“Choose a job you love, an you will never have to work a day in your life.”-Confucius

Disclaimer: The chapters are meant to be read in order for better understanding, but with that said, each chapter can also be read on its own.

Disclaimer: The chapters are meant to be read in order for better understanding, but with that said, each chapter can also be read on its own.

Kim slides an envelope across the table and I quickly snatch it up.

“Thank you for all your hard work,” she says.

I reach into the envelope and pull out two crisp one hundred dollar bills.

My heart sings as I say, “You have no idea how much I appreciate this.”

When she says, “We are so happy with the photos you did for us today,” my whole body smiles.

I grab my camera bag and luggage and walk toward the hotel’s exit with a little extra pep in my step.  The bellman holds the door for me and asks, “Sir, do you need a taxi?”

Singapore’s sweltering heat quickly gobbles me up the second I step outside.

I tell him that I’m headed to the Link Hotel, which is roughly 2 miles away.  Then I set my camera bag down and fan myself with my shirt, “Boy it’s smoldering out here this afternoon.”

While he waits for my answer, I quickly do the math; it’s probably about a 10-dollar cab ride or about a forty-five-minute walk through this soupy humidity.  I reach into my pocket and rub the two hundreds together and say, “It’d be nice to get a taxi, but I think I’ll walk.”

I hitch my camera bag up onto my shoulders and wheel my trusty duffel bag by my side as I set off on foot.

Once I get my bearings, I head down East Tong Sen Street and when I cut up Merchant Road a few minutes later it hits me just what a big decision that just was.  It may not seem like it, but the decision to turn down a taxi and to walk through this sidewalk melting heat with all my belongings epitomizes what I can feel myself becoming.

In my old life, I wouldn’t have even thought twice about that decision.  If anything, I would have insisted on a taxi, but that was then, and this is now.

You see, this cool two hundred dollars in my pocket is the first money I’ve ever made taking photos for a hotel.



I had three hotels in Singapore agree to my standard offer, but I only have time to stay at two of the three hotels while I’m here.  So, I emailed Kim and asked her if instead of exchanging a room for the photos, if she would be willing to pay me for my work.  When she said yes, I nearly leapt out of my skin. I couldn’t believe that I was actually going to make money for my photography.

I’ve worked with over two hundred hotels at this point. I’ve gone from Cape Town to Singapore without making a single dollar.  All that I’ve ever asked for in exchange is a place to sleep.

During that time though I’ve been relentlessly practicing my craft, taking each hotel photo shoot more seriously than the last.  I’m constantly trying to raise my game to create unique photographs for each hotel.  I’ve photographed everything from hotel staff and hotel grounds to every menu item and cocktail a hotel can concoct.  And I’ll bet that if you asked any of the hotels I’ve ever worked with to describe what I’m like to work with in one word, I’m sure they’d all pick the same one, “intense”.

While hotel photography is not my passion, I’ve never once mailed it in.  I’ll work just as hard for a hostel as I will a five-star resort because I know that what I learn doing that type of photography will ultimately help me with the creative travel shots I like to do on my own, the ones that fill me with purpose.  So, it would have been really easy to just go ahead and think that I’ve finally “made it” and that I should reward myself with a 10-dollar taxi ride.  I mean today is the hottest, most disgustingly humid day I’ve ever spent on earth.  But I just couldn’t let myself do it.

I turn off Merchant Road and head north on Chin Swee Road, which is directly in line with the sun.  I’ll have to immediately change clothes once I get to my next hotel; it looks like I jumped in a pool this afternoon as sweat cascades down my arms.

As my bags get heavier, I begin to question my decision to walk.

But I just couldn’t part with 10 dollars because there’s been an elephant in the room that I’ve been trying to avoid since day one.  Well, I don’t know if trying to avoid it is the right thing to say, it’s more like there is an elephant in the room and I’m just kind of trying to keep it entertained enough to distract it from pooping on the carpet.

That elephant’s name is money and the carpet is my life.



The only thing people ever seem to want to know about my journey around the world is, how do I afford it and how do I make money while traveling.  No one has ever asked about Sudan or the Syrian refuges, there’s never been a question about my favorite foreign food, nor has anyone been curious how I’m coping with all the tiny hotel beds.  This is a shame because it feels like the only thing that will truly validate my transformation and journey is to come back home with more money than I started with.

And here’s the thing, I know there are ways to make money while traveling, but I only want to make money doing things that I love.  I didn’t quit my corporate life only to get sucked back into doing something similar while out here on the road.  I’m not trying to teach online or do graphic design work on the side or any sort of job like that that allows me to work remotely.

I’ll even go so far as to say that I don’t want to go on press trips to really nice resorts or write articles for online travel magazines.  That defeats the whole purpose.  Call me crazy, but I just want to write, film and photograph for myself and then somehow earn an income from that, kind of like what Bill Cunningham did.

Bill Cunningham was a fashion photographer for the New York Times, known for his candid street photography.  He had a regular series that ran in the paper called On The Street.  For over forty years he would wake up every morning and ride his bicycle around Manhattan in his blue workman’s jacket and black sneakers.  The only thing he carried with him was his camera.  He would photograph people as they moved about the city streets, but not as paparazzi.  He was more interested in capturing clothing as each individual’s personal expression.

He made a career taking unexpected photographs of every-day people, socialites and fashion personalities, many of whom valued his company.  He won many awards for his work and is considered a pioneer in the industry.  He was a humble man only concerned with his passion.  He lived in a tiny apartment in the Carnegie Hall building on 41st and West Ave.  The apartment had no closet, kitchen, or private bathroom.  It had just a bed and his photographs.

When talking about his personal philosophy he once said, “You see if you don’t take the money, they can’t tell you what to do, kid.”

This to me is a man who refused to compromise his passion; I’m willing to bet that he would have taken all those photographs the exact same way even if he had not worked for the New York Times.

Link Hotel, Singapore.

Link Hotel, Singapore.

When it comes to money itself, I’ve always just believed in two things.  The first is the idea of abundance, meaning that I will always have enough of what I need when I need it.  And the second theory I subscribe to is to do what you love, and the money will find you, kind of like Bill Cunningham.  Well, after 600 days traveling and earning less than a single paycheck at my old corporate job, I can officially say that I’m testing both of these theories to the max.

When the cargo ship I was supposed to take from Singapore to Australia was cancelled last month I had to find an alternative way to go. The only other option this time of year was a cruise that Princess Cruise Lines offered.  It’s a 14-day trip up and around South East Asia that eventually docks in Fremantle.  I couldn’t wait six months for the next cargo ship (that would take passengers) to Australia, which meant that I had to pay the inflated price Princess set.

While I am looking forward to the cruise, the problem with it is that it’s three times the price of the cargo ship.  Since I am traveling alone they are charging me the price of two passengers because their policy insists on two people to a room.  But since I have no one to split the room with, I also have no one to share the costs with.  The second I forked over the payment to Princess it meant that my funds had officially dipped down to half of what I started with, and so the elephant started looking a bit bloated, like he just cleaned out a Taco Bell at 2AM.  He started bumping into tables, knocking paintings off the walls, and he was circling the same spot on the carpet like he was getting ready to mark his territory.

Up until this point I just haven’t been too concerned with money.  It’s like the deeper and deeper I get into doing things that I love, the less and less important money seems to become.  It just seems so trivial, so soul sucking, so meaningless, but I don’t know what I’d do if I ran out of it.  I purposely have no plan B.  I don’t want one.  I’ve put all my eggs into one basket because what I’m trying to do has to work.

I’ve decided that now is finally the right time to shift some of my attention towards making some money.  Here’s the thing, there are strings attached and it matters how I make the money.

When I told my Mother that I am finally going to get paid to take hotel photos, she enthusiastically said, “Oh that’s great, this is the pot at the end of the rainbow!”



With all due respect, I had to disagree with her and so I said, “This is alright for now, but I won’t let this be the pot at the end of the rainbow and if it is then I have failed.”

While I am so grateful for getting paid today, this is not my goal.  Sure, it sounds great to travel the world and make money as a hotel photographer, but that’s exactly what I don’t want to wind up doing.  That’s what I’ve written about in the past when I mentioned the term ‘shadow artist’, which Julia Cameron coined in her book, The Artist Way.

A ‘shadow artist’ is when an intending artist settles for a shadow career.  It’s a career that is close to the desired art, even parallel to it, but not the art itself.  An example would be when a writer wants to write his or her own novels, but settles for writing high school musicals.  In my case, in terms of my photography, I want to be a photographer that only takes the kinds of creative photos that I want to take like Bill Cunningham did, but instead of doing that, I end up taking family portraits at Sears.

I’m finding that it takes a great deal of honesty and courage to push past this point, especially when it felt so good to open that envelope today.  I’d be lying if I didn’t have visions of doing thousand-dollar photo shoots for five-star hotels in the Maldives the moment that money touched my fingers.  But, ultimately ‘shadow artists’ go through life discontented, filled with a sense of missed purpose and unfilled promise, and I refuse to let that happen.

So, that’s why I’m walking, that’s why I’m schlepping my bags up a steep hill and over gravel stones.  That’s why cars are whizzing by me on this busy highway where the sidewalks run out in 90-degree heat with 100 percent humidity.

As usual I’m the only person on the road right now, which makes me smile with a pride that cannot be explained. I’m grinding my way up this hill for a reason that’s bigger than 10 dollars.  It’s to remind myself that this is not the goal, that while yes, today was a step in the right direction and small victory, the goal is much bigger than this and it will remain much bigger than this.

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