With the large increase of jobs turning remote since the COVID-19 pandemic began in early 2020, there has also been an increase in individuals working two remote jobs, AT ONCE.
Without their bosses knowing.
My friend… let’s call her… “Pam” took on this venture last year.
We had many conversations leading up to it about logistics, fears, and goals.
She has been in her position for about 8 months now and I wanted to interview her and share it will you all!
We chat about:
- Why she chose to pursue this
- Financial goals, including paying off debt
- The norm of working two jobs
- And everything in between
Where do you work?
I am going to keep the names of my employers anonymous but I will say one is in education and the other is in healthcare.
When did you start these roles?
I started working in my education role in July 2019 and I started working for the healthcare company in June 2022.
What kind of education do you need for these roles?
For the education role, I needed a certification because I worked more for the IT department, and for the healthcare role, I needed both experience and a bachelor’s. I did not need a master’s for either of these roles but I do have a Master’s in Health Administration. I graduated in October 2022.
Are they both remote roles?
The healthcare role is 100% remote and the education position turned into a hybrid role post-COVID.
Why did you decide to pursue a second position?
I choose to pursue this second position because I found myself having a lot of free time in my current role and I wanted to make more money. I had debts that I wanted to pay off. I had just gotten married and wanted to find a way to bring in more income so I could attack my debt more aggressively.
I read a lot about logistics on the blog Overemployed. They have a frequently asked questions section that goes over taxes, withholding, how people balance, and ethics and I got a lot of my questions answered by the FAQ and by people’s comments to different articles. I do remember seeing one guy, who got caught and fired from both jobs, but he was working in two competing IT companies.
What is your salary?
Combined, I make over $100,000.
Wow! You have more than doubled your salary.
I have and I just feel grateful. I feel really humble but I just feel like, it literally brings me to tears how grateful I feel. Because I used to pray so hard, write it down, and put it on every vision board. I didn’t know how it was going to happen and now I look up and it has happened, wow. I just feel grateful. And I try to live in the moment because I can’t work these two jobs forever. My mindset is, do what you do while you can because this can’t be forever.
It’s cool to be making this much but it’s like dang, I have to be working TWO full-time jobs to do that. I read this tweet once and this girl said, “Things that are not a flex: working two jobs.” She is so right though. Imagine if I was able to earn this much with one job. Sometimes you know it’s like, wow that was a tough day, or I get tired of having to think about both jobs.
How much debt did you pay off in the past 8 months?
I paid off about $12,000 of credit card debt. There was no way I was going to pay that off of my one salary, with interest?! There’s no way.
I remember you mentioning when you were first considering pursuing this, you said you thought it might feel ethically wrong to keep your other job a secret from your bosses. How are you feeling about it now being 8 months in?
I feel a lot better than I did when I first started. I realized now that it’s not as uncommon as I once thought. I looked into both employee handbooks and you can work another job as long as they are not competitors. I am working in education and health care and those are two completely different sectors so that made me feel a lot better about working both jobs.
I also recently received my annual review and reviewed high praise from both managers. That also made me feel better about it because I am not taking away from one job to give to the other, I am honestly able to balance both adequately.
How do you manage your time in both positions?
It takes a lot of organization and pre-planning. If I am going to be on-site for my education position, I have to make sure my meetings don’t overlap. I have to make sure I am organized in that I am thinking 10 steps ahead. That’s really important. For instance, if I am in a meeting, and someone says, “Hey, are you free at this time”, I have to know my schedule so I don’t overbook myself.
Do you feel like having these two jobs has been interfering with having a life outside of work?
No, I don’t. I never work overtime. When it’s 5:30 pm, I am done with both jobs. So, I am not working more hours than I worked with one job. Has it interfered with my daily naps? Yes. Do I get to sleep in? No. But other than that, an average 8-hour day is what I work.
What has been challenging?
It becomes challenging when you are just constantly thinking about your jobs. You’re constantly thinking ahead. For both of my jobs, I have to travel about 5-20% of the time. Those things give me anxiety because how do you travel and work at the same time? I think some of the difficulties are just trying to balance and make sure you are organized enough to where things aren’t overlapping. That’s honestly the hardest part.
