Several years ago, Sean Ogle spent a significant portion of his life sitting at a desk in Portland, Oregon, wearing a suit and tie, and crunching numbers as a financial analyst.

The job itself wasn't horrible. Sean had a nice view of the city from his office window, and people were often impressed when they heard his job title; however, he felt unfulfilled. So he quit.

Less than nine months later, he was on his way to Thailand to begin living the life he had always dreamed of.

Sean tells us about how difficult it was to leave his 9-5 job, shares the importance of creating a bucket list, and even reveals his most embarrassing story.

Today's 20 questions is with someone who truly is "living the dream."

20 questions with Sean Ogle

1 - How would you describe yourself in one sentence?

Sean - Someone who likes a good adventure, enjoys helping people, and doesn’t take life too seriously.

2 - For those who aren't familiar with Location Rebel, what is it all about?

Sean - Location Rebel and Location Rebel Academy are about helping people build small businesses that allow them to travel and do more of the stuff that makes them happy in life.

3 - Clearly your decision to leave a cushy job paid off; however, how difficult was that initial decision to actually quit?

Sean - Oh it was incredibly difficult. It took over a year to work up the nerve to start pushing things in that direction. I felt a sense of obligation to my boss, which I think was the hardest thing to get over.

4 - How did you get "The Desk" to all of those remote locations for the video shoot?

Sean - With great difficulty. In the snow, we were about ½ mile from where we parked, so we had to do 3 trips out to get all of the gear there - all through pretty deep snow.

We also got a lot of weird looks unloading the desk and carrying it around some of the spots - like the cliff over the ocean and the waterfall shot.

5 - On top of many things, you're clearly a successful blogger. What advice would you give to someone who is looking to start his/her own blog?

Sean - Two things:

1 - Figure out what makes you different. There are millions of blogs out there now, and chances are the niche you want to enter has thousands of people doing something similar. What sets you apart? Why would someone pay attention to you over someone else? Figure out what that is and latch onto it.

2 - Be consistent. That’s it. Put in at least a little bit of work, every single day, and eventually you’ll see success.

6 - In Step 1 of your three-step process, you mention several skills, such as: copywriting, search engine optimization, creating a website with WordPress, social media for business, fundamentals of design and online marketing essentials. If you had to choose one of these as the most critical skill to learn, which would you choose? Why?

Sean - Copywriting. If you can be persuasive with your words, you’ll never have trouble making money. Whether it’s through selling your own products, affiliate products, or simply being able to write a cover letter and resume that gets attention.

Copywriting is one the most important skills not just in business, but in life.

7 - Which item on your bucket list do you believe will be most difficult to achieve?

Sean - Right now flying in a Virgin Galactic Spaceship is looking pretty difficult, but I’ve got plenty of pretty cool things to keep me busy until that materializes :)

8 - I understand you began creating your bucket list in 2009. Would you recommend that others also create bucket lists of their own? Why?

Sean - 100% yes.

Until you write down your goals, they often don’t become real. They become that thing you’ll do “someday” - that you never actually do. By creating the list, and finding some accountability for it (for me it was publishing it on the site), you’ll begin to do things you never thought would actually happen.

Going to Cuba and smoking a cigar was one of those things for me.

9 - Number 89 on your bucket list suggests you created your own drink called "The Ogle." What's in it?

Sean - Dolin Dry Vermouth, orange zest infused maple syrup, maraska, and Ardbeg scotch.

But there are a couple variations now that are a little easier to make :)

10 - Who is your favorite band/musician?

Sean - That’s a really tough question, but my stock answer is blues guitarist Joe Bonamassa.

11 - What is your favorite song?

Sean - Man, that changes daily. But right this second it’s probably Beat the Machine by Quaker City Night Hawks.

12 - What's your biggest pet peeve?

Sean - When people who I’m doing a Skype call with or podcast with don’t specify it’s video beforehand - then turn on their video and expect me to do the same, ha.

13 - Where is one place that you've not yet traveled, that is on the top of your list to visit?

Sean - Croatia. Definitely Croatia.

14 - Who inspires you?

Sean - I think you can gain inspiration from everyone depending on how you frame it. But my wife, Tate, inspires me to be a better person every day.

15 - What's your greatest fear?

Sean - Man, tough questions! These days it’s the thought of not being able to continue with the lifestyle I’ve had over the past 7 years. But that’s also where a lot of my motivation to work harder comes from as well.

16 - Who is your favorite author?

Sean - I could name a couple dozen non-fiction writers, but I really enjoy Clive Cussler adventure novels when I need an escape.

17 - What's your favorite quote?

Sean - "Comparison is the thief of joy."

Or, "There are only seven days in a week and someday isn’t one of them." I still believe I coined that term in a blog post back in 2009. Now it’s been attributed to everyone from Kate Spade to Shaw haha.

18 - You get to have dinner with three people, living or dead. Who are you eating with?

Sean - Jimi Hendrix, Casey Neistat, Tiger Woods.

19 - What's your most embarrassing moment?

Sean - I rapped a rewritten version of The Fresh Prince of Bel Air theme song in front of 3,000 people on stage at a conference once. That was up there.

20 - What is one thing very few people know about you?

Sean - I can ride a six foot tall unicycle.

Thanks, Sean, for taking time out of your busy schedule to answer these 20 questions!

As always, thanks to all of you for taking the time to read.

Who would you like to see me throw 20 questions at? Drop me a comment below and I'll work on setting up the interview.

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Previous "20 questions" interviews: