How to Work Remotely While Having the Adventure of a Lifetime

By Sean Ogle •  Updated: 02/09/15 •  12 min read

Undulating cornfields in Nebraska drove home the reality: I can work from anywhere, even while ticking off a bucket list goal. And with a fresh new year officially here, what better time to talk about all the things you want to accomplish?

Wait a second. Why (oh why), you ask, was Nebraska on my bucket list?

Because just west of Omaha marked halfway for a 4,000 mile bicycle tour this summer. And unlike most people who take months off work to ride across the country, my bank balance increased while we (my wife and I) traveled, all thanks to technology and planning.

Biking in Glacier National Park

Biking in Glacier National Park

Much ink is spilled discussing working remotely. These days, it’s possible pretty much anywhere.

This post is about taking it to the next level: running your own business wherever you choose, making a solid income, and ticking off extended, bucket-list caliber goals at the same time. I’ll cover my business story, the tech tools I use, and the mindset that got me here. I hope to provide a framework to help you tackle your own bucket list goals.

Maybe you want to volunteer for three months in Borneo rescuing orangutans, or traverse the El Camino pilgrimage in Spain. Or there’s that novel in your head seeking to fill a book. It’s all possible, and you don’t have to retire first.

Making It Happen

Even as recently as ten years ago, bicycling from Washington to Maine while managing my business and six full-time employees would have a) sucked or b) been impossible. (Faxing from a bike seat is a difficult task.)

Back then, I’d be a stationary desk jockey working from the same location every day and chucking life goals into the Someday Bin to mold and disappear. Instead, the last 15 months included:

  1. An extended road trip in our campervan to mountain bike the best trails in the western US
  2. An unsupported bicycle tour from Washington to Maine
  3. Big city living in Manhattan (we saw seven Broadway shows!)
  4. A Spanish language immersion course in Tulum, Mexico
  5. Exploring the islands and jungles of Belize (I’m literally writing this swinging in a hammock with a view of the Caribbean)

It wasn’t always this way.

Far from it.

Six years ago, I was chained to a desk as a mechanical engineer, working for The Man. Other than “optional” lunch trainings, I sat through eye-gougingly-boring meetings and was forced to stay late on pointless projects while missing birthday and anniversary dinners. Two of those and I was out of there.

Catalyzed by the book “The Four Hour Work Week,” my vision of earning money changed dramatically. I quit, spent six glorious months cycling and rock climbing, and then threw myself into creating my own business using blog posts just like this one as a guide.

I needed an enterprise solid enough to build a life around. That work also needed to be flexible enough to allow bucket list trips whenever we felt like it. Looking back now, I was searching for that Holy Grail of work: lots of free time and plenty of money.

Reaching this goal was a combination of two things: technology and deliberate action.

My first effort was looking into various combinations of sustainability and technology. Two months later, I shelved that focus and wasted a month on a Multi-Level Marketing company that a business partner talked me into.

Bonus Lesson: Don’t. Ever. Do. MLMs.


Finally, in a method that works for many entrepreneurs, I combined two things I knew well (finance and engineering) and faked *cough* learned all the rest of how to run a business. About a year of intense work later, I could actually pay the mortgage with cash flow instead of savings!

My business, which provides financing for energy-efficiency home upgrades such as heating systems and solar panels, plus mortgages for homes, lies in a field where people wear suits and report to executive suites at 8 a.m. sharp. It’s white-collar, “How-was-Cancun-for-the-long-weekend.” I had other goals.

Initially I worked my butt off. Like a desperate octopus, I grabbed any project – small, tedious, time-sucking. I’d work with any client who needed my services. And then, gradually, I built systems (see below tech tools) and whittled down extraneous BS that didn’t deliver results. My lean, profitable company now affords me the luxury to work as little as a few hours per week while adventuring, or more when I choose.

Enough fanfare: here’s how I run my business to allow me to pursue bucket list goals while still working anywhere, whether it’s a mountain pass in Montana or a beach in Thailand. My base tech is simple – slim laptop and iPhone – so it comes down to how I use the technology paired with online services, many that you probably know of but may not use.

The Technology

1) WiFi Hotspot

First, and most importantly: a wifi hotspot – two ways to go here.

You can run directly from your phone’s hotspot, or buy something like the Verizon MiFi Jetpack 4620. DON’T spend $200 on it, or sign up for a contract – it’s super cheap on Ebay or Amazon. #1 thing to free yourself from a desk: WIFI.

Luckily, this is plentiful in almost all foreign countries. If you are traveling overseas, each country differs dramatically in the cost of data, so search for specific info if you need lots of mobile data.

2) Google apps

Forget Microsoft Exchange. Go with Google Apps – I power the back-end to my email, calendar, documents, and chat with Google Apps.

It’s cheap, ties most daily functions together seamlessly, and I’d be a wandering hobo in the desert without it. (As compared to a hobo anywhere I choose. Mountain biking in the desert sand sucks.)

