29yo here. I was born a naturally confident guy. Played sports all the way up to college. Getting girls was easy for me in High School due to my confidence. If you asked around, Johnny was the most confident dude around. Large friends group, multiple options with girls, and even my teachers liked me. I felt like the man. I didn't really have the most healthy home life (narcissistic mother and weak father made the family dynamic rot from the inside) so I got validation from the streets. After HS I went to play D1 football in Idaho as a (real) 6'0 190lbs lightskin Wide Receiver. I don't think I was ever an NFL caliber player. I definitely knew that I could be a starter by my senior year and maybe go undrafted and get cut by some team. That was my expectation. I didn't worry about it. I had a lot of fun until I got a girl pregnant in my sophomore year. I failed all my classes and dropped out. This was the beginning of the end.
I decided to just say fuck it. I'll go joint he military and start training for SEALs. Went to the recruiter, they don't allow single parents. So it was either not join or marry my daughters mother.
For the rest of my 20s, my confidence was still higher than normal, but slowly diminished. I still was motivated. I made a series of poor decisions. Quitting job after job. Starting businesses and failing due to refusing to have a job. I was overly confident that my natural abilities and hustle was enough to build a million dollar business with nothing. Years went by as I went from job to job and from one idea to the next idea. I was still a hustler in my head though. I broke the record at my commercial gym for the strongest bench at 375 and I held the squat record for about 2 weeks. I was going downtown making out and hooking up with random girls having a blast, while my confidence slowly withered away year by year.
Once I turned 27, I felt like a loser and I went back to school. This is the age where I started lying about how much money I made. Not about anything crazy, but just to seem normal. No one knew that I was unemployed and living with my ltr at the time and she was funding my lifestyle. I didn't want anyone to know that I was just a good looking loser. I definitely felt like one. I even lied to my parents and siblings.
I studied my ass off and graduated earlier this year with a bachelors and found a job paying 75k/yr remote. I immediately enrolled in a masters program in Data Science and I should be finished by the time I'm 30. In addition, a business partner and I will be buying a mom and pop popular restaurant in my city very soon. I'm still in great shape and I have an ok social life but I still feel like a loser inside. Over the past few months I've had my first irrational fear of approaching a woman who was showing interest. I almost had this feeling like I wasn't enough. When talking to people they hype me up but something inside me feels like they're lying because they're just being good friends. What they're saying makes complete sense but I just don't feel that chin to the sky type of confidence I used to have.
On paper, I should be "ahead" of the average person, but I feel like I haven't measured up to all my lies and it's making me feel like a loser and a liar. I want to shake this feeling and get back to my younger self. Before all the mistakes.
Be as critical as possible. I need to hear it.
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