Why This “Old Man” Ditched the Office and Became His Own Boss


Meetings almost swallowed me whole. Sucked the life out of me in jobs I loved and brought me to the brink of exhaustion.

For much of my career I had jobs I really enjoyed, people I enjoyed working with, and general good times. But, like many Baby Boomers, as I advanced in my career, along came the inevitable increases in responsibility and expectations of greater performance.

As I approached my 50s, the hair was thinning (and the remaining brave follicles were going gray) and things began to shift.

I didn’t get the assignments I wanted. I didn’t get the travel I wanted. I didn’t get the responsibility I wanted…but I did get “volunteered” to attend more meetings. And the digital paperwork seemingly became more important, and more strangling.

Sound familiar?

It wasn’t that bad at the beginning, but I did have that sense that this was the beginning of the long, slow decline into work I disliked, punctuated with the occasional slice of work I enjoyed, interrupted by an endless stream of emails. And I struggled with this.

At first you rationalize…Well, the stock plan…well, the health insurance…well, the security…well, the company….Well, well, well.

You can go from being the “go to” person with the action plan to the older person who probably “needs a nap”…a comment directed at me in jest, that stung with fury.

It motivated me to hack my way out of the career jungle with the equivalent of a dull machete. I made lots of mistakes, went down blind alleys and wandered in the desert of despair before I pieced together a plan that began to work.

Fast forward a bunch of years…

Now, I work for myself. I live where I want to live (mostly Mexico now). And my work takes me around the world (12 countries last year) and I get to pick the assignments that are most interesting to me.

And maybe most important, most of my work today gets done on my time schedule rather than someone else’s.

Quite a different future to the one my “career-self” saw as inevitable not so many years ago.

From travel photographers, to freelance writers, to people who sell goods online, countless people have done the same as me and left their office job for a more exciting, stress-free career. If you like the idea of having an income that goes with you wherever in the world you want to be—this could be perfect for you.

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