About Bobby
My career in my twenties didn’t exactly set the world on fire. Around 30, I was referred for a job I was wildly underqualified for. Within a month of starting, my boss asked, “You don’t know much about what we do here, do you?”
He was right. Exactly zero clue.
Once I got past the initial “WTF do I do now?” phase, I asked him for a list of the 10 things I needed to master to reach the next level. Credit to him, that list turned out to be the blueprint. He also told me promotions took 18 to 24 months at a minimum.
So I turned that list into a little game: how quickly could I get really good at each one?
I went all in on learning every item and building proof that I could do them well. Eight months later I walked back into his office holding that same list. This time, I had proof for every line showing what I had accomplished.
That conversation ultimately led to my first significant pay increase.
Clueless or not, that was the moment the curtain lifted.
From then on, this became my operating system: figure out what actually matters, turn those things into clear goals, break those goals into daily actions, build proof, and repeat the cycle.
Over the next decade I moved from an entry-level role to Director positions at three different companies, eventually managing more than $300MM in annual revenue and leading over 100 people along the way.
But the most meaningful shift wasn’t the titles or the numbers. It was realizing how many talented people around me felt stuck. Not because they lacked effort, but because nobody had ever shown them how the system actually works.
Helping people see those patterns and make smarter moves because of them became the part of work I enjoyed most.
New Game Careers grew out of that realization.
It takes the process I learned through experience and turns it into something practical: clear goals, daily actions, and measurable proof that help people build the skills leaders actually reward.
Your career lasts about 50 years.
It’s a lot more fun when you understand the rules of the game you’re already playing.