Dean Jackson

You’re Playing a Game You Can Never Win

You’re Playing a Game You Can Never Win

Most entrepreneurs have this vision of one day in the future where they lean back in a their chair, kick their feet up on their desk made of rich mahogany and lazily stare out the window of their 42nd floor corner office window. Life will be so wonderful for them once they are successful.

I think that’s shit.

The Ultimate Goal for Work


My love for Quora has already been well documented, but for those of you who haven’t made the plunge to become full blown Quora addicts yet, I will share one of my answers from this morning.

The question was “What would you do with your time if you could afford to quit your job?”

Here is my answer


I think Dean Jackson has a wonderful perspective on this question. He says that one of his main goals is to “live like an artist with a $50,000 / month trust fund.” That way he could wake up every day and ask himself the question, “What would I like to do today?” and then focus on the thing that is most important to him for that day.

The goal is to get to the point where you don’t have to work, but you want to work. You want to work on things that you find incredibly rewarding and valuable. Most often this includes things that help others, improve something, make the world a better place, etc.

When you get to that point where you are able to truly focus all of your time and attention on a project that motivates and inspires you — like an artist — that is when you will produce your best work. If you ever have a chance to watch the “New Money Masters” video with Dean Jackson and Tony Robbins, I would highly suggest it.

I know it doesn’t answer the question of what I personally would do, but I think the point of this question is really to figure out what you would do. This answer and approach is definitely something I am working towards every single day.

I can’t imagine retiring.. One of the great joys in life is working. I enjoy being productive. I enjoy making a difference for people. I enjoy contributing.

via Dean Jackson

Dean Jackson is a real estate coach and internet marketer and has one of the greatest perspectives on achieving success I have ever heard. His approach to “his ultimate lifestyle” is so unique and refreshing.

Side note: I would link to his website but it looks awful and he doesn’t have any online profiles, because that’s just how he rolls. If you really want to know more about him, hit me up.