Living and Surfing your Dreams and Not Failing

"I’m 29, and failing at doing something I love"

This is the story of someone currently in the process of pursuing one’s passion, and failing.

I am 29 and was once diagnosed with anxiety after working in New York for a year. I’m generally risk-averse but understand taking big risks are necessary. I’d however rather watch someone else take that risk from the sidelines because I was once told "Don’t be a hero. Heroes die young." I’m an indecisive dreamer with lots of ideas. The word 'execution' is foreign to me.  Some would say I’m lost and I’d retort defensively, “I just go with the flow”. All said, let’s say for fun, half a year ago I left my stable 6 year career in the pharmaceutical market research industry to pursue a volatile and unpredictable passion combining film and surf.

After having done so, as a once youthful-looking Asian, people can correctly guess my age now.

First I’ll explain what drove me to embark on this journey to help those in similar situations, then I’ll divulge details on how I planned and executed it, and finally cap it off with real takeaways for those looking to take the big leap and to avoid my mistakes.

It started with a big dream early on in college to one day move to New York and work on Wall St. I wanted to say “Yes Richard, we have a deal” and chuckle like a fat balding man wearing suspenders. A big delusion that seemed glorious at the time.

After being severely distracted in college, chasing fun rather than education, the lucrative Wall St. opportunity evaporated. While I can say placing value on such fleeting thrills is honestly my biggest regret, I was extremely fortunate to meet friends that connected me with the ocean through surfing and that has been one of life’s biggest rewards.

After graduation I settled into an entry level data entry position with a tiny firm in San Diego where I was allowed to wear shorts and sandals, and received free lunches and a below average pay. I used the perks to rationalize that everything was fine, sharing Snapchats of my bare feet in the office to demonstrate how great I had it to my friends. Then three long painful years of catching four second beach break waves passed. One morning, with the help of a very good friend, Mr Johnson, I was grabbed by the shoulders and shaken not violently, but enough to be galvanized. He didn’t ask but rather demanded of me simply “What are you doing with your life??”. After I told him I’d probably move to North County San Diego because the surf was better, he encouraged me to explore an opportunity I had in New York which I had boasted about once, but never had the gut to pursue. It would be a sales job, wearing a suit, talking to company directors and executives about our services and solutions. Maybe I could one day say, Richard, we have a deal, and chuckle loudly.

Coincidentally or maybe by fate, the Director of Sales was just starting to build a team based in the Big Apple to support our clients. After three brutal rounds of mock-sales calls, he accepted me as the second member of the team, with no sales experience at that. I just happened to be a guy who knew how our products worked in a very technical industry. While not exactly Wall St., it was Vanderbilt Ave. right next to Grand Central, which I once accidentally referred to as “The Grand Central”.

Thus I became an account manager, responsible for nearly 100 of our clients. From the very start it was a rollercoaster ride, one day having a wonderful conversation about someone’s ski trip in some small expensive town in the Swiss Alps, to the next call being verbally abused on the phone by a sizable investment firm because the subscription price had gone up $100. In between was  “Hi Richard, just checking in. Wanted to know if you received my previous email. Please let me know when works best to chat. Thanks, Dan.” followed by “Dan. Now’s not a good time”.

Day in and day out we were reminded of our performance numbers posted above whole sales floor, like a Times Square billboard. If we were below target, the number was written in red. It was an easy way for the higher-ups to gently or rudely remind us that we had work to do.

My soft Californian skin grew thick and my patience wore thin. What was I doing?

It wasn't until I had walked through Grand Central twice a day for 593 days, head down, rubbing shoulders with a few million people, that I was able to take my first real vacation - a last minute surf trip to Nicaragua. 10 days in Playa Maderas to be exact.

