So I’m Retired Now?

So the wife and I talked a few months back about if I should take early social security benefits or not. She always jokes I’ve been retired for a long time now so I might as well get paid for it. lol.. Such is the roller coaster life style of being self employed my entire life.

One thing that consumes me from time to time as I age is the endless “what if” scenarios I self impose on my thought process. And one of those is “what if I had a regular job and just brought in a stable income instead of being self employed?” I did have a couple of decent jobs for a while when I was younger. But due to my ego I was destined to be self employed because I could never embrace the concept of giving my intellect away to someone else, even if the money was good. I would rather fail or succeed on my own rather than sell my creativity to the highest offer. I don’t even know if my brain was capable of working for someone else long term to be honest. But looking back… there is no doubt having a stable income instead of the endless cycles of random waves of income, would have made things much easier on my wife. My wife as usual would provide the stability in both our personal life and financially.

But being self employed had a financial fun side to it. Almost any money I would bring in, would be “play money” because the wife’s income would pretty much pay for all of our monthly bills. Sure there would be some gaps in my income, but it seemed…. for about 20 years or so… I would go through a cycle of little income followed by a financial tsunami. lol.. Looking back this was simply a “research & development cycle” followed by a “deploy and sell” cycle. lol..

In the early days of software marketing, a clever strategy for developers was to create websites centered around software similar to their own. By using various search engine tricks / hacks, they could push those sites higher in search rankings. And of course prominently feature their own software. 😉

I had made several websites that I would end up selling once my personal interests or investments were no longer warranted. I recall selling a particular website and then non nonchalantly telling my wife I just sold it for 6 figures. yah… good times. lol..

So I’ve struggled with the thought process of taking early retirement. Long story short… I’m not convinced I’m in the best health long term so regardless how long I live, we decided we might as well take the payments now while we can fully enjoy the extra income. My first SS benefit check was deposited in July 2025.

You read about so many people getting sick, dying, etc, shortly after retiring. I can honestly say I understand it now because wow.. if you don’t find something to do both mentally and physically after retiring, you can just end up withering away rapidly. I can’t imagine the toll it must take on people that had a regular 9-5 job all their life and all of a sudden find themselves with nothing to do. Maybe I was lucky being self employed because not being tethered to any schedule allowed me the flexibility to pursue my various hobbies.

Since the main goal of my blog is to keep it real… I freely admit the past 2 months I am struggling with a side effect of being retired. Mainly because my wife is still working. Even though we have discussed the fact that she could retire right now (she’s 3 years younger than me), but she has decided she wants to keep working for another couple of years then take early retirement a year later. But maybe I’ll talk her into retiring earlier. 😉

So I’m so happy I’m sad? I mean… right now I’m probably the most stress free I have ever been my entire life. My 3 kids are all very successful, my grandkids are simply beautiful, financially we’re comfortable. I can literally do anything I want, go anywhere I want, whenever I want. So what’s the problem? Maybe it’s part of my mental ups and downs, but I question now if I deserve to be this happy. My wife says to just roll with it and enjoy life as much as possible. Do as much fishing as I want, play disc golf, make some music, just be happy. As I sit here typing this I’m a bit melancholy. So yah.. to answer the blog’s question…

So I’m retired now? Yah… I am. But it feels a bit undeserving. Maybe I’ll lose myself in a software project and start programming 18 hours a day again. You know… it’s been a while so that potential cerebral orgasm might feel pretty good! hmm…. nah… I think I’ll go fishing instead. 😉 lol… Actually I need to start practicing disc golf again, I’ve taken the summer off, lots of good tournaments coming up!

To close out the post and end on a high note, here’s a couple of photos I took with my phone. My beautiful granddaughter Olive and a nice photo of the ocean I took while in Florida.