I haven’t posted anything here in almost 3 years. The main reason is that because after a grueling job search in 2024, I lucked into joining a Big Tech / FAANG company as a senior software engineer. I felt like this was the opportunity of a lifetime, and didn’t want to jeopardize it with some “edgy” writing I may have written years ago.
Since it’s been so long, let’s recap my life journey:
University
- 2008 – enter university as a computer science major because I want to make video games
- 2009 – do a software engineering internship, think it’s boring like the movie Office Space. One day in the computer science lounge I get fed up with all the geeks around me (this was before CS was cool, though in hindsight I wasn’t cool either) and I switch my major to math.
- 2011 – intern at a bank in NYC. I hated the job and it made me think working for corporations was lame, but I fell in love with NYC
- 2012 – move to NYC to do a master’s at Columbia university. Why? Because I had no idea what to do with my life, and wanted the pedigree (terrible reasons to do grad school). I told myself if I ended up becoming a software engineer, I’m a failure. Graduate with $135k in student loan debt, which leaves me bitter of America, and despising “prestige”.
- 2014 – After various internships, realize the only thing I don’t completely suck at is software engineering, and upon graduation decide I should just get a software engineering job. But I think Leetcode interviews are stupid and refuse to interview for companies who do those stupid interviews. Also I only want to live in NYC.
Real World
- 2014 – Join a random company because I liked the people. Quit after 5 months because (a) they’d nag me if I showed up at 9:35am instead of their mandated 9:30am (b) I wanted to make electronic music
- 2014 – Realize I can’t afford to live in NYC making music (and that having to make money from it would kill any joy from it), and start applying for tech jobs again. Join a music company. Jumped from $70k salary -> $100k salary + 20% bonus. The job was great, though at some point got boring, and then when management changed and they suddenly started having issue with me working from home from time-to-time on Fridays (something the previous TL who’d left had told me was fine before I joined), I decide to leave.
- 2016 – Have $30k saved up and want to leave NYC and travel the world. Join a series D “startup” (that’s not really a startup) that verbally tells me I can work remotely while traveling the world ($140k/yr salary). I don’t end up taking them up on that, though I AirBnB around NYC for a while in preparation before ended up at a month to month sublet.
- 2016 – 2017 The job itself was me being the first employee in the NYC HQ and having the opportunity to rewrite their ecommerce website, which appealed to me because I was into 0->1 work. I rewrite the website, get promoted, am leading a team. CEO tells me the new website is fantastic. Feels good. But turns out the website isn’t actually getting that much traffic, and isn’t really that important for the company. I start getting bored, and also annoyed at this other guy who like my previous job wants to start cracking down on remote work policies. The CIO who hired me gets fired. I should’ve left, but had two good friends there that kept it fun, and just wanted to save $100k before leaving to travel the world. Make a bunch of meh Youtube videos, including one called “How to cope with a boring 9-5 job” that my company finds and fires me. Blessing in disguise and I go off and travel the world with $100k in savings
Traveling the World
- 2018 – 2019 – Travel the world. South America, Europe, Asia. Amazing time. Though to be honest, some of the highest highs and lowest lows. I refuse to move back to the U.S or work another in-person job. I tell myself if I become a software engineer again I’m a failure. My initial plan was to be a Youtuber so I was posting a decent amount in the beginning, but they required a ton of work, never got that many views, and weren’t that great so I lost interest in it. I thought my purpose of being on this planet was to evangelize universal basic income especially in the wake of job automation (I canvassed for Andrew Yang for the 2020 presidential election while in Korea).
- 2019 – Girlfriend convinces me to get a job, so I post on this “looking for work” website. Immediately I’m hounded with inbound requests, and within a couple weeks I have a remote contract job. After that contract ends, I look again and within a couple weeks I’m working for a NYC startup that lets me work remotely from anywhere in the world (I was in Korea), paying me $190k/yr. I was spending very little in these countries (<$2-3k/month), so I could live and save very well on this.
- 2020 – I quickly realized this was a dead end job. The flip side of the privilege of being able to work from a completely opposite timezone with no meetings is that the founder didn’t really care about me. As they built out their in-office presence I felt more and more sidelined. I’d gotten a recruiter message from a FAANG, and now that everyone was remote due to COVID (I always hated mandatory 5 days/week in office), I thought maybe it was time to suck it up and do my Leetcode grinding to get my first “big boy” job.
- 2020 – 2022 – Crypto boom. I go from $200k -> $1m in assets within a few months. I lose interest in job hunting, and start preparing for the fact that I may never have to work for money again. But I’m pissed because that easily could’ve been $3-4m+ had I not sold too early, so I double down at the top, and end up falling back down to where I started ($200-300k).
- 2022 – Being remote at this startup was a dead end job, and I became marginalized even more as they built out their in-person presence. I should’ve looked for new opportunities, but it was hard to walk away from getting paid $190k/yr and only having to work 1 hour/day while being able to live anywhere in the world (my friends would joke that I already had a basic income). This dragged on far longer than it should’ve, and one day while I was alone in an AirBnB in Lisbon they finally cut the cord. I didn’t even notice until the next day.
