeze, the third party who does the background check won’t be able to pull your profile. They will ask you to provide your last paystubs as proof. Important: they will only check what you put on your resume. So if you don’t mention J2/J3, they won’t ask about it.”
3. Meeting overlaps gone wrong
- Client happens to be in both meetings
- Screen share reveals wrong company’s Slack/email
- Calendar conflicts create impossible scheduling
- Video background reveals you’re in same room for “different office”
Solution: Obsessive calendar management, separate devices, elaborate blocking strategies
4. Performance deterioration
- Missed deadlines raise red flags
- Quality decline noticed by managers
- Unavailability patterns emerge
- Managers start investigating why you’re distracted
Solution:
“Do not give your employers a reason to look into you. I strongly believe that if you do your job and do it well, no one is going to try and fire you.”
5. Accidental disclosure
- Wrong laptop screen shared in meeting
- Email sent from J2 account to J1 colleague
- Slack message posted in wrong workspace
- Mentioned J2 project details in J1 standup
- Kids/spouse mentions “dad’s other job” on hot mic
Solution from community:
“KVM is great. Consider using it. Raspberry Pi is also cool if you want to be a bit more involved.”
Translation: Hardware solutions to control multiple computers from single setup
6. W2 forms at tax time
- Spouse discovers multiple W2 forms
- Accountant asks questions about second income
- HR benefit enrollment crosses employers
Solution: Can’t hide from your own taxes—some keep spouse in the dark about amounts
7. Colleague recognition
- Someone from J1 knows someone at J2
- Small industry, word travels fast
- Conference attendance reveals dual employment
- Professional network overlap
Solution: Work in completely different industries or geographies
8. Wellness check / Emergency contact
- Company tries to reach you in emergency
- Can’t explain why you’re unavailable during work hours
- Emergency contact reveals you’re at “other job”
9. Reference checks
- Former manager mentions your “other job”
- LinkedIn recommendations reveal timeline conflicts
- Casual conversation betrays dual employment
10. Audit / Layoff Investigation
- Company does retention review
- IT department notices VPN usage patterns
- Equipment audits reveal access anomalies
- Severance negotiation triggers background investigation
Section 12: The “Full Disclosure” Fantasy
Why transparency doesn’t work:
Some people wonder: “What if I just tell both employers upfront? Wouldn’t that solve everything?”
The employer’s perspective on disclosed dual employment:
Risk Assessment:
- “This candidate will have access to our confidential information AND our competitor’s”
- “How do we ensure they won’t inadvertently share our strategies?”
- “What happens when we both pitch the same client?”
- “Will they truly be available when we need them?”
- “Are they giving us their B-game while fresh at the other job?”
Legal liability concerns:
- Company could be sued by clients for conflicts of interest
- NDA violations become the company’s problem
- Professional negligence claims
- Fiduciary duty breaches
- Malpractice insurance won’t cover known conflicts
Team dynamics issues:
- “Why should I work 40 focused hours when they’re splitting attention?”
- “Is this person really giving us their best work?”
- “What if they leave for the other job during our critical deadline?”
- Morale impact on colleagues working single jobs
Practical concerns:
- Meeting availability nightmares
- Response time expectations unmet
- Professional development and training commitment
- Team building and culture participation
- Emergency/urgent situation responsiveness
The proof it doesn’t work:
The entire 201,000-member r/overemployed community operates in complete secrecy. That’s the evidence.
If disclosure worked, there would be no need for:
- Frozen background checks
- Multiple versions of resumes
- Fake LinkedIn profiles
- Elaborate OPSEC procedures
- Constant anxiety about discovery
The bottom line:
Transparency = immediate rejection for any roles that:
- Compete in the same industry
- Serve overlapping client bases
- Require significant time commitment
- Involve confidential information
- Demand loyalty and full attention
Section 13: When Dual Employment IS Acceptable
Legitimate scenarios where multiple jobs work:
1. Completely different industries with zero overlap
- Full-time teacher + weekend wedding photographer ✅
- Nurse + rental property manager ✅
- Software engineer + yoga instructor ✅
- Accountant + musician ✅
- Corporate lawyer + adjunct professor (non-competing) ✅
2. Part-time + part-time combinations
- Two 20-hour/week positions = one full-time equivalent
- Usually disclosed to both employers
- No deception required
- Common in retail, food service, gig economy
3. Full-time + disclosed side business
- Many companies explicitly allow non-competing side work
- Requires formal approval process
- Usually covered in employment contract
- Clear boundaries on time and conflicts
- Example: Software engineer with weekend landscaping business
4. Contract/freelance work (1099)
- Multiple clients are expected and normalized
- No expectation of exclusivity
- Disclosure is standard practice
- 1099 vs W2 changes entire dynamic
- Portfolio careers increasingly common
5. Jobs with explicit moonlighting approval
- Some progressive companies actively allow dual employment
- Requires written permission from management
- Clear boundaries established on conflicts
- Annual review of outside employment
- Examples: Some tech companies, academia, creative fields
6. Seasonal work combinations
- Tax preparer (Jan-Apr) + teacher (Sep-Jun) ✅
- Ski instructor (winter) + camp counselor (summer) ✅
- Agricultural work seasonal overlaps ✅
7. Advisory/board positions
- Full-time job + advisory board membership
- Usually disclosed and approved
- Limited time commitment (hours per month)
- Often seen as professional development
8. Academic combinations
- Tenured professor + consulting work
- Often explicitly permitted in contracts
- Keeps academics connected to industry
- Usually has limits (1 day/week consulting)
