remote work

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8 Books and podcasts that will help you build your remote business

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It's taken me a long time to admit that I'm a read-about-it-first learner. I've always admired tactile learners, who learn by just jumping into things and figuring them out as they go. I, on the other hand, find that stressful and decidedly un-fun. When I want to learn something completely foreign to me, it comforts me to hear stories about how other people have done the thing I want to do. I'll read every book, article and listen to every story about the thing that interests me until I feel ready to make an educated move. Colleagues and friends often comment on how decisive I am to take action. In reality, I take quick action on new projects because I've secretly spent weeks or months researching the best way to move forward.  

Are you like me? If you are, I've pulled together the list of books, articles and podcasts that I used to teach myself how to logistically convert my skills into a business, manage finances and otherwise figure out how to pay for my adventuring.

What do you love that I'm missing here? I'm always looking for new things to dig into! 

Books

I'm fully aware that starting this list off with Tim Ferriss' classic is a cliche, and since I hate being a cliche, I waited YEARS to read this book. Don't be like me. If nothing else, swallow whole the message of working smarter, not harder, and start thining about ways to outsource your life. The mental calculus of how much time I was spending on small tasks that were keeping me from doing big things vs. paying someone else to do them for me was a game-changer and allowed me to build up my personal projects and business while maintaining a day job. 

Berkun's breakdown of his year working at the distributed tech company, Wordpress, is an excellent primer for remote work technologies and structures, especially if you already or want to work closely with other team members. His breakdown of holocratic work structures and rules for asynchronous work management are thought provoking and worth a read, even if you're an IRL manager. This book is best for people who have to keep working and managing people on the road, but definitely a peek in to the future of work for anyone who's curious. 

Part memoir, part Pixar business manual, I found this book an essential guide to building a business where employees have autonomy and a sense of self-fulfillment that will allow bosses to step back and be more hands off. 

Podcasts

There's a podcast for literally every interest. I find podcasts about business-building, marketing and detailed descriptions of how people financially have made big things happen totally engrossing. I am, however, allergic to the sound of loud bros and gushing women, who oddly make up a large contingent of this kind of podcast. There isn't much middle ground between "get off your ass" and "reach your dreams!" so what you listen to comes down to your personal tolerance for those kinds of diatribes. 

Pat Flynn's Smart Passive Income

Ultimately, the goal of working while traveling is always in some part to increase passive income, so that you can spend more time doing what you want... even if that's working on something else. Pat Flynn has a weird, nichy empire built on the topic, and I found his podcasts to be interesting, well-edited and without the hyperbolic broeyness of many of his counterparts. He has a blog as well, but I preferred to listen to his interviews with business owners. Start with his three-part intro series and then go from there -- the people he interviews all basically have taken his advice and adapted it to the things that they're good at. I love the frank money discussions here, which really break down where to spend your time per dollar.  

Sail Loot

Specific to sailing in content, but helpful for working while adventuring in general, Sail Loot interviews cruisers on the gory financial details of what it took to ship off with cash in the bank. Part financial podcast, part gossip fest with bloggers whom many cruisers may recognize, the podcast is useful in the way that it shows a hugely wide variety of ways people have gotten to their lives aboard. For some people it took a year, for others it took 20. I give a lot of credit to podcast host, Teddy, who's trying to set sail himself, and thusly asks crazy specific financial questions of all his guests. 

The Sailing Podcast

Not a financial blog, per se, The Sailing Podcast is basically an open space for hosts David and Carina to have long, winding conversation with people who have sailed the world. By default, those conversations often devolve into "but how can you afford it" territory. It's a fun listen for the wild yarns. 

Keep Your Daydream

In this sometimes winding podcast, adventurers of all kinds are interviewed about their crazy life stories leaving behind 9-5 jobs and how they were able to afford doing so. I appreciate the broad array of guests but take note that the podcast tends to be heavy on the inspirational takeaways. 

Startup

Perhaps the most well-known of the trying-to-make-it podcast set, Startup chronicles a journalist's effort to break into the startup tech industry. While not directly applicable to funding a way to escape, it's a solid introduction into the startup universe if you've never worked in it. 

