financial freedom, as easy as taking pasta from a jar

Check My Privilege: Here’s everything you can use to discredit me.

I may be a weirdo but I’m not oblivious. Let me help you check my privilege.

So often I’ll wade into the comments on a personal finance site/article/whatever, and I inevitably see angry or dismissive posts like “oh sure *you* can do it, but you made X amount of money or got a college scholarship or graduated into a hot job market..” or whatever. Which, sure! That person *did* have it easier than you.

It doesn’t mean you should give up. Being mad that someone had an easier time isn’t going to get you any closer to your goals.

Anybody that says “all it takes is hard work” is a fucking idiot. There are hundreds of millions of people doing hard work every day that are underpaid (or worse). Privilege and luck were required for my hard work to pay off, I harbor no delusions.

– me, just now

With that, let me acknowledge ‘my story’ as it were. I fully appreciate that I’ve gotten lucky breaks, accidentally timed things really well, had the right amount of knowledge in negotiations, and sometimes even fallen ass-backwards into a situation that totally changed my trajectory. Too often people complain and (rightly) get told to check their privilege, so here we go…

How it Started – Woe is me

I’m a high-school dropout. Not the “Bill Gates had so many opportunities he dropped out of Harvard!” kind. I got in trouble constantly, I hadn’t passed a grade since middle school, and eventually after getting shuffled along to the next grade after failing, I decided after 9th grade I was just going to drop out. Yes, somewhere underneath I was intelligent/undiagnosed ADHD/whatever. That’s the first and ultimate privilege.

I worked a bunch of terrible jobs and lived with my parents until I turned 18. I think I had at least one full-time job from the end of 9th grade until the week I went to bootcamp.

Lucky Break #1 – The US Air Force

Without a doubt – no single event changed my trajectory more radically than enlisting. I was lucky enough to be healthy, and after waiting for a GED slot to open up (the AF would only allow 1% of the force to have a GED at any time), I went off and learned to work on cars. More importantly, it gave me a work ethic and opened a ton of opportunities that I wouldn’t fully appreciate until much later. Say what you will about the dystopian reality that you have to join the military to afford training/education/whatever.

Lucky Break #2 – The Blessing in Disguise

At some point a few years into my enlistment, I did some questionable things and a supervisor ‘punished’ me by essentially forcing me out of the career field (vehicle mechanic). I was supposed to be discharged but was given a chance to fill out a ‘dream sheet’ of jobs. I didn’t know anything about computers (or even own one) but I picked ‘computer programming’ because it sounded nice to be indoors. They told me I couldn’t pick only one and that one was hard/impossible to get into, so I’d likely be discharged.

So yes, I essentially fell ass-backwards into being a computer programmer in the mid 2000s, received free training, and had 18 months of on-the-job training/experience before entering the civilian workforce. Couldn’t possibly have gone better and is unlikely to be a common story, I am aware of this.

“We did it ourselves.” Really? Now just how did you arrange to be born in the United States of America?

Jack Bogle, “Enough”

TL;DR – I’ve Had All These Advantages

  • I enlisted at a young age, and at a time when my peers were taking loans to pay for their education, I learned a trade and got paid to do it
    • This had the side effect of teaching me to work on cars, which has been a massive financial boost over the years. I can afford to buy used cars and make them reliable again, saving a ton of money
  • I got to learn about personal finance/adulting with guardrails
    • You can get into financial trouble as a young enlisted person, but you’re never going to go hungry or homeless
  • I eventually got a degree in computer science, at no cost to me (GI Bill!)
    • (this isn’t really necessary as a developer, it’s more a holdover because of mgmt-level boomers in charge of hiring and pay)
  • I entered the civilian workforce as a programmer with a security clearance and enough experience to get a great entry-level-ish job
  • I had a VA loan that let us buy our first house with no money down
  • I earned/saved enough that when we wanted to move, I was able to take a 401k loan to buy a condo
  • I very naively followed the first bit of investment advice I got, it just happened to be about index funds. If someone had told me that onion futures were the way to get rich I’d have done that. I knew so little that I was not at all skeptical and it turned out to be great advice, but could have gone horribly.

So there you have it. I’ve lucked out, I know I’ve lucked out, and I’m not here to ask anyone else why they can’t do what I did or claim I bootstrapped my way up out of the gutter. But with that out of the way, it also kinda doesn’t matter. We each have our own stories/setbacks/advantages, but what you do or don’t have compared to someone else isn’t going to reach your goal for you. It’s time to put in the work.

What are some of the lucky breaks, privileges, and opportunities you were fortunate enough to have along the way?

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