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This is my story published as part of The Remote Working Chronicles


1. Hey, can you please introduce yourself?


My name is Sean Ogle, and I’ve been remote working since the beginning of 2010. For work I run three websites around personal interests of mine:

  • Location Rebel - Is about travel and entrepreneurship. I teach people how to build small businesses that quickly make $3-5k a month that can be run from anywhere. I earn most of my income through my Academy community on this site.
  • Breaking Eighty - This started with a quest to play the top 100 golf courses in the world. I now do golf course and product reviews, and also have a membership site for members of private golf clubs around the world. I monetize Breaking Eighty through display ads, affiliate links, and through a membership community for private golf club members.
  • Slightly Pretentious - I have another (ridiculous) quest to visit the top 100 bars in the world. This site documents it, and shares recipes for some of the best cocktails in the world. I monetize Slightly Pretentious through affiliate links and display ads.

On occasion I also do freelance copywriting and marketing in the golf industry. Portland, Oregon is my home base, and I travel about 4 months out of the year.

2. What motivated you to choose remote working?


It was a total fluke, to be honest. I graduated from college and began working as a financial analyst in July of 2007. Not exactly the best time to be getting into finance.

By February of 2009, the market had collapsed, my bosses were unhappy, our clients were unhappy, and not the least of which, I was unhappy.

I needed a change. I saved up all of my vacation time for the year to go to Rio de Janeiro, Brazil with my best friend Ryan for Carnival. We spent two weeks traveling around, and had some spectacular experiences like hang-gliding over the city, dancing in the Carnival parade, and visiting Iguazu Falls, one of the seven natural wonders of the world.

Carnival Parade
Carnival Parade

On our last day we were sitting on Ipanema Beach drinking out of a coconut, when we said to each other “we should be able to do this whenever we want.”


A couple months later, I started my website Location Rebel, and by the end of the year, I’d left my job, sold my car, and moved to Thailand to have an adventure, learn how to do online marketing, and build my brand.

I expected the trip to last a few months and then I’d have to go back home and get a day job. But the reality is I realized just how attainable remote work really was. I did freelance SEO and freelance writing for a few years while I waited for my websites to take off.

I continued to travel about 4 months out of the year and work wherever I went. I spent the better part of that first year in Thailand, 2 months in Bali the next year, a month in China the next year, and hit dozens of places in between.

3. What were your initial months like? Did it live up to your expectations?


It probably exceeded my expectations. I don’t want to sound like the stereotypical digital nomad backpacker, but living in Bangkok opened up a whole new world to me. I lived in a horrible $200 a month apartment, and I worked out of a co-working space 3 days out of the week. There were a group of two dozen or so expat/digital nomad types that were also there, and simply being around them encouraged me to want to learn more about entrepreneurship, and grow everything I was doing.

During this time I had an apprenticeship with a guy named Dan who was running an experiment called the Tropical MBA. They paid me $800 a month for living expenses, and I spent about 20 hours a week working on their brands while I learned all about online marketing. Twice a month I’d travel either down to the Thai islands, or over to the Philippines to work directly with Dan. It was 50/50 work and play. And it was eye opening to see that when you worked smart you could have success and have fun at the same time. I didn’t mind the rundown apartment, because the whole thing was such an adventure. There wasn’t a single time I walked out my front door, where I didn’t have some interesting or memorable experience.

4. How did you find remote working roles?


There were two primary ways I found remote work roles. The first one is through starting a blog. I began Location Rebel in May of 2009, and I found that with every post I created, it was essentially serving as a resume for myself. As I grew an audience, and began to find my voice with my writing, I’d get a few inquiries a month asking me if I did freelance writing or SEO - as those were topics I talked about a fair amount on the site. I found it’s pretty powerful if you can get people to come to you, rather than you having to always seek it out.

Even once I started my golf brand Breaking Eighty in 2012, I’ve had a handful of people reach out specifically to ask me to do freelance marketing and copywriting in the golf industry, as I had a unique background that’s hard to find (understand golf, travel for golf, and direct response marketing). Two of those in particular turned into six figure clients over their lifespan.

The second thing I did early on was go to in person meetups in complementary industries.
If you go to just say, SEO meetups you’re going to find a lot of people all looking for the same thing: SEO jobs. But I found going to meetups in industries that were complimentary to my own to be even more valuable. For instance, if I went to a web-design meetup, I’d often find a bunch of designers who had clients that wanted to make sure their new sites were optimized for search. But often the designers didn’t have expertise there, so they would hire me to do that side of things.

