Is there such a thing as too much freedom?

I’ve always used freedom as the compass to guide my decisions.

We moved a lot when I was a kid. I lived in five states and countries by the time I was 5.

I left home at 17 and went off to college as far away as I could.

I joined a circus for 10 years. Then I quit my last job in 1992, vowing to make a living making music and never have a job again.

A few years after I started my company, I delegated all of my responsibilities, making myself unnecessary to the operations of my company, so that I was free to go live anywhere and do anything.

My email was filtered by the customer service staff. Hardly any needed my personal reply, so I was free to go days without checking email.

I gave nobody my phone number, and said no to all meeting requests, so I was free to work on my own schedule with no appointments to interrupt.

I gave away most of my stuff, including my entire recording studio, to my employees. So all I had left were some clothes and my laptop. Free to travel lightly.

I eliminated all physical mail, setting my necessary bills to electronic payments, and had tax forms go to my accountant. I was free to move without notice.

I moved to London for a year, just because I could. I hardly told anyone I was gone. Most people thought I was still in Portland. Then I went to San Francisco for a few months, India for a month, and Iceland for a month.

Friends back home would say, “So what did you do in Iceland?” I’d say, “Same thing as you. Same thing I’d be doing anywhere else. Just programming, working, writing, reading, living.” Living the laptop life. Location agnostic.

Switching countries was like switching rooms in your house. Why not go sit in the den for a while? Why not do some writing in the kitchen for a change How about the back yard?

How about Berlin for a while? Brazil? Buenos Aires? Beijing? It’s a big world. Why not do my work in each of these places?

I could be anywhere, but didn’t have to be anywhere.

But even though I had freedom of location, I still had some responsibilities to my company — CEO/owner type stuff. And I was still the main programmer, so in all of these places, I’d still be working mostly on the backend programming, improving the site and service.

My company grew 1000% while I was gone, from 2002 to 2008. But once I left for good in 2008, I really had no more responsibilities at all, and might never again.

I had done it! I’d reached the final destination of my life-long pursuit of freedom! Awesome, and overwhelming. So… Wow. Now what?

Where do you go, when you can be anywhere, and don’t have to be anywhere?

What do you do, when you can do anything, and don’t have to do anything?

What if you had no ties? Nothing holding you to any one place. What if you had unlimited plane tickets? What if you never had to work again?

Is there such a thing as too much freedom?

This story isn’t coming to some conclusion where I answer the question. I’m still living the question.