- 2022 – Up till now I’d always been able to find remote jobs within weeks by simply posting a job ad on this one site, but this time when I posted, I got crickets. Was it the market? Or did I screw up my resume?
- 2022 – Eventually I find some work, but it’s low level work – the type that might be embarrassing to even mention in a job interview – and it’s paying less than what I previously made per hour. I’m inspired by “indie hackers” like Pieter Levels, and build my own projects, so I start working on things like mindgarden.app.
- 2022 – Get a remote job at a seed stage startup about to go through YC. I was hesitant to join, but they sold me pretty hard, so I thought about it and decided this might be a great opportunity for me to reset my career. They fired me 2 months later, 1 week after starting YC. It caught me by total surprise, and I was pretty devastated and embarrassed since it was the day after I’d returned home.
- 2023 – A friend / ex-coworker and his designer friend are doing a web3 dev agency, have some client projects lined up, and are looking for a CTO to handle the technical part and manage the contractors. I join, and head to Bali because he’s there and Bali is awesome. The contractors are terrible, so I end up doing all the work. It’s a lot of work, and the money isn’t that great. Again it’s also “low level” work. After these projects are complete, we decide it’s not worth it. I resume working on Mindgarden.
Back to the U.S
- 2023 – With the job market being trash, my career in the toilet, me being too old for hostels, and tired of aimlessly traveling around without much to show for it, I decide it’s time to return to the U.S, get a proper job, and return to reality. AI is getting really good now, and it’s clear that the window of opportunity for humans is starting to close. For the first time in my life, I want to optimize for the best job I can get instead of the best city (NYC), remote work policy, being chill, most money, etc.
- 2023 – I move to SF to join a seed startup with some pretty hardcore founders. Upon arrival to SF, I walk through the sh!thole that is the Tenderloin with fentanyl addicts bent over everywhere (I’d never seen this before), and post a tweet that goes viral, leading to Fox News interviewing me the following day. I start my first day at work the next day.
- 2024 – The founders want me and the other guy they just hired there M-F from 10am-7pm. I think that’s crazy. They fire us both a few months later, though the CEO generously offers to provide references and puts me in touch with other startups. Though to be honest I’m getting sick of startups now, and hate SF.
- 2024 – I fail final round “onsite” interviews from something like 7 startups at the same time. One slightly suspicious seed stage startup that I would never otherwise consider gives me an offer, but when I say I need more time reneges on it (I believe they folded a few months after). I’m totally demoralized. I’m getting rejected by random crappy startups I don’t even want to work for. One “onsite” might entail 4-5 interviews, and all interviews can feel like they went well except for one interview where one person dings me for something that feels stupid or even unjust. Most of the time companies give no feedback, so you might not even know what went wrong. Sometimes the feedback was actually positive, but they just went with another candidate. I’m often getting rejected by people with way less experience than me. I feel like a complete failure.
- 2024 – The one silver lining is that at least I’m getting interviews. Mostly crap companies, but I did get Scale AI. I failed a Leetcode style coding interview in the final round and it pissed me off so much because I felt I could’ve completed it if I hadn’t been as nervous. My girlfriend asked me what company I really wanted to work for, I mentioned a FAANG, but added that there’s no way I’d get an interview without a referral. So she told me to get a referral. So I cold messaged people on LinkedIn until a got a reference, and a recruiter contacted me the next day.
- 2024 – With the FAANG interview scheduled, it was game on. I went hardcore on the interview prep, doing almost 500 Leetcode problems and 4 paid systems design mock interviews (I neglected behavioral, which was the biggest mistake). Just having the FAANG interview opportunity gave me the confidence to apply for other top companies, which to my complete surprise I landed.
- 2024 – I ended up with final rounds at FAANG, OpenAI, and xAI at the same time. I thought I did reasonably well except for maybe some of the behavioral interviews which I took the least seriously (huge mistake in hindsight). After passing the final round technicals and doing a presentation on myself to the team, they asked me to do a followup interview with some early 20s person. I felt from the beginning she was just looking for an excuse to cut me, and afterwards I got the automated rejection. OpenAI rejected me. I didn’t hear anything from the FAANG after a week. I was devastated. All this work and many months of intense preparation for nothing?
- 2024 – I lucked out and was given the senior FAANG offer. I performed well on the technical interviews, but my behavioral was not up to par. I would’ve been downleveled to IC4 and thus not given any offer because there was a hiring freeze at the time for IC4 SWEs, but by chance I’d gone on LinkedIn and found that an ex-coworker of mine worked at this company, and he was graciously able to give me a good reference. If not for this, I would not have gotten this job.
I write this in 2026 now from the Bay Area where I’m still working at the FAANG. I’ll save that story for the next post because this one is already very long.
I’ve gone through some of the highest highs and lowest lows here, but overall I’m in a good place now and feel blessed. I feel like I slipped in through the cracks right before the window was closing, both in terms of career and relationship.
My mission remains the same – to keep evolving every day, and hopefully one day give back to this world more than I took.
I’ll be writing regularly again because I genuinely feel that writing is the best form of expression, and also because it beats doomscrolling.
Until next time
– J
(also please do reply if you got anything from this – it’s more fun that way)
J. Savage 