End of Summer Book Review

One of the great things about no longer having a company or a farm to run is that I’ve been reading a new book every week or two. I’ll save the fiction reviews for Goodreads, but a few of them are worth writing about here.

  1. Lean UX: Designing Great Products With Agile Teams

I’ve worked at giant companies where everything was so hierarchical and top-down that if the employees wanted to get anything cross-functional done, they basically had to bribe co-workers from other departments with favors or after-work drinks. I have also worked at a tiny start-up where everyone worked on everything, all ideas were considered, and we moved extremely fast. I knew we used tools like Trello and Asana and Google Docs, but I found that I had trouble explaining why we did it that way. When people threw terms around like Waterfall or Agile, I Googled them, but until I read this book, I never really understood the history behind these vastly different methodologies. When I mentioned this gap in my understanding, a friend suggested I check out the Agile Manifesto, the Scrum Guide, and read Lean UX, and I’m really glad I did.

The book borrows heavily from existing Scrum concepts, but expands on it to ensure that research and design (and legal and whoever is needed to ensure the thing works) have a voice within that ritualized framework. There are a lot of great examples of how to incorporate diverse thought into the ideation process, and how to ensure that the desires of the end user (and not just developer bias) are honored in the final product. Best of all, there is no dogma. They recognize that some organizations are hierarchical, and maybe it’s ok to be inefficient in certain contexts. The point is not to adhere to some perfect process, it’s producing great products quickly, and realistically.

As an intuitive autodidact, I’m all for faking things until you find yourself making things, but there comes a time to backfill whatever you figured out on your own with some book learning. When I have cluttered, unorganized thoughts, and I know everything seems to work, but I don’t really know why, I absolutely love it when a book comes along with a framework that allows me to tidy all those thoughts up, declutter my brain, and store them away. Lean UX is like the Marie Kondo of software development. It’s a framework for working with a team, keeping just the bare bones of what’s needed, and chucking all the unnecessary documentation and bureaucracy. To borrow from Marie, it brings me joy to know that the next time someone tells me about the pain of their waterfall process, I can simply hand them my copy of Lean UX.  P.S. Go read this too.

2.   The Challenger Sale: Taking Control of the Customer Conversation

One of the hardest things about stepping up from my back-office analyst roles to client-facing executive roles was learning to sell. My method of selling was to learn everything I could about a problem, then walk into a conference room and drop a knowledge bomb on my prospective client. I’d deliver a fully-fleshed out analysis of what they were doing well, what they were doing wrong, and a plan to fix it, then shake hands and walk away. I think this approach terrified my co-workers, who were afraid I’d offend the client. We were all a little surprised to discover that my approach worked about 75% of the time. But why?

In my mind, sales people are supposed to be annoyingly nice, calling all the time, bothering people, never taking no for an answer. I, on the other hand, encouraged clients to tell me no. I considered myself the anti-sales guy. This dissonance of disliking sales yet having to sell, and yet somehow having it work out… it was a problem for me. I couldn’t wrap my head around what was happening. So, I decided to face things head on and be the best darn sales guy I could be. I made an effort to be friendly and bought lunches and emailed interesting articles…and I sold nothing. What was I doing wrong?

I asked my friend Alex Boyd, CEO of RevenueZen.com, to suggest some books that would help me learn how to finally be one of those nice but annoying sales people. Instead, he told me to read The Challenger Sale. What I found was not a how-to guide to bug people, but hard data that helped me understand why my no-nonsense style had worked, while my overly-friendly style had failed.

The premise of The Challenger Sale, to paraphrase aggressively, is that the best sales people tend to do the hard work of becoming experts before they try to sell anything, then fundamentally challenge the way the client is doing business, reframing the way their clients think about their business. Before pitching anything related to what you have for sale, you need to make sure the client understands the solution – not your solution. It turns out I had meandered accidentally into doing the right thing, but I needed a book like this to give me a framework in which to think about it and help me understand why being direct worked, and why my attempts to “act like a sales person” generally failed. Right or wrong way, I have a lot more empathy for sales people these days, and no longer experience that dissonance when it’s time for me to sell.

3.  Animal, Vegetable, Miracle: A Year of Food Life

OK, so I know the last two were business books, and this is a book about what Barbara Kingsolver ate for a year. I promise, there’s a reason for this.

This book follows the Kingsolver family as they grow or locally source all their food for a year on their small Appalachian farm, preaching about the absurdity of flying bananas 6000 miles, or the even more absurd practice of trucking lettuce 3000 miles when there’s perfectly good lettuce available at a farm down the road, or in your own backyard.

