five jobs in IT millionaire

Story: $1.2M With Five IT Jobs – u/SweetMullet

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

From $16 Per Hour To $1.2 Million A Year

I am in IT. I have a niche title that everybody wants right now. I have five full-time jobs, four of which are Fortune 500 companies. If I manage all five jobs for a year, I will make around $1.2 million in 2022. Just for some perspective, I made $16 per hour in 2016. I’m still struggling to grasp the sheer amount of money dumping into my bank account.

My Path To Becoming An IT Millionaire

At the start of 2021, I got a new job. It paid ~170k, which was around 70k more than I was making at my previous job. I had the inside scoop from a previous coworker, so I was able to name-drop and negotiate effectively. I was tempted to keep both jobs since both were fully remote because of Covid. My fiancée is incredibly risk-averse, so she talked me out of it. As I got situated in my new position, I became increasingly set on getting a second job. I played video games from 8-4 and sat in meetings barely paying attention. I’ve probably done around 15 hours of real work since I started in January 2021.

In April, I opened my resume to the world on Dice. By June, I bagged job 2 at $82/hour. Holy crap! Two jobs! I was giddy with the money, terrified of meetings overlapping, and horrified if they found out about each other. As I settled into job 2, I found the meetings to be tedious. There were around 4 hours of meetings each day for job 2. I suffered through them, agreeing to job 3.

Always Be Interviewing

I never stopped interviewing. I just made my salary expectations higher and waited for something to fall in my lap. My thought process was that job 3 ($90/hour corp-to-corp) would likely replace job 2, as job 1 is a laughable cakewalk.

However, since I am now in a position of power, I decided to try to flex a bit. I told my project manager that the meetings were a waste of my time. They got nothing done, and they didn’t contribute to my work at all. I now participate in an average of 45 minutes of meetings each week for job 2. Job 3 is also a cakewalk – around 1.5 hours a week of meetings, probably 5 hours a week worth of real work.

I continue to field any interviews that will meet my salary expectations. I am now saying $95/hour is my salary expectation. Another corp-to-corp gig came around, and the hiring manager loves me. Once again, being in the position of power, I am able to simply flex my expectations with ZERO fear of the results.

Me: “Given the scope of the work, my salary expectation is $105 (per hour).”

Recruiter: “The highest we can go is $100 (per hour).”

Me: “Nope, that doesn’t work for me.”

u/SweetMullet

They gave into my request. They then tried to push back my start date by a week. I told them “I had already given my two weeks at my previous job, so you will need to pay me for the absent week.” They hemmed and hawed and tried to say no. I simply told them that I wouldn’t work there then. They paid me $4,200 for a week that I didn’t even sign in.

I expected this job to fold quickly, as it’s with a VERY prestigious company and there is quite a bit of spotlight on my role. It turns out that I haven’t done sh*t at all since I started mid-October. With $4,200 per week to go to a standup each morning and say I have nothing to do, job 4 is somehow an even bigger cakewalk than job 1.

Now Onto Job #5

On Monday, I start job 5. Initially having agreed to $115/hour, I tried to press them for $127/hour but ended up at $120. Not bad for someone earning $16/hour five years ago. This appears to be another job that I will just sort of expect to get fired from, but hopefully, it turns into another easy $5,000 a week for doing jack sh*t.

My 5 jobs “assembly line” setup.

Let’s Talk About Things That Are Working For Me

1. Be fearless. After all, once you get job 2, your risk absolutely plummets. It is ingrained in you to be terrified of getting fired. That fear can f*cking die when you move into your second role. The amount of relief of not having to worry about what your boss thinks of you, or how you accidentally overslept and that might piss off some clown in charge, it all fades. It’s beyond freeing, this feeling of empowerment.

2. Be willing to get fired. I have the luxury of having job 1 be a cakewalk with incredible benefits. So, from there, who gives a f*ck about getting fired from job x? I try to keep job 1 happy (like not saying “I am going to actively find a new job” – that was stupid) and don’t really give a sh*t about the others. I try to do the absolute bare minimum to keep all the jobs, since replacing one is a pain, but any fear of getting fired just isn’t there.