5. What have been the best, good and worst aspects of remote working for you?


The best aspects have been the stories I’ve been able to create and people. I’ve been fortunate enough to meet.

I mentioned earlier I had a goal of visiting the top 100 bars in the world, and playing the top 100 golf courses in the world.

Cocktail at 28 Hong Kong St
Cocktail at 28 Hong Kong St

Those two things alone have led me to dozens of interesting places I never would have visited otherwise. By working for myself and being able to do it remotely, I’ve also been able to jump at the chance to take last minute trips and work on the road that I simply would never have been able to do were it not for the flexibility this lifestyle has afforded me.

However, it’s not always without its downside. It can definitely get lonely. Often you’ll go days without actually seeing other people in person, which has only been exacerbated by COVID this past year. Working in person with a team is definitely something that I miss doing. As a solo business owner who works remotely, there’s also added stress of being solely responsible for your success. Sure it’s liberating much of the time, but we also all go through phases where we’re less motivated - and if I don't work on the business, no one is going to do that for me. When you don’t have an office to go into, there are distractions everywhere. So if you hit a funk like that, it can often take some time to get out of it - and your work, and psyche can suffer in the process.

6. What tools do you swear by while working remotely?


There are a number of tools that I swear by, but here are a few:

  • Notion - I think of Notion as my extended brain. This is where I do my daily journaling, create databases for personal items (food recipes, cocktails etc), it’s where I dump notes, draft blog posts, write video scripts. It all goes here.
  • Asana - I still prefer Asana to more collaborative task management. So if we’re working on a big product launch, or running our editorial calendar for any of the sites, it’s all done in here.
  • Spotify - Not only do you have just about every song ever at your fingertips, the “Focus” playlists are usually what I listen to while working. Pair this with….
  • Bose QC35ii Headphones - These noise canceling headphones are absolutely amazing, and whenever I put them on it’s like i'm instantly transported into work mode.
  • Dropbox - I find myself using this more and more. Whether it’s to upload video files to my editor, add photos so that I can then edit them on my ipad, or simply store stuff I want to access from multiple devices, this is my go to for cloud storage.
  • Apple Everything - I hate that I’ve become such an Apple fanboy, but I truly am a fan. I have an iPhone 12 Pro, iPad Air with Magic Keyboard, and 15” Macbook Pro, and I use all of those every single day both at home and on the road. Syncing between each device has become so seamless that it’s easy to start on my phone and then pick it up on my iPad or computer later on.

7. Your most exciting/ hilarious experience since you started working remotely.


There are so many of them I wouldn’t even know where to begin.

1) The biggest would probably have to be filming “The Desk” this started as just a random idea of proving you really could work from “anywhere.”

Everything was on location, no greenscreens or special effects:

2) A few years ago I used some American Express points to fly on Singapore Airlines A380 in Suites Class from Singapore to Tokyo, and then Tokyo to Los Angeles. 

After boarding I went to the upper level of the plane to look at the business class cabin, and when walking back down to my seat, the flight attendant said “Excuse me sir, you’re not allowed to be down here, please go back to your seat!”

To which I replied “I’m sorry could you check my ticket and let me know where that is?”

Needless to say, the apologies that came were plentiful after that.

Suites Class
Suites Class

3) I did a TEDx talk at Carnegie Melon University not long after I started working remotely. It was a wild experience to look out at the audience and simply think “every single person in this audience is smarter than me, so how did I get invited up here to talk??”

4) I was working in Monterrey for a couple days, and had the chance to play Pebble Beach for the first time. We had a spectacular round, and as a golfer, this is kind of the holy grail of rounds you can play.

We were in the pub afterwards, and these 3 guys came down and sat next to us. I didn’t pay them any attention, as we were still geeking out over the fact we’d just played Pebble Beach.

20 minutes later I overhear one of them saying they were trying to decide if it’s worth driving up north to play Royal Dornoch on an upcoming Scotland trip.

Royal Dornoch is one of the best golf courses in the world, and it happens to be a personal favorite - so naturally I turned to interrupt them to tell him it’s absolutely worth the trip.

