How I Afford My Life of Travel

I made the decision to move to Bali at the end of 2015, because I wanted more color in my life. I wanted to push myself across through boundaries and ignite a new chapter in my life.

For the last 14 months, I have been living the life of a digital nomad in SE Asia. I stayed in Bali for 4 months and found the tourist season too busy for my taste. Since then, I have taken up base in Koh Lanta (Thailand), Penang (Malaysia) and Pokhara (Nepal). Along the way I have trekked through the high valleys of the Himalayas, dived with car-sized manta rays in the pristine waters of Indonesia, meditated in the jungles of south Thailand, and watched powerful life and death ceremonies in small villages. I have done all of this while figuring out how to make an income remotely – on the go.

Snow trekking through the Annapurnas | Photo by Jason Joscon

I attribute my current life of travel to a few key areas:

  1. Passive Income – which allows me to generate income at any time and anywhere in the world.
  2. Automation – building a system to free up my personal time so I can work as little or as much as I need to.
  3. Flying Free – a guarantee that I can fly free international twice a year.
  4. Slow Travel – find deeper meaning in my travel experiences with less money

Passive Income

I was first introduced to the idea of passive income through Tim Ferris in the 4 Hour Workweek. The idea is simple – instead of making money by the hour, find a means to generate income when you are not actively working. This comes in many forms from renting out your apartment, selling an eBook, or in my case – operating an online web store. Whether it’s incoming rent, royalties or sales, once you have the logistics setup you can have an ongoing income while you’re sleeping or vacation.

My passive income comes through Shopify through a dropship commerce model. I operate two stores where I sell items I have designed or items made by other vendors. The product are fulfilled through the vendor or through fulfillment centers like Shipwire. This keeps me hands off on shipping, packing and inventory logistics.

BBS – Bamboo Bicycle Kits

My work is similar to an art curator. I specialize in a certain niche of products and I use my experience in design and sales to showcase the products from various vendors. All of this is done online through an ecommerce store, which is essentially a digital gallery for artistic goods. Once the ‘gallery’ is setup, anyone can come in and out and buy things as will. Myself or someone else is there to answer questions and help the customers in their selection.

Checkout Pay Flynn’s SPI (Smart Passive Income) podcast for ideas on how to get out of the paycheck to paycheck way of valuing our time and income.


Up until January of this year I have been operating both my business on my own. The hours have tapered off over time but I have a great of trial and error over the first year. When I first arrived in Bali I would work 40-60 hours a week trying to get my sales in the green. Keep in mind this was a new business model for me and I had no idea what I was doing. I was pulling out all the guns making sure things would stick.

Since I’m based in Asia, most of these sales happen while I sleep during daytime hours the US, which presents some logistical problems. I have been through a few months of late night shifts from 7pm-12am after dinner or been up at 6am pre-surfing to get a few emails out. Just like bartenders choose to work at night, you have a choice to work the hours you want to work and find ways to not work.

This has shifted drastically over the last year and has entailed a good bit of experimenting with my personal lifestyle and where I have traveled. I now can work 1-2 hour a day to maintain my business with the help of an online assistant and occasional hire other freelancers help me with design and office work. This has been a tremendous shift in my lifestyle. Instead of worrying about orders, returns and customer emails I can do things like hike in the Himalayas for a month.

I use Upwork and Fiverr to find my team. I interviewed and distilled over a dozen applicants until I found a few individuals that work well with me. Make sure you test things out with a few projects and keep tabs on things that are important to you.

Outsourcing on Upwork – divide and conquer your time

Flying Free

The biggest cost of travel is often flying. Unless you have a hookup with an airline, chances are you spend a few hundred to a few thousand flying across the world. I can not tell you how having 1-2 free flights waiting for your without the thought of dipping into your savings or travel funds can be to your you mindset. It’s like growing wings. When I first did this at the age of 22, I couldn’t sleep at night as I kept dreaming of all the places I could be fly to for free.

Flying into Nepal – seeing eye to eye with the Himalayas

The secret to flying free? Knowing your Airline Miles. The truth is you don’t have to spend $10,000 to get a few hundred points and wait forever to redeem your miles. The smart way is to accumulate just enough miles for your traveling needs and do so with a clear plan.

I usually fly one or two international trips a year which means I need enough miles for 1-2 flights a year. That’s about 60,000 to 120,000 points if I’m flying US to Asia twice, less if I’m traveling shorter routes to say Europe or South America. I use Chase credit cards to accumulate United Airline Miles to use with any Star Alliance carriers. If you look for promotion signups for the Chase InkPlus (Business), United Mileplus Explorer, Sapphire Preferred or Sapphire Reserve you will likely be able to accumulate around 50-75k per signup.

Of course you’ll need to meet the spending requirements. This means you need to spend $3000 to $5000 in 90 days to get a 50,000 points bonus. The trick to this is to figure out what you’re spending it on before you get the card so you don’t go on a crazy spending spree and put yourself in debt.

My go to sources for spending is rent, utility, insurance, and if the occasional electronic purchase (new phone or laptop). Currently, I place most of this on business spending. You may even opt to pre-pay your insurance or utility a month in advance to simplify the process or pay a friend via PayPal (although you’ll be charged around 3% for using a credit card). Regardless, there’s plenty of options out there to active spend a chunk of credit without having to pay for it – give it some thought.


Slow Travel

Moving slow doesn’t mean seeing less. Most people who visit San Francisco never make it to Oakland, Santa Cruz or Marin. Instead they spend a few days around the Mission and checkout Fisherman’s Wharf, then head down to LA to get a glimpse of Hollywood and Disneyland.

What about old the redwood forests, wine country and the best surf town in California?

I like to travel with a base and find the small hole in the wall places, try local foods and inject myself into the local culture. This means 2-12 weeks somewhere. This also means more genuine connections, deeper conversations and getting a glimpse at local life without the big crowd of tourism. The best thing is it’s also easy on the wallet.

Ask for rentals by the month or by the week. Even if you only stay 5 days or 20 days somewhere, you have the upper hand in bargaining power. Same applies for motorbikes, bicycles, surfboard and any equipment. I was able to find a private 1 bedroom suite for $188 / month in Cangu, Bali when the daily rate for the place was $22 / day. That’s near 90% cheaper! More time for venturing and surfing 🙂

Walking home with Mt Agung towering over the sunset – Bali

Plus locals love when you stay longer, often giving you tips, food and added help to make your stay more enjoyable. Wouldn’t you do the same if a Costa Rican or Nepalese fella moved into your neighborhood for a few weeks? We tend to be curious and welcoming of people from distant places who spend a period in our lives. The same treatment is possible, but harder to give to tourist who spend 1-2 days somewhere before hopping on to the next hotspot.

Slow down and see more… prioritize the deeper connections over checking off the travel bucklist.



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