3. Flex. Your. Power. Be willing to say “I can’t make that meeting” or “this meeting is a waste of my time.” People don’t want to rock the boat. They don’t want to do something that might be stupid. Use the fact that most people also want to do the bare minimum to get by. I have had zero pushback when I’ve asked meetings to be moved, or say “Hey, I can’t make the standup today.”

4. Stand up for yourself. Just say “I can’t make it.” I have gotten zero pushback on this. Don’t need to even make up a lame excuse – just own it.

5. Use your new negotiation power. You don’t need to listen about the job that is offering a paltry $65/hour. Recruiters have a range. Demand the range. If it doesn’t fit $10-15/hour more than your current job, tell them no. I EAGERLY accepted a role at $82/hour six months ago. Christmas Eve, I accepted a position for nearly 50% more than that. Flex. Your. Power. Job 2 takes the power out of your employer’s hands and plants it firmly in your own. Use it to climb, grow, and make your life what you want.

Thoughts On This Crazy, Empowering Lifestyle

I have paid off all my debt already, bought a second house, and have enough money to fully renovate both houses by the end of February. I plan on snowbirding from a rather cold home location to a sunny state for the foreseeable future – at the ripe age of 35.

Since this is all debt-free, maybe I want to cut it down to 2 jobs? Or maybe I will just dump all the money into retirement. Maybe I don’t really give a f*ck? Because the world, for the first time in my life, is MY f*cking oyster. Sidenote: when you’re banking over $1M, start your own S-Corp by talking to a tax lawyer.

I’m more than willing to answer any questions. Even though I have four jobs right now (five by the time you read this), I still play video games for 4-5 hours a day. I have plenty of time. Hopefully, this empowers someone to take the leap into this incredible lifestyle. Overemployment for the win.

75 comments

  1. your “crazy, empowering lifestyle” sounds a lot like time theft. which is theft. You make it seem like you skate by and just take people’s money because f*CK them?

  2. I have focused on one job for my career and have earned over $300 million. I’ve become really good at my craft, so much so, that a major sports network has offered me a contract after I retire for $375 million over 10 years.

  3. I applied for a 3rd job and got the job but the hiring manager looked at my background check and reached out to my current employer and asked if I left that job.

    How do I avoid this?

    1. When did they reach out to your current employer? After you started? Need more details.

  4. Looking forward to your follow-up blog post where you tell the story of how some of these companies sued you for well more than you were paid if their terms of employment specifically forbid such activity.

    1. Sure thing, can’t wait for an employer to care enough to waste their time, energy, and money for it. Great for their employer branding too.

  5. You’re my idol man. Here I am. Struggling to keep me afloat with 2 full time jobs and trying to help my wife with our newborn baby.

  6. Hey. I was wondering if anyone had multiple jobs at a time while having green card then applied for US Citizenship. Do you think USCIS officer will make a big deal about this?

  7. I have been doing two jobs for over a year now and it is very manageable.
    I am now interviewing for job 3 right now.
    In IT you need to look for jobs where the IT department has a high budget with no clear goals defined.
    You want companies that are not too large and not too small either since you don’t want to be the only one there for them to bother and also you don’t want companies with too much structure because generally there is more documentation and processes required and this takes more of your time.
    I will post back here after I start job 3, hopefully it will be a walk in the park as well.
    Who knows, if job 3 goes well then I might go for job 4 later but I plan on doing this gradually as I get acclimated.
    If you think 5 jobs is a lot, this guy is working 10 jobs: https://news.ycombinator.com/item?id=27454589
    Crazy dude!
    Also make sure to visit https://theworknumber.com and ask Equifax to freeze your work history so other employers cannot find out about multiple jobs.

