business

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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:

 

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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.