I can honestly say, every day, at the end of my day, I feel like, “Woo! We did it.” I take it one day at a time. Some days I am a little more anxious than others, but I have gotten to the point where I know it’s going to work itself out. I am now 8 months into my second job, so I am comfortable in it. I am comfortable enough to ask to change a meeting time if needed. Also, having to schedule personal appointments is difficult sometimes because you have to coordinate taking time off for two jobs.
What are your future money goals?
I have some collections that total about $5,500 that I need to take care of. And then I want to start saving for my family and start investing.
What are your goals for the next 2 years? Do you see yourself continuing to work both positions?
My goals for the next 2 years are to not be working two jobs still. When I started this, I did a lot of research on it (shoutout to Overemployed, again!) and I read other people’s experiences and perspectives. What I took away from it was that this should not be the long-term thing that you do. It should be short-term and with a goal in mind. So for me, my goal was to pay off my debt.
I just don’t think it’s something I should balance long-term because it’s like constant anxiety. I do have anxiety from it, and I can imagine if I were to start a family it would kind of be unhealthy to balance both jobs and a family. I feel that way because I do think about work a lot when I am not working. And I do get antsy sometimes when I feel like my two worlds might collide. In a perfect world, my goal would be to find one position that could pay me what I am currently making.
I don’t want to make less than I make now, I like making this much money, it’s a comfortable space for me. And then, I kind of feel guilty in a sense of well, shouldn’t you want more for yourself? But I think this is a good pay for me. I don’t need more. I am satisfied here.
This is the first time in a long time that I’m not stressed, sad or have any negative feelings related to money. And it makes me sad because that’s how everybody should feel. There are people that don’t even make a fraction of what you and I make and they have like three kids to take care of. I really don’t know how people do it.
Do you have any regrets? Would you recommend this to others? What would be your advice to them?
I don’t have any regrets, absolutely no regrets, especially after my annual evaluations. I know that I made the right decision and it just works for me in my life.
Would I recommend It to other people? No.
I am surprised to hear you say that you wouldn’t recommend it to someone else.
I wouldn’t because I feel like I had a very rare situation. Like think about it, you know how my job was, we were having parties, dancing in Soul Train lines… like most people don’t have a job like that where they have so much time to work another job. Normally people have to account for all their hours at their first job. For my first job, I could be at work for eight hours and literally do 30 minutes of legit work. And I should note that that role was salaried, the healthcare job is hourly. But to answer your question, I wouldn’t recommend it to just anyone.
Both jobs have to fit in with each other’s schedule and to make that happen it’s kind of difficult. But if you are able to manage that and it’s not too stressful or causing you strife at home or anywhere else in your life, then yeah, go for it.
Extra income is great but overall, I would say it makes me sad that you know, how the economy is right now, like a lot of people work two jobs and most people don’t know it. I think working two jobs is becoming more and more common. I feel like working two jobs has historically been common for individuals of lower socioeconomic status and now I think it’s becoming the norm for people who would be classified as middle class. It says something about our society and economy that more and more people are feeling the need to work two jobs to get by. I personally know about 4 people in my close circle working 2 jobs.
And most of the people in America are in these two classes. A lot of people that I know have two jobs, too.
It’s becoming the norm now. I don’t remember it being the norm for people in the middle class working two jobs. If you met someone back then who was working two jobs it was like, “OK you’re ambitious” or “you hustlin’, you’re doing it.” It wasn’t common but now it’s totally normal. Now when I meet someone and they are working two jobs, I’m just like, “Oh, OK gotcha.”
Anything else you’d like to share?
Overall, if you’re going to work two jobs, make sure you do your research. Even if you make friends at work, be careful who you share it with. You don’t want to upset that person or for them to tell others. I’d recommend telling the least amount of people. Have a goal and a plan B in case it doesn’t work out.
Are you working two remote or semi-remote jobs? Would love to hear about your experience in the comments below!