multiple contract jobs

Story: From Unemployed To 3 Jobs In 6 Months – u/OEaholic

The following is a success story from u/OEaholic with some light edits. Visit our Reddit community r/Overemployed.

Hey everyone! I felt it was time to share my story of how I went from unemployed to having three jobs in a span of six months. If I can do it, anyone with interest, skill, and hunger for money can achieve it. Of course, experience is important as well. I hope this will help anyone who is looking to take advantage of OE. I am a US citizen who has immigrated from a South Asian country when I was young. I completed my MBA from a top 50 university and graduated in January 2021. Isaac’s note: also see our how to break into tech in your 30s.

$30k of Debt and Jobless

From January, I had a loan of about $30k from my MBA program and I found it difficult to get a job for three months. I was doing part-time jobs while searching for jobs using LinkedIn and Blind. I applied and got interviews for all kinds of companies. The roles I was looking to get were Data Analyst/Business Analyst type roles. I had done more than a dozen interviews from January to March of 2021 and my expenses were piling up. That propelled me to dig in and find a job.

The Hidden Gem: Contract Roles

I started looking into contracting roles which were a game-changer for me. I have found that contracting roles had less strict criteria and require only one or two interviews before you are hired. Isaac’s note: very true, just understand the other side is looking for someone who is plug-and-play and experienced.

I was always interested in getting multiple jobs, so I found that finding contracting jobs was the way to go. Of course, there were negatives which I will explain later in the post.

J1: A contracting job at a FAANG company.

This was March 2021 and by this time I was desperate. Since it was an interview for a FAANG company, I barely had any hopes of getting the job and this was also my first contracting interview. The company did two rounds of interviews and hired me the same day of my second interview! I was hyped. This was a business analyst role and the annual pay was $127K. I immediately accepted and worked only at this job from March, 2021 to May, 2021. In these three months, I got accustomed to the work, my team, and my manager. Luckily, I had one of the best teams one could ask for, my manager was amazing at what she does, and the team was extremely flexible. I am good at what I do and my team completely trusted me. We had a daily stand-up, but other than that, no one bothered me or asked me what I was doing as long as I got my work done. I never worked over 20 hrs per week except for a few times but got paid for all 40 hrs.

By May, I started looking for J2. Again, I only looked for contracting roles and was able to find a job within 2 weeks from search to hire (it helped I had FAANG on my resume).

J2 and J3 enter the game

J2 is a contract business analyst role at another FAANG company paying $141k. The work here is a little bit more hectic than J1 but still manageable. Luckily, this job only has two meetings per week. And as long as I show results, no one questioned or bothered me. This is a plus for being a contractor.

In July 2021, I started looking for J3. This was another contracting role and the recruiter reached out on LinkedIn. I couldn’t resist saying no and interviewed for the role. This was a PM role at a major social media company paying $134k. The team is really good and since it is a PM role I have quite a few meetings at the end of each quarter but other than that manageable with a lot of freedom.

I have been working three jobs since July 2021. Even though it’s difficult at times, I found a way to manage and now it’s easy for me to handle. Of course, I have been fortunate enough to get three jobs that have good teams and manageable workloads.

Total Compensation Breakdown

  • J1: $127k
  • J2: $141k
  • J3: $134k

Total: $402k/year

Since it’s contracting, I don’t have other benefits such as allowance, stocks, company insurance, etc. I have noticed that when you are a contractor, the focus on you is a little less than FTE. I also feel that this gives me leniency to work multiple jobs. Isaac’s note: the flexibility and balance of contract work can make up for the lack in RSUs and other benefits, OE is all about prioritizing you.

OE Tech Tips

I use Logitech MX Master keyboard and mouse since it gives me a chance to connect to all three laptops at once and I can switch between them easily at the click of a button. I also have all work related apps on a separate work phone that gives me the chance to respond to any chats/emails immediately. Check out our other tech tips that have worked for countless others in our OE community.


  1. If you are FTE at one place and decide to tack on a FAANG contract role, what’s involved in the background check? I want to make sure my full time employer doesn’t find out.

    1. Just went though this… the “background check” has become the most invasive thing I have ever seen but when it required prior jobs and dates it exempted my present position entirely. The new gig just started but I have not heard boo from J1, and I find it odd it didn’t even want to verify your employment at the job you are “leaving”.

  2. Great story! I’ve followed a similar path utilizing a combination of FT/Contract and Online Ventures (Multiple Income Streams) on/off since being downsized in early 2000’s in Silicon Valley and since then have made more money by taking on multiple projects, outsourcing all/most of my admin/research portion of jobs to people on Freelance sites like Upwork & Fiverr to free up my bandwidth, and had more time off with no commute and couldn’t imagine any othe way of life now. I’ve been able to earn all over the globe in dream tropical destinations NOW while being able to write quite a few of items as business expenses via my CPA. Who said you had to wait for a two week vacation to enjoy life?, Live it now and find a variety of group/communities that support this way of work. Tim

    1. Same. I wonder this person left that part out–it seems like an important part of this whole thing. If this person wasn’t remote, then were they able to handle 4 positions solely because it was all contract work, therefore it was able to be juggled?

  3. Inspiring read through and through!
    I was looking at some global contract jobs and most of them ask for notice period.
    How do you guys bypass that question or go around it? Or do you tell your second company (contract job) that you are already employed? Let me know, it will be really helpful.

    1. Hi there, last year I held 4 contract jobs and was able to pay off my house.
      Now I only have two I had to give one away due to micromaging I love my three jobs that I have right now they are not stressful plus I no longer live pay check to pay check. I have a nice savings in the bank.

    1. Nope. No employer can see what the other is paying you or withholding. Just leave it alone, and you’ll get the excess contributions paid back at tax time. See the blog post here on tax surprises.

    1. Yes there are look at staffing companies also do a search on job boards. I currently work three contract jobs and make over $10,000 a month.

  4. I might try for three for a brief overlap, but 2 feels much more sustainable. It’s a marathon, not a sprint. Well, unless you have a lot of debt at the moment. Then sprint away.

    But the more tax years you spread your OE gains over, the less you will pay in taxes. Better from a tax perspective to do 2 jobs for 4 years than 3 jobs for two and then only 1 for two. In both cases you averaged two jobs over the 4 years and you DID front-load your income (time value of money and all that), but on the margin taxes just keep going up.

    So many things to think through, but it’s great to have this community to refer to.

  5. Many people in the community say wait and get to senior level and then start to OE from what I can see but you did it straight out of your MBA program. Should someone breaking into tech wait or just pull the trigger like you? What’s your take on the pros vs cons?

    1. Desperate times call for desperate measures. We’ve some who were pushed into OE out of recovering financially from a layoff, health issues, and amongst other situations as well.

    2. Yeah, how do you negotiate a high-salary job right after your degree program? I’m thinking of getting into software development, no more student loans and if I put my heart and soul and blood and sweat and teeeeaars… seems like I got a chance to have financial stability for the first time of my life.

      I chose the wrong field, got my degrees in biomedical sciences’ research… money is only in pharma/biotech companies but no one (to me anyway) seems to hire fresh graduates and academia reseach pays $20/hour. And yes, that was with negotiation!!!!!

Leave a Reply

Your email address will not be published. Required fields are marked *