try two remote jobs

Overlapping Jobs To Try Two Full-Time Remote Jobs

So you’re thinking about working two remote tech jobs but unsure if you can do it? Having overlapping jobs when you’re job switching is the best way to get a taste of the two job lifestyle. To be honest, working two jobs is not for everyone, but overlapping jobs is the closest experience you can get.

Like many of us that first thought about working two jobs, there’s a lot of initial fear about the risks and uncertainties. The good news is that you can try it to see if it works for you. Read on to find out how you can overlap jobs to get a taste of working two remote jobs with low risk.

“What if I get caught?”

“How do I manage two conflicting meetings?”

“Can I really handle two jobs without messing up?”

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Overlapping Jobs: Low-Risk Way To Try Two Full-Time Remote Jobs

The best way to get your feet wet working two remote tech jobs is to simply overlap jobs when you are switching jobs. True, you will need to find a second job first, but this is a great experience if the timing is right. That’s how many of us fell into it. We didn’t set out to do two jobs but ended up overlapping jobs coincidentally and got hooked on the dual-income. Why not eventually hold 2 full-time jobs and get dual incomes for longer than a month?

overlapping two jobs

Different Ways to Create Overlaps In Employment

1. Give a longer resignation notice

Think about this, why do we all give a “2-week notice?”. Why not three or four weeks? Why stay “customary” when you can be weird? Everyone gives two weeks because that’s what society tells us. We’re supposed to stick with the established norms when changing jobs. We can use this to our advantage by giving a month’s notice instead. Actually, why not two month’s notice?

The reason for an elongated resignation? You’re helping to ensure a smooth transition while you figure out what you want to do next in your career. Such a great person! 

While you’re counting down to your extended resignation, you can start your second job. Since you are most likely transitioning your knowledge and ramping down your old projects, you can use this time to start and focus on your new job. This timing is perfect since there will be low expectations from your outgoing employer but still required to work.

2. Use vacation days and other paid time off to overlap jobs

Another strategy is to leverage your vacation days to create an overlapping job situation. If giving an extended resignation notice is not your thing, you can leverage your vacation days to effectively push out your net resignation date. This will retain a 2-week notice for resignation. This vacation strategy is great for companies with unlimited vacation days. If you’re afraid you will miss out on cashing in on your remaining vacation days, remember you will be working two jobs and therefore doubling your salary during that time!

3. Get a short term consulting engagement

An alternative to creating a job overlap is getting a consulting engagement. Consulting gigs are temporary for a few months through the agency. Through that, you can achieve two remote jobs in a non-committal way to see if working two jobs is right for you. 

The End game: Long-term job overlap a.k.a two full-time jobs

How some of us got into working two jobs was simply never telling our employer we were quitting, even though that was our initial intention. You can start your new job and feel out how comfortable you are with working two jobs. Remember, you can quit your old job at any time when it becomes too much. Though each day you overlap, you’re receiving 2x the salary. Keep in mind the longer the job overlaps, the harder it is to explain the overlap should someone ask. In this case, you might just be better off staying at your original job and never mentioning the second one on your resume or linked in.

How Do I Explain Overlapping Jobs If Someone Asks?

Getting “caught” with an overlapping job is the biggest concern for most people. Simple job verifications will surface the end date or month for your former employers. We advocate being truthful on your resume, and it should match the verification dates. The strategy here is to create overlaps only for a month or so which are easily explainable. We only use months on resumes, so as long as it’s the same month or month +1, it’s not as noticeable.

We think this is low risk. Even if someone asks, there are commonly accepted business explanations for job overlaps during a job transition. These occurrences are normalized in today’s work environment. There are multiple stories from colleagues that we’ve seen that can help explain away overlapping job situations. Think about your own colleagues and examples from the workplace; have you heard any of these? Here are a few.

1. An employer needs you to start immediately

Your new employer may request you start immediately, but you still need to give two weeks’ notice. There are many occasions where this happens. Even if you say no, you can not start. Your new employer might still send you some material (non-confidential) to read before your official start. Does this sound familiar?

2. Extended vacation while starting your new job

It’s not uncommon to be on an extended vacation with your old company, while your new company needs to start immediately. There are many reasons for this including formalities and milestones that you want to reach such as a stock vesting date. Many employers are open to negotiation for you to extend your last day so you may meet some milestone.

3. Extending resignation date for insurance coverage

Insurance coverage in the US lasts for the month as long as you’re employed on the 1st of the month. It’s common that employees stretch out their last day to the first of the next month to ensure they’re covered. Sometimes people go on an extended vacation in between jobs. You can just say that was your initial plan, but instead of taking time off, you decided to start your next job early.

4. Consulting with the old employer part-time

In some instances, a former employer would try to retain you to finish a project on a consulting basis. You are kept on the payroll but not expected to work all 8 hours but to help out as needed with the skills only you know.

As an example, I’ve had my new employer invite me to a team offsite with my new team, knowing I was still employed at my old job. The point here is employers don’t care if you overlap jobs for a bit while transitioning, especially if they’re the new employer. They know your intent is to leave, eventually. It is explainable and won’t cause any red flags for most companies.

Purpose of Overlapping Jobs and How to Maximize Your Experience

The primary purpose of this exercise is to clear your way to achieve a 2x take-home salary by working two remote jobs. Maximize the overlapping job experience to get comfortable with the fears you may have with this setup. Here are some things to be conscious of to get the most of this experience.

  • Managing meetings – See how comfortable you are to juggle two conflicting calendars. Some strategies to get comfortable are to push back, ask if we need a meeting or email, rescheduling, and blocking calendars. Check our post on managing meetings.
  • Managing workload – Check if the type of roles and the mix of companies are a good fit for working two jobs. How demanding is the workload at the combined roles? This will help if you either continue or decide to try this again in the future.
  • Get a taste of double income – Working two jobs is all about trade-offs. Use this opportunity to assess whether having a double income is worth the effort to juggle both jobs. The answer is different for everyone.

Try overlapping jobs for yourself! (disclaimer)

As a disclaimer, everyone’s situation is different, and you’ll have to do your own trade-off and risk analysis. Also, we’d caveat, we are not HR professionals. There may be risks that we have not covered. We are merely basing this on our experiences and stories from colleagues. Overlapping jobs short term is quite common and normalized, and their occurrences are easily explainable. If you are wondering what to do about your LinkedIn with two full-time remote jobs, check out our article here.

Overlapping jobs when you’re naturally changing jobs is a low-risk way to see if holding two jobs is right for you. You need to set expectations low with your manager, but the rewards are plentiful if you can manage two jobs. Either you can stress to get one really well-paying job, or 2 easy ones, the choice is up to you. 

2 comments

  1. I have been working two overlapping jobs now the first of which I now am strictly on an ‘on call’ basis but receiving a higher hourly rate for being ‘available’ – I am contemplating a new ‘remote’ job but the two will have widely different hours since they will be about 9 time zones apart. And I am about half way in between! Perhaps I have not found it yet on this wonderful website but I would like to see more about requiring each client to provide me with laptops exclusively theirs. Each has offered or is offering me some stipend to pay for my upgraded internet but how do I gauge that?

    1. It’s best to take the corporate laptops and cell phones if offered. If not, I’d keep both jobs separated, e.g. on two personal laptops and two burner phones (Walmart pre-paid types). This is probably overly cautious, but better safe than sorry.

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