3) Dropbox

Dropbox – this is my favorite file sharing service. It automatically keeps everything synced to both computers and to the web, plus backs it up. It also avoids having to email secure info or big attachments.

4) Echosign

Echosign – many people assume legal documents need to be signed in person. Nope! Almost everything, thanks to President Clinton back in the late 90s, can actually be signed electronically.

Echosign delivers clearly labeled electronic documents that are easily signed. I L-O-V-E electronic signatures for avoiding missed signatures, hungry fax machines eating client documents, and other technical difficulties.

Another good option for signing contracts: Our Deal. There are many others as well.

5) Efax

Efax – an old standby at this point. Instead of sending/receiving faxes, it’s just delivered to your email inbox. I use this rarely, but when needed, it’s a lifesaver. works great.

6) YouMail

YouMail – this is a great, free visual voicemail service that allows custom voicemails (a fun, or annoying, way to let your friends and colleagues know you care) and also lets you receive voicemails as emailed MP3s, which is great for someone like me who filters, labels and saves all emails for reference later.

7) Boomerang for Gmail

Boomerang for Gmail – an awesome productivity tool that allows you to schedule when you send an emails, or set up reminders related to an individual email. The best thing about this? You won’t get into the instant-messenger-style email chats with people, but can still clear out your inbox by hitting “send in 2 hours” immediately after receiving the email.

8) Toggl

Toggl – time tracking software. For years, I’ve tracked all my work time down to the minute as a way to maximize productivity. I got the idea from Jim Collins, the author of “Good To Great,” a seminal business book. I recommend picking three categories to keep it simple (I chose clients, business development, and admin).

My work hours decreased dramatically as I nixed the stuff that was wasting my time, not producing revenue, or creating satisfaction for me. Classic Pareto simplification. Can’t recommend this highly enough.

9) Skype

Skype – Pretty much the defacto online phone and chat system. It’s perfect for international clients or for when you’re overseas yourself. It seems most podcast interviews are now conducted using Skype these days.

I run this via wifi and my outgoing number shows my cell phone number. Who cares if you’re beachside in Mexico or in your office? Same same, not different. It’s cheap, effective and doesn’t even (usually) have a time lag these days.

Note: There are dozens of free calling services. Skype is simply my favorite.

10) – a great tool to run tutorials remotely. I use this to train employees on the tools mentioned above.

11) Evernote + GTD

Evernote – I use this to keep track of everything in my life.

Can’t recommend it enough. Paired with “Getting Things Done (GTD),” the method I use is called “The Secret Weapon.” It easily lets me dial in work, travel, writing, and photography projects, plus reference materials from all the reading I do.

See this post for some Evernote Hacks: How to Use IFTTT to Automate Your Business

The Mindset

Technology doesn’t solve a damn thing if you don’t apply some mental juice to why you’re doing a task.

Put another way, being efficient gets you nowhere if you didn’t effectively choose the project. For instance, I could have figured out efficient ways to attend final document signings with my clients. Instead I tested not attending them at all, which worked fine. A magic gift to myself of 5-10 hours per week (!) freed up simply by asking the right question. That’s a day per week mountain biking instead of sitting in a conference room.

In the end, it’s about having a choice about how you spend your time. Whether it’s time off or space to focus on bigger, higher value-added efforts for your business, the below items put you in command and allow you to be in control, not just be a harried self-employed person. Ask yourself this: are you running your business or is your business running you?

Here are some of the things I’ve learned that made me more effective.

1) Be willing to let some clients go

It took awhile, and still is painful every time (progressively less though), but you can’t work with everyone. And you don’t want to.

For my work, some clients want to sit down and meet in person. I have all the online tools to make this unnecessary in a purely practical sense, yet completely understand when this is a request. It’s one of those trade-offs. Lose some revenue, gain some inspiration and happiness points working remotely. (GDP ain’t the only measure of one’s success in life.) For me, flexibility trumps gross revenue.

2) Don’t do it all yourself

Hire people, even when you don’t think you can afford it! Trust that your freed-up time will yield benefits. Hiring my first employee was one of the scariest things I’ve ever done, and one of the best. (HOW to hire amazing people is another subject entirely! I’ve been blessed with fantastic people joining my team.)

Don’t want to bring someone on payroll? No worries. I’ve outsourced via and; both are great for temporary workers to save you time or crank out a project you can’t do yourself. (Kevin Kelly, founder of Wired Magazine, says his advice to himself at 20 would be to hire out projects whenever possible.)

3) Challenge yourself to see how little you can be involved with your company

Initially, it was all me. Then I cranked hard on the 80/20 Pareto lever using #1 above.

Over the last year, my goal was Pareto squared: 4% of the hours while still making 64% of the revenue compared to doing all the work myself.

I challenge you to do the same.

