What Am I Doing? …When To Call It Quits

When you grow up in Baltimore City as I did, the school of life comes at you fast.  Unless you’ve experienced that kind of atmosphere, and I’m sure a minority reading this have, it’s something that’s hard to convey.  It couldn’t be further from the typical suburban lifestyle that most of my readers likely experienced. 

When I was around 20, I started bonding more with my friend Rob.  Rob’s Dad had abandoned him at a young age and his Mom worked two waitress jobs to just try to get by.  They were on welfare. 

My Dad had just died and left lots of unhealed wounds that I was struggling with.  So Rob and I now had this shared thing, and we’d sit around at the Italian sub shop every night, get drunk, and talk shit about what we’d do to anyone who dared mess with our Moms.

One day Rob got jumped on the street by a group of other kids and beat up pretty badly.  He was a mess.  Me and some other friends vowed revenge, that’s how things worked where I’m from. 

The kids who did it heard that we were coming for them and a big fight got brewing a few nights later.  We brought ourselves, but many of the other kids brought hockey sticks and baseball bats. 

I was so pissed about my buddy Rob that I instigated things, and chaos ensued.  Blood, bodies thrown about, it was street fighting at it’s ugliest. 

Then someone screamed “Gun!” and I looked up to see a kid pointing a pistol at my chest. 

Our eyes locked and I almost pissed my pants.  I remember thinking “stay calm, but this could be it”.  I then said something like “really dude? it’s not worth it..” or something like that, I can’t exactly recall.  We both backed away and the fight ended promptly. 

Nothing like a gun to stop a good street brawl. 

My clan ran to my friend Tiffany’s house around the corner and she iced my wounds and yelled at me.  Tiffany wanted to go out with me I found out later, but I was just too caught up in being a lost kid.  The next day, bruised, bloodied, and sore in a way that only street fighting inflicts, I did a lot of thinking. 

“What am I doing?  What the fuck am I doing?  I could have been killed.  For what, Rob’s honor?” 

The event clearly and unequivocally was a quitting point.  A quitting point for my life as a hell-raiser.  I still went on drinking and partying heavily for a long time, but that fight ended my involvement in the fabricated and bullshit world of the romanticized and tough inner-city kid. 

I called it quits, and have never been in another fight since.

When To Call It Quits

I’m now financially independent and semi-retired from a successful W2 career.  Things worked out.  I made it out of Baltimore, worked hard, saved my money, and got rich.  I never got shot. 

So how did I reach the decision to quit full time work and semi-retire from my W2 job? 

My office job makes me feel caged, trapped

It was 2017 and I had just split with a serious girlfriend.  I wasn’t emotionally in a great place, and my job as a big-wig manager with all the associated stresses was compounding things. 

I remember going to an area of my building that had windows and just staring outside.  It was a beautiful spring day after a long winter with a breakup and a knee surgery.  My office itself had no windows, and I faced another 7 hours of sitting and clicking a mouse under the sorrowful glow of fluorescent lights. 

Suddenly, the voice in my head blurted it out.  “What am I doing?”

Being stuck in that office made me feel like my emotions were being trapped, stifled.  I knew what I needed, I needed nature.  To be running and cycling, moving my body.  The movement and exertion in those activities is how I heal and mentally process life.  Not in a cold, sterile office clicking a mouse to turn the wheels of useless bureaucracy.  

And I also knew I was fully FI.  So I did it, I decided to go part time that day.  I had reached my breaking point.

Not Sure I Can Help You

At this point you might think I’m going to advise you as to when to quit your job, or some other aspect of life that you find intolerable.

Well, my advise isn’t great, so take it or leave it.  In my experience, if it gets to the point where you’re saying “what am I doing?”, then it might be time to pull chocks. 

I realize this isn’t measurable or even meaningful to others in any tangible way.  

Sorry.

I liken it to the “I know it when I see it” test used in 1964 by United States Supreme Court Justice Potter Stewart to describe his threshold test for pornography.  What Justice Stewart considered porn at the time might have been very very different than someone else.  His statement wasn’t particularly helpful, but he was just conveying the system he used.

The breaking point isn’t quantifiable, there’s no clear threshold to reach.  But you have to find your own “what am I doing?” point in life to know when to call it quits.

You’ll know it when you feel it.