Away from the concrete jungle the vitamin D was plentiful and work emails limited. The board-shorts-temperature water could be enjoyed as the sky caught fire each sunset. From the top of the jungled hills surrounding the beach, you could look down into a splendid bay. Each hostel bar played that Bob Marley reggae and Sublime ska punk which paired so well with a beer after a surf session. And there were waves EVERY. DAY.  Due to Maderas' unique location, featuring the Pacific on the west, and a huge lake some kilometers to the east, the wind howls offshore. This was the moment that allowed me to catch my breath and meet carefree smiling people for the first time since the move to New York. I remember distinctly a hostel owner named Ted who was in his mid-40’s, and had a striking smile, with no discernible wrinkles on his face. I also met a man who had created instructional snowboard videos on Youtube which afforded him an annual extended trip to Nicaragua, and a man who ran a brewery in San Juan Del Sur. They all worked for themselves, answered to no one, and reaped all the rewards. These guys had managed to escape and were doing well.

As a naturally risk-averse person, I wanted to know what was the hardest part about running their own businesses. If I were to mimic their individual spirit, what would I have to endure? I was expecting them to answer with something along the lines of divorce followed by drug rehab.

But all three gave the same answer: The hardest part was just going for it.

I mulled it over. That was it?  No one had elaborated on it, but I continued to encounter this common theme during a few more trips abroad.

Looking back and having gone through with it now, just going for it has been the hardest part because the fear of loss is at its greatest right before taking the plunge. It had taken 28 years to be finally holding my own in the greatest city on Earth. Now I was going to leave that behind and burn through my savings for some unproven venture?

When I returned to work from Nicaragua, my mind was churning for a solution so that I would no longer have to wake up to an alarm clock. There was an article I once read regarding Scott Adams, the author of the business comic strip Dilbert, where he posited that it is nearly impossible to be the best ever at one thing (think Michael Jordan for basketball). But if you’re good enough in two things, you have a chance to succeed. He mentioned while he was not the funniest person, nor the best business person, by combining the two areas into a comic strip, Dilbert is now printed in over 2,000 newspapers weekly.

Another surf trip later, after filming a really poor taste surf lifestyle mock video with friends (think Alana Blanchard bikini shots and really shit GoPro-attached-to-the-nose footage in 2 ft waves), I found myself in a flow stitching the video together. The same flow when I’m surfing.

Lightbulb!  Make a living from filming surfers.

My thought process (and unlicensed idea):

1. Everyone loves a great surf picture of themselves. What about video footage? Priceless.

2. There were already lots of surf photographers

3. There were very few people filming surf videos with drones

4. With the footage I could sell, I should be able support myself in affordable surf countries (Nicaragua and Indonesia were my top two choices).

Next was calculating my expenses for the venture. Let’s get super serious for a second.

1. I decided to give myself one year to test my idea.  Roughly $18,000 to cover living expenses. The expenditures rule of thumb for travellers is $50/person/day. This includes airfare, travel, food, lodging and entertainment. You can definitely get by on $1,000 a month if you stay put in places longer.

2. I also needed to purchase gear. Film equipment, film course, and laptop.

Once I had those two numbers in mind, I knew how much longer I needed to put up with “how many contracts did you close today?” This would take me a very non-committal year of back and forth between, “now is the time!” and “but I could work for another year, get a promotion and take a few surf trips a year instead!” During my conversation with my Director about my plans, he actually encouraged me while offering a position should I have to come back tail tucked between my legs. So the leap became less frightening.

Ideas are easy. Execution is not because I didn’t have a concrete plan. I implore you to create one.

Here’s my failure. In six months so far, I’ve produced 11 videos grossing $162 in sales. No, it’s not missing any additional zeros or commas. I’m also about 75% of the way through my savings.

So what happened? I started planning too late. I learned two hard truths once I started. Drones are banned in Nicaragua and it is hard to stay in Indonesia longer than 60 days at a time. The latter seemed too unstable for me. Boom. Two of my top spots crossed off the list. Without the affordable surf spots to stretch my savings, and without a concrete plan, my partner and I decided we’d go to Europe first to attend a wedding.  We ended up sticking around a few months visiting friends and family in landlocked areas. With the Euro strengthening against the dollar, talk about cash burn! Keeping up with the ill-prepared theme, without knowing where we’d go until the last minute, booking becomes an expensive affair. You don’t want to be too rigid with your planning, but there’s a cost to pay if you’re too loose.

