How I Failed at Everything I Tried and Then Discovered I Was Winning at Life

From Epic Fails to Unexpected Wins and My Journey to Self-Discovery

Dec 02, 2024

I’ve always felt like a failure. School, relationships, work, family–I messed up in every area of my life. But looking back, I realize those failures were stepping stones to success. This is my story.

Epic Fails in High School

I played basketball in high school. Or at least I tried to. My tryout was so bad it’s probably still talked about in coaching circles. That was my first major failure, but not the last.

Basketball Tryout Disaster: Worst tryout in Montreal history. It was so bad, it’s probably legendary.
Early Lessons in Humility: Quickly learned that natural talent wasn’t everything.
First Taste of Failure: This early experience set the stage for many more “learning opportunities” to come.

CEGEP and Gambling Away My Future

I went to CEGEP (pre-university in Quebec) and quickly found some cool dudes. They introduced me to card gambling, and I was hooked. I lost money I didn’t have and failed tests I should have passed.

Card Shark Wannabe: Fell in with the wrong crowd and got hooked on card gambling.
Losing Streak: Lost money I didn’t have and failed tests I should have passed.
Failing to Balance: Couldn’t find the balance between having fun and taking responsibility.

Art School Dropout

My next stop was art school. I thought I could thrive in a more creative environment. Boy, was I wrong!

Second Chance, Same Result: My second attempt at post-secondary education went about as well as the first.
Distracted and Unfocused: Couldn’t stay motivated or interested enough in my studies.
Another Missed Opportunity: This time I crashed out in the second semester.

Relationship Mistakes and Heartbreak

Somewhere in this mess, I met a beautiful girl who lived out of town. I have no idea what she saw in me, but somehow I knew I didn’t deserve her. Two months into our relationship, I cheated on her. She gave me a second chance, and I cheated again. That was the end of that.

Long-Distance Love Gone Wrong: Met a wonderful girl in a long-distance relationship, but couldn’t stay faithful.
Infidelity and Consequences: Cheated on her not once, but twice.
Learning About Trust: The relationship ended, teaching me a hard lesson about trust and commitment.

Business Blunders and Missed Opportunities

I finally had time to use my writing skills and make some money as a copywriter. It was a rare opportunity, but my work ethic was terrible, and my writing wasn’t great.

Content writing Flops: Landed a copywriting job, a rare opportunity for a newbie.
Lackluster Performance: Poor work ethic and mediocre copy led to failure.
Missed the Mark: Failed to capitalize on a chance to learn and grow professionally.

Family Friction and Failed Connections

My relationship with my father wasn’t great either. My dad wanted one type of son(type A, jock), and I was another (cerebral and artsy without the talent). We never connected.

My dad and I had a complicated relationship.

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