5 years ago, I never would have thought I could live a laptop lifestyle – one that would allow me to make money online – some from freelancing, some from passive income — from anywhere in the world.

In fact, when we first started thinking about selling the house and going cruising, my biggest fear was what we’d do for money.

At the time, I was working for a small marketing company that I’d been at for 7 years. I worked from a small windowless office (which was a huge upgrade from my former cubicle), and my salary was meager at best. I did not have a big savings account, and I knew I’d never touch my 401k, so the day I went in to tell my boss I needed to quit because of this whole moving-onto-a-boat thing, I started to doubt every decision we had made.

What was I thinking? What the f#ck did I agree to? I must be INSANE!

I thought about backing out and finding some way to put off our plan, or just go bury my face in a monster sized glass of wine instead, but I summoned my inner rockstar, knocked on my boss’ door and upon getting permission to come in, I sat across the desk from him…

…and broke into tears.

Yep — totally profesh.

Luckily, my boss was a really kind and understanding family man with a wife and teenage daughter (so I’m sure he’s seen his fair share of tears), and that was the only thing that kept me from walking out of his office and going to throw myself off a bridge out of embarassment at my spectacle.

But after I wiped away the salty mess on my face, I explained this super scary, but exciting adventure we were going on, and to my relief, he was really excited for me.

I then I said the words I had been so scared to say… out of fear of the future, and of guilt for letting down these people who had been really great to work with.

I need to quit.

He sat and thought about it for a few seconds, then said, “Hmmm… well… could you work from the boat?”

WHAT? Could I work from the boat?

He then went on. “All you really need is a phone and a computer, so if you think you could find a way to work from the boat, we can try it out for a year to see how it goes, and then reassess from there. If you want to, of course.”

And that was the magic answer. I could work from the boat — I would find a way. It wouldn’t be without its headaches, of course, but it was a paycheck, and it eliminated my biggest fear about jumping into this lifestyle and then not having any money to pay for it or enjoy it.

I gotta say — my being able to work remotely from the boat was our saving grace for the first year or so, because as Murphy’s Law goes, everything seemed to break that first year, and had we not had jobs, we would have been screwed.

Not all it was cracked up to be

I was super stoked for having this set up where I could work from the boat. I’d pass people who were on their way to the beach and they would tell me how lucky I was to have a company that allowed me to work remotely. But as time went on, I realized that while it was awesome to have a steady paycheck, and I was very lucky that my employer did this for me, I wasn’t living the life I thought I would be.

Because of the particular job I had, I needed constant wifi connectivity, at least 8-10 hours a day. My entire job was centered around email, and I probably exchanged about 300 emails a day on average. That’s one email sent or received every minute and a half for 8 hours a day.

I honestly don’t know how I stayed sane for so long.

Not only was the work constant and didn’t allow me to do things like even go hang out at the pool for an afternoon, but because my work required reliable wifi at all times, we weren’t able to sail to the Bahamas with our friends, or do anything that was much fun. In fact, not much had changed at all — I worked just as hard. I just had a better view.

Now I know that sounds like I’m a spoiled brat. I was still on a boat and I still had a job. Oh, boo hoo. I know I didn’t have any reason to complain, BUT when you take a big leap like we did, you want to enjoy it. And I wasn’t enjoying it very much.

My aha moment

One day, I was browsing for books on my Kindle and saw a book called The 4-Hour Work Week by Tim Ferriss. It introduced something I hadn’t really thought of when it came to working — setting up a business that is systematized and more automated, so you can earn seemingly passive income with just a few hours a week of hard work.

I devoured that book in a weekend, and I gotta say it changed my whole mindset. While I was happy for being able to work remotely (which I am still grateful for), other people were setting up these “freedom businesses” that allowed them to live a laptop lifestyle and travel the world!

If you haven’t read the book, I highly recommend it — even if only for some of the killer information on the 80/20 rule, which states that 80% of our results come from just 20% of the work, so the other 80% of the work you do is almost inconsequential. If you can figure out how to leverage that concept to your advantage in all facets of your life, you could become infinitely more productive, and yet have more free time on your hands.

Living a laptop lifestyle

After reading that book, my entire way of thinking shifted, and I started thinking more and more about the laptop lifestyle. I began studying ways to earn money on the side, and it paved the way for the direction this blog has taken.

I have since quit that job with the marketing company. I have my own online jewelry business. I’ve taken online courses on how to build better websites and started doing some freelance web design on the side. I’ve taken classes on writing and marketing, and now I have clients who pay me to write for their company blog and websites.

I am a firm believer in diversifying your income streams because you never know when one might go away, or when you might hate one so much that you want to leave. If you have other income streams, it’s not so scary.

That’s the benefit of having a laptop lifestyle. You can do so much from anywhere with nothing more than your skillsets and your laptop. I can’t imagine ever working in another cubicle again. Having a laptop lifestyle allows me to design a life that allows me to make my work work for me — not the other way around.

Now it’s your turn — have you ever thought about a laptop lifestyle? What would a laptop lifestyle allow you to do? Leave a comment and let me know!