    1. That was very interesting! Thank you so much, I will be talking to you soon if I have any questions

  8. Hello Sir, I have a few questions about your five IT jobs. I watched a youtube video discussing how it is extremely prevalent in the IT space to have workers burnout. That was more or less the basis for what the author of that video discussed because you work so hard for so long with so many different tasks, that it is always hard to keep up. How do you stay so efficient that you are able to stay on top of your tasks and play video games 4-5 hours a day? Also, with working alone, how do you solve your programming problems? I have learned that through collaboration, I can solve any problem that I am facing because a few brains are always better than one. Or do you already have a team for each company that you work for?

  9. No way this is real . I bet each of them companies have a policy and he certainly is getting paid for doing nothing. And that I wonder doesn’t it have to be illegal? To charge your employer for work you aren’t getting done? I would think so …

  10. To those asking what to put on your resume, I just have “Independent Consultant” on there for the past 2+ years. No questions asked that way.

  11. THIS! I have been looking for people who do similar things – overemployment and I thought I was the only one. I have to say that you need to be expert in what you do and you need to be great in communication skills – at least thats what helped me. I am working in Quality Assurance in software and the fact that not many people know how to set estimates for QA is helpful. Currently starting a Job 4. NEVER STOP INTERVIEWING

  12. I am doing the same but my rates are 115 an hour, 130 an hour, 140 and my top is 150 hour. Not bad considering i am 50 years old. But it helps to have an IQ of 145+. Secret sauce: keep learning and keep growing plus 4 college degrees of which I put myself through school. I would say only the hiring manager knows what I am about. Also, I keep my ego in check at the entrance. At work, I am just a “worker bee associate”. No high falutin titles.

    1. Is it illegal? Like conflict of interest contracts etc? Or does that depend on the type of role?

  13. My question would be if working multiple jobs with multiple W2s would be a problem when it comes to doing your taxes. Is there a chance that one of your employers might find out about your other jobs from any of the government entities such as IRS, Department of Labor, etc?

    1. Nope. Not from the payroll processors, either. None of their business. You will end up paying excess social security tax because the employers are not coordinating and don’t know when you go over the income limit, but you get the money back when you file your taxes.

    1. Exactly my question too. Are you in cybersecurity? DevOps? CloudOps? QA? Can’t be Software Engineer because you need to get a lot of good quality of work done every week.

  14. Nice job on making this work, Your assembly-line set up is similar to mine. I have two full-time W-2 jobs and one $80/hr 1099 job. Each of those jobs pays around $130K/year. I deposit all of these salaries into brokerage accounts, invest in dividend stocks using leverage, and am able to generate an additional six figures of passive income on an annual basis. All told, it’s about half a million a year. I’ve been doing some version of this working remotely since 2017, long before COVID. I don’t post my job history anywhere online.

    In any case, I wanted to point out that I have encountered one BIG impediment: GETTING REFERENCES necessary to keep getting more jobs (I’m sure I could do four). The problem is that all of the people who could give me good references (at least 5-10) are current employers and/or coworkers who would obviously assume I was leaving their employ if I asked for a reference. Given that this won’t work, I’m sort of stuck.

    I’m pretty good at interviewing, but it’s quite frustrating to get to the end of the process and then when asked for references not be able to deliver on them. The HR depts in most companies require these, so no matter how persuasive/enthusiastic I am, they will never let it slide, otherwise it looks like they aren’t doing their jobs.

    I’d be curious to hear how you deal with getting references or, if you don’t, how you manage to get out of it.

    1. I don’t think I’ve ever had a prospective employer ask for a reference. I didn’t think employers did that anymore, because anyone smart won’t say anything.

      But just ask for a reference and if they ask why you’re still around say you didn’t get the job, or the pay wasn’t right or whatever.

    2. Regarding the references, there should be a way to get them. I was able to reach out on LinkedIn to two developers that I used to work with at my current job. They had left 6 months ago for other opportunities. The HR lady got the positive recommendation through LinkedIn messaging.

      In a previous job that I was still working at, I was able to ask a few developers to give a phone referral to the recruiter and they agreed. I told them it was for an interesting opportunity that came my way, and they understood that it doesn’t hurt to keep open to new opportunities. I think developers understand that the job market is really hot and it doesn’t hurt to explore what’s out there.

