My Biggest Mistakes in Life

1. I got a girlfriend way too soon in life and got married way too soon.

Most of you who know my story know this already. When I was a young, dumb, inexperienced beta male at age 25, I married an older single mother. This one decision caused the following long-term problems in my life:

A. The marriage set me back financially at least ten years even without the divorce. Read this.

B. Being married almost put my business under. Read this.

C. The relationship and subsequent marriage caused me to gain over 50 pounds, some of which Iâm still struggling to lose 20+ years later.

D. Being married caused a decent amount of regular drama and stress in my life that lasted almost a decade.

E. Being married murdered my sex life. Before getting married I was having sex on regular basis with FBs and it was good sex. Once I was married for about a year that dropped in frequency and stayed low until the divorce nine years later.

F. I got divorced, which cost me a decent amount of money in alimony and legal bills. It wasnât horrible and I didnât get âdivorce raped.â Some people seem to think I did, and I didnât. I was able to survive it financially and we didnât have any sort of custody battle. But it was still a massive disruption in my life that lasted several years and cost me a lot of money for no reason.

G. It set back my pick-up and dating skills by at least ten years. I would have been far more skilled with women by age 35 had I never gotten married. Today Iâm fine, but as many of you know, it took me several years of hard work to get my woman skills up. That would have been much less of an issue if I had stayed unmarried throughout my twenties and thirties.

2. I had children way too soon in life.

I love my kids. Theyâre a source of great pride and joy for me. But I could have had them later in life and should have. Iâm a man, which means I can have kids pretty much whenever the hell I want. I made the utterly ridiculous and unforgivable mistake of having my kids in my mid-twenties when I was not much older than a kid myself. It caused the following problems:

A. It set me back financially at least five years (and yes, this is on top of the ten years the marriage set me back). Read this.

B. It made my marriage far worse. By far, the number one source of big arguments I had with my first wife during my first marriage were directly caused by the fact that we had children. Most married couples with kids will tell you the same thing. It was brutal. The marriage would have been far better if there were no kids. (It still wouldnât have worked because it was monogamous, but it would have been much, much better.)

C. I made errors in raising my kids back then because I was far too young to be a proper dad. Guys in their twenties should not be dads!

3. I stupidly waited until my early twenties to lose my virginity.

Some guys seem to think that waiting a longer time to lose your virginity makes you a better man, or a more moral man, or a safer man, or a more focused man. All wrong. Itâs all bullshit right-wing Societal Programming. 

Likely the biggest source of angst and inner pain during my teenage years and early twenties was due to the fact that I wasnât having any sex. Man, it hurt, and on multiple levels. 

It was very good that I didnât have a girlfriend during that time. That was something I did right. But I should have been having sex with an FB or two on a regular basis. I would have been happier, less stressed, more confident, had better self-esteem, and yes, more focused at my work and a more effective man overall. 

I still remember how much better I felt overall once I started having sex on a regular basis (at least before I got married!). It was a world of difference. Losing my virginity in my teenage years would have had a huge and positive effect on my entire twenties, and perhaps my thirties as well. What a monumental mistake.

4. I didnât spend any time abroad during my twenties.

I still regret this a little to this day. During my early and mid-twenties, I was very excited about traveling abroad and even perhaps living abroad for a year or two before returning to the USA. I read a lot of books about it and got very excited. Back then I was looking at doing this with Japan (it was the early 90s and Japan had not entered their zombie economy yet). 

Alas, I didnât go anywhere because I was scared. It would be almost 15 years later before I started regularly traveling to other countries. Way, way too long. 

Had I lived abroad for a year or two way back in my early twenties, regardless of what country it was, it would have had a massive positive effect on the rest of my life going forward.

5. I chose to follow a âselling hours for dollarsâ model for my first business.

Iâm very proud of my first business, my little computer consulting practice way back in the mid-90s. It was my first business success. I got to a six-figure income in 1990s dollars by the age of 27 because of that business. I did a lot right with it. 

However, I made the massive and common error of getting into a business where I traded dollars for hours, rather than leveraging my time by decoupling what I sold to the hours I actually put in. I sold per-hour consulting services. This was fine, and made me some good money, but it also put me in the position where the only way I could feasibly increase my income was to put in more hours. That is pretty much the stupidest business model you could come up with, regardless of how much money you make. 

I should have sold flat-fee services, retainer services, information, and/or products instead of per-hour services. I could have been a millionaire much sooner in life, and with a lot less stress and pain.

6. I waited too long to lose weight.

Younger men can get fat, get drunk a lot, eat like shit, do drugs to a degree, and pretty much fuck up their bodies without having it damage too much of the rest of their life. Once you hit age 35, you canât do that anymore, and certainly not past 40.  

I wanted to address my weight when I was in my early 30s, but I didnât, at least not completely. While I have never again weighed what I weighed back then (which was a lot), I should have gotten down to my ideal weight at or around age 35. I was too focused on other areas of my life to make that happen, which is not an excuse.  

Now I have to focus very hard on getting my body fat down at age 47. Not fun. It would have been much easier 17 years ago.

7. I charged way too low for my products and services for way too long.

Throughout most of my business career, in all of my businesses, I got stuck in the trap many entrepreneurs do of underestimating A) how valuable my products, information, and services really were and B) how much money my customer base was willing to spend.  

Iâve lost millions of dollars over the past 20 years or so by charging too low for the things Iâve sold in my businesses. Even now I still donât do this as well as I should (though Iâm much better at it today). I could have made much more money on far less work hours had I figured this out and/or had the balls to actually raise my prices 25 years ago. 

So, none of us are perfect. Iâve done a lot of dumb shit throughout my life. The above seven items arenât even one percent of all the mistakes Iâve made. I just kept going despite my mistakes. 

No one needs to be perfect to be happy.