 

Interested in reading more? While it's not about money or business per se, I also found that a book on decluttering helped me rearrange my financial goals.

You can also read the first and second part in this series about working remotely:

 

How to build a remote team that won't trip your business up.

Last week I published a beginner's guide to working while cruising, detailing how I structure my  days as a remote business owner. One unsurprising piece of feedback I got was that many people have tried to hire remote workers or people who travel while working, and have found them to be less reliable than traditional workers.

If this rings true to you, I feel your pain.

I've run several remote businesses and between them I've culled through thousands of cold applications for remote positions. It took lots of trial and error to pick the right people to work in a distributed or remote environment. It also takes a lot of work to be a good manager to remote employees. With that said, here are my major guiding principles for building a remote team of people who travel. 

Hire remotely (or in other time zones) only for jobs that can be done asynchronously. 

The nitty gritty of this depends on your industry, but I've found in editorial that short turnaround work like breaking news, social media for breaking news and coordinating with teams that need to work together closely on tight deadlines (sales pitches) needed to stay on a US timezone to work well. However, remote workers can be a boon if you need to expand your workday reach. I've seen great success in hiring people from Europe to break stories earlier than East Coasters would be able to. 

Build a job application that tests responsiveness as part of the interview process. 

I've hired roughly 100 people in the last 5 years and for the last few positions the ratio was about 2000 applicants to every open position. Eek!

I had to remake how I hired and it's now super effective.

First, determine the four to five qualities you need in the position and then develop 2 levels of application questions.

The first level should be for ability to handle details and responsiveness -- my favorite tricks are to ask them to deliver their application back by a certain time, add a specific word in their cover letter and to have them send something in PDF format. That rules out about 80 percent of applicants and you can auto-search those responses in applications (Protip: in greenhouse.io you can bulk search applications.)

Essentially, you shouldn't have to look at your fist round applications to weed out the worst of the bunch. Use the second round app to ask questions and give challenges that illuminate their skill set.

Read those applications and take notes on where they're weak, then use your actual interview only to clarify what you've already learned and drill down on weaknesses. I find in those interviews that asking them questions about real experiences rather than hypothetical situations gives you a better idea of what kind of person they are. For example, "tell me about a time you made a mistake and how you fixed it" can really tell you a lot about a person. 

This application process can work for any kind of employee, but it's especially important for remote workers, who need to be extra detail-oriented, resourceful and tech-savvy, as well as responsive. 

In your interviews, ask for details of travel and routine.

People who are good at this aren't good by chance. They, like me, have really strong plans around getting internet, building structure into their days, and they think A LOT about how to do their jobs well. I think it's totally fair to ask that stuff as part of the interview process. I can talk all day about our wifi and cell boosting rigs! If they're new travelers, I'm more likely to pass on hiring because they haven't figured their you-know-what out yet.

Never hire someone for their first job as a remote worker.

They haven't been broken in yet into work norms in general. I totally believe in giving people first chances, but new workers need to be socialized before they're set free! (And sorry, someone else can do that.)

The more senior the position, the better a full-time traveler will work for you.

The longer someone has done this and the more they know about their area of expertise, the more likely they are to be able to handle both at the same time.

When you're working with new people, give them a really clear set of guidelines for cultural norms and behavior for remote work. 

Go over a one-sheet on your employee's first day with a clear set of consequences for what happens if they break these norms. This sounds like kindergarten, but it actually is quite relieving to remote workers to have guidelines to follow and they usually follow them well. Remember that they're in their own kind of vacuum from your business, and following rules allows them to have a stronger sense of job security.

Never let people *start* traveling at the same time they start working for you. 

I had a two-month ban on traveling for new workers at the last couple of roles I ran, and it worked really well for those people wanted to use their remote work to travel. This harkens back to the advice I gave on my last post, which is to give yourself time to figure out your travel and build a business. The people who work for you should do the same.

Traveling while working means slow travel.

Some may quibble with this, but in my experience, you need to build in lots of time for working and if you don't, you'll always run into problems. If people have ambitious travel plans while working, I get a little suspicious and ask for more details. 

Let your like recognize like.

