Stepping out of my comfort zone: The Turning Point


With radical transparency in mind, this is a blog series providing ongoing insights into my transition from being stuck in the corporate world to the challenging freedom of entrepreneurship.

Kodak-fork-in-the-roadWhen I look back on it the real turning point happened a couple of years ago. Minette and I were driving home after meeting with our financial advisers having done some long-term planning for our investments. As is their wont, they asked questions about when the kids would be starting in university, how often we would get another car, whether we would move once the kids moved out, etc. This data allows them to plan out what money goes where, when. We were halfway home before one of the questions hit me hard: “Brad, where do you see yourself in 5 years?” I looked at Minette and told he there’s no way I’m still working at my same job when I’m 50. I think she gulped and then said she had better get her butt in gear.

She had already been working hard to ramp up her coaching business with the eventual hope of allowing me to get out of my job. We had made a couple of different coaching investments to help her up her game. I’d been working in software for 25 years and at the same company for the last 15. It had become a set of golden handcuffs: 5+ weeks vacation per year, excellent salary, full-time telecommuting, great benefits, lots of self-directed work. Others would kill for that opportunity, but what good was it if I was stagnating and unhappy?

As we continued our drive home we agreed that I’d be done with my job in five years no matter what. Once the wheels were in motion things kind of .. accelerated :-)

Brad Dobson
Brad Dobson is a co-founder of the Path to Profit Academy, and husband of Minette Riordan. He handles all the techy stuff and shares parenting duties. He is a 2-time marathon and 2-time Ironman finisher and for some reason enjoys endurance athletics. After 25 years in the software industry he quit his job to become an entrepreneur alongside Minette.

About Brad Dobson

Brad Dobson is a co-founder of the Path to Profit Academy, and husband of Minette Riordan. He handles all the techy stuff and shares parenting duties. He is a 2-time marathon and 2-time Ironman finisher and for some reason enjoys endurance athletics. After 25 years in the software industry he quit his job to become an entrepreneur alongside Minette.

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