The good: I love the insistence on thinking about petroleum as an input when growing food, both when used on the field as a fertilizer or pesticide and as gas in transportation. I love the idea of eating food that’s been grown locally without pesticides. I love the idea of eating heirloom varietals of plants that were bred for taste rather than ease of transport. I agree that processed foods are a huge part of the obesity epidemic and think we should shift our diets towards high quality foods. I agree that we, as a society, need a much better understanding of where the ingredients in our food are coming from, even if it’s just to become better shoppers.

The bad: The book really downplays just how much work this family of four had to put in to extract roughly half of their yearly calories from the animals and plants they cared for. The work of farming was presented as a benefit: it’s like meditation, yoga, and you can cancel your gym membership for the price of a shovel! Nope. I had a farm. I grew my own food. It was really, really hard, and the reason I stopped going to the gym was because my joints hurt too much after all that repetitive physical labor.

The frustrating: There is a puritanical insistence on eating extremely seasonally throughout the book. Mason jars and freezers are offered as the only acceptable way to consume warm-weather plants during cold-weather months. While I get that seasonality is important to think about when picking up a tub of strawberries in January at a grocery store in Minneapolis, real farmers use all sorts of greenhouse-esque contraptions to grow plants out of season, and are rewarded for doing so. It’s very normal to extend the growing season in cold climates with hoop houses, shield the sun in hot climates with screens, use hydroponics in dry environments…etc. If the Kingsolvers had employed a little technology, they might have been able to grow their own indoor oranges and bananas, and they definitely could have been eating fresh greens in February, the lack of which was much lamented throughout the book.

Now, why am I writing about this at all? I can’t stop thinking about the idea of employing tech in urban agriculture. If 2 out of 3 Americans live in cities, and we all agree that eating locally sourced food makes sense, why aren’t we growing food for cities in or immediately around them? Is it really easier to fly food across the world than to figure out how to grow it on your roof? I am fascinated by startups in this space, and have been checking out a bunch of them. I think whoever figures out how to grow high-quality veggies on a large scale, year-round, in a place like Chicago, using winter sunlight (or other low-energy methods), inside dense, automated growing facilities, is going to revolutionize how we eat, and where a big chunk of our food comes from. I think it’s very telling that Jeff Bezos, the proud new owner of Whole Foods, has invested in Plenty.ag, and that IronOx.com came out of Y Combinator. This is very exciting stuff, and I think scaled urban agriculture is an industry that is just getting started.


That was fast

Less than a year after we launched EmotionReader, another company, Kairos, came along and bought it. I am continually amazed by the whiplash pace that tech moves at. Startup life truly is a bit like riding a tiger. It demands your full attention, and there is room for little else once the ride starts.

The last couple of months have been a bit odd, as I was still publicly the COO of a company, yet anyone paying attention to my Instagram account knew full-well that I had sold my farm in Portland and was living the high life in France, Spain, and British Columbia. I knew the company sale was happening, but until the sale went through, I couldn’t announce anything. So, I just mysteriously retired at 40, explaining little to anyone for months.

I first realized that the news was public when I suddenly got a wave of financial advisors trying to add me on LinkedIn. I did a quick search, and sure enough, TechCrunch had broken the news. These enterprising folks were hoping to take advantage of my newfound riches, and all rushed to get to me first. I politely declined, but as a marketer, did appreciate the effort.

I now find myself in an interesting spot. I went from owning a farm and part of a company, totally asset heavy, to being nearly free of possessions. Just about the only thing I actually own now is a new (used) surf van (it’s a minivan, I’m not that cool). I’m living out of Airbnbs, and working out of coffee shops. Making this massive transition, nearly overnight, was breathtaking, but I did it all for a specific, strategic reason.

Today, I’m in Santa Cruz, riding my bike from coffee shop to cafe, stalking respecting the privacy of my favorite author, Jonathan Franzen, visiting the outsite.co co-working house, hanging with friends eager to convince me to be their neighbor, and looking at rentals to see how far my buck would go here. I love that I get to try on Santa Cruz like a pair of pants, seeing how it fits, seeing if I look different in the mirror. Tomorrow I’ll be in Sonoma. All the while, I’m scanning for the next opportunity.

As much as I look forward to whatever the next version of my life looks like, and have trouble imagining being a nomad forever, I love these interludes. I know full-well that too many options lead to analysis paralysis, but as I ping-pong around the universe this summer, I am careful to appreciate such infinite options. I do not rush through the afternoons spent napping in the surf van with a view of the waves and the setting sun. I do this because I know I’m resting up for a reason.

The next tiger is right around the corner.



It may seem like a silly thing to go all the way to Costa Rica to pull out your computer and work, but after my first experience with Nomad House, I’m hooked. I’ve spent a lot of time working on the road, from Chiang Mai to the south of France. Friends and relatives assume I’m ruining a perfectly good vacation by working from these locations, but the reality is that without work I get bored. Maybe it’s just me, but I can only sip so many pina coladas on the beach before I get antsy and start looking for problems to solve.
2017-01-22 16.27.19

When I work from the road, I’m intensely focused. I tend to stay in a place for at least a week or two, and after I figure out where the grocery store is and how to get around, there’s a lot of down time. It’s easy to carve out five or six hours of time each day with almost no distractions. In fact, when traveling alone, I often wished for more distraction. My main complaint on solo trips was that it was hard to meet interesting people.

