Step 1: Quit Job

Quitting a Great Job

For the past year and a half I’ve been working at a small software startup in San Francisco, and today was my last day. I didn’t quit to go to a higher paying job, because I was unhappy with the way I was treated, or anything else like that. Working here was actually the best job I’ve ever had; good pay, smart people, challenging problems, independence, flexible work hours and location, etc. The reason I quit was because I had a longing for adventure that this job was no longer fulfilling. When I moved to San Francisco 3 years ago and started working in the tech startup world, it was an extremely exciting and invigorating undertaking. It was an awesome challenge as well as an adventure.

Eventually, however, it became too comfortable, and grew restless. I’ve always enjoyed being on the road, going on adventures, and meeting new people in new places. These past 3 years in San Francisco are actually the longest I’ve consecutively lived in a single city since I graduated high school 10 years ago. I quit so I could go on an adventure, push outside my comfort zone, and have the time of my life.


view from my office

view from my office

What To Do

Making the decision to quit a job I enjoyed and leave a city and friends that I love was the hard part, planning what to do during my travels is the fun part. The three things I really love, and that I want to spend as much time as possible doing, are surfing, sailing, and (spear)fishing. So the tropics were the obvious destination to start with. I’ve spent time traveling all over South East Asian but the one place I’ve never been and always wanted to go is Indonesia. It has the most diverse marine life on the planet, world class waves, and is a pretty popular yachting destination. I bought a 1-way ticket to Bali, with a week-long lay over in Taiwan, leaving June 1. That gives me about 4 weeks to move out of my house, put my stuff in storage, and spend some time adventuring around California doing things I’ve wanted to do but never got around to.

While I have a list of destinations I hope to make it to, I purposefully haven’t planned anything more than the first stop in Indonesia. I’m hoping to travel as much as possible by sailboat, and I want the people I meet to dictate the places I go as much as possible, and if I have any sort of set itinerary that will make this pretty much impossible. That being said, I do have a lists of places I hope to visit, including: other Indonesian islands, Australia, New Zealand, China, Namibia, South Africa, Mozambique, Madagascar,  Botswana, and hopefully many more far off and remote islands.


What about money?

In order to do something like this, money is obviously essential. Though tech jobs in San Francisco typically pay extremely well, rent and cost of living are super high as well, so it’s not always easy to save. I was, however, able to save up more than enough money to easily travel for 6 months without putting myself on a budget and living a pretty good life.

I’ve lived in a nice 4 bedroom house for the past 2 years with two roommates (they’re a couple and shared one room). We rented out the other two rooms on AirBnB which basically let me live in SF rent free (when you account for taxes I did have to pay a little bit of rent, but it wasn’t much). This situation, combined with a good job, let me save up money while also going out to eat/drink all the time, traveling often, and in general having fun and not pinching pennies. Having a job that has unlimited vacation and allows remote work definitely helps with this as well. Over the past year I took week+ trips to Spain/France, Hawaii, Cabo, and Vietnam along with shorter trips to Vegas, Portland, Austin, LA, San Diego, and others.

How the whole AirBnB situation came to be is worth a whole other post which I’ll write at some point.

As I walked out of my office for the last time, and set off on the first adventure of my newly unemployed life, there was definitely a tinge of sadness at leaving a job I’d really enjoyed, but it was overshadowed by a surging feeling of enthusiasm and anticipation for the adventures that I have in front of me.

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