About

I don’t really like writing about myself, because I’d rather share practical advice to implement, or ideas to think about.

But readers tell me they love this page, so I guess it’s somehow useful.

My story goes like this. After graduating college I took a job in corporate America. A few years later, after saving some money, I bought a little condo to live in and BMW to drive.

Yeah, blissfully living the American dream.

But then one day, sitting in my drab cubicle at work, I thought, “So I have to do this 40 more years?”

And that’s when I realized I had a choice. That you don’t have to work, get money, spend money, and work again, repeating the cycle forever. Instead, you can work to save, save to invest, and someday quit working because your invested money is working for you. So, that’s the unconventional journey I decided to take.

Fortunately, by age 35 I’d accumulated enough, and at 37 quit working. That landed me a profile in The New York Times.

That’s the short version. I figured I might as well start writing the longer version for my obituary.

Timeline:

1979: born in Illinois
1989: became a shareholder of Wrigley stock
1994: started working as a dishwasher
1997: began college at tiny Millikin University, as a Finance major
1999: changed major to Management Information Systems
2000: started a business developing websites
2001: graduated college, moved to Madison, Wisconsin to work at SecurePipe (now Trustwave), started investing in index funds
2002: created the cybersecurity site packetfu.org, publishing articles and research papers
2003: quit my job, and started working at Alliant Energy
2004: became certified as a perimeter and intrusion analyst
2006: started investing in individual stocks
2008: became a private pilot (single engine land)
2010: decided to maximize savings rate
2012: became a certified Lean Six Sigma Green Belt, created chrisreining.com
2015: promoted to Business/Enterprise Architect
2016: quit my “day job”, started living off investments
2021 to present: had a kid, mostly on sabbatical parenting until 2026

I’m an INTJ

People wear me out. So I’m usually happier spending a few hours a day alone so I can get immersed in whatever I’m learning or studying, whatever I’m creating or making.

In my career I was interested in things like linux, OpenBSD, programming. I would spend eight hours on these things at my job and come home and spend eight hours tinkering.

Eventually I got bored with it. There was nothing big left to learn, and I enjoy learning, growing, and stretching or I’m not satisfied.

That’s why my life’s work really is investing. I’m a passionate reader and learner, and the more you read and learn about investing the more you realize how little you know (“the sea gets deeper as you go further into it”).

Investing is the one thing that can hold my attention forever.

I’m a minimalist

I’m wary about bringing things into my life. It’s easy to buy new things, but much harder to get rid of them, so I’d just rather not participate.

And I’m always asking myself if I’m using the things I own. If the answer is no I get rid of it. Always consolidating and optimizing.

This is a common theme throughout my life. During the week I usually eat the same meals for breakfast, lunch, and dinner. Grocery shopping and meal prep is so simple, and I don’t have to think about what to eat.

Or how my entire net worth is like 8 stocks and a checking account. It doesn’t need to be more complicated than that.

I’m an investor

I’ve loved investing in stock since I was 10. The idea that you can sit there doing nothing while your money works for you is extremely appealing to me.

The problem was that I didn’t grow up rich. I started with nothing, and so my career was the way for me to acquire the capital to invest.

After quitting corporate America I started living off investments. Roughly 95% of my money is always invested, the remainder in cash equivalents.

Oh, and I don’t pay attention to financial media, macro events, predictions. What I believe is that American business will probably be worth more in the future than it is today.

Also:

I’m not easily distracted. When I’m performing a task it gets 100% of my focus. Writing, learning, creating, whatever. If we’re meeting you won’t see my phone. In fact, my phone has been on silent since the day I got it.

I don’t have an assistant or anyone who helps me. People don’t believe this, but every article I write or email I send is done right here on this keyboard (never ever AI). Everything takes me way longer this way, but so what?

I walk away and never look back. I practice non-attachment, because it makes me more resilient. I’ll walk away from silly little things like my barber or dentist, to bigger things like my car or career. I don’t like feeling dependent on anyone, or anything.

I’m disciplined and methodical. If some action has a positive impact on my life, or gets me to where I want to go, I try building a long-term habit around it. On the other hand, if something is addictive or has a deleterious effect, I stay away.

I don’t follow trends or think short term. I don’t get caught up with what’s flashy and novel. Instead, I live a simple life, eat healthy, work out, do yoga, and read and write. But none of this is for me, it’s always for my future self.

Any questions? Contact me.