This is why my most recent trip was so great! Nomad House set up a trip to Costa Rica, where thirteen people came together to work and hang out in paradise. From day one we were riffing on startup ideas, and it was clear that this was not your normal group of tourists. It was completely normal for people to go for a run or do some yoga in the morning, then work for a few hours in the air-conditioned co-working space, before surfing or grabbing a few beers to watch the sun set over the ocean.

Think about the best conference you’ve ever been to–the kind where you left with a pocket full of business cards, inspired to take on new challenges. Did you actually follow up with all those people? Have you ever talked to them again? Now think about what it would have been like to spend a couple weeks with those people, talking shop over dinner, taking time to get to know each other. It’s a totally different and far more meaningful experience.

Back on my farm in Portland, it’s hard not to eye the pasture and wonder how many yurts I could fit out there, as I scheme about the best ways to blanket the property with fast wifi.

Coding Bootcamp: The Best Terrible Decision

When yet another friend asked me “is coding bootcamp worth it,” wondering whether they should learn to code too, I found myself giving a very long and convoluted answer that I realized would probably be better off written down. I know that before I signed up for bootcamp, I had trouble finding a straight answer myself. So, my answer is: Yes, but…

1. Upon graduating, be prepared to be a specialist of limited use or a master of little

Building a decent software app is kind of like building a house. The electrician knows very little about installing plumbing or sewage. The roofer probably can’t lay the foundation. A software app combines lots of independent skills. As a developer, you have to make a choice whether to be a decent plumber right away (focus on one thing) or be a general contractor, and know a little bit about everything, but not really be expert at anything for a very long time.

2. It takes a huge amount of time

This may seem laughably naive to long-time software developers, but I don’t think regular people realize the sheer volume of information a person needs to absorb in order to be even a mediocre developer. To be a decent coder, you need to learn three to six code languages and be able to read and write them with some fluency. Code languages are just as hard to learn as, say, a European language. If you wanted to learn to speak French, German, Spanish, Italian, Greek, and Portuguese all at once, would you try to learn them all in four very intense months? No? Because that is essentially what I tried to do.

Too many screens!
Too many screens!

My bootcamp was four months, or sixteen weeks long, with five hour classes every weeknight (fridays too). To keep up with the pace of the class, I had to read coding books, do online coding exercises, and write code for my class projects outside of class. When you add in all that study/coding time outside of class, it added up to about fifty hour weeks spent coding. In other words, it’s about as difficult as a mentally demanding full-time job.

I was freelancing and working part-time, and I was completely brain-fried and had no social life during those four months. I felt incredibly sorry for my fellow students who had full-time jobs on top of school. I watched them put on weight and grow increasingly haggard by month four. We all agreed we were seeing ones and zeros in our dreams.

3. It’s expensive

I’ve heard people say that coding bootcamp is a waste of money since you can teach yourself everything online for free. The thing is, even in coding bootcamp you’re still teaching yourself to code, and you’re still using those free resources. The difference is that in bootcamp you have an experienced developer guiding you and a structure that limits the complexity and chaos of coding. Realistically, a coding bootcamp is just going to take months 6-18 of your coding education and compress them into months 6-10. What is the price for 8 months of your life? That’s really up to you. I spent $3,400 on tuition, and that seemed like a bargain to me. If you have more time than money, by all means, figure it out on your own.

4. The hard way is probably the only way

Zed Shaw’s “Learn Python the Hard Way” is generally considered the best course for those trying to teach themselves Python. He intentionally makes the course difficult. When a piece of code doesn’t work, his answer is “Google it”. Realistically, learning to code is as much about rote memory as it is about training yourself to be patient and resilient. You have to first spend lots of time practicing writing code so that you can memorize and internalize the patterns. However, that’s the easy part. The hard part is figuring out what to do when you think you’ve done everything right and your code still won’t run correctly. It’s easy to copy and paste someone else’s code. It’s hard to know why it isn’t working in the context of your project.

I heartily recommend going all-in. The more time you can invest, the better. I spent 50 hours per week, but I recommend spending 80 hours per week the first few weeks you’re learning. Mix it up, and read books on coding, then go to online practice sites like Codecademy.org or Treehouse.com, then write some actual code. Every program does something different, so when you’re done with one, write another one. Tear apart an old program you wrote and write it better. Like playing the violin, the more you practice, the more you’ll internalize the skill. If you want to learn quickly, the only way to do so is to devote yourself.

