Portal Vells, Mallorca

If there’s one thing I hate, it’s having to lug too much stuff around on my travels. Ever since my pair of Air Jordan 6s got replaced with stinky old shoes after I checked in my luggage 23 years ago, I’ve never checked in another bag again! I saved up all summer for them $120 Jordans and I was devastated as a 13 year old kid.

It’s been a year since I officially retired from Corporate America and I finally took a grand 4 week trip to NYC, Switzerland, Mallorca, and Germany. I took several weeks here and there to Hawaii, Tahoe, and a cruise up the Gulf of Finland to St. Petersburg over the past 12 months, but I had never gone on trip for longer than 2.5 weeks since college 14 years ago.

The main reasons for this trip were the following: 1) I wanted to see family and friends in NYC I haven’t seen in over two years, 2) To test the extent of being able to run an online business from anywhere in the world for an extended period of time, 3) To see if I could run my business without a laptop, 4) To test the limits of how long I can last away until I start feeling overly homesick, and 5) To learn and explore!

I’ve written two posts about my trip already in “How Do People Comfortably Live On Less Than Six Figures In Expensive Cities Like New York?“, and “Do You Suffer From Apathy? (Swiss portion)” with a couple more posts to come this summer. For this post, I’d like to share with you my strategies and thoughts on running a business with just my iPhone while traveling for four weeks.


I’ve always fancied the idea of being able to run a business anywhere in the world there’s internet access. It’s admittedly fun to tell people about this freedom. The truth of the matter is that I’ve only tested a location independent business lifestyle for a maximum of 2.5 weeks at a time since the most I could take off was 6 weeks a year thanks to work. Although I was able to run the business fine during this time period, was 2.5 weeks really a statistically large enough sample set? I wasn’t so sure.

It bums me out to have to lug around a four pound laptop and take it out for the scanners at every airport. Hence, I rationed if I could just go on a four week long trip without a laptop, I could without guilty conscience say that I truly have a location independent business. Here are the steps I took:


Posts: We’re in the business of generating content and typing 1,500 word articles on an iPhone is not ideal. Given every single one of my posts on Financial Samurai contains a picture or two, it was imperative that I prep and schedule at least three weeks worth of posts. This took a mind numbing long time given I didn’t want to have to edit errors like I normally do after a post is published while I’m away. Preparing each of the 10 posts took about 20 minutes, equaling about three hours of time after they were all written. This process will really test your patience.

Business: Every single business contact was contacted two weeks before my trip to either tie up loose ends such as outstanding payments or lock down future campaigns or advertising agreements. I keep a spreadsheet of outstanding business follow up items in Google Docs, which is also an app on my iPhone. The key to business is keeping the flow going. Conversion cycles may be one day or two months, but so long as the flow keeps coming, it doesn’t really matter because sooner or later you will get paid.

Checking Ahead: Taking just a smartphone on a four week trip is a gamble because I can’t easily do a lot of things I can with a laptop, and that causes stress. But in a tech savvy world where everybody I know has at least a desktop, I decided to take the risk. During the first week in NYC I was able to use two laptops to write three more posts and cement a couple business deals before going to Europe for 2.5 weeks. I just needed to make sure I had all my login details intact, which is easy due to the cloud and my smartphone. Another great thing is the proliferation of WiFi access. Each day that goes by makes location independent business owners happier.


The Mega Out Of Office Reply E-mail: I make it a point to be as thorough as possible with my Out Of Office Reply e-mail. The below OOO encapsulates all the major points someone contacting me will inquire about. If someone can’t find an answer from my OOO, then God help them! E-mail gets out of hand and I will miss important messages while traveling. Putting in a disclaimer to resend me an e-mail after five days is a way to buy me some time and make sure all really important messages are sent. Here is my latest OOO:


I’ll be overseas on vacation until July 21. As a result, e-mail correspondence will be slower than normal. If you haven’t heard back from me within five days, please feel free to resend me the e-mail.

1) For advertising inquiries, please send an e-mail with your rate offer, specific advertisement, and duration of advertisement. I only host advertisement that is relevant and helpful to my readers. 

2) To buy the #1 book on the web that teaches you how to negotiate a severance package in order to profitably quit your job, please see How To Engineer Your Layoff.

