Headed To The Philippines For October!

People often wonder why I devote energy to examining how I spend my time or optimizing my physical possessions. While it provides some immediate intrigue and satisfaction, it can’t really connect to my long-term goals, can it? I’m here to say that it absolutely does. Remember, small choices lead to big victories. Developing more intentionality at all levels of your life will empower you in pursuing challenging or counter-cultural decisions in the future. Through this process, I decided to spend the month of October on an overseas adventure.

Making Time to Travel

In all reality, the simple acts of intentionality themselves will not guarantee you more freedom or world travel (or whatever your ideal life is). Developing a sensible meditation routine to create mindfulness, or organizing your closet to create space are fantastic in and of themselves, but there’s a greater force in motion. You are changing the way in which you view the world; this is the most important element of Designing Essential. You are rewiring the filter through which you interpret time, money, and energy. You choose to create space for reflection. You identify what is or is not important in your life. Your relationships become more intentional; you rekindle old connections. You feel less rushed and spend more time on meaningful activities.

Here at DE, I provide stories, exercises, and strategies that worked for me. Things that enriched my life with meaning, connection, financial stability, and community. They may or may not work for you. But as mentioned, they lay the groundwork for redesigning a gratifying and purposeful life. It is this higher-order thinking that translates to large change.

During the last six months of my life, I actively evaluated habits and routines, but also looked at what I value, what I want, and what my life could be.

So here I am 10 weeks into my second “life sabbatical” from work and school–the first being a four-month respite after graduating college. Over the past few months, I’ve continued growing the Simplicity Project community, creating freelance photography opportunities, developing self-motivation, and reading tons of books. I’ve downsized my material possessions dramatically and visited close friends throughout the country. My finances are in check and I have a safety net in place. The choices leading up to this October were small and large, but more importantly, they were intentional.

While the analytical qualities of my personality provide great value, it can also cause “decision paralysis”.  Making this decision to head to Asia was no different. However, as I often remind myself, all the lights will never be green. You can’t live life in a hyper-structured and optimized fashion. There is an art–an ebb and flow–to making any lifestyle shift. Moving across the country, traveling out of the country, or even running a country come with their fair share of choices. I was making a seemingly large commitment, albeit it was not one to be afraid of. I had no clue what my employment situation would look like come October, but I knew I would carve a path. Those whom recognize fear, deal with it in a healthy manner, and move forward, will prosper.

The Philippines

So why the Philippines? It’s a reasonable question for sure. I had been tracking flights to Asia for a few months knowing this fall would provide a mix of reduced flight prices and good weather. Equally attractive, I considered visiting Central or South America. Heading due south would give me excellent Spanish practice, but I would’ve coughed up quite a few airline miles as I didn’t see any great flight prices. Shortly after seeing a fantastic round-trip deal to the Philippines, I pulled the trigger.

Thanks to an avid flight price scanning and travel hacking lifestyle, I landed a $469 round-trip ticket to Manila. I’ll be flying EVA Air through Taipei with a very reasonable layover: four hours outbound, and two hours returning to the States. Both total travel times will be less than 20 hours. Knowing I’ve spent more flying Seattle to Detroit, I was quite curious as to why the flights were steeply discounted. As it turns out, the price drop is largely due to a lift on fuel surcharge fees into and out of the Philippines.

Soon after departure, I’ll land in the capital city of Manila for a 29-day adventure around this massive archipelago–well over 7,000 islands in total! As an aside, always check visa requirements before purchasing a ticket. I almost bought a 32-day itinerary which would’ve crossed the 30-day “free visa” threshold and set me back around $150 bucks. Not something you want to discover moments after purchasing an international flight. Shortly after learning this, I adjusted my flights to return on October 27th.


The Philippines is divided into three principal regions: Luzon, the Visayas, and Mindanao. Luzon is the largest and most populous island in the Philippines located at the north end of the map below. The country’s capital Manila is located here. The Visayas are the large dotting of islands throughout the center of the Philippines. This is where a majority of my travel will be. The final region Mindanao is the large island at the southern end of the Philippines. Given the decades-long conflict occurring there, I’ll be avoiding Mindanao per many state travel websites’ recommendation. Below is a spacial representation of the places I hope to visit during my four-week trip throughout the country.

I created a map in Google Drive to plot out my anticipated destinations. All of my trip will take place in the regions of Luzon and the Visayas.

After targeting these two major regions, I started dropping pins of recommended or favorite places. Although I rarely travel with a guide book, a friend of mine lent me a Lonely Planet book which was helpful for finding a few overlooked destinations. I also learned quite a bit of cultural context thanks to the book’s traveling tip section. I also reached out to a travel blogger who lived in the Philippines off and on for over three years. My final and most useful source of information was a few friends I made in Seattle. They are a couple folks I overheard speaking about their pending returning to the Philippines. Naturally I struck up a conversation, shared my vision with them, and proceeded to be welcomed into their world.

After parsing through all the information, I’ve narrowed my time down to five major locations, all of which I will fly between. Anything within each of these regions will be accessible by bus:

At the time of this writing, the above list strikes me as a tad ambitious. I’ve been confronted with similar situations before and often opted to reduce destinations to improve my sanity. It has paid off in the past and may he necessary for this trip as well. Flights are readily available between islands, so changing plans on the fly is a small financial burden, but one I’ll take in stride. Furthermore, October is typically the tailing end of typhoon season which means weather can change on a dime. Just another reason to remain flexible and open to unforeseen adventures.

Following Along

Similar to my recent road trip to New Zealand, I’ll be sharing my experiences through the wonderful medium of photography. Additionally, I’ll detail my time in the Philippines with observations and thoughts on this site.  I look forward to entwining images and musings on both Instagram and Twitter as well. I encourage you to follow along and reach out with questions and messages of encouragement. Here’s to the start of an incredible adventure!

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