5. Pick your language carefully

Back in high school I decided to learn Italian. In college, I took Japanese. Not to knock these languages, but I use them so rarely I’ve forgotten most of what I learned. In retrospect, I really should have learned a practical language I can use all the time like Spanish. Picking a coding language works similarly.

Before you pick a flavor, know that everyone needs to learn HTML and CSS. Before you even think about enrolling in a bootcamp, teach yourself these languages. Once you can construct a static HTML page writing raw HTML and CSS code and get it up on a server, you’re ready to pick a path.

Python, JavaScript, and Ruby are currently the most common open-source options offered by bootcamps, but they are by no means the only languages out there. You can write software using any of these three languages, but committing to one is sort of like choosing Apple vs. Microsoft. They can work in parallel, but for the most part are incompatible, and the software written for one won’t work on the other. As owners of Microsoft Phone users know well, none of those awesome apps that work great on iPhones have been written for their Windows phone. Code generally works the same way. Personally, I deal with a lot of data, and much smarter people than me have written great libraries for handling data in Python. I decided to code primarily in Python to take advantage of libraries like iPython and Pandas, which do complex math for me. It’s sort of like plugging in a calculator app into your raw code.

You will need to figure out what you want to do with the software you write, and which language will best support that task. If your primary goal is to make a lot of money right away, you could learn the languages that high-salary finance companies use, like Scala, Java, and .NET. If, on the other hand, you want to work at a hipster start-up, learn Ruby, Python, or C++. It’s not a bad idea to look at the job postings for the companies you want to work for first to see what they’re asking for.

Once you pick a language, then you have to pick a version of that language. New versions will be relevant longer, have cleaner code and do some cool new stuff, but old versions are more stable and have more libraries built for them. Every choice is a trade-off, and nothing will work 100% of the time.

6. Get used to frustration

One of the most profound things my teacher told our class is that we weren’t really learning to code, we were learning to debug. As normal consumers, even tech power-users, we’re used to stuff just working. Restarting a computer once a month to update some software seems like a huge hassle. Well, guess what, programming is about 10,000,000x more annoying. The code you write that works great locally won’t run on the server. Why? Who knows. And to find out, you’ll need to individually tweak each of the fifty things that could be causing a glitch until you figure out the cause, and when you finally fix that thing, your fix will probably break something else. That is coding.

Have you ever punched a hole in a wall, thrown your phone across the room, or (egads) sent a computer tumbling? If so, coding is not for you. But if you’re still with me, you must be a mellow individual that can handle frustration without smashing a screen. You have the calm demeanor to simply copy error messages, paste them into google, and spend thirty minutes reading five different and contradictory stackoverflow.com suggestions, trying three to find that the first doesn’t work with one of the drivers your app has running in the background and produces new errors, the second actually does the wrong thing, while the third sort of fixes your problem, but forces you to update some other seemingly unrelated part of your code for it to work.

When I was learning to use git and github, I was stoked to find out about the ability to clone projects in github and add them to my own. Similar to code libraries, you can just grab someone else’s code and incorporate it into whatever you’re working on. Sounds easy, right? So after weeks of work, customizing the clone with all my own code, I decided I would create a git repository and upload my project back to github, so other people could see my work. But, when I tried, there was a weird error telling me I had duplicate repositories. I hopped on stackoverflow, followed the directions I found, and… erased all my work. Yes, while attempting to back up my project, I erased it, all by following directions. It turns out, when you clone code from github, it automatically creates an invisible repository. This is just a thing you’re supposed to know, and since I didn’t know I had created a repository at the time I downloaded the clone, I didn’t understand that by resetting my repository, I would wipe out all changes made over the weeks since I added it. Want to know what I did? I sat down, and calmly spent the next three days recoding all my work from memory. And THAT is what coding is like.

7. Get used to very little help

I had a boss who once described his management style as “handing you a fortune cookie, then leaving you alone in the woods.” It turns out this was good training for coding. Most tutorials tend to fall into one of two types: those meant for week 1 beginners that are far too simplistic to be of much use, or those that are written by experts for other experts. These experts have been coding for decades and will intentionally leave out steps they find to be obvious (you will probably not find the missing steps so obvious). This is actually a big reason why I signed up for bootcamp, and why I recommend it. It is incredibly helpful to have someone around to fill in all those missing pieces for you and help guide you during that intermediary phase.

Much to my surprise, living a mostly digital life, coding books (made from trees!) are actually extremely helpful once you’re done being a beginner and get to the novice/intermediary phase. They provide a coherent level of structure that is hard to find online, and are good for reference when you forget something specific. However, they still assume a basic level of know-how that will constantly trip up the novice developer.

