Part 2: The Grind Behind The Curtain

Read Part 1: Love & A Dream Here

We arrived in Panama and were genuinely impressed with ourselves and everything we encountered. Grocery shopping was exciting, negotiating a taxi price in broken Spanish was a thrill, and eating fried red snapper, with sweet plantains, was a dream.

We were sold on location independence and knew we wanted to continue traveling, which, of course, would require self-sufficiency. In short, we needed to learn how to make money on our own. As I did with travel, Jarrell took on his goal of entrepreneurship and led the way (thankfully).

Admittedly, I was one of the many people that graduates from college and thinks they know it all. You weren’t going to tell me about business, because I had dedicated 5 years of my life to memorizing formulas and sitting through accounting lectures. Luckily, my partner was patient with my arrogance.

Jarrell was very adamant about his learning never ending. He was a lifetime student and the world was his classroom. There was no piece of paper, award or graduation date that was going to make him feel as though he no longer needed to learn, and his behavior reflected that.

While I streamed my favorite television shows from our studio apartment in Nicaragua, in between stalking our dwindling bank account, Jarrell binge-watched seminars and motivational speeches, while spending our last dollars on books. I was confused and scared, but I (kinda) trusted him.

Our entrepreneurial journey can be traced by revelations Jarrell experienced from the books he read and lectures he watched. I should mention that when we sold everything before our departure, there were a handful of items we just couldn’t part with. For me it was my collection of photographs and recently worn wedding dress (actually a suit), for Jarrell it was his books. He refused to sell his literary collection and ended up storing hundreds of books in his mother’s attic.

Revelation #1: “We Only Have to Find One Person to Help.” 

Simple enough. We were running out of money, with all of the ships burned, when Jarrell went online, searching for a person to help. He found a client on the other side of the world that wanted a custom tattoo design. He made his first $100. Because we were down to our last hundred dollars, it was about much more than the monetary amount. It was proof that we could make it, we could survive without the ships, and it came minutes before we drowned.

From that point, I watched him work through the night as we traveled through Central America, before settling in Cancun for a month. He designed movie storyboards, logos, tattoos, album covers, everything. I was beyond impressed; it was as if he were printing money. We were receiving daily PayPal notifications of payment, and we could have begun to relax and enjoy the beaches.

But that wasn’t us, so we kept pushing.

Jarrell appeared to be tireless, lost in his two passions – creating visual art and independently making money. He was working so hard that I had to begin to schedule breaks for him so that he didn’t burn out, though that seemed unlikely.

Revelation #2: “We Have to Turn Our Dollars Into Soldiers and Make Them Work for Us.”

It wasn’t about making money and spending it. That was the rat race, and if we wanted to live that way, we could’ve just kept our careers in Corporate America. Jarrell was determined to make money passively. While his creativity was successfully funding our trip, he was exchanging his time for money and that wasn’t the plan.

So we decided to work smarter, not harder. We knew that this was going to take sacrifice and dedication, so we made another pact to give it a go with everything we had. This meant that every dollar we made was to be invested, rather than simply expensed. Basically, outside of necessities, if it didn’t have the potential to make us more money, it wasn’t happening. 

I am a cheapskate accountant, so I took control of minimizing our expenses so that we could invest as much of our income as possible. By this time I was freelance writing and blogging, though my blog was not making any money yet.

This is where I should insert the struggle stories. Maybe how we volunteered to work exchange in several countries – we would work 4 hours a day, a couple of days a week, in exchange for free accommodation and all of our food expenses. But I was so good at vetting great hosts, that our work exchange experiences were rather exceptional, which is not always the case for travelers.

Once, we had a private villa in Italy for three months, with unlimited wine, access to a private pool, and any food we requested – in exchange for learning Italian recipes and cooking 4 days a week for guests of the B&B. Another one was dog sitting two shit tzus in London. I still miss those dogs. We dog sat in Mallorca, cat sat in the English countryside, painted a mural in a quaint English village, all sorts of stuff. Again, I would schedule the travel dates and arrangements, and Jarrell would focus on the businesses.

Maybe I should talk about how we didn’t buy a new pair of shoes for a year. Something that was unheard of for two shoe addicts. But we didn’t care. We were so happy, so free, gallivanting around the world, together, launching businesses and chasing Jarrell’s dream, together.

We both understood that it was bigger than us. We always said that our ‘indefinite honeymoon’ was our boot camp to parenthood. While that meant checking off my shallow desires like having a white sofa and enjoying a guilt-free adult only trip to Disneyland, it also meant becoming self-sufficient. We don’t want to choose between missing moments in our children’s lives and making money.

So we kept pushing, kept trying, kept budgeting and kept sacrificing.

Revelation #3: “Your Goals Are Limiting Us.”

We’ve always agreed that I am the linear thinker and Jarrell is the creative. I make excel sheets, and Jarrell snickers at said excel sheets.

I go looking for apartments with a price filter within our budget, while Jarrell peruses luxury real estate as a past time. I am the realist and he is the dreamer, which is hard for me to admit as a hopeless romantic daydreamer who writes fictional short stories for fun.

Every month we had a goal for revenue and a detailed budget – an allotment for investments into each venture, an allotment for groceries, a travel expense account – and a pretty color-coded excel sheet, that only I could understand, explaining where every dollar would go.

We were house sitting in Mallorca, caring for two loving Labradors in an apartment not big enough for two shit tzus. Drinking a carton of 60-cent wine, Jarrell proclaimed that it was time to step it up. We had to take it to the next level. No more house sitting, no more work exchange. We had spent an entire year learning how to make money on our own, subsequently building online businesses. Part of the reason that they weren’t exceling was because they didn’t have to.

We only needed to make enough to cover small bills, because a major expense – accommodation – was covered. My monthly goals were never missed, whatever amount I deemed necessary for survival, we would find a way to make. My budgets were effectively serving as training wheels. And it was time to take the training wheels off.

In an analogy that I will never forget I was taught why my goals were limiting us. By setting a benchmark of $5,000 a month, I was saying that $10,000 a month was too much, out of the question. I was more concerned with reaching my goals than succeeding. Was it more successful to achieve 100% of a $5,000 goal, or 50% of a $20,000 goal? By focusing on surviving I was preventing us from thriving.

So, naturally, we burned the ships again. No more house sitting or work exchange. We were going to run these businesses like our life(styles) depended on it. We were going to live our dreams, and goddammit, we were gonna do it in style!

There’s nothing wrong with tasting your dream and realizing that you’d like it sweeter. At one point we both thought that if we had the chance to travel the world, and make money on our own, we would be completely satisfied.

But that wasn’t us. So we decided to have our cake and eat it too.

Part 2 of 3.

Read Part 3: The Roadmap to Success Now


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  1. “In an analogy that I will never forget I was taught why my goals were limiting us. By setting a benchmark of $5,000 a month, I was saying that $10,000 a month was too much, out of the question. I was more concerned with reaching my goals than succeeding. Was it more successful to achieve 100% of a $5,000 goal, or 50% of a $20,000 goal? By focusing on surviving I was preventing us from thriving.”


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