Software Engineers Need a Backup Plan


My first job was as an Associate Engineer in an Artificial Intelligence lab at a large company. Still, I was dabbling around in software development back then, doing just enough not to get fired.

Following that humble start, I ventured out to try my hand in Silicon Valley with my first start-up developer role.

For that first decade of my career, I designed, architected, developed, and deployed software solutions for large and small companies alike.

As I reached my second decade, I transitioned into a cybersecurity consulting role for companies worldwide—less technical hands-on work, more reports, and talking with other industry players.

After 20 years of working in IT companies (or the IT role in a regular company), I decided it was time to figure out how I was going to survive in IT now that I was approaching 40 years old and becoming a bit old, at least, according to Silicon Valley norms.

No Man’s Land

The IT industry is trench warfare in WWI. When you’re the new conscript in the trench, getting your soldier shit done, it’s not too bad.

But, at some point, you’re going to be the senior soldier, and you’re the next one called out to go over the top into no man’s land.

And nobody comes back from no man’s land.

Colleagues could not move to new companies as they once had, not because they didn’t have the experience, but because they had experience and Silicon Valley is bombastically proud of its history of discrimination against older workers.

Most of us had “achieved” ourselves out of our own jobs because companies can hire any recent college grad who will take anything to have that first job.

Like the next soldier over the wall, death was all that was in front of us.

The Two Rules of this Website

How to get around this problem so I could survive once I hit 40 years old? It was a tough question, but one I knew I had to figure out eventually.

I don’t remember the first thing I realized regarding my future career, but I remember the last thing I realized.

I finally realized that if I was trying to own a successful business where I was in charge, I was doing everything wrong.

Rule 1) If I wanted to be successful, I needed to stop ever again trying to start my own business.

Overwhelming evidence proves that we will all fail if we keep doing it repeatedly (just like I failed too).

Rule 2) If I wanted to be successful, I needed to be buying my own businesses, not starting them. 

It doesn’t matter how large or small the purchase is at first, but learning the buying, operating, and selling lifecycle of business provides a much greater chance of success than trying to start a business on your own.

Once I figured those two facts out, I had a game plan for my future success.

I’m in my mid-40’s and manage a portfolio of online assets, mainly software businesses, that I purchased over the last few years.

I keep my businesses simple, lean, and narrowly focused. I am the only boss (just kidding, honey) and only hire specific tasks that I am either not very good at or don’t desire to learn.

I’m protected from employer discrimination, firings, furloughs, downsizing, rightsizing, layoffs, government shutdowns, and even pandemics.

I control my own destiny, for better or worse.

This website will capture how I have reached that point today and what I’ve learned along the way.

Hopefully, it can help anyone else out that might be interested in doing the same thing in the future as they transition from early career to mid-career in the IT industry, or any industry, for that matter.

If you believe I can be of any help, I suggest you Start Here.