8. Bootcamp is just the beginning

Coding languages are constantly changing and evolving. Code you wrote a few years ago may not be supported in another few years. The code language you learn first may become out-dated or go out of fashion. A new code language or library may make a lot of the old code language obsolete. For example, JQuery is just a better, more condensed way of writing certain kinds of JavaScript, Rails does something similar for Ruby.

The point I’m trying to make is that bootcamp is a great way to kickstart a career change, and really a life change, but your first job out of school is probably going to be entry level, because your skills will only be entry level. If you make less than $50k now, you’ll probably be able to make that much or more with an entry-level software job after going through a bootcamp program. However, expecting to be a full-fledged software developer making six figures and signing bonuses after a four month program is sort of like expecting to be a successful novelist after a summer creative writing program.

9. Learn to learn

The most important thing bootcamp taught me was how to teach myself. Learning to debug, see patterns in my mistakes, and knowing where to go for answers was absolutely worth the time, money, and effort. I am continuing my education by taking classes through Udacity, Coursera, Codecademy, Udemy and whatever other books or online tutorials make sense. I also continue to meet with my bootcamp teacher for mentoring. I’m still doing difficult stuff, but the pace of my learning is continually speeding up. While it may take a novice coder months to learn a language, an experienced coder can probably pick it up in a few days (or so I’ve been told). This virtuous cycle will continue the longer you code, but you have to keep at it for years.

10. Always be building

The best way to learn, and to keep learning, is to keep building. Pick a project and go for it. Start small with HTML and CSS. Tear it down and rebuild it better. Add something dynamic using JQuery or JavaScript. Make your CSS responsive for mobile devices. After a few months, your old code will look as dated and silly to you as the bad poetry you wrote in high school. Rewrite it. Learn backend languages and try incorporating dynamic forms and data. Then tear that down and make it better. Pick a backend framework and drop your old code into that…

You get the idea. Now go code something.  And remember…

The best time to plant a tree is 30 years ago. The second best time to plant a tree is today.

The Tiny Farm Experiment


Seen in Portland
Seen in Portland

In May of 2015, I bought a small (tiny, some would say) 3-acre horse property on the edge of Portland, Oregon. We’re bordered on two sides by butte cliffs, in one of the few agrarian valleys inside the city limits that remain untouched by development. Many friends have wondered why a city kid like me would do such an odd thing. I’ve heard assumptions that my motives are naiveutopian, or even dystopian. But, I can assure you the scheme that led me to owning adorable animals and digging in the dirt are as cut-throat and capitalist as any Manhattanite’s designs on a rent-controlled pre-war apartment.

It started with a question: how can I afford to fail, to make stuff that nobody wants to buy? Taking a quick look at my finances, housing stood out as my biggest expense. That led to another question: what if I can live in a house that pays for itself? It occurred to me that if I could live in a home that is also a business, I could take the time to go back to school, learn new skills, build software, write books, and maybe even start a company…in other words, I’d be free to fail. By eliminating the neccessity of working to pay the mortgate or rent, I’d be able to work on whatever I want, or not work at all, right? That was my theory, at least.

I started looking at apartment buildings with an eye on becoming a landlord, but the buildings I could afford in the places I wanted to live tended to have an intimidating number of problems with them. Next, I looked at big rural farms, the kinds of places with orchards and fields full of crops, but upon crunching the numbers, it became obvious pretty quickly that low-margin crops require a huge amount of work for very little profit, and (at least in Oregon) zoning laws make it very difficult to use the land for anything more profitable than farming or ranching. I took it for granted that if we bought 30 acres, we could host weddings or rent out a cabin on AirBnB, but zoning laws in most Oregon counties forbid them. You know those tiny houses that get so many likes on Facebook? Turns out they’re illegal in most places. Finally, we looked at small farms closer to urban centers. Zoning near Portland is much friendlier to AirBnB operations, anything you grow can be sold directly to consumers at relatively high prices, and getting people to come to your property for events gets easier the closer you are to the city. Looking at profit margin, life-style, and initial affordability, a small urban farm made a lot of sense.

Farm Boss
The cure for computer work: a chainsaw

Now, I have to admit that there is big upfront cost, and no guarantee that I’ll recoup them. I’m building out a guest cottage, planting trees, painting the barn, building fences, building a chicken coop, buying animals, etc… And, I’m working harder than ever doing a lot of this upfront work myself. It is physically demanding work, shoveling, hauling heavy things, covered in dirt, and most nights I fall asleep exhausted. However, I have plenty of time for freelance work, and (if all goes as planned) it will only be a few more months before the income the farm generates will pay the mortgage (while feeding us like kings).

