Baking in Layers of Challenge Makes a Sweeter Life

Paulie’s Wild Life
6 min readJul 14, 2020

How well do we really know ourselves? Do we really know what drives us deep down? For me, I didn’t find out until much later in life. I didn’t realize a lot of things straight away about myself. For example, I didn’t realize I was talented mathematically until I was 25. I also didn’t realize my love of the outdoors until well after that. It also took quite a number of people asking me why I would do certain things the way I did them, such as hiking in the desert in the middle of the July heat as I wrote about in a prior post. It wasn’t until much later that I realized that life was more about the challenge than the goal.

In college, I didn’t really know what I wanted to do for a career. I don’t think anyone truly knows, save a select few. I double majored in economics and politics and off I went into the real world. Little did I know, this was the first inkling into a personality trait I recently realized I had. My first job wasn’t particularly interesting, though I was glad I had it at the time. Within a few weeks, I automated my entire job and went off on the Wikipedia tour. We’ve all been there: keep clicking links to see where we wind up on the online intellectual journey. I realized then, that not only did I need something more challenging, I needed to do the most challenging job in finance.

In the field of finance, the most respected people, at least from a point of intellect, are the quants. These are the math whizzes, the ones that come up with the best solutions to the hardest problems using quantitative methods. In my 20’s, it was all about getting respect. I would end up gaining a whole lot more than respect, I would get a whole new taste for life.

One cannot just become a quant by wishing upon a star. Most of us have to go through some form of graduate-level training. I applied to a few math programs and was summarily dismissed from every single one. My first stumble along the way was to not have all the prerequisite classes. Silly me, jumping in head first without looking. But this did not deter me. Not only did I get the minimum prerequisites, but I also ended up picking up a third major, in mathematics. Going well beyond the minimum became the norm.

After dusting myself off from my stumble, I was admitted into a few programs. I’m not really sure what prompted me to do so at the time, but I ended up doing two masters degrees, simultaneously. As if one wasn’t enough, I guess I needed another challenge. While most people took maybe 3 classes per semester and complained about the difficulty, I took 6, like a champ.

In my first master’s degree, my thesis paper on mathematical finance was where I learned to enjoy really enjoy the process of these challenges. My friend had exclaimed that the professor in this class added additional layers of “tedious” just to torture us all. I had to model out an esoteric financial instrument with some added complexities. I had to code the whole thing up in C++. I had to write the whole thing up, not in Microsoft Word mind you, but in a word processing language called Latex. However, I didn’t view this as layers of tedious, but as additional levels of challenge. For me it wasn’t torture, but just another challenge to overcome. That became the mantra for my life from then on.

Now I thrive on putting myself through these additional levels of challenge.

Living in New York, my hiking and outdoor options are fairly limited. While hiking in the Hudson Valley is nice in the fall to watch the leaves turn colors, it just doesn’t have that rigor for which I clamor. There are some steep trails with some decent elevation gain, but if I’m not getting above a tree line and gasping for air, it doesn’t count. In order to assuage that lame elevation issue, as well as escape the summer humidity, I escape to Colorado almost every year.

Colorado provides me with those additional layers of challenge I thrive on. You always hear the term “Mile High City” yet you rarely hear the term 14’er. Colorado is home to the largest collection of mountain peaks over 14,000 feet (4,267 meters) in the lower 48 states. This is a perfect place for someone looking for a challenge.

The first time I went to Colorado was to climb its highest peak, Mount Elbert. Why start small? Doing some cursory research, I saw that it was a simple walk up. At the time, a good friend of mine from graduate school was living in Denver so I recruited him on this little escapade. We spent some time in Denver, and then we drove out to Leadville, elevation 10,151 feet (3,094 meters). I didn’t feel any different in the Mile-High City, but I certainly started feeling the effects of the nearly two mile high city of Leadville. We checked into our motel and went to dinner at a nearby pub. Something very strange happened, beers seemed to have an inversely proportional effect. After drinking just half a beer, it felt like I had two beers! When we got back to the hotel and in the parking lot, I walked through someone’s cigarette smoke, and I couldn’t stop coughing for about 15 minutes. This was not the oxygen rich environment I had been used to!

The next morning, we got up early around 4am and drove out to the Mount Elbert trailhead. It was still dark when we arrived. We laced up our boots, got on all our layers, and we trotted off through the dawn. The sun began to peek through the trees which were themselves beginning to thin out the further we were on the trail.

Above a certain elevation, vegetation becomes sparse. When we broke the tree line, we saw these rolling mountains full of fantastical shades of green, blue, gray, and even yellow from the hay-like grass. This is where we stashed our bags, as the higher we went, the tougher it became to hike due to the thinning oxygen.

My friend, who I must admit, is much stronger than I am, paced ahead and made it to the summit about a half hour before I did. In the final half hour of my ascent, my steps became miniscule; I stopped every 10 or so steps to rest. I didn’t think I would make it. But then I saw my friend descending. He gave me some words of encouragement before descending to warm up. Even for an August day, it was fairly cold at this elevation.

I trudged up on what seemed like a death march, but then I finally made it to the top of Colorado. What a sight it was to behold! I saw all the mountains around me and felt as if I had conquered them all. After taking a few pictures and enjoying the view, snow began to fall and my hands were freezing. I began my descent.

On the way down from that mountain on that day, I finally realized that it wasn’t the goal, but rather the type of journey that I enjoyed. To me, the journey was that much more enjoyable if I added in some extra difficulties like doing two masters degrees simultaneously and hiking in high alpine environments. The extra challenges I imposed on myself added in the flavor that had been missing in my life. Like a chef at a high-priced Michelin star restaurant, I began to add in these flavors into other areas of my life. I realized that adding in these layers of challenge just makes achieving your goal that much sweeter. I have to say, I developed one hell of a sweet tooth!

I summited Mount Elbert, at 14,440 feet (4,400 meters) it is tallest peak in Colorado on August 31, 2014.

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Paulie’s Wild Life

I am a lover of the outdoors and everything you can do outside. Maintaining an active and healthy lifestyle while having fun is my passion.