Success Stories (formerly OE Journal)

Anxious or nervous about taking the plunge? Follow our community members as they start new jobs, navigate conflicting meetings, get out of debt, and become financially free.

Interested in sharing your story? Email content (at) overemployed (dot) com or direct message “Chloe” on Discord.

Latest Stories

OG Success Stories

Mr. 4-Jobs sidegigs

He’s a Sr. Engineering Manager with 20+ years of experience killing it with four jobs. His total base is around 670k with small sign-on bonuses from jobs #3 & #4 below.

I’ve been lurking around for past couple of months; great to be part of this community and good to see contribution. Here’s my scenario. Background – 20+ years in different software engineeing roles.

Job #1 – FTE Sr. Management for past 5 years, 99% in cruise mode, mostly delegation. Waiting for parachute payment.

Job #2 – Contracting at FAANG, lead role with a bit of hands on but not too much. Since Oct’2020.

Job #3 – FTE Manager role, fully remote team. This company competes with job #1 in literally every product. Since Nov’2020

Job #4 – FTE Sr Manager since Apr’2021. In fact, negotiated with boss for promotion in next 6 months. No competition with any of the above companies.

Funny thing is I am [a hiring manager and] recruiting in all the companies. Why am I doing this? Got bored and wanted to check how far can I go. Do I still have free time? Absolutely, I enjoy all evenings & weekends. Ocassionaly work on weekends for 1-2 hrs to catch up on job#4. Usually work between 7:30 – 5 PM, very hectic on Wednesday & Thursday. Have couple of 9 PM calls 1-2 days in a week.


Bonjour 2jobssaucethegeneral

Hailing from Europe, he’s a software engineer with 5 years of experience. A young free agent shattering corporate and social norms.

I’ve always been the type of person who tries to game the system and I’ve always been actively looking for jobs that don’t require too much effort. Since the beginning of my career, I’ve always wondered why everyone looked so busy while there was seemingly nothing getting done. I had even contemplated the idea of having some kind of superior intelligence, allowing me to get things done quicker than the others. Then, one random day in 2018, something clicked in my head: THEY ARE JUST PRETENDING TO BE BUSY!

At the same time, I came across some juicy contracting offers from London, I tried my best but I eventually gave in to a very insisting recruiter. The contract, unfortunately, required me to be physically present at the client’s location. My old job had some kind of flexibility but clearly, I had to come up with a good excuse if I wanted to be away for several months. So I told my manager that I was going to take a cybersecurity course in London and that I would try my best to conciliate work and study, I told him that it was going to be an expensive course but that I was willing to make this sacrifice. To my surprise, my manager blindly believed me and offered to pay for at least part of the costs (~1,200€), apologizing for not being able to cover a bigger part of the costs.

And that was it, a week later, I was in London, working as a contractor while secretly working my normal 9-5 job in my home country. I kept working hard and saving as much money as possible, after about 3 months (the contract was 6 months) I had enough. I hated my existence in London and I was convinced that no money in the world would ever be enough to justify my miserable existence, I had enough and I wanted to go back to my home country. So one day I scheduled a 121 meeting with my manager, I told her that I had just received a remote job offer (obviously a lie) and that I going to resign unless they let me work remotely.

After a couple of weeks, to my disbelieve, she agreed to let me work from home on a permanent basis. That’s how, 3 years ago, my double-job-fuck-capitalism adventure started! Since then, I changed 4 employers, earning more and doing less at each iteration. In the last 12 months alone, I’ve managed to save more than 70,000€ and I’m on track for early retirement. Right now I pull in roughly 8,000€/month after taxes while spending only ~1,500€/month (roughly double the average monthly wage of the country I’m from). I’m only 27 and I feel like I’m living life with cheat codes, please tell me that I’m not the only one gaming the system so hard!


Meet Grimmjow

He’s a cloud architect who couldn’t decide between two offers so he took both jobs! Then came the biggest surprise of all, after he started the two jobs he got an offer from one of the FAANG (Facebook, Apple, Amazon, Netflix, Google). So, now he’s doing all three jobs! His only regret is it didn’t occur to him to work two jobs at once (or now three) in his old job before he had quit.

Hello Mars

She’s in analytics and a soon-to-be-mom who’s hustling hard for her baby. After taking on a second job as a contractor paid as W-2 through an agency, Mars landed another full-time offer and is planning to work all three jobs while weighing which of the jobs to keep. We’ll see what she does after maternity leave. Maybe she’ll keep all three or turn the contacting job into a permanent client!

👋 Derek Who Thought He Was Alone

He’s the old information security pro who has mastered the Overemployed art of keeping a cash cow on hand while seasonally rotating two other jobs, always making sure he has cash flow redundancy. Derek’s been three-job hustling for the last three to four years and now he’s not alone!

Game recognizes game. Grab your 💰💰💰!