As I’m turning, I realize who it was I was interrupting:

It was Steph Curry and the two owners of the Golden State Warriors. This was their celebratory round of golf after winning the 2015 NBA Championships.

Steph Curry
Steph Curry

5) My wife also got a 2 month sabbatical from work after being at her job for 10 years. So we took a round the world trip for two months with stops in NYC, Munich for Oktoberfest, hiking in the Dolomites, and we even volunteered at a panda reserve in rural China. Being able to work 3-4 hours a day throughout that adventure was a blessing.

Working in Germany
Working in Germany

I could go on, but those are a few highlights that come to mind.

8. What is your golden advice to a new remote worker?


The absolute best advice I can give is to set a schedule and create boundaries. When you work remotely, it becomes easy for your whole life to turn into work. There’s always something you could be or should be doing. And if you’re not careful, you’ll let yourself fall into the trap of working all the time. I’ve found that even though I have the most flexible schedule in the world, the best way to both maintain my sanity, and be productive is to create a schedule just as I would if I weren’t a remote worker.

Put everything in the calendar. Detail when you’re going to work, what you’re going to work on, and where you’re going to do it. If I don’t do that, and I just roll out of bed and say “hmmm, what should I do today” there’s a high likelihood either nothing of substance will get done, or I’ll simply work on the wrong things.

9. How do you see your career shaping up and your goals?


At this point, remote work has given me the time to cultivate a skill set which has allowed me to create businesses around the things I love to do. Travel, golf, cocktails, entrepreneurship. I’m excited to get to spend everyday working on the things I love. And because I do this, I’m constantly meeting new people who share those same interests. What are the odds you sit down at a bar, and you share the exact same hobbies and passions as the person next to you? Probably pretty slim. But when you have a remote business around something you love, everyday people with those same passions are finding you. So success for me is to essentially be able to continue doing exactly what I’m doing right now 5, 10, 20 years from now. Sure aspects will change, new businesses may arise from it, but I just want to be able to help other people get what they want, in the hope that I’ll continue to be able to do the things I want in my life.

10. How do you expect remote working to evolve in the future?


I think we’re on the cusp of the biggest shift we’ve ever seen as it relates to remote work. All of a sudden due to COVID, we’ve seen millions of people working remotely who never thought it would be a possibility for them. Even my wife who works for a large Fortune 100 company had said “I could never do my job remotely.” Their business is doing better than ever not despite working remotely, but in large part because of it.

We’re seeing so many companies thriving with remote employees, where they can be more efficient, have better work life balance, and cost the company far less money than having to always be in the office. So I think we’re going to see a huge shift towards remote work becoming the rule rather than the exception. I also think we’re going to see this trickle all the way down from the largest businesses in the world, to the solopreneur like myself, who all of a sudden realizes that they no longer need to be in say NYC or San Francisco. They can just as easily be anywhere they want, and live a more affordable, and at times more adventurous and interesting life. So I’m excited to see how it evolves in the coming years.

11. Where can we follow you on?


1. Location Rebel
2. Breaking Eighty
3. Slightly Pretentious

1. Twitter
2. Instagram
3. YouTube

Some of my posts that you may find helpful:
1. How to become a freelance writer in 2021
2. 24 Things I Learned from Taking a Two Month Global Sabbatical

P.S: Originally published here


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    Great story, Sean! You mentioned that distractions are everywhere, so how do you stay focused during the day?

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      Thanks Mark, appreciate the comment! There are a few specific things I do:

      1. Be realistic about my goals for the day. When I have a to do list a mile long, it's easy lose focus on the 1-3 things I REALLY need to get done for the day. So I try not to be realistic about what I can actually do during each work day.

      2. I schedule everything in advance. Every Sunday I figure out when my blocks of work are going to be and make a note of what specifically I'm planning to do in each session. This helps minimize the time wasted saying "hmmm, what should I work on now?" I'll then re-evaluate on Weds to adjust as necessary.

      3. Specifically for writing I put on classical music from spotify, noise-canceling headphones and light a candle. Those things basically shift me into writing/work mode.

      Hope that helps!

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        Thanks for sharing! @sean-1458

        I do something similar by planning out my day in the morning and blocking time off my calendar. That way, I can keep myself on track and avoid any major distractions.

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      What's the newest cocktail that you're most excited about these days? (not your favorite, but one that's caught your eye recently).

      And, which bar are you going to visit when the world opens back up?