The Constant Quest For A Clean Slate

Stepping out of my apartment building on a sunny morning in Cheonan, South Korea I started my new daily walk on the shared use path that leads all the way to my English teaching job in the village about half a mile away. I was there for a new beginning, or rather a clean break from what I had been struggling to establish for the past 8 years since graduating undergrad.

I lived above a 7/11 convenience store, for which the novelty of shopping had not quite worn off yet as convenience stores in South Korea were so totally different from anything I had experienced in the US. These were places that people came quite literally around the clock. Stuffed rice balls for breakfast, pre-packaged sandwiches that were actually tasty for lunch, the lukewarm vitamin C drinks held in tiny specialized warming boxes for when the germs from working with kids started to wear down your immune system and to the beer and soju with accompanied drinking snacks for the wee hours after work. I thought about stepping in the store, but remembered that I was going to meet up with a few of my fellow English teachers at the cafe downstairs from the English Academy about an hour before we needed to punch in for the day.

The walking path was paved with a softer, more spongy material than the rest of the concrete surrounding the sidewalks and roads with polished handrails leading you as you walked through the outdoor playgrounds and exercise stations scattered throughout the neighborhood. The building that I lived in was situated within an older neighborhood, probably built about ten years prior to my arrival in 2014. I never got to know any of my neighbors in a meaningful way, but greeted anyone who made eye contact with me with a smile, nod and “anyang haseo” as I slowly made my way to work. The building I worked in was a high rise within a much newer neighborhood that I would learn was home to mostly wealthy families, many of whose children studied at the hagwon, or academy, that I taught at.

I didn’t quite know it yet, but this was approximately the last time I’d have that clean reset on life that I had managed to enjoy several times throughout my 20’s. Growing up in a tightly packed urban neighborhood in Worcester, Massachusetts, I always had the sense that I needed more space and opportunity than my home or origin would provide. Graduating undergrad in 2006 I was quickly met with the reality that in Boston I was simultaneously the type of curious, earnest and hard working person that had a lot to offer the world, with relatively few if any distinguishing academic or social connections to be of much use to me as the economy quickly descended in into a bad recession within a year from me getting my diploma.

The early days of social media had excited me greatly – not because I had some idea that personal branding and social networking would be the actual currency that would carry me forward in my career and life into the future, but because it gave me a chance to explore who I was and discover my own voice and share my story. I loved writing but struggled to get published beyond my college newspaper which I was the managing editor of. I would pick up literary journals at the bookstores near Harvard Square and Downtown Crossing in Boston, pour over them page to page and be electrified by the power of the creative writing in them.

I even played with the idea of doing a Masters of Fine Arts degree, getting a job at a newspaper or some other type of creative endeavor as a way to continue to hone my own writing abilities, however as the job market and economy steadily got worse and the student loan statements I’d receive showed a huge payment due each month with interest accruing forced me to curb my creative hopes for a career in self expression. I simply had to get as much work as possible to pay rent and my student loan and hope that I could find some slack in my own life to become the type of creative person I believed myself to be.

To be honest I have not read much good creative writing on the topics of student loans, however my own had become quite the literary device for my own character development from the beginning of my journey out of the apartment building I had grown up in with my mother and sister. As a single mother, my mom did just about everything she could to keep my sister and I in a small private Catholic school downtown in the city from kindergarten, all the way through our respective high school years. Though we were raised Catholic, being of some Irish Catholic descent, I wouldn’t say the lifestyle of the devout was something my family or many others of similar background I knew kept us in Catholic school. My mom worked nights as a secretary at the labor and delivery department of a local hospital while my grandparents who lived in the apartment below us would look after us while she was away.

With my father being out of the picture since I was 2 years old, the path for my sister and I to find our way in the local public schools as latch key kids was not one my mom wanted for us. Many of the Catholic schools in the city were places where people of pretty much any social, racial, economic or even religious background could find a secure place to learn if they demonstrated a willingness to learn, comply with some religious behavioral norms and of course share work. My mom was a trained seamstress before she began what would become her career as a medical secretary and sewed costumes for the many musicals and plays put on by my school. The schools offered meal support with breakfast and lunch if needed, childcare before and after school and it generally was a place my mom felt safe leaving us while she was either working or sleeping off the stress of her night shifts. The work she did in exchange for a greatly reduced tuition created about as stable of an environment for my sister and I to grow up in among an inner city marred by turmoil in the 90’s and 2000’s and despite my fundamentally rebellious nature which got me in trouble a lot, I was grateful.