There's a certain vibe that really good remote-working travelers exude and I can smell it for miles (insert dirty backpacker joke here.) You probably know what I'm talking about, and don't ignore it! 

It takes years and commitment to get a good groove and a lot of people, often really excellent workers in in-office environments, never get there. Remote business management and working isn't for everyone, but for the people it works for, you can expect more loyal employees, a stronger work ethic and often a discounted cost of work. Providing your employees and contractors freedom in exchange for them earning your trust is a foundation of building a great business, and remote working can truly accelerate that. 

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We're leaving New York for a life of remote work and sailing adventures.

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Throughout the spring, you may have seen a few sprigs of big changes aboard The Scallywag. We hauled the boat out for upgrades, quit our jobs, we went notably quiet on our blog. 

And now, in the throes of early summer, our plan is ready to meet the full light of day: We’re casting off the lines to become full-time sailors. 

While our decision may seem out of the blue, the preparation and intention behind it have taken months of deliberate work. More importantly, it’s taken a hundred conversations between Jon and myself about what we love to do, and what we want our lives to look like now and as we grow older. 

Before moving to New York two years ago, Jon and I worked remotely for five years. Sometimes running a business together, sometimes working separately. This wasn’t gig economy work, but rather traditional companies that were trying a new format of working. And it worked. I completely and emotionally bought into this idea and lifestyle. It felt natural to us to pace our days and weeks around the work we needed to do and the life we wanted to live rather than a more traditional schedule. 

While working this way, we lived by the flexibility to travel while getting things done. We rarely ever took vacations, but instead set up in coffee shops while we were on the move, sometimes so flawlessly that the only way our coworkers would know was by the change in background when we video chatted. 

Without jobs that tied us to a place, we kept having the same conversation: where did we want to live, and what kind of people would that make us? Were we LA people? San Francisco people? Would we fit in better on the East Coast or somewhere in South America? As all our friends started to settle down, finding the answer seemed more urgent, and that’s when we bought a boat. We had a home that could take us anywhere. 

Fast forward three years and we found ourselves living in New York, an amazing city where we could be anything, but only in one place. As we hit the two-year mark of residency, we were once again itching for change and we took interviews for jobs we could have only imagined being recruited for. But each time, we came home to each other and asked ourselves… then what? We have that awesome job and... then what? 

The paradox of choice is a weird, wonderful and very “now” problem to have. 

As a woman who wants to have kids someday, I found this indecision particularly challenging. Smarter women than I have told me the key to great work-life balance is to lock down baller job a couple of years before having kids so that you have deeper job security for your maternity leave. But a really big part of my heart wanted to build a flexible career that kids could be warmly welcomed into, rather than interrupt. I wanted to start that career before it was 9-months-urgent and continue it after, on my own time. 

So the answer, for us, continues to be to pursue careers that don’t have geographic limits. It’s never been a better time to go that route — most places finally have the infrastructure to support digital nomadism and the speed with which things are changing is breathtaking. Five years ago, I got my first smartphone — in Iraq. During a recent trip to Myanmar, we learned that though the internet essentially didn’t exist there year ago, there are now more people connected via smartphones than there are houses wired to an electrical grid. 

And on a recent vacation to the French Caribbean, we found pockets of internet where fellow boaters said nothing had existed just months ago. 

The ability to work anywhere, and work well, is here — even if it takes extra time and inconvenience to figure it out. 

This is the freedom that today’s technology provides, and yet to embrace it can still make you an implausible hire and a weirdo. 

So, we’re ready to be weirdos. 

We’ve launched businesses (his, mine) that allow us to do the work we love while we travel, with the assumption that there will be frequent trips to metro hubs to see our clients face to face. We’ve outfitted our boat with solar panels, a wind generator, cell and wifi boosters, we’ve upped our data across multiple networks. And we’ve hungrily read the stories of people who have gone before us to figure out just how much we can pull off without risking our sanity and quality of work. 

Our plan is to sail back to California, the long way. First north, perhaps as far as Nova Scotia, then south to the Caribbean and through the Panama Canal. We don’t have a set itinerary or time span, though we think it’ll take about a year. We’re excited to explore parts of this continent and its surrounding isles we’ve never seen before, to take it slow and to make lots of mistakes as full-time cruisers. 