3) For Yakezie Network and Blogging related questions, please visit the Yakezie Forum and ask one of the 100+ Yakezie Members for help. 

4) For career and personal finance 1X1 consulting with me, see my FS Online Services page. I will review your application and get back to you when I return. Please also e-mail me if you have filled out an application. 

Have a great summer!

Technology Contingencies: Something seems to always go wrong when you’re away and it’s more important than ever to have a tech backup plan. My friend Jesse from AntiNecktie is my tech guru and I let him know about my time away as well as my goals and things to look out for while I’m away. The main thing we worked on was making sure the newly launched FS Forum stayed working and added a bunch of helpful new features. The other main issue was to make sure the sites stayed up for as long as possible, which I’m happy to say they did. Andrea from Nuts and Bolts Media is also a fantastic resource who I know would gladly help as well. In fact, when you are a part of the Yakezie Network, you have the entire community to help out!

Business Contingencies: Business really slows down during the summer because we are all in cahoots together! It’s a domino effect where if we see business slowdown 10%, we decide to take some time off, and business slows down some more. We discussed pushing through the online hump and surviving a seasonal online traffic downturn earlier on Yakezie.com. Despite a slowdown, there is still business to be had! I like contacting fellow Yakezie bloggers who will be around while I’m gone and giving them my business to run so they can earn a profit. It’s a win-win as I’ll get to do the same when they are gone and I’m around.


Interacting with readers. Using a smartphone to approve comments (80% of all my comments get stuck in my spam filter for some reason), responding to comments, responding to e-mails, and sharing content over social media is a breeze. It’s way easier to share pictures on Twitter and Facebook using a smartphone than with a laptop for example. I found using my smartphone to be easier overall since I was always on the go. The area that suffers is interaction with other sites and owners through commenting since you only have so much time.

Adjusting scheduling of content. I ended up prepping three weeks worth of posts, but during my time away I ended up writing five more posts, three of which were on my iPhone. As a result, I had to do a little rescheduling of content which worked just fine. The WordPress app works just fine, but I still just login to my dashboard going the normal web route.

Follow ups. With Reminders, Google Docs, and Notes, I stayed on top with all outstanding items using my smartphone. Remember that it’s all about keeping the flow going.


There’s always a little sense that something will go wrong if you are traveling overseas without a laptop. The most common fears I had were a post not getting published as scheduled, a post getting inadvertenantly published because I pressed the wrong button on my phone, or missing out on some lucrative deal because I missed the notification. Thankfully, all posts came out as scheduled thanks to preparation and backup help. The content quality stayed the same as well.

Although the blog business is largely passive once the content is created, I would say at least 20% of my business is due to hustling in search for more business. I hate spending much more than 30 minutes on work while I’m traveling, so I’m sure I missed some business opportunities. That said, I don’t know what I missed, so did I really miss anything? Maybe not. It’s summer after all with traffic and revenue both down.

It’s been three weeks since I touched a laptop and it feels absolutely strange. Productivity is certainly much higher, but I long for the simplicity of just using an iPhone again. If I can type HTML code without having to think, I think I’d happily go for six months to a year without a laptop. Becoming proficient in HTML is now my goal for the next six months before I attempt to go on an even longer trip.

The real ass kicking is the hours of preparation before the trip if you just want to run your business with a smartphone. But if you put in the time, you’ll be able to rest easier and truly enjoy your time away. Bringing a laptop on my travels just feels like I have to work, and that’s not something I want to feel. Three hours of preparation for four weeks away plus 30 minutes of maintenance on average a day was all it took. Let’s see if things get easier on the next trip to my vacation rental up in Lake Tahoe!


I never thought I’d be able to quit my job in 2012 just three years after starting Financial Samurai. But by starting one financial crisis day in 2009, Financial Samurai actually makes more than my entire passive income total that took 15 years to build. If you enjoy writing, creating, connecting with people online, and enjoying more freedom, learn how you can set up a WordPress blog in 15 minutes like this one. 

Leverage the 3+ billion internet users and build your brand online. There are professional bloggers now who make way more than bankers, doctors, lawyers, and entrepreneurs while having much more fun, much more freedom, and doing less work. Get started. You never know where the journey will take you!

Updated for 2017 and beyond.