Business-wise, I’ve found drone filming is less practical than using a camera. For example, I can only capture around 12 waves each session with the six batteries I have. The ocean will provide waves on its own time and doesn’t care you only have one battery left to film.  It’s also hard to track down the surfers I’ve filmed afterwards because I’m not entirely sure who I’m filming, sometimes posted at a spot 500m away. And while those super shredder locals aren’t exactly the BMW-wielding-established-career type with extra dollars to spend on a video, these shredders are the ones that make for awesome footage. These are the guys I’d rather film.  I can’t be bothered standing under the sun, filming tourists on foam tops catching white wash, their top half leaning forward, butt jutted out, face fully dialed in on focused, about to faceplant. To date, I have not sold any footage to individuals yet.

And finally, one of the biggest difficulties on the road is staying disciplined with all the distractions of people and places. It’s important to build a routine, otherwise you’ll decide to meet some people for coffee in the afternoon and you’ll end up staying out until midnight. This isn’t good when you have footage that needs to be edited, uploaded, shared with witty comments on FB or Instagram on a consistent basis. I have constant reminders on Facebook, telling me, “VitaminDan, your audience hasn’t heard from you in over two weeks”.  Oftentimes, lethargy can be a problem as well without a stable regiment of exercise or consistent diet. You can’t eat like you do at home without all the conveniences of your local grocery store and kitchen or go to your local rock climbing gym either to take a boot camp class.

So what should you do?

1. As early on as possible, invest in yourself to develop valuable skills that will generate as much income as possible. Even if it sucks. The pain is temporary. On those days I could barely wake up for work, I reminded myself that each new day presented new opportunities to learn to get me closer to my goal. I have not met anyone successful who did not put in the work.

2. Read. Feed your brain with ideas. This is also Bill Gates’ and Warren Buffet’s advice.

3. Get out of your comfort zone with baby steps. This will prepare you to push your limits further. Personally, my journey started by going away from home for university. I then decided to study abroad in Hong Kong and Beijing, two of the busiest places on earth. A few years later I tried stand up comedy in LA once, moved to New York where I held a stressful sales job for three years, and tried stand up thrice more (each time feeling like vomiting on stage). People will shy away from living in New York, or public speaking, but I found it prepared me to take the biggest leap of my life.

4. Have a detailed plan of what you want to do, and how you’ll do it. Think of your end goal, how much you’d need to make to support yourself, and work backwards.

5. Stay disciplined and do not be distracted. When your friends are out on a Thursday night, tell them you can’t make it. Instead, get involved in activities that will increase your growth. You’ll have so much more meaningful fun later on.

6. Save your money but spend it on travel. If you seek knowledge abroad, you’ll get perspectives from travellers who have done what you want to do.

7. Once you’ve built a safety net of savings and skills and gone out of your comfort zone enough times, you’ll feel more liberated to do your own thing.

8. Be adaptable. What you initially planned will not go accordingly. With your safety net, you can adjust your sails. Whether you adjust them calmly or in a fit of panic, depends on how well you’ve planned.

I’m now trying to correct the ship by setting a new course towards the island of Travel Videos and Story Telling with the aim of exposing Earth’s beauty so viewers can decide “Hey, let’s not ruin it”. There’s some on-the-fly learning I’ll have to do. And rather than being sad that I haven’t sold my footage to any individuals yet, I’m focusing on building up my portfolio with quality content. At the moment I’m looking for surf camps that have an awesome story waiting to be told because surf camps can be a great source of inspiration. Don't despair I’ll still throw together some fun surf edits! Here is something I threw together at Supertubos, Portugal.

This is not a story with a happy ending, because it’s not over yet! But use it as a cautionary tale if you will.

If you would like to learn more about the work I’m doing or have any questions on the above, feel free to contact me by email: [email protected], or if you like my videos,  please subscribe to and follow me on my youtube channel here.