Living Da Life…of a Lifestyle Entrepreneur



“Life begins at the end of your comfort zone.”

― Neale Donald Walsch

In hindsight, I probably made a mistake. When I left my last corporate job, because I’m still relatively young, I sent a note to my family, friends and associates that I was “semi-retired”.  This is a hard thing for many people to wrap their head around. It’s a little like a “semi” truck. When you look at it, it’s still just a big truck.

Now, one of the most annoying parts of being retired is that every time I pick up a computer or look at my IPhone, people inevitably ask, “What are you doing? You’re supposed to be retired.”

They act as if, somehow in retirement, that you shouldn’t do anything meaningful and that you should never work on a project or have a desire for anything outside of sitting in your backyard picking up dog poop ever again.

As a result, when people ask what I do, I say that technically I’m retired and there is an awkward silence. When I was a kid, I wanted to be independently wealthy, but this sounds arrogant and what the heck does that really mean these days anyway?

Ironically, I actually planned on retiring when I was 40, but kids and marriage tends to rearrange your priorities. Of course , none of you would have any experience in this area, right?

Truth is, I never intended to retire in the way that my parents or grandparents did. When I was a kid watching my grandfather retire, retirement meant sitting in the house on your recliner or easy chair, while watching your favorite game show and/or soap opera. Are any of you old enough to remember how they covered the nice furniture with plastic covers?

I watched my grandfather retire in his 70’s, after more than  30 years, get a gold watch, survive a very painful heart bypass surgery only to die less than two years later. This was wrong on so many levels. I didn’t want to be that guy.

I didn’t want to be the guy who had to rely on such a low fixed income that I would be reliant on eating pork and beans and bologna. What’s that stuff made of anyway? I never liked either of these and I like having choices.

On the other hand, I also didn’t want to “retire” only to create another stressful full-time occupation for myself. I retired to focus on things that were important to me.

If we can work 10-12 hours days to do what’s important to our corporate employers, why is it strange that we would spend 6 hours on causes and projects that are important specifically to us? Think about this.

At some part, I started thinking I should use some other term and I ran across the term “lifestyle  entrepreneur”.  The first definition of a lifestyle entrepreneur I found was “a business owner who prioritizes lifestyle benefits over profits.”

Scott Fox, the author of Click Millionaires describes it this way:

“Lifestyle entrepreneurs are known for organizing their work and business activities around their own lifestyle goals. These goals often including flexible hours, fulfilling work, spending time with family and friends, hobbies, charity work.

How do Lifestyle Entrepreneurs differ?

Lifestyle entrepreneurs differ from most start-up founders or executives because they deliberately balance their work and their play to create lifestyle businesses that support their favorite activities while also making money. Pleasing their venture capital investors or shareholders takes a back seat to doing the work they were born to do, and having a good time doing it. “

Still not totally sure if this totally describes who I am today, but it is definitely getting closer. 🙂