  15. My CV is becoming a problem. I can’t mention my 2 current employers. So even casual conversations with recruiters result in me looking under employed over the last year. Any advise?

    1. You can’t mention >>either one<<? Just pick the one that suits your story best and deal with the background check when it comes up.

  16. my mind is being blown and real time is being spent on this newfound blog, wow. This is amazing especially since both of my jobs are remote. I found this blog searching ‘is it legal to have two jobs’ :0 Thank you!

  17. What roles did you work in? My background is project management and I find it tremendously tedious working as a project management and hoping you can shed light. Can two project management jobs be handled?

    1. In some ways, project management could be ideal for this, especially if you get to determine the meeting cadence and attendees. They key to OE is time management, particularly avoiding overlapping engagements.

      Remember as well that OE is predicated not on being “great” but on being “adequate.” Don’t think of project management as you do it NOW, but as you would do it if all you wanted to do was avoid being fired. Layoffs are an inevitability no matter how good you are, so no use trying to be a top performer to avoid them. Use OE to create income redundancy and breathing room for the inevitable.

    2. I am working one project management job and one business analyst job. Both of these jobs require that I set and take a lot of meetings, which I find to be a little painful. I’m not sure if I could possibly take another job right now because some days I am just wall to wall meetings. Two PM jobs might be possible though. Think of it this way, how many times have you had to manage two projects at the same time anyway?

  18. Quick question about resume and Linkedin when having multiple Jobs, when having multiple Jobs what would be the best way to show that you worked those roles with those companies to show you have experience, but at the same time don’t get fired for having multiple jobs.
    Or just don’t update your resume and linkedin?
    Thank you!

    1. See the blog post on linkedin and associated comments. Don’t put overlaps on your resume or LinkedIn, IMO. Match your resume to the job opportunity at hand, and consider putting LinkedIn on ice.

  19. Man this article was so good! this guy has no fear. I wish more could adapt his mindset but especially when you are in a certain demographic its hard and fear is real. Kudos to you

  20. With 3 offers waiting for my response, I am tempted but don’t think I can handle it. As a developer I can’t simply say no to meetings of daily standup, spring planning, demo and the discussion session of my items.

    1. Exactly. Thats my point too. How can you avoid all of these. When you are doing two jobs you need to attend all these meetings from those two jobs. Imagine third job on top of these two.
      if its waterfall methodology somewhat manageable.

    2. You never know until you try. Other posts here have some suggestions on how to handle that. Push to be involved in fewer meetings. Take a week off from your current job to get moving on J2 and try a two-job overlap to get your rhythm for a few months. If it doesn’t work, drop one.

    3. I moved straight from one job to 3 all at once – not my initial intention. Got two offers when I was looking for one and decided to just give it a shot at both of them. J3 was hourly contract as a temp but for an awful company and massive time requirement. It wasn’t going to allow me to meet my starting job requirements at J2 (what I now consider primary as it pays best and has great long-term potential) so after one week I simply dropped J3. Onboarding with 2 jobs at once was simply too much. But I am definitely planning on adding on the right J3 in 6-9 months when I’m in a good groove and have the ability to dictate my schedule at my new J2 without raising eyebrows. The lesson for me was to not rush out of greed. Who knows, maybe I’ll be at 5 j’s eventually, but I’m definitely only going to add one at a time from now on.

  21. Similar boat here ( not quite in the millions here ) but the taxes are crazy. I’m curious about your S-Corp suggestions. How would an S-Corp help alleviate income tax given that by the time your paycheck lands in your account, it’s already been voided of taxes.

    1. 1099, file as an LLC in your state and register as S-corp federally. Pay out a “reasonable salary” and take the rest as “distributions” (which aren’t income taxed).

      Talk to a CPA and a tax lawyer.

    2. You’re right. S-Corp only helps you if you are 1099. So the author of this post must not actually have five “jobs”; some or all of those are 1099 contractor positions if he is funneling the income into an LLC/S-Corp.