The key difference in ALL acceptable scenarios:
- ✅ Transparency – both employers know
- ✅ Non-competing – different industries/markets
- ✅ Time boundaries – clear separation of hours
- ✅ No conflicts – completely different stakeholders
- ✅ Disclosed – written approval obtained
Section 14: The Alternatives to OE
If you need more income without the deception:
1. Negotiate aggressively at current job
- Market rate research using levels.fyi, Glassdoor, Payscale
- Document your achievements quantitatively
- Time negotiations with performance reviews or competing offers
- Ask for 15-20% increase with justification
- Less risky than OE, transparent
2. Switch to a significantly higher-paying job
- Job hopping = fastest path to higher salary in most fields
- 10-30% increases common when switching companies
- No deception required
- Focus all energy on one high-paying role
3. Develop legitimate freelance/consulting business
- Disclose to employer and get approval
- Build client base in non-competing space
- 1099 income, different tax treatment
- Scalable over time
- Can eventually replace W2 income
4. Create passive income streams
- Real estate investing (rentals, REITs)
- Dividend-focused stock portfolio
- Digital products (courses, ebooks, templates)
- Affiliate marketing
- YouTube/content monetization
- Takes time to build but sustainable
5. Side businesses with low time commitment
- Dropshipping (4-6 hours/week)
- Print-on-demand products
- Automated digital services
- Vending machines or ATMs
- Storage unit rentals
6. Skill arbitrage
- Learn high-demand skill (coding, data analysis, video editing)
- Freelance evenings/weekends
- Disclosed to employer
- Can command $50-150/hour
- Scale to full-time transition
7. Career advancement strategy
- Get promoted rather than adding jobs
- Senior roles often pay 40-60% more
- Leadership positions = higher comp
- Less time-intensive than juggling multiple jobs
8. Geographic arbitrage
- Work remotely for high-paying market (SF, NYC wages)
- Live in low cost-of-living area
- Legitimate and increasingly common
- Effective 30-50% “raise” via cost reduction
9. Professional certifications
- CPA, PMP, CFA, AWS, etc.
- Often = $10-30K salary bump
- One-time investment of time
- Permanent credential
10. Start legitimate side business with disclosure
- Get it in writing that employer approves
- Weekend/evening hours
- Non-competing industry
- Can grow into full-time venture
The key advantage of these alternatives:
- No deception required
- No risk of losing everything simultaneously
- Better for mental health and sleep
- Sustainable long-term
- Build reputation rather than damage it
Conclusion: The Truth About Overemployment
Can you legally work two full-time jobs?
Yes. There’s no law in most jurisdictions that prevents it.
Should you?
That’s a more complex question that depends on:
- Your risk tolerance – Can you handle losing all income if discovered?
- Your ethical framework – Are you comfortable with systematic deception?
- Your financial situation – Is this desperation or optimization?
- Your industry – Tech possible, healthcare nearly impossible
- Your performance capacity – Can you actually excel at both?
- Your conflict situation – Are the jobs genuinely non-competing?
- Your stress resilience – Can you sustain constant vigilance?
- Your long-term goals – Is this a sprint to a financial target?
Will it work if you’re transparent about it?
Almost certainly not—especially if the jobs:
- Compete in the same market
- Serve overlapping client bases
- Both require significant availability
- Involve confidential or proprietary information
- Are in regulated industries
The reality check:
The overemployment movement exists because transparency doesn’t work. The 201,000-member community built an entire infrastructure of deception—frozen background checks, multiple resumes, elaborate OPSEC, separate devices—precisely because employers will not knowingly accept dual employment in demanding or competing roles.
What the data shows:
- Practitioners can earn $200K-$1M+ annually
- Requires exceptional time management and performance
- Primarily viable in remote tech/knowledge work
- Average duration: 1-2 years before burnout or discovery
- Most treat it as a sprint to financial goal, not lifestyle
- Community explicitly warns about unsustainability
The sustainable path forward:
For those considering OE:
- Understand the real risks (termination, legal action, reputation damage, stress)
- Avoid conflicts of interest obsessively
- Have a concrete exit plan and financial goal
- Accept it’s not sustainable long-term
- Never underestimate the mental health toll
- Consider whether legal alternatives achieve your goals
For those who need additional income:
- Negotiate aggressively at current role
- Switch to higher-paying job (often easier than OE)
- Build disclosed, non-competing side income
- Pursue passive income strategies
- Invest in career advancement
- Consider geographic arbitrage
The ethical question remains open:
Is overemployment:
- Workers finally getting fair compensation for productivity gains?
- A justified response to corporate layoffs despite record profits?
- An inevitable exploitation of remote work loopholes?
Or is it:
- Systematic deception that erodes employment trust?
- Theft of time and attention from employers?
- Creating harm for colleagues who pick up the slack?
There’s no consensus, even within the OE community.
Final thought:
The gap between “legal” and “allowed” is where this entire phenomenon lives. Working two jobs isn’t against criminal law. But it’s almost certainly against your employment contract. And that contract—not the law—is what matters when you’re trying to keep multiple jobs simultaneously.
The 201,000 members of r/overemployed have shown it’s possible. Whether it’s advisable is a question only you can answer.
Resources:
- r/overemployed (primary community)
- The Work Number (freeze employment verification)
- TrueWork (alternative verification service)
- Your employment contract (actually read it)
- Local employment attorney (jurisdiction-specific advice)
- levels.fyi (salary comparison for negotiation)
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