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!
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.
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.
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.
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.
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.
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.
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:
- A beginner's guide to working full-time while cruising
- How to build a remote team that won't trip your business up