It was right around this time I stumbled across a guy by the name of Chris Guillebeau.

These days he’s a multiple New York Times Bestselling author, entrepreneur, and founder of the World Domination Summit.

At the time though, he was just a blogger on his site The Art of Non-Conformity.

In 2009 he was quickly making a name for himself, and I still remember the first time I stumbled across the site.

I read every blog post he’d written in a single afternoon.

At the time he posted every Monday and Thursday and every day I’d hit refresh repeatedly waiting for that new post.

He was on a quest to visit every country in the world by the time he turned 35. He had a business where he put his interests and lifestyle first, and most importantly he could work wherever he wanted – with no suit and tie.

As it happened, he had just moved to Portland – so on a whim, I sent him this email hoping he would meet me for coffee:

My email to Chris.

He agreed, and the following week I lied to my boss, said I had a doctor’s appointment, and headed to the hipster neighborhood of Hawthorne to meet Chris.

I walked into the coffee shop fully decked out in my awful suit, and when he first saw me – he just laughed.

I was the only person in a 30 block radius actually wearing a suit.

It was during this meeting that the concept for Location Rebel was first born.

Chris, knowing how much I wanted to make a change in my life, recommended I start a blog and begin writing about my desire to make that change.

He also encouraged me to think about the things I really wanted to do in life and publicize them for increased accountability.

A few weeks later I’d secured the domain locationrebel.com, and written out my bucket list.

Over the course of the next year, Chris and I met every month or two. I’d do what he told me to, come back, and get more advice.

A Leap of Faith

By the end of the summer, things were starting to come to a head.

Location Rebel was slowly starting to gain some traction, I was increasingly unhappy in my job, and Ryan was putting the pressure on for me to join him on his round the world trip.

During this time I was making progress on the bucket list:

And that August, as I was walking away from a meet-up Chris was hosting he yelled to me and said:

“Hey, Sean! You better follow through with all of that stuff you said you were going to do because I’d hate to have to rewrite your chapter in my book.”

Note: He really did write about my story in that book. Check out chapter 3 in The Art of Non-Conformity :) (Affiliate Link).

Pressure on.

He knew I wanted to quit. He knew I wanted to sell my car and travel.

Now I just had to find a way to work up the nerve to actually do it.

The markets were still in the dumps at this time, and at one point my boss came up to me and said: “If you can think of any creative ways to save the company money, I’d love to hear them.”

So me being full of ingenuity and quite frankly, thinking I was a genius – I put together a plan to save the company money!

I set up a meeting a few weeks after he said that and gave him a five-page proposal.

The gist of it was that I offered to take a 50% pay cut for 3 months to work remotely from Hawaii on a trial basis.

The move would save the company thousands of dollars in salary and miscellaneous expenses. It’d open us up to a new client base. It’d make the company more secure and allow my bosses to travel more, and it’d give me the little bit of adventure that I needed.

They thought about it for a month, and we had a couple of follow-up meetings to talk about logistics and how it could work.

Finally one day they called me into their office and my boss said:

“Sean, we’ve decided not to accept your proposal…but we will accept this as your resignation.”

I was shocked.

I get creative, and instead of a simple “no, this won’t work” I got the boot at a time where I felt very unprepared to leave.

Over the next week, we continued talking, and I had the opportunity to save my job and stick around.

But at that point, I realized it was now or never. There would never be a perfect time, and I opted to leave.

I had no idea where I’d be leaving, or what would happen, but I was terrified and excited all at the same time.

I was terrified of the uncertainty, as I always had been, but quickly learned that this was something I’d have to embrace if I were to be successful as an entrepreneur.

A Lesson from the Alchemist

“And, when you want something, all the universe conspires in helping you to achieve it.”

– Paulo Coelho (The Alchemist)

I went home on my last day (which didn’t exactly end on good terms) and cried. I had no idea where things were going to go from here, how I was going to pay the bills, and what lay ahead.

But over the next week, I quickly began to realize the truth in that quote from The Alchemist.

The world was conspiring in my favor.

For 6 months I’d been writing on Location Rebel. I’d been proving that I was someone willing to take action, and letting the world know that I was open to opportunities.

Within that first week, two incredible things happened.

The first was Chris offering me a job as his affiliate manager. “This won’t solve all of your money questions, but it’s a start.” He said after I told him about leaving my job.

The second was an email I received after publishing the post “My Last Day.”

It was from a guy named Dan Andrews, who at the time had a startup podcast called the “Lifestyle Business Podcast” with about 6 episodes in the bank.

Here was the email:

At the time, the Tropical MBA was a simple landing page with a video of this guy in the Philippines talking about an experimental internship, where he wanted to bring someone out to Asia, teach them internet marketing, and pay for their basic living expenses ($800/month).

Considering I had no idea what was next in my life, it seemed like the perfect adventure.

About two months later, I’d landed at the Bangkok Airport at 1 am and met this random dude from the internet.

And it ended up being one of the best decisions I’d ever make.

We spent the next 3 weeks traveling through the Thai islands, and I even convinced my buddy Ryan to start his world trip in Asia rather than Central America as he’d planned.

We didn’t get much work done those first few weeks, but we sure did have a hell of a time.

At the end of it, he said you can stay down here in the islands, head back to the Philippines with him, go back to Bangkok – or really go wherever I wanted.

I ended up getting an apartment in Bangkok where I’d live for 7 months and truly become a lifestyle entrepreneur.

And so began over a decade of working remotely, building lifestyle businesses, and helping others do the exact same thing.

Ready to get started? Awesome, me too!