Frequently Asked Questions

New to working multiple jobs? Welcome to the Overemployed lifestyle. Start here with our list of the most frequently asked questions. Or, jump straight to background checks (our winner of most frequently asked questions).

Need more? Join us on Discord or subscribe to our newsletter to stay up to date.

Overemployed FAQ working multiple jobs gif
We know. First-time is scary.

Job Hunting

1. What do I put on my resume? Can I tailor it to leave out some job experience?

Yes, you can tailor it to fit the job you’re interviewing for. If you’re going after a more junior role for J2 or J3, you might want to leave out experiences that make you overqualified. That might mean leaving out J1 entirely if you’re already in a senior role. One thing you shouldn’t do is lie or alter the nature of your role (omission is ok) – a background check will reveal it.

2. Is working multiple jobs even legal? What about non-compete clauses and company policies?

Yes, generally it’s legal to work multiple remote jobs, period – enforceability of your contracts depends on the country. But laws across different jurisdictions and countries can be tricky, so yes, we recommend consulting an employment lawyer to fully understand your risks. Don’t ever accept a role that will create a conflict of interest, though.

3. Do I look for a larger or smaller company for my second job?

This really depends on the individual work culture of the company you’re looking at. Generally, startups tend to get a bad rap in the Overemployed community because they require you to wear several hats (read: a lot more work), but not all of them are like that.

On the other hand, larger companies usually don’t need as much face time and you can get away with less involvement, but it also really depends on the company itself and your own direct supervisor. We recommend asking about the work culture in the interview and reading Glassdoor and Blind reviews to gauge how much involvement is expected.

Ultimately, it’s a judgment call. There are no right or wrong answers.

4. Can I look for a second job in another country? What considerations would I have to take into account?

Yes, you definitely can, and others have done so in our community. However, there are a few things to take into account:

  • Time zones. This shouldn’t really matter if your team is already international and has a results-oriented culture, but avoid those that require you to clock in at a set time or have a lot of meetings.
  • Taxes. This varies depending on the country, so find out the details ahead of time by asking around.
  • Different work cultures. As much as we don’t like to stereotype, there are some unavoidable differences in work culture across regions. Some require a lot more communication, while others are more hands-off. Again, find out as much as you can about the work culture early on before committing to the job.

Hello geo-arbitrage! Just make sure to operate like Family Inc. and consult the experts, e.g. employment and tax attorneys.

5. What counts as potential conflicts of interest?

It’s natural to want to work multiple jobs in the same industry because it requires less mental switching. But if it’s in a very specialized field, you run the risk of conflicts. Common potential conflicts of interest include companies that are direct competitors or have a vendor-client relationship.

This is especially important if your J1 and J2 are both people-facing jobs. One member of our community shared a real-life example of having to meet the same client twice while representing two different companies – a nightmare situation we’d all rather avoid.

Managing Interviews

1. What are some interview red flags to look out for?

Generally, anything that indicates micromanagement. Ask about meeting culture, accountability, and what a typical workday looks like. You don’t want a company that requires having the camera on all day, for instance.

In the job description, look out for terms like “looking for candidates who thrive in a fast-paced environment”, “expected to wear multiple hats”, “hands-on”, “team player”. Not necessarily bad things, but they indicate a higher level of involvement that might not work for working multiple jobs.

Then again, you never really know how the job is until you get on board. So, if push comes to shove, we advocate the “try before your buy” strategy. Just like how companies put new employees on the unspoken 90-day probation, now it’s you putting the company, culture, and job on a probationary period. Kick the burner jobs to the curb if they don’t suit your lifestyle design.

2. What do I say when they ask when I’m planning to leave my current job?

Tell them the truth, but frame it carefully. If they ask when you’re planning to leave (or when can you start), for instance, tell them what your notice period is, e.g. ranging from two weeks to thirty or ninety days.

If you’re new to 2xing, you can try overlapping jobs first before deciding if you want to pursue the Overemployed lifestyle from there.