Once I get to that tipping point where my home becomes a profitable business, I won’t really need a job; I can finally hop off the tread-mill of having to work a full-time job just to pay the mortgage. That said, I’ve never worked harder in my life, and don’t see the work slowing down any time soon. Instead of mindlessly surfing Facebook to while away a slow afternoon in my cubicle, the moment my computer work is done I’m out in my wood shop. When everything I do is an investment in myself, it’s easy to work all day and not feel burnt out. Early morning emails and conference calls mean happy East Coast clients for my business. Working in the mid-day sun out in the pasture means increased equity and income for my farm. Working late nights writing tricky code is an investment in my own skills and the IP of my company. I feel like I used to be a consumer, but have turned into a producer, and it feels good.

Ironically, by giving myself the space and permission to fail, I finally feel like I’m succeeding.

How I traveled around the world for six months (and made money doing it)

My wife and I packed, leaving behind the apartment and furniture we sold
My wife and I packed, leaving behind the apartment and furniture we sold

My wife and I knew we wanted to travel, and with about $10,000 in the honeyfund account we set up in lieu of a wedding registry, we had enough for a pretty epic honeymoon. I, however, like to stretch the limits of possiblity. Why have an epic two-week trip when we could stretch it out into an even more epic six month trip? All we had to do, I reasoned, was spend our money wisely and work a little while on the road.

Now, just for perspective, $5,000 per person (what we had in the honeyfund) is about what a normal American might spend for a nice trip to one or two European countries, including airfare, hotel, ground transport, entertainment, drinks, and meals in restaurants for two weeks. We managed to travel to dozens of cities in seventeen countries across four continents and went all the way around the globe. Here’s how.

1. Control your expenses

My two biggest expenses were my apartment and my car. So, I got rid of them. I sold the car and house. The reason to sell your things is not to use that money for travel (put it in a savings account and don’t touch it!), but to stop having to spend money on a life at home you’re no longer living. Without a mortgage, utility bills, car payment, or car insurance, my monthly bills dropped from thousands to hundreds, which freed up a lot of money to travel with. We put all our stuff that we didn’t sell in a month-to-month storage warehouse, which only cost $120/month, and I paid the bill each month via PayPal from wherever I was at the time. If you want to do a short trip, try renting out your car and/or home (just be really careful you don’t invalidate your auto insurance or lease in the process). If you rent your home or lease your car, you probably can’t legally sub-let them, which is why I highly recommend that you…

2. Travel longer

Getting rid of or renting out your home is more hassle than it’s worth for a short trip, but is worth it if you want to travel for many months or even years. If you do a longer trip, you only pay for the bed you’re sleeping in, and not the bed you left behind at home. By paying for one bed to sleep in instead of two, you avoid doubling your daily expenses.

If you’re working part time and earning income while you travel, that’s time you won’t be able to spend out and about in your new surroundings. If you’re working half the time, spend two or three times as long in each place as you normally would.

3. Maximize your income

By working while you travel, you can live on your earnings instead of your savings, which is definitely preferable. Arranging a job you can do while traveling is tricky, however. Getting a job with a foreign company will just tie you down all over again, assuming you can even get a work visa and decent wage.

To keep working while you travel, it’s best if you can keep a job you already have. This takes some time to set up and a little luck, but it’s doable. If you are able to do your job remotely (online or over the phone) from your home while living in the US, there’s no compelling reason why you can’t just keep doing that job from a different country. The only hard part is getting whoever is paying you to believe this. If you are able to get set up with some sort of online business before you go, that would definitely be the best way to do it. If your current job can’t be done remotely, try getting a part-time job as a virtual assistant either on your own or through a company like Zirtual.com a few months before you leave, then keep it while you travel. Just be prepared to work US hours when overseas. This might mean working in the middle of the night, however, the upside of working nights is that you have your days free to explore whatever country you happen to be in.

If you happen to be a computer programmer, you can find all sorts of interesting jobs that can be done from anywhere. remoteok.io is a good source, and is curated by Pieter Levels, the guy who runs nomadlist.com, which is another good resource for globe trotting techies.

My office in Bangkok, Thailand, working well into the night for my US client that was 11 hours behind
My office in Bangkok, Thailand, working well into the night for my US client who was 11 hours behind

I essentially out-sourced a job to myself. My company needed to hire someone with very specific computer and research skills but was having trouble finding that person, so I quit my full-time job as a VP managing staff, then in the same meeting asked my boss to hire me back as a freelancer doing this other job that could be done entirely online and over the phone. This was a big gamble, since they could have said no, and they could have ended my freelance employment at any time while I was traveling. I assumed the arrangement would last about three months and budgeted for that, but it lasted eight months before they found a full-time person to take over the job. In other words, I was employed the entire time I was traveling, which meant I never had to dip into savings and could pay “rent” (a.k.a. hotel and airbnb) and “car payments” (a.k.a. planes/trains/rental cars) out of my monthly income, just like I would any normal month living at home.