At 30 hours a week, it’s hard to find the mind space to really create. At 2 hours a week, time in spades floods in and allows you to create, connect and envision your next challenge or contribution to the world.

And that’s not to say you can’t work more when you want to – it’s all about creating choices for yourself. Even hedge fund managers with billions in their funds use the Pareto principle. It’s all about being more effective with your time.

4) Have confidence that following your inner compass results in everything working out, even if it doesn’t seem that way at the time.

This is probably the most important. Ping mentors and close friends for their opinions, but trust your gut. Change leads to dislocation, which is always uncomfortable. And that’s where the good stuff is.

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Wrapping It Up

For me, the simple lens through which to view work is this: does it contribute to living the life I seek? There are periods where busy work and boring projects are required, but focus on a long-term goal, while appreciating what you’re building at the moment, and power forward.

In the end, ask yourself whether you’re building an intentional life that allows you to pursue goals that make your heart sing. If you’re doing that, life is good.

Here’s to a 2015 filled with deliberate work and awesome bucket list adventures. I’ll see you out there!

Dakota is an adventurer, business owner, writer and photographer. When not on the road, he enjoys exploring the fantastic city of Portland, Oregon and digging into various sustainability projects. Find more on his blog,

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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14 comments on "How to Work Remotely While Having the Adventure of a Lifetime"

  1. Ragnar says:

    Wow Dakota, sounds like you’re on a great journey. I decided to ‘take the plunge’ but ended up settling on the ‘halfway point’ of teaching English out of lack of momentum on many fronts.

    Thanks for the tips, I’m back at it again, but I’m definitely not efficient enough. Implementing some of what you’ve mentioned here could be the missing piece.

    1. Dakota says:

      I’ve found that simple, short trials of tech tools is a good way to test whether it works. Even if it doesn’t, the process of evaluating your processes can how you approach certain aspects of your work. Hope some of these things can become permanent fixtures in your life – they have certainly helped me out a lot.

  2. Mathias says:

    Awesome article! Just the motivational boost I needed to stay on track with my travel/working goals.

    Love the efficiency tools, I definitely need to work a lot on that area!

  3. Sara Stein says:

    Motivation factor is huge with any self employed professional. It can be so hard to work from home and find the time that isn’t devoted to anything else to get the work done, and still have time to go where you want and see what you want. The key to all of that I’m sure is in the details but for a lot of us, I’m sure we’d like to see that happen before we’re 80 years old and wondering where the time went.

  4. Jack says:

    Great post, particularly the reference to the Pareto principle! Particularly liked the idea of ‘squaring’ it – continuously boiling down to the most effective action you could be taking, and dedicating all your time to it. With sufficient awareness, this even takes care of all the *minor* things you could do as well; if you really do need to keep track on top of them, they will eventually become part of the 20% of things you could do to get 80% of the results!

    This sort of metacognition (not just acting, but *thinking about* the way you act) is a core focus of my own website. Hope it follows a similar trajectory to yours!

    1. Dakota says:

      Glad you liked it! Taking it to the next level with Pareto squared made me think outside the typical box of running a business or being self-employed. It really freed me up for greater adventure and other pursuits. Good luck with your project! Looks like a good one.

  5. Great article! I enjoyed the combination of hearing about your story, coupled with very actionable advice. Chuckled to myself when I read about MLM – I hear you on that, never again!

    1. Dakota says:

      Yeah man, MLMs=bad news. Anything that promises get-rich-quickly results is (in my experience) something to avoid at all costs. Even the overnight successes are never such a thing – lots of hard work behind any success.

  6. Eric Rondeau says:

    Sorry you feel so negative about MLM. It has been the best thing for me, my family and friends and 1000’s of people I helped for over 20 years. Not all MLM companies are bad. “Did you ever have a bad meal or service in a restaurant? Sure you have…. Does that stop you from eating some place else?” I’m excited for you and wish you the best.

  7. Kenny Ruby says:

    I found this article rather inspiring. I’m still stuck on finding a business I could run. I finally got my website set up, but not sure what it’s really going to be about or what I could offer that would bring in enough income to support a travelling lifestyle. Ideally having more time to do the things I want to do would be a much more fulfilling, enjoyable life. Still looking for that spark to get there.

    1. Dakota says:

      Hi Kenny,

      I’d say the best thing to do is look at the interests and current skills you have, things that light you up, and what the world needs. The intersection of those three things is a great place to start. As they say, do SOMEthing…anything…to get momentum going.

      Sean’s Location Rebel course is a great way to do some fact finding. I also recommend Michael over at as a way to figure out a business that can support you, and doing so before you make the leap to self-employed.

      Good luck!

      1. Kenny Ruby says:

        Great thanks! Some of the skills I feel I’m good at are writing, things like love poetry, funny stories from my observations of people, especially when I’m on vacation. I do love to write!

        Some of my interests are basketball, music, and I’m a HUGE Disney fan! So I’m not sure where I go with things like that… :/

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