3. Can a company legally inquire about my employment without my consent?

No, they have to get your permission first. You can state during the interview that your current employer doesn’t know you’re interviewing for other jobs; this is pretty standard. In some states like California and Illinois, it’s even illegal for a company to ask about your salary history.

4. How do I handle reference checks? Whose names should I give?

It’s rare that a company will ask for references, but in tech, it happens. For software engineers, work experience is actually pretty easy to fabricate – some of our community members just create a web app and get a friend to give a reference. Alternatively, give them a reference from an older job and explain that your current job doesn’t know you’re interviewing.

We also recommend letting your references know ahead of time that someone might be calling them up so they know what to say. The reference doesn’t need to know you’re working multiple jobs – they just need to know what you’re applying for and the kind of experience you want them to highlight.

As you can see, if you churn and burn jobs, your references are going to be wondering what’s going on. So, play chess and think ahead of your strategy.

5. What do I say when an interviewer asks if I have another full-time job at the moment?

This one is obvious. Again, you don’t have to lie. You can say that you do have another full-time job at the moment – just leave out the part where you’re not planning on quitting. Wink wink.

6. How do you ask about the meeting culture during interviews?

Bring it up in the larger context of managing your work efficiently. You can say that your working style involves batching or minimizing meetings in order to have focused deep work time and go from there. Also, this question is a good follow-up to the “how do you prioritize” question.

If conflicting meetings are unavoidable, use our GREAT strategy to manage them.

Background Checks

1. I’m in the interviewing stage for J2. Will they perform a background check on me and find out I’m still doing J1?

As far as we know, all background checks require consent and most are simple criminal checks and verifying the veracity of your resume and credentials. It’s standard for a company to run a background check towards the final stage of interviewing or after you’ve accepted the offer, but it’s mostly just a formality to ensure you’re not lying about the experiences you’ve had. Depending on your industries, some may do more intrusive background checks, like a credit check or interviewing your neighbors when a security clearance is required.

2. Do companies run random background checks on their employees?

It’s very rare that employers do this unless you’re in a very sensitive role. It also depends on the industry you’re in – if you’re working in compliance, for instance, then there’s a higher chance of random background checks. However, you shouldn’t run into this issue if you stick with big, well-known companies.

3. What shows up in a background check?

Background checks validate things like your educational and employment history, criminal records, addresses, and general public records. They might also include interviews with your co-workers, neighbors, associates, educational institutions, or anything else necessary to verify that you are the person you say you are.

Usually, these checks only validate what you fill out in the application (they’re a company, not FBI). They verify what you have said, so our advice is to list only what’s necessary, i.e. J1.

Managing Identity

1. Can I tell my partner about working multiple jobs?

If you’re already married, you can make your partner the exception to the rule (again, judgment call here). But don’t tell someone you’re dating about your multiple jobs. You don’t want to run the risk of a bitter ex calling your bosses to out you. For now, it’s generally good Family Inc. policy to not talk about working multiple jobs.

While we’re on the topic, don’t tell your family or anyone else. We’ve heard of jealous relatives calling companies to expose 2xers in the name of “doing the honest thing”.

2. What do I do with my LinkedIn once I’m 2xing?

LinkedIn can be an awkward topic of conversation if your new colleagues ask why you haven’t added them yet or updated your profile to reflect your new role. We’ve found that the best way of avoiding this is just to hibernate your profile – you can just say you’re doing a social media cleanse or that you’re just not very active.

Same for other social media. Make all accounts private and tell colleagues you prefer to keep personal and work lives separate. You can sound smart and cite what you’ve learned from Cal Newport’s book Digital Minimalism.

Dealing with Taxes and 401K

1. How do I manage taxes for both jobs? Will either of them find out?

Taxes get pretty complicated when you’re working multiple jobs. We’d recommend reading this post on the top 5 tax surprises when you have multiple jobs so you know what to expect ahead of time.

A lot of people have asked how they should file their W4’s, and if HR or payroll will “find out” if you work multiple jobs. The short answer is no one cares about your taxes. W4 is about your taxes.

