Introduction
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 my personal interests of mine:
- Location Rebel – This 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 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.
Motivation for Remote Work
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.
Carnival Parade
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.
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.”
Coconut
A couple of 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.
Initial Months and Expectations
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 was 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 in 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.
Finding Remote Work Roles
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 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 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. However, I found going to meetups in industries that were complementary 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 who 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.
The Good, Bad and Ugly of Remote Work
What have been the best, good, and worst aspects of remote working for you?
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.
The best aspects have been the stories I’ve been able to create and people I’ve been fortunate enough to meet.
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 the 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.
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, with no green screens or studio, which meant tons of travel. It’s the first major project that Location Rebel produced and it garnered a fair amount of press and helped grow the brand considerably.
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
3. I did a TEDx talk at Carnegie Mellon 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 of 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 afterward, and these three 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.
Twenty minutes later, I overheard one of them saying they were trying to decide if it was 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 was turning, I realized 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
5. My wife also got a two-month sabbatical from work after being at her job for ten 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.
Remote Work Tech Stack
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, and create databases for personal items (food recipes, cocktails, etc), it’s where I dump notes, draft blog posts, and 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, but 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.
Advice for Remote Workers
What is your golden advice to a new remote worker?
Find something you’re passionate about, and then see if there is a way to make a living around it.
When I first started remote working I was doing freelance writing and SEO, and it was a way to make a living while I was building my own brands. But eventually, I started getting paid for doing things I really cared about – travel, golf, and cocktails. If you’re in a job you hate, and you want to work remotely, I’d advise finding something you enjoy and getting started with it on the side. If you don’t have a passion, you can always find a way to make it work, but it will take longer and be more difficult.
Start small, and don’t be afraid to experiment. That’s how I started out, and it’s how I’ve continued to find new ways to make money online. The remote work lifestyle isn’t as difficult as it seems, but it requires a willingness to step outside your comfort zone and take some risks.
Looking Ahead
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 that has allowed me to create businesses around the things I love to do. Travel, golf, cocktails, entrepreneurship. I’m excited to get to spend every day 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, and 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.
How do you expect remote working to evolve in the future?
The future of remote working is incredibly bright. The pandemic accelerated a trend that was already well underway, and more and more companies are seeing that remote work can be just as productive, if not more so, than working in an office.
The shift towards hybrid work models is likely to continue, where employees can work from home part-time and come into the office as needed. This allows companies to save on real estate costs and employees to benefit from a better work-life balance.
Additionally, technology will continue to improve, making remote work even more seamless and efficient. Virtual reality meetings and advanced collaboration tools will further bridge the gap between remote and in-office work.
Overall, remote work is here to stay, and it will only become more integrated into the way we work and live.
Where can we follow you?
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Some of my posts that you may find helpful: