About Bobby
The path here has not been a straight line. In my 20’s, my career felt like an inescapable 40-hour-per-week time vampire. In my 30’s, I found a way to make it give back.
The shift came when I realized that if you can just identify what actually matters and get really good at it, your background and imposter syndrome don’t matter nearly as much as you think.
I am a walking example of this.
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?” I said, “No, but I made it through 9 interviews, including one with you, so I’m guessing I still have a career in sales.” He laughed, but he was right… precisely 0 clue what I was doing.
Once I got past the “WTF do I do now?” phase, I asked for a list of the top ten things I needed to do to be successful. Credit to him, it turned out to be a great roadmap. I obsessed over mastering it, building tangible proof for each of the 10 items. Shortly after, I traded that proof in for my first significant pay increase. Clueless or not, it was one of those life moments that felt like a curtain had been pulled back.
So I shifted into the “do this” phase: figure out what actually matters, turn those things into goals, break those goals into daily actions, provide proof, and repeat the cycle relentlessly.
Since then, it’s been a wild ride. I climbed from an account sidekick to Director roles at three different companies, eventually managing $300MM+ in yearly revenue and leading over 100 people along the way. But the real shift wasn’t the title or the numbers. It was helping people realize they also have control over their careers, clueless or not.
New Game Careers is my way of turning that process into something useful, and breaking the mold of what people expect career advice to be. It makes the idea playable through exact daily actions to build specific skills, and measurable proof to help people reach whatever their next level is.
I built this because I’ve lived it, and it made work finally feel like something positive in my life. And it should be — your career is around 50 years. It’s a lot more fun when it feels like a game you can actually win.