My first year of law school I was paired up with a mentor. His name was Jeff, a very nice guy actually and we kept in contact with each other throughout the years. Fast forward to today and our lives are very, very different.

You see Jeff ended up marrying a girl who happened to be very rich, attractive and nice. They now have several kids, live in a palatial estate in a well-to-do suburb of Chicago and partake in a traditional life where he works and she stay home with the kids. I’m far from the family lifestyle as you know.

Every so often I have some work out in Chicago and every time Jeff would invite me to stay at his house. And every time I would decline, opting for a hotel to either do some light gaming while traveling for work, or just relaxing and enjoying some alone time.

A few weeks ago I had to be in Chicago again and like clockwork I got the invitation from Jeff again. Except this time I accepted it.

Why I Accepted

I enjoy my lifestyle. There is always room for improvement but I am generally content overall. But that doesn’t stop me from both hearing externally from numerous people about how what I’m doing is wrong (remaining single, traveling all the time, not having “roots”) and once in a while questioning myself about the same thing — which I view as healthy. I don’t want to just pull a blanket over my head and blindly assume all my decisions are correct.

So I wanted to see what life was like for someone that not only got married, but got married to an attractive girl who was rich, traditional and extremely nice. I wanted to see if this would also make me happy, to have chosen a path that most would consider a high standard of familial life.

On The Surface

Let’s get the main observable negative out of the way immediately — his wife is now fat. Granted she’s been pregnant for a large portion of the past decade (6 kids), but I’ve seen enough thin girls during pregnancy that I don’t buy that excuse. She does now take boot camp classes multiple times a week however since finishing up her last pregnancy, so there is that. Putting that admittedly large negative aside, she is still extremely nice (as far as I can tell), takes care of the kids and cooks elaborate and delicious meals from scratch.

Back to the other easily observable positives in Jeff’s life. He lives on a 15+ acre estate. There are so many rooms here I’ve gotten lost trying to find my bedroom multiple times. There’s close to a million dollars worth of cars in his driveway, which itself is so long you can’t see the main road from the house. He has two live-in housekeepers. As easily as your friends would offer you a Bud Light he offers me glasses of Blue Label (which I gladly accepted). Basically, money is of no concern.


Even his kids are amazing and I don’t even like kids. Granted they are still kids so there were a few crying incidents, but overall they are insanely well-behaved. More than that they are all good-looking and extremely smart. I had a conversation with his 3-year old girl that was more substantive than some dates I’ve been on. If I ever have kids his would be the ideal I would strive for.

But On The Inside…

He was a dead man. At dinner one night I watched him as he held his youngest son, an infant, and for minutes on end he would just stare into space with empty eyes. You can tell when someone is looking off to the side thinking about something. This was not it. It was a robotic, dead gaze.

One of the mornings on his way to work his wife innocuously asked him about a bill and whether it was paid. He snapped at her in an angry voice that seemed to be unwarranted and something that happens after months of being passive-aggressive. Healthy minds don’t react like this.

Random family and friends showed up during my few days there and everyone was having a great time besides him. I felt bad. Here is a guy who will never have to worry about money in his life, has probably the best kids a person could ever ask for, and aside from his wife’s weight gain which will hopefully be reversed with the start of a new exercise regimen, she still is nice and very traditional. Yet he is the unhappiest person I’ve interacted with in a while.

My Thoughts

I’m very happy I finally accepted Jeff’s invitation. I had a chance to see what my life could have been like had I not only veered down a traditional path, but one that at least superficially is about as ideal as one can ask for.

It would be an absolute lie for me to say that I’m 100% certain that my chosen lifestyle is the right one. I believe it is but I keep an open mind and welcome thoughts to the contrary. When people ask me about my lifestyle, I tell them about it but don’t preach it because everyone is different.

And while I realize one example does not make a rule, there is no escaping a few undeniable truths. If I really wanted to just get up and go to Europe for a month, I could. In a few weeks I’d arrange for work to be taken care of, sublet my place out and off I go. Jeff has six young kids and a wife — it’s highly doubtful he can even escape for one evening let alone a month.

For some having a Bentley in your driveway makes you happy. For others like myself, it’s freedom. Having a coffee in a random Siberian cafe puts a smile on my face. One probably much larger than any Jeff has had for a while.

Read Next: A Tale Of Two Men


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