4. Spend money upfront to make working on the road easy

It is amazingly easy to work from anywhere in the world if your job is done on a computer, but you need to invest in a flexible mobile hardware and software set-up that is fully backed up to the cloud should your gear get lost or stolen. I used a MacBook Air (running Windows as a virtual PC with VMWare, Adobe Acrobat Pro to “sign and scan” documents digitally, and Dropbox for full back-ups) and an unlocked iPhone.

My office in Dubrovnic Croatia
My office in Dubrovnic Croatia

I got a global data plan from AT&T, which allowed me to answer calls, tether my computer, or quickly respond to emails anywhere in the world. To avoid burning through too much cellular data, I would do most of my backups over hotel wifi and would often use Skype for calls or video chats and screen-sharing. It was necessary to have the option to tether my computer to my phone and use cellular data, or use wifi, since cellular data gets expensive but wifi isn’t always available. With both options available, it was truly rare that I had trouble getting online as long as I stayed in decent sized cities. Just like in the US, however, once you get out into the countryside, finding a cell signal gets a lot harder. When choosing between that mountaintop Tuscan villa or a Parisian loft, exchange a few emails with your hosts first to see what the cellular phone, cellular data, and wifi situation is. I learned the hard way that many hotels “with wifi” only had it in the lobby. AirBnB hosts, on the other hand, tended to have great wifi right in the apartment.

I found the global data plans offered by US carriers to be underpowered and/or expensive, and any normal user will burn through their allotment of data very quickly. So, before I left, I unlocked my iPhone, which meant I could swap out my AT&T SIM card and get on a network anywhere in the world. When I landed in a country, I would use my global data plan for the first day (mostly for Google Maps, Facebook check-ins, and translation apps), but then quickly find a local cell phone store and get a new SIM card. Deals will vary by country and carrier, but I would usually pre-pay for 5 to 50 gigs of data, whatever about $50 would buy me. Once you have your local data plan, you can forward your US cell number to a Skype number, and answer or make calls on the mobile Skype app.

5. Make your bank accounts globally accessible

First, establish a “home” setup that works for paper mail. It’s important to make sure you set up and maintain a US-based home address while you’re traveling, particularly if you are working on the road. Ironically, you can’t get a global cell phone plan, global bank account, or travel insurance without a home address. You can pick a mail service, or a relative’s house, but you have to have a US address to send paper bills and checks to (and so the state and federal governments get their cut of your taxes since you’re still a US-based worker, remember?). Make sure someone you trust is there to open your mail in case something important shows up. If you can, arrange for pay via direct deposit before you leave the states.

Next, make sure you can access your cash wherever you are in the world. I opted for a Schwab Checking account, which allows you to get cash out with no foreign fees or ATM fees, anywhere in the world, and got a credit card with no foreign transaction fees, and pin and chip functionality. Make sure to call all your banks and credit card companies the first of every month to let them know when and where you will be traveling over the next month so they don’t shut down your accounts because of a fake fraud trigger. It’s also a good idea to use one card for your recurring bill payments, and a different card for everyday purchases. That way if you lose your everyday card and need a replacement, you won’t have to update the card on file with every auto-pay account.

6. Pay for travel with travel on credit

There are lots of points systems out there, but we opted for the Chase Sapphire card. It has a chip and pin, which means you can use it just about anywhere in Europe (they will not accept swipe and signature credit cards most places), it has no foreign transaction fees, and you get double points for buying anything travel related, which means that if you book all your travel for the first half of the trip on the card, you will quickly earn enough points to travel free for the second half of the trip. We paid for all our travel on the card up until we got to India (half-way around the world) but booked all our flights from there on out with free miles. Also, if you have to stay in hotels, try booking through hotels.com, since they will give you one night free for every ten nights you book through them. Sure, you could use a hotel rewards program like Starwood or Marriott, but that will really limit your experiences abroad, which completely defeats the purpose of travel.

7. Stay safe for cheap

American health insurance is really expensive, but travel insurance is actually quite cheap. If you can, get rid of your US health insurance and get travel health insurance. We got a plan through WorldNomads.com that was super-cheap and covered us anywhere in the world. It even covered our belongings if they were stolen. If you read the fine print, however, there was a big catch with the travel health insurance plan we got. It would not cover us in the event that we injured ourselves while under the influence of drugs or alcohol. Make sure to read the fine print!

When you return home, you will probably want to get a new US-based health insurance plan, but this can be tricky. Open enrollment periods only happen during November to January, which means if you get back from your travels in June you’re stuck without insurance until January 1st. A good way around this is to plan ahead to make sure you have what’s called a qualifying life event. Qualifying life events include marriage/divorce, getting a new job, and (very helpfully for the traveler) moving to a new state. If you lived in, say, New York, and designate a relative’s house in Ohio as your permanent address while traveling for six months, then go back to New York and change your permanent residence back to New York, then you technically just moved from New York to Ohio, then back to New York, which is a qualifying life event. Don’t hate the player, hate the game.