Also, our simple default recommendation is, when starting out, to file your W4 as single or married filing separately and put zero for everything else. That way, you have semi-conservative withholdings and can compare and pay the difference, if any, as estimated taxes (just like 1099 self-employed) at the end of each tax quarter.

Still confused about your taxes? Act like a Family Inc. and consult an expert, e.g. certified public accountant (CPA) or tax attorney.

2. What if my jobs are in different countries?

Check with a CPA who’s well-versed in the tax system of the other country, since there are different tax laws. However, as a rule of thumb, remote workers pay taxes to their country or state of residence. Some countries, like the USA, have a minimum global tax.

3. How can I maximize my 401k while working multiple remote jobs?

This needs an entire post, so you can read how to maximize your 401ks and benefits while Overemployed. TL;DR if you manage it carefully, you can capture all or almost all of your 401K matchings across multiple employers. Nice huh?

Managing Healthcare and Insurance

1. Can I have secondary insurance from J2 if I already have it from J1?

Yes, you can have multiple health insurance plans from different employers. Check out all you need to know about health insurance with multiple jobs here.

2. Will my employers know about each other if I have insurance plans from both?

No, they won’t. No one will care about your insurance except you, so you’re safe. Another nice perk of Overemployed is having multiple free life (death) and disability insurances, a standard employee benefit given by tech companies.

Maximizing Productivity

1. Should I take time off in J1 to deal with orientation for J2?

If possible, take a couple of days off while you get adjusted. We recommend taking at least a whole week off. Most orientations for remote work involve briefings and get-to-know-you sessions (depending on the culture of your J2 company) and it’s important to make great first impressions by being present. It’s also a good opportunity to learn more about their expectations so you can ramp up and meet those expectations accordingly.

2. What if both jobs require multi-factor authentication on your phone?

Simple: if either of your jobs requires multi-factor authentication (MFA), get another phone on the cheapest cell plan possible. This helps you avoid mixing things up. You can also just do without the cell plan and authenticate through Wi-Fi.

3. I have multiple laptops but want to keep the same setup. Can I work multiple jobs from one setup?

It’s possible, though tricky, usually accomplished through virtual machines and/or IP KVM. There are much more complicated but check out the discussion on our Discord #tech-setup.

For a simpler setup that meets 95% of 2xers’ needs, check out our post on how to switch between laptops efficiently.

4. What happens if friends or family come over and see my 2x setup?

We prefer to just close the study door. But if it’s unavoidable, tell them you do some freelancing on the side, or just prefer to have separate setups for work and personal stuff. They usually don’t question it further.

5. How do you get focused work done when 2xing?

It’s all about efficiency. If you can, delegate administrative tasks to someone else or hire a virtual assistant, so you’re free to focus on the high-value tasks that only you can do. If you can’t delegate, try to batch tasks within each job so that you can get them done faster without having to do mental switching.

Since 2xing requires some mental agility for task-switching, you don’t have to schedule out every hour. But we recommend using the Pomodoro method by setting yourself three or four stretches of 60-90 minutes to get tasks done.

6. How can I deal with meeting conflicts across jobs?

If you get advance notice of an upcoming meeting at one job, block out time in your other job’s calendar. This can be “deep work” (we recommend regularly scheduling blocks of deep work time from the onset, so it becomes a habit no one questions), a client meeting, or anything else that looks legit. Here’s our post on managing meeting conflicts across two remote jobs.

This requires some juggling when working multiple jobs, so we’d recommend either coming up with a mitigation strategy (like telling one or both companies that your connection or camera isn’t working) or switching on the camera only when you have to answer a question. Just don’t be a repeat offender. The key to managing meeting conflicts is NOT to have meeting conflicts in the first place. That’s OE mastery in working multiple jobs.

7. What techniques can I use if I have conflicting meetings that both require having the camera on?

That being said, having the camera on during meetings is one of those remote work rules that we should question. If you can, set expectations early on by not having your camera on all the time even in non-conflicting meetings.

Got a burning question you think we should answer here? Tell us in the comments.