(Our first, for example, was to set a hard date for leaving, which we promptly blew after having a camera crew see us off. ::Facepalm::)

That’s our plan. Subject to lots and lots of changes. By this time next week, we should be somewhere in the Long Island Sound, with many more stories to come. 

 

How traveling solo helped this woman find love and a beautiful guesthouse business in Peru.

As part of an ongoing series, Sail Me Om presents the stories and practical advice of people who have made daring life choices about how they live and work. If you know of an adventurer whose story should be told, tell us about them.  

Megan Youngmee is a talented graphic designer who worked full-time and freelance for more than 150 startups and Fortune 500s in Los Angeles. Three years ago, she ended a 2.5 year relationship, sold her furniture, cashed in her retirement fund and left on a trip of a lifetime. Eventually, Megan landed -- married, a mom to one and a guesthouse proprietor -- in the Sacred Valley in Peru. 

This is Megan's story, in her own words. 

The spirit quest

For quite a few years I had felt unsettled. The further I moved into my career, the more I realized the job, titles and money weren't actually going to make me happy. Finally, at 29, I decided to do a bit of travel and soul searching because after having everything I thought I wanted and worked for, I had never felt more disconnected, stressed and empty. 

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The spirit quest started with a cross-country road trip with just my dog, some clothes and my computer. I connected with friends across the country and spent a month in my home state of Pennsylvania. On the very first night back in my hometown, I reconnected with my middle school crush, after 18 years apart. It was the beginning of my trip, but by its end, Eric would be my husband and the father of our 4-month-old. 

I spent that time at home reconnecting with him, friends and family, and planning a six-month international sabbatical. I looked at this trip as a time to ask myself who I was and what I wanted, discover the meaning of home and connect with my roots. The trip led me to Peru, Bolivia, Brazil, and the UK. It took me finally to South Korea, where I was born and hadn't been back in the 28 years since my adoption. 

Overall, I spent one year traveling internationally and all over the country. 

I spent a month in Beopjusa Temple in the Songnisan mountains, chanting with monks under the stars, and connecting with my roots. There were so many strong Korean women who felt like adoptive mothers. They taught me about Buddhism, motherhood, gentleness, self-love and the history and culture of my land. 

I saw the mountain ranges of Huaraz, Salar de Uyuni in Bolivia, Foz de Iguaçu, Brazil and the epic landscapes and ruins of Peru. 

I was alone for all but three weeks, which was a great time to reflect, spend time in meditation, and really ask myself what I wanted every day.  

During the trip I had never felt so alive and healthy. I also was doing freelance work on the road and realized that I could make money anywhere and be home anywhere. I was writing business plans, doing design, writing, learning the ukelele and spending lots of time in nature.  Plant medicine ceremonies also were part of giving me a clearer sense of who I was and where I wanted to be. 

The decision to move to Peru

The final decision to really make this lifestyle a reality happened when I returned to The States. I had left my life for a year and came back to a few amazing job offers.

Eric proposed, and he, like me, felt that his life was in transition.

Then, he asked me, point blank, "What do you really want?" 

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I had spent the majority of my travels in Peru where I had fallen in love with people, language, delicious organic food, fresh air and glacier drinking water. 

"Honestly, I keep thinking about Peru,” I told him.

He said simply, “let's get our tickets.” 

I had secretly hoped he'd say that. But I was also terrified he hadn’t urged me to take the jobs and money in NYC or LA. 

We decided that we would take a chance and try traveling for two years. If we didn’t find something stable in that time, we could always move back and jump back into the grind. 

We found an insanely cheap one-way ticket and in one week we had a job offer to work at a hostel in Peru. The tourist season was coming and we built our wedding around our life plans. We planned our wedding and got married in three weeks, and then, just one week later, we found ourselves in Peru. 

In hindsight, I think that if we overthought the decision, we might never have never made the move. Something about stepping out into the abyss with a partner and doing it without too much rumination over the "what ifs" made the decision easier. 

