Jason Flamm
3 min readFeb 20, 2019

“Did you ever think you’d be where you are today?”

Without hesitation, I said “No.”

“Why? You’re smart, you’re talented. You work hard. Seriously, I’m curious why.”

This made me stop to think for a minute. Why had I never considered success in my future?

After a few beats, I replied,

“I never thought I was smart or, really, any of those things you just said about me.”

Growing up poor, and in poor company, the only role models I had around me were service workers and teachers.

No one was educated. No one was wealthy or even middle class. Everyone lived paycheck to paycheck and barely scraped by.

I went to inner-city public schools which only graduated about 60% of their students in the late 90s. I was fortunate to be one of those that stuck it out and got my diploma.

After HS, I attended a college about 2 1/2 hours away and fell into a deep depression that brought me back home after a failed semester. My family was going through rough times and I felt guilty for leaving.

Over the next decade of my life, I’d go to community college off and on, changing majors and trying to figure out how to get out of the same situations I’d seen my entire life. 19 years after taking my first college class, I’m still trying to get my Bachelor’s degree.

I would sabotage any chance for success by making poor choices and quitting school before any true progress was made. Late into my 20s and early 30s, I lived paycheck to paycheck and worked in fast food.

An interesting thing happened to me then. I began to surround myself with different people. People who had jobs I’d never even heard of:

  • Copywriters
  • Designers
  • Account & Project Managers
  • Administrative Coordinators

Growing up, I had never even heard of any of these jobs. My relatives were janitors, cooks, dishwashers, factory workers, movie store clerks, laundromat attendants, and, for a time, my mom taught pre-school.

I had always heard that some people had office jobs, but I didn’t know them.

And, now I did.

Fortunately, a few of them took notice of me because we were running in similar circles. First, it was in improv comedy, then sketch comedy, then a few of us would talk about business leadership on Saturday mornings at a local coffee house.

I read every book I could get my hands on about management, leadership, behavioral psychology, and any form of self-help.

Eventually, one of these friends stuck their neck out for me and told their boss she should interview me.

I knew the importance of the interview and I dreaded the thought of failing. This was a chance to truly change my life.

I would later hear from the person who interviewed me that, within the first 10 minutes, she knew I would be great.

Four years later, I’m anticipating a job offer that will put me in a position to manage and lead creative teams.

Over these last four years, I’ve more than tripled my salary and I’ve developed marketable skills that should keep me in my current industry for as long as I want.

Recently, I turned down a job at a great place because I wanted to pursue a better opportunity. Something that the old me would’ve… well, the old me wouldn’t even know what that job actually was… so nevermind.

A previous coworker called it my “Glow-Up.”

And a coworker of my wife made a comment about my luck, saying that I always seem to land “jelly side up.”

For 30 years of my life, the environment around me limited my world view of what was possible.

I was lucky to have people around me who told me I was smart. Who told me better things were possible. I was very fortunate to feel a lot of love from some key people throughout my first 30 years.

But, it wasn’t until I diversified the environment around me and really started learning about new things, that everything began to change.

Now, I believe anything is possible for my life and my career.

But, did I ever think that I’d be here today?

No.

But, now that I am, I don’t ever plan on leaving. And I hope that I can help and encourage others to believe in better things for themselves.

Jason Flamm

Author of Keep Creating: 83 Ways to Keep Creating the Things You Love. My day job is a copywriter and content director. Jasonflamm.com and Keepcreating.io