Career Path 3.0: Don't Listen to Your Mother

I am finally in a position where I am truly happy with my professional life. That doesn’t mean that everything is perfect or that I’m even remotely satisfied — far from it. Shit is more complicated and difficult now than ever, but I love it. I love what we are building, I’m incredibly fortunate to work with super smart people, and I walk into work every day fired up and ready for world domination. This makes me truly happy. I had no grand plan to be building MVPs at the NYC Dev Shop. It certainly wasn’t a direct path, but it’s been a fun ride so far. So here is my unabridged 4 Part answer to how it all came to be:

Career Path 3.0 Don’t Listen to Your Mother


I woke up one morning and realized that I hated my job.

That is a devastating realization. I never ever ever imagined I would be one of those people that absolutely despised waking up to go to work. That’s not my style. I’m too ambitious, I have too much to accomplish, and I’m generally a very easy going and laid back person. So you can imagine how miserable I was when I finally came to terms with this.

It was a slow, grinding series of soul crushing events strung together in the most painful and numbing way possible. The system had won. They had taken all of the fight out of me. I was showing up for work at 9am-ish, going to the gym at noon, going to the lunch after that, and then trying desperately to find ways to leave before 5pm.

It was an incredible transformation as just 18 months early, I was the first one in the office every morning and by far the last one to leave at night.

I had lost my purpose.

I had lost my ambition to do great things.

It was time to make a change…

I explored just about every option imaginable for my next steps — I clearly had all the time in the world to browse the internet like the rest of my colleagues.

Primary Objective: Find a position that would reward me for the value that I create.

This simple objective eliminated so many possibilities. My ultimate direction was clear. I had to find a position where I could bust my ass and it meant more than a pat on the back.

I had to become an entrepreneur.

My mother hated this idea. Secretly, I almost agreed with her a bit because I was afraid. I was going to throw away everything I had worked so hard to accomplish. I was making good money, not great, but more than almost all of my friends. I was in a secure position where my employer’s loved me. This was in 2009. The unemployment rate was through the roof and people would kill for my job. And here I am about to quit because I was bored.

I know why my mom didn’t want me to leave my comfortable position. She didn’t want me to be a fuck up and become homeless. Totally reasonable. She just could never truly understand how painful it was to go to work at a soulless job every single day.

Regardless of her advice, I knew (and she knew) deep down in my heart that it was time.

Time to leave my cushy job. Time to find out what it’s like to live without a steady paycheck. Time to try and find my place in the world.

Time for Career 4.0: Learn. Improve. Adapt.