      I would think this also means that you’d have to work for the various jobs as an LLC instead of as your actual person, but I could be wrong about that. Maybe there’s a way to be hired as a contractor under your own name but still direct the income to an LLC.

  22. Amazing post about being aggresive and saying ‘no’ to meetings – my J1 is also a cakewalk with great benefits so I completely get where you’re coming from.

    I’m currently doing 3 FT + one PT teaching gig (which I love) and honestly the PT gig is more work than the other 3 combined.

  23. Really curious to know what “niche title” this guy has to be making this much money for this little work. This story seems a little farfetched to me, honestly.

  24. What type of IT job do you with so little workload? Did you get a certification to increase your pay from $16 an hr to your current wage? Or just getting a new job was the only thing to boost your salary. This awesome lifestyle you have created for yourself! Tfs

  25. Seriously 1.2$ million, I am doing 2 jobs right now but the taxes would be higher right. How do you end up working across that?

    1. I’m not a CPA and this is not advice from a professional. But you can do the calculations yourself. Federal tax system is not incredibly hard. Just don’t include any deductions which will like you to over estimating on your calculations.

      You could always talk to a CPA to have the actual numbers ran.

  26. I dont want to believe this story. How can one work in 5 IT jobs when companies expect you to work more than 40 hours a week . They dump all the work on develepers. What are you? Are you dev or tech lead or architect or manager? Not even a single company among 5 companies asking you for status updates for the user stories and to do unit testing and peer reviews?

    1. I don’t do 40 hours of work COMBINED between my 3 remote jobs, it’s never even close.

      I may once every few month have to do a little work on weekend to hit a deadline that’s about it

    2. I can say from experience that this is absolutely possible. I have been doing 5 since Jan though not as highly paid as the author(75$-85$ /hr) and it is not as difficult as people are making it to be. Of course this takes a month to get used to, but definitely doable. I work as a PM in my J1 and Business architect(J2/ J3) and as a Business analyst in the last 2.

  27. Congratulation for your 5 jobs.
    On my side, I have 3 jobs and it’s not easy to handle but I can do it. I don’t know if I could manage 4 jobs. Plus I have children and wife that take times so 3 jobs is enough for me and I earn so much money that my family can’t believe it…
    3 jobs and no vaccine mandate ! Remote IT job is liberty ! I have time to enjoy my life and to pray God.

  28. How do you get around j2 wanting to contact either your j1 hR department for a start/end date or a reference? My J1 has amazing bennies and a pension which I’m 3 years away from being able to leverage, and I don’t want to lose it. Thanks!

    1. Does your J1 use a third party for employment verification? Most places do. HR doesn’t want to field calls like that for a variety of reasons.

    1. You don’t have to work 65 hours a week! You can estimate your job accordingly – don’t have to be a superstar to finish job on time. Always do bare minimal – worst case scenario – you get fired, you still have other income coming in.

  29. You’re my hero! I want to rock it like you. I take it you don’t have any kids? Just curious. You still rock either way.

  30. This is awesome stuff. Wishing you best of luck on your journey. I am about to accept J2 and would like to try a J3 later on once i settle into the OE routines with J1 & J2. My question is when i apply for J3 i will already be on J1 & J2 full time wouldn’t the background check by potential J3 employer reveal i already have J1 & J2? how do i go about it. Thanks.

    1. Yeah this actually burned me on J2 they checked with J1 and found that I had not left. But I got 4 weeks of pay 8K, Thank You.

  31. WOW !!! ALL I CAN SAY is truly WOW. Dude, 5 Full time jobs. I dont have words on this…. I feel like i want to do this but FEAR is keeping me back and the brainwashing of feeling fearful of what bosses will scold me .

  32. Awesome post, thank you. What do you recommend I do with my Linkedin?

    This website recommends closing it but is it possible get new jobs without it?

    1. You can keep it, but don’t update it. Use an updated resume (if it makes sense) for subsequent applications. No requirement to keep LI up to date. Just use it to connect.

Leave a Reply

Your email address will not be published.