Another loophole I found in travel health insurance is that it will cover you until you get within 100 miles of your home. However, your home is just where your stuff is and where your mail goes. Upon returning to the states, if you sublet a place more than 100 miles from “home”, then you’re technically still traveling and can be covered by travel health insurance while in the USA.

8. Live like a local

At the time of our travels, we found AirBnB locations to be common throughout the world, though more prevalent in big cities and more developed locations. In destinations like London or the south of France, hotel prices tended to run upwards of $300 per night, but renting someone’s apartment on AirBnB was roughly $80-$120 per night, came with wifi, laundry, a kitchen, and was in a neighborhood full of locals instead of tourists.

Having a kitchen will save you a lot of money over a six month period, since you can shop at the local grocery store and cook for yourself. In my opinion, exploratory eating is one of the best parts of being in a new place. It may take a week before you find the best local market, but haggling in the market for fresh meat and veggies, or inviting new friends over for a dinner party, are some of the most rewarding experiences you can have as a traveler. If you want to speed up the process, spend a little money on a cooking class the first or second night you’re in a new place, then grill your teacher for info on where to shop and where the best non-touristy restaurants are. Cooking classes are a great way to get educated on the local cuisine while making friends.

The TripAdvisor app is a great way to find cooking classes with high ratings and reasonable prices. It’s also a good way to find tourist-friendly businesses in smaller towns. However, in big cities, the app will steer you towards the same sights everyone else is waiting in line to see.

When getting around, find out how the locals do it. Most cities with trains have smartphone apps you can use to navigate them, or come pre-loaded on Google Maps, which can really help when navigating a strange system. Taking the train or bus usually costs a fraction of what you’ll spend on cabs, and many cities have “tourist passes” which offer unlimited rides for a week or a month. Just budget lots of extra time at first so you can figure it out, and don’t be afraid to ask for help. Save all that cab fare money for the 2am trip home from a bar or the frantic dash to the airport for an early flight.

9. Travel to the deal, not the destination

Europe and Asia are full of discount airlines that offer cheap local flights. If you’re flying from the US, try booking your initial one-way flight to an interesting city that is also a big airline hub, like Copenhagen or London. Scanning the European flight deals, you can find dirt cheap flights from these cities to destinations all over Europe and Asia.

We used an app called SkyScanner, and very rarely booked our flights more than two weeks in advance. With SkyScanner.com, you simply put the dates you want to travel, and the city you are starting from, then it will list out every flight leaving from that city to every location around the world, in order of price. Perhaps Aix en Provance wasn’t initially on your radar, but you see on SkyScanner that there’s a $50 flight from Copenhagen. Book it! Then, figure out where you can go to cheaply from Aix. Check the local train systems for deals too. Just Google “French Train” or “Spanish Train” and you’ll quickly find the local websites (SNCF in France, RENFE in Spain, etc.). Be advised that each country has it’s own system, and you’ll want to book based on the country you’re leaving from. Train deals will be scarce during the prime summer vacation months, but you’ll find lots of deals during the fall and spring off-season. Sure, you could buy a Eurail pass, but you’re  really unlikely to save much money, and then you’re locked into train travel and can’t hop on the $80 last-minute flight to Morocco.

One caveat, before you book that last minute flight to Russia (or anywhere else), check the US State Department website to see what the visa requirements are. It’s no fun arriving in a new country only to be put back on the plane and sent home because you don’t have the required visa. We went to considerable trouble to get a tourist visa for India before we left the US.

10. Stay longer in each city

Spending two weeks in a city might feel like a luxuriously long time, but trust me, it will take a week and a half just to feel like you have the place figured out, especially if you’re stuck working on your computer for three or four days at a time. I highly recommend spending four weeks or more in big cities, and two weeks or more in small towns.

By moving less, you save a lot on airfare, you’ll find more locals-only deals, you’ll make more friends, and you’ll have a much more authentic experience. If you insist on excitement, try booking a different AirBnB apartment every week in different neighborhoods. That way you can cover much more ground around a city and really get a feel for the difference between the laid-back residential neighborhoods and the up-all-night trendy urban neighborhoods. Or, slum it one week and go posh the next. The point is that you can travel to very different experiences with just a $2 train fare.

If you find a place you really like, stay or come back. If the place you scheduled three weeks in is terrible, leave. Most hotels will refund a cancelation up to the day before you booked, and when booking AirBnB homes, you can set the search parameter to exclude locations with strict cancellation policies.


This list is certainly not comprehensive or static. The world is a quickly changing place, and you should do your own research before blindly trusting anything above. I will readily admit that this advice is meant for neither the budget traveler or the luxury vacationer. What I hope is that this helps people in a middle-class situation similar to my own realize that travel can be a comfortable way of life, rather than just a break from life.