Up through grade school and into the all-boys Catholic high school I got into just outside of the city, I worked hard to achieve what I could academically and grow into a young man that I’d recognize as being decent despite an often rocky home life. While my school was a haven for me as an insecure boy growing up, there were still many potential dangers I faced on a day to day basis, whether walking home a few blocks from the bus stop to seeing drug use and criminal activity around and within the apartment building I grew up in, I saw my path to bettering myself and making a better life as not guaranteed but something I’d need to focus on with intense dedication and steadfastness if I was going to avoid the pitfalls that some in my extended family and friend groups would.

Truthfully I wasn’t always steadfast – despite deep down appreciating what my mother sacrificed for my sister and I with the help of my grandparents and some other generous and more well off extended family members, I was more often than not uncomfortable with my situation and myself as a person. Having a father who’d pop in and out of my life with little explanation for his reappearance and just as little about his eventual departure, I’d be left questioning my own worthiness as a person and as a child. My relationship with my mother was strained as well throughout my childhood into adulthood as the toll from her work and unhealthy lifestyle of late nights and poor health choices left her with little energy to interact with my sister and I on a day to day basis. Though I’d eventually grow extremely close with my sister and could rely on my grandmother downstairs to always lend a caring ear to me, I often felt alone in my desire to discover and nurture who I was.

While I was not an all star academic, I was above average in spurts throughout my schooling. Some years the depression resulting from family problems lead me to withdraw and barely eek by a passing grade, yet in the years that would define my admission into high school and college I managed to rally and focus on achieving the grades I was capable of and get to the next step of what I hoped would be my chance to pass to the next stage of my development. High school was a big opportunity for me as it was the first time I had mustered the courage to aim for a specific goal that I didn’t quite believe I was capable of. My high school was one of the best in the region and was very expensive – I would need to perform well on the admissions test and keep my grades up to have enough financial aid for it to be feasible financially for my mother. With encouragement and some financial help from extended family members, my mother was able to get me through high school financially while I tried to paint a picture for myself of how college could change my life and put me on the path I so desperately wanted.

After high school I learned that I enjoyed nothing more than new beginnings. Up until I was about 18 I was just shifting about my own social circles and circumstances – college was very different. College was like going to summer camp, and therein lies the problem, for me at least.

I got into a variety of decent colleges and after touring a bunch of them with my best friends' parents. They both were Harvard graduates with PhDs and had very strong opinions about my chance at becoming something greater through college. One of the more life altering pieces of advice they gave me that I clearly remember is being told that college debt was “good debt.” This wasn’t an idiom that they themselves invented, as I’d heard it before, but they insisted that picking a school based on how affordable it was or wasn’t was a terrible idea and that I should put the idea of money aside entirely and think of the experience holistically.

Obviously a 17 year old kid is impressionable, but I don’t for a second blame anyone for my decision to take on six figures of student debt but myself. I was desperate for some opportunity for a bigger and better life, I wanted to make my family proud of me (which was a goal I didn’t know was so misguided), and honestly, if I had accepted my lot in life and not pursued higher education I have not clue where I would be right now – and given the examples of other family members life paths, I’d guess it wouldn’t be what I’d want.

I got into and accepted admission from UMass Dartmouth, a state school in Massachusetts. My initial course of study was accounting because I read on an aptitude test I took in high school that it was well suited for my personality and paid relatively well. I had no clue if I liked it, I did no experiments or research on the topic – I just went for it. I got into other schools as well and even got a full scholarship to a school in New Jersey that I was told by multiple people was just a party haven and not actually a school. As I’d come to find out, pretty much all colleges are and can be defined that way – it’s what you as an attending student choose to do when you get there.

