On Being Rich-ish: Lessons I learned becoming suddenly middle-class

As you likely know, you are at the point where more money won't change these feelings.

Therapy or meditation, likely both may help induce a shift. As the grip loosens you will find many things begin to change.

"Sleeping well at night", is likely the single most important thing you can focus on. If you choose to focus on that, it likely will permeate many aspects of your life..

You may find a deeper and more authentic experience and through that you may find that you actually have won the lottery. You are safe. You have 5 years of expenses - I guarantee you that you could figure out solutions to just about anything that comes your way in 5 years.

You're no longer trying to survive. It's now time to learn how to live.

20 years ago I was living in a $100 car with 3 immovable doors that I had to push start and repair every day. I was working 80 hour weeks doing day labor in the mornings and telemarketing in the evenings. I also sometimes did truck deliveries, street magic, random tech gigs from craigslist, PC repair. If there was a craigslist ad with a problem I would learn enough to solve it well enough to get paid and get referrals.

Any free day I was trying to get better at programming on college library computers I was able to use by copying other peoples student IDs off sign in sheets.

I made maybe $1500 a month which barely covered food, gas, and helping out people even poorer than me while trying to slowly save for a vehicle that could make a cross country trip to somewhere with other work options.

I eventually got a $1000 vehicle that only needed weekly repair, used it to relocate to a more populated area, upgraded to an abandoned trailer with borrowed electricity and no septic, and got a retail job.

Now I had more time to build tech skills. Eventually got the confidence to take on contract coding jobs, and then the confidence to do that full time.

Eventually I knew enough to pass interviews and get a salaried software engineering role. Then another. Turns out there was plenty of demand for some of the skills developed along the way doing random coding and infosec gigs, managing cheap DIY servers for thousands of users of random open source side projects of mine, and building custom Linux kernels for whatever random old hardware I could find.

Worked my from software engineering roles into running security departments for a series of well known companies by finding major security bugs at every employer. Turns out security is one of those things everyone seems to think is someone else's job, so I always made it mine.

Now I own a home and have a family in Silicon Valley. I own a security consulting company where my team and I have several audit projects and retainer contracts at any given time helping major companies spot security flaws, and build defenses.

Going from homeless to the comfort I currently enjoy was a long road. I never fully shake the fear I could lose it all and be back on the streets at any time. That is only amplified now that others depend on me. I never took 401ks because I expect life or the institutions will fail me before I ever see it back. Never 100% trust banks because I worry funds will be stolen via identity theft or go negative into overdraft hell I can never pay back, no matter how high the balance. I always have the need to have multiple income sources so no single one of them drying up can sink me. The need to learn new skills constantly so I always deliver results most others cannot so people keep paying me. The need to prep for every worst case scenario I can think of always for myself and those that pay me.

In the end, I think this pressure of always feeling a bit chased has served me well and still does. I also do not know that I would recommend this path to anyone, but I am generally pretty happy these days so I will take it.

I grew up upper middle class and earn a mid-low six figure salary. I used to be quite frugal. Now I'm just apathetic to it. I don't care at all about money. I have no particular financial goals. I save a lot without trying. But savings scale linearly in non risky comp scenarios. And that's kind of boring because there's nothing that I could imagine wanting that doesn't require orders of magnitude more money than I have now. Aside from the vague "retire early" thing.

Not a complaint.

> There’s something that people with money say that doesn’t make sense: that regardless of how much money you have, you run out of it just as soon.

This is just a weird thing to me. I didn't feel this was true on a five digit salary much less what I have now.

We can help you out and roll that into the loan for the new car.