Why Quitting My Six Figure Job Was Easier Than Choosing An Ice Cream Flavor

Growing up, my family didn’t have much money, so we never took any holidays. What I knew of places like Paris, Cairo, New York, or Venice, I learned from hopping from one casino to the next whenever we drove from Los Angeles to Las Vegas. I didn’t leave the US until I was 20. In fact, prior to flying away to go to college in Philadelphia, I had only been on two flights in my life.

So what I missed out on before this point, I’ve been making up for ever since. I’ve now traveled to over 70 countries, many of them multiple times, and more and more now for extended periods in one place. I’ve met so many incredible people along and have shared countless adventures with them.

I’ve turned a hobby of taking photographs into a way of life where I can tell stories and inspire others to reach for something just a little bit out of their reach. I’ve done it pretty economically too, and that’s made all the difference.

Time vs Money

I studied economics at the Wharton School of Business, and perhaps the most important lesson I’ve learned from my time there and subsequently working at the largest asset management firm in the world is this: time is your most precious commodity.

Sure, in our world, it’s pretty tough to live without money, but it’s time that levels the playing field between everyone. I learned this in the most random of ways.

While earning a fairly good salary at the age of 23, I was able to squeeze out of every last vacation day I had to go backpacking to new countries. I stayed in hostels, I bargained for everything, and I took the cheaper form of transportation whenever it made sense. It rejuvenated me to return to the grind each time. Until I was went to Costa Rica. There I became friends with a random group of people, who didn’t care what I “did”. The question never came up.

After a week together, they asked if I wanted to head over to Nicaragua with them for a few days for some adventuring. It seemed so simple, but reluctantly, I told them I had to go home to a chorus of “boos” and “whys.” I explained that I had a meeting with Deutsche Bank on Monday to figure out our pricing contracts for a new group of funds…

No one cared. They were bummed. I was bummed, but that’s just how it goes. I got it, but it still bugged me. For the first time, I was earning enough to be able to go almost anywhere I wanted, and still I couldn’t.

But Why I Can’t Travel More?

And then I remembered meeting others before who somehow had this freedom I didn’t. I remembered a feeling of jealousy grow whenever I heard that they had been on the road for 4 months or 6 months or in the case of this one girl traveling on her own, 15 months. They all worked for a bit to save up for the trip and then found a country to work in when they ran out of money. And then they were off again. Rinse and repeat.

I ran the numbers in my head and this is what came out. As much as I was making, a large part was taken out to pay Uncle Sam, and then a chunk for my San Francisco rent. And then some for all the happy hours, the eating out, the taxi rides, the new clothes, and the new gadgets. I made a little more each year, but also spent more. At the end of the year, I saved up a bit, but not nearly as much as I thought. For some of my colleagues, they hardly saved anything at all.

So despite a six figure salary, for which I gave up 48 weeks out of the year, I had very little to show for it, other than that I made it through the year. But so did ‘dreadlocks’ from Australia who I met in Vietnam. Except, he worked for a grand total of 16 weeks, across a few different jobs in a few different countries. He too had very little to show for it, other than the fact that he was traveling and just having fun for the other 36 weeks. This made very little sense at all.

And it made perfect sense sometime in the fall of 2010.

I had been working pretty hard and getting recognition in the company. The next promotion I was gunning was for was to leapfrog for a Director position, running my own group. A group that I’d be in charge of. No more sneaking out. No more two weeks away from my Blackberry. Definitely no more backpacking and staying in hostels walking barefoot everywhere. How would that look for the company?

I worked out the numbers and there was a definitely a number for which I was about to mortgage away the rest of my twenties. When everything was accounted for, it was not a very impressive number.

So About Ice Cream

I love good ice cream. You always have to get it in a waffle cone. Two scoops. Completely different flavors like hazelnut gelato and mango sorbet, or mint pistachio and strawberry rhubarb. You pick the dominant flavor and put that in first. And you never eat it with a spoon. By licking it, you maximize the surface area contact to volume ratio.

When you put a spoonful of ice cream in your mouth, you’re just tasting the outside surface area. The rest is mostly swallowed away. What a waste. You’re taking in the calories and missing out on the potential mouth/tongue contact. Amateur hour.

When I’m on the road and find an ice cream place, it’s incredibly difficult for me to choose a flavor or two. There are so many to choose from, and I want to make sure I’ve made the right decision for the next 10-15 minutes of enjoyment. Who knows when I’ll be back again. Why not just get more you ask? Because Carl, there is too much of a good thing.

It’s agonizingly difficult and the stress is unnecessarily high, save for knowing that as soon as I decide, I will embark on a flavor trip fo velvety goodness. Unless I made the wrong choice. You get the point.

So on that fateful day in the fall of 2010, I had a moment of clarity. If I stayed and locked myself in for that Director position, I’d be looking at 3-5 years before I can make another decision. I’d be giving up the rest of my twenties to this job. Of course I can always earn a lot of money and then travel at some point in the future (maybe), but it became suffocatingly clear that if I stayed, I could never do so again in my twenties. It was an existential dilemma I was facing.

But of course I had done the math, and so the decision was pretty clear. At the moment, it simply wasn’t worth it for me to stay. I didn’t know what to do next, but I felt like my time was just more valuable doing something else other than working. The decision was easier than figuring out which two ice cream flavors to pick the next time I was at Salt & Straw in Portland.

I Quit.

So I quit. It was a little more complicated than that, but for all intents and purposes, I was no longer an employee of the company. And then I bought a one way ticket to London to begin what would become a year of traveling around the world. That part was a logical decision too. If I hadn’t figured out what I wanted to do next already, sitting there wouldn’t change that. I needed to be somewhere else. Doing something else. So why not travel and figure it out abroad.

It’s coming on 9 years now and I haven’t stopped traveling. Somewhere between Morocco and Indonesia, I decided to pursue photography full time. And then somewhere between Thailand and Argentina, I decided to create a blog so I can document the journey. So here we are. I’ve learned a lot of things about how all this works and I’ve had a damn good time doing it. It’s definitely been a learning process. Some things came easier than others and I’ve certainly made mistakes a long the way. Some sucked, others were learning experiences, and a few turned into some of the most wonderful, unexpected things I could not have planned for if I had crystal ball. Hopefully I can help you avoid some of easy pitfalls if you are looking to do the same thing. Feel free to engage and reach out.