Into the inn business

First, we started in Cusco, working at a hostel. When I was traveling, I noticed there weren't many places that didn't cater to just gap-year kids or folks in their golden retirement years. There was a huge price and age divide.  

We had friends in the Sacred Valley who were renting a house in the hopes of making it an inn and it just wasn’t working. Eric and I somehow both had a sense that we were home when we were there. We visited every couple months, and then found out they were about to leave the house and the business. We saw an opportunity.

We moved in to see how it felt to live with lots of people. And we needed to get an idea of how much work we'd have to put into the property to be able to start filling rooms. 

After a couple months, we signed a lease and started doing major construction on the house. We tore up old carpet, refinished the hardwood floors, upgraded the plumbing, changed out lighting fixtures, we spackled, rebuilt broken walls and painted.

When creating this place, we wanted to make something that was homey — a place that had the benefits of community but was quiet and off the main tourist path. It has an open vibe that a traveler can make of what they want — some hike, while others explore the local culture. Some take time to learn the language, many people find what makes them happy and healthy.

Even though it was irrational to think people would come to a tiny town in the middle of the Andes, we also had the sense of ”If you build it they will come.” And people have found us. In a less than year and a half we've had over 300 people from 30 countries, of all different ages.

Most people find us by word of mouth. Travelers find us through Trip Advisor, Facebook and Airbnb, but most discover the house from a suggestion from a friend. 

The majority of our travelers are people in transition, looking to spend some down time doing some soul-searching, working on a passion project like writing a book, creating art, or getting in shape and reflecting on what they want to make of their life. Most friends stay for over a month and end up feeling like family.

4 ways Megan’s days have changed:

I tend to flow with where the day goes. 

I've never known a life where we weren't forced to live by the clock. Time doesn't exist the same way down here. We still work hard, cook, clean, take reservations, communicate with future guests, are present for current guests, design logos and websites, and build furniture. But nothing is forced. 

I find myself much more focused when it is time to write or design. 

People connect on a much deeper level when they aren't behind the glow of a screen. We don't have internet in the house right now. Then I go to use internet with a list of things I need to accomplish. 

I get to be a momma. 

I'm momma to travelers and my amazing son. In the hectic life of LA living, I don't know how i would have found the presence of mind to be here for others the way I can be now. I found the joy of caretaking, nurturing, listening and seeing people through great triumphs or challenges. I am so stinking grateful for not having to worry about maternity leave or the crushing costs of healthcare with having my little baby. 

I get to be partners with my partner. 

We get a lot of time to work together, work things out, learn and grow without constant distractions, stresses and "real" jobs.

Second-guessing is part of the job

I have never been particularly spiritual, but stepping out into the abyss builds your faith in yourself and the universe in a way I have never known. There were moments where we were down to our last penny but felt somewhere deep down, we should keep going. Many times we had no idea how we would make things work and then someone would come in and donate money, give gifts or bring in friends to cover the rent.  

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I’m reminded of a part in the I Ching about how to make progress. It says that a wind that constantly shifts directions just stirs things up. A wind that moves in a slow constant direction shapes the world. Sometimes we'd think of changing directions, about giving up or starting something new. But by slowly building, we have created a beautiful house full of the most amazing people I've ever met.  

I also think of an expression that is used a lot by the indigenous people here: "poco a poco" or little by little. The best businesses I've seen are built brick by brick with a solid foundation. They create a great service at a reasonable price that people are willing to pay because of what they receive in return.

We've learned not to become too attached to anything but simply go with the flow and take the path of least resistance.  What used to sound like bohemian cliches have become very real to us in our simple life. We learn lessons, we make decisions, we shift slowly and purposely.

I've learned to truly listen to my inner voice of what I want and need and to honor it, rather than "shoulding" myself. Based on paper, taking a high-paying, high-powered job made much more sense, but I’ve discovered that creating my life with intention and thoughtfulness brings the rewards of being part of something i believe in. It's really the best gift I've ever given to myself.

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Need To Know

If you visit one place, Megan recommends Iguazu Falls, Brazil.

Follow Tres Osos' gorgeous Instagram @casatresosos and Twitter @tresososperu.

It has a Facebook page you should follow too. 

Also, learn more about Megan Youngmee's creative work.