1. How did you start working remotely?
This was something I’ve wanted to do for ages. The 4 Hour Workweek gave me the travel/work for yourself bug when I first read it back in 2007, and I started leveraging what I learned in there in 2009 to sort of test the waters.
I’ve worked remotely off and on since 2009, but left a startup job and went full time remote in August 2017 and haven’t gone back to an office since 🙂
My wife is a writer, I’m a consultant and a writer, we both work from our laptops. My kid is 8, and lives off his iPad, does all his homeschool/unschool from there, we don’t have a lot of stuff, and we’re not super close to family…there just wasn’t a good reason not to travel and work remotely, so here we are.
2. What do you think are the main advantages of remote work?
There are so many! Flexibility, being able to work whenever and wherever I feel productive. Not having to worry about vacation days, sick days, commuting, office distractions, pointless meetings, etc. Being able to spend more time doing fun things with my wife and son, not having to spend some of the best years of my life trapped in an office.
There are of course huge productivity advantages. I get as much work done working 10 hours a week as I ever did working 40+ in an office, because I have no distractions, and I’m highly motivated to be efficient since the faster I work, the more time I have to play!
I love being able to live and work from anywhere I can find an internet connection, and I can’t think of a better way to live than this.
3. Do you think there are disadvantages or that you’re missing something by working remotely?
Not at all. I’m an introvert, so remote work is pretty much my happy place. Technology makes it incredibly easy to do everything I need to do from my phone and laptop. If I feel like I need camaraderie, I play online games with friends from all over the world, do stuff with my wife and son, go to networking events, conferences, chat with folks on Twitter, etc.
4. From which cities or countries have you worked since you have become remote?
Long list! Playa Ocotal, Costa Rica; Rome, Florence and Venice, Italy; Seattle, WA; Vancouver, Canada; Miami, Florida; Barcelona and Madrid, Spain; Paris, France; Sofia, Bulgaria; Bucharest, Romania; Amsterdam, Netherlands; Zagreb, Croatia. I should hit another 4-5 cities at least in 2019.
My favorite city so far has been Barcelona, though Amsterdam was a close second, and Florence is probably a close third.
5. From which type of place do you prefer to work?
Home, always. I hate the distraction of working around other people, so I work from home. Also, I like working in my pajamas, or boxers, which still doesn’t fly at offices or coworking spaces or coffee shops 😉
6. Which places would you like to travel to while working remotely?
I have a really long list of places to visit still…Hungary, Czechia, Morocco, Germany, Poland, Turkey, Greece, Cyprus, England, Scotland, Ireland…I’ve barely scratched the surface of Europe (the whole Schengen thing makes it pretty hard for a US citizen to see everything I want to see in my time-frame). I also want to travel around South America at some point, and maybe if I can make myself brave the insanely long flight, Australia and New Zealand.
7. What would you say to the companies that don’t believe in hiring employees who work remotely?
They’re insane. If you only hire in a specific city, your talent pool is limited to those who live there or whom you can attract there…which means there’s competition, which raises prices. You can get amazing talent, anywhere in the world, probably for less than what a local employee would cost, with less overhead, fewer taxes…the reasons are numerous.
Think about this: if you’re in the San Francisco area, with the insane cost of living, you have to pay insane salaries to local employees, radically increasing your overhead. Or, you can hire a world class dev team in Tallinn, Estonia, for a fraction of the cost, and get everything you need. You could literally hire an entire dev team in Tallinn for the cost of a single senior developer in Silicon Valley…why wouldn’t you do that?
Also, it makes your employees happier and more productive. Having employees who love their job and have amazing work-life balance is awesome. Less turnover, better work, more loyalty. I could go on.
8. Which tools do you use to work remotely?
I use dozens of tools for various purposes, but for communicating remotely, mostly:
- Uber Conference
- and of course email.
Things like PayPal, Stripe and Transferwise are great for payments, Pipedrive for managing sales, and HelloSign is brilliant for getting contracts signed easily.
9. How do you manage your business and taxes as a remote working professional?
I have a law firm who manages my business registration, which is in a very tax favorable offshore country (I don’t live or work in the US, so this made the most sense), and I use a tax firm that specializes in digital nomads/expats for the tax side of things. I think both combined end up costing me less than $1,000 USD per year to take all of that off my plate, which is totally worth it.
As a US citizen, we’re normally taxed on any worldwide income, regardless of where we live or work or where the money is earned…unless we spend 330+ days of the year outside the US, in which case we have the Foreign Earned Income Exclusion (FEIE). With the FEIE, you can deduct up to $104,000 per adult in income from taxation, plus another 30% for housing if you rent. For a lot of US expats and digital nomads who make decent money, the tax savings of living outside the US can fund a good chunk of your trip 🙂
The same goes for most countries; as long as you spend less than 183 days a year in any one country, and don’t earn your money from that country while living in that country, it’s generally not taxable.
There’s some nuance of course, so folks should consult a tax professional…but it’s worth digging into. If you want to go down a fun rabbit hole, dig into Perpetual Travel (PT)/Flag Theory.
10. What advice would you give to people looking to work remotely and companies making the remote switch?
DO IT DO IT DO IT!!! Seriously, I can’t think of a single valid reason not to work remotely, whether as an employee or self-employed, the benefits vastly outweigh any potential negatives. There are tons of books to help wrap your head around it, such as ReWork or It Doesn’t Have To Be Crazy At Work, both by the founders of Basecamp, who run a hugely successful mostly remote company which is a shining example of how to do it.