UMass Dartmouth was a rough start for my adult years. As I said before, it felt like I was in summer camp and I acted accordingly. I wound up being paired with a roommate in the dorms that I knew from high school, who I wouldn’t say was a friend, but someone I felt more comfortable with than a stranger. Overwhelmed by the newness of everything I over extended myself socially and created a persona of a fun guy with a rough edge, as I was from a rough neighborhood in a rough city after all. Well actually I just wanted to compensate for the fact that I felt I didn’t have much to offer the world from my inner self and I had no prominent family accolades to lean on. I was lost.

Simply put, I drank too much, socialized with exciting people who also seemed to not actually care about being in college and followed the crowd into the likely end – poor grades, poor physical and mental health and an existential crisis of what I was even doing there. I cringe to think that the friends I thought I had made liked me because I was entertaining to be around when I was drunk, willing to do anything to be liked and laughed at because I didn’t think I was worthy of being appreciated otherwise. By the end of my second year I had a hard depressing look at myself and questioned what the end goal of all of this was. I wasn’t enjoying the subjects I was studying, I wasn’t on a good path in terms of academic performance and I wanted out.

In the evenings at Umass I’d drive the campus shuttle bus, which was a decent job to pass time and make some extra money. One night I parked the van on a service road away from the main part of campus and called my mom and started crying, telling her that I felt lost and I didn’t know what I was doing anymore. She told me that I should consider transferring schools and studying something I would be more interested in. At the risk of making another change that would cost me even more money, I decided to apply to schools elsewhere. I was limited to where I could transfer given my poor grades, but I found Suffolk University in Boston as a school I could likely get admitted to and study a subject I knew I liked from a very young age – writing.

I left UMass without much fanfare, eventually realizing that most of my friends there were not going to be long-lasting. I increased my student loan massively by borrowing tuition costs plus living expenses in the Boston area and began my studies.

My family and friends from high school were thrilled at my choice initially – I had an old apartment in the North End of Boston, a lively Italian neighborhood with lots of restaurants and tourists day and night. Everyone I knew was excited to visit, which felt good. I felt like I was once again worthy of being someone in this new-new beginning. The opportunities for fun and partying were still there and part of me was worried I’d fall into the old ways I found myself at Umass, however things were different enough this time for me to have an entirely different experience.

The Suffolk campus in Boston was distributed among the old neighborhood of Beacon Hill, where the State House and many government and business buildings were mixed among swanky but small apartments on cobblestone roads. Unlike Umass I wasn’t living in any sort of dormitory but instead an apartment about a mile off campus that I’d walk from every day. My roommate was a Freshman, but somehow a remarkable hybrid of serious political science student and occasional party animal. It was nice having someone to talk about intellectual topics with and learn from even though he was younger and seemingly less mature than me. On campus I was among my peers mostly in class only. In ways that I’d act out and try to be overly social in the dormitory at Umass by forcing new relationships by fake extroversion and eventual partying, I’d strike up conversations from time to time with other students in the classroom, often about subjects we were studying and only if I thought there was some interesting connection I’d make the effort to hang out with them outside of school hours. Otherwise after class it was mostly straight back to my apartment to study or to the part time jobs I’d eventually find for extra money.

As time passed I found myself much more comfortable in this new routine, being able to have the alone time to myself required to recharge my social battery, explore new books, write more and actually delve deep into my course work that I learned to really enjoy. After my first semester I was surprised to learn that except for one B I had received in a required math class, I had managed to get A’s on everything else in the class I took. I worked up the courage to apply to the student newspaper as a writer and started publishing weekly rather than just writing essays in my journal about my personal feelings on life. My best friend’s mom also helped me get an internship at a state agency she ran adjacent to the State House doing some writing work.

This period is where I started to feel like I was starting to put my true self into the world and developing on a path that meant something to me, rather than appearing outwardly similar to whatever social group I was in and seeking approval through being the crazy, fun, often stupid acting guy who drank too much at parties and said and did things he normally wished he hadn’t otherwise.

Additionally after two semesters of getting better grades than I ever had in my prior academic career I made the dean's list and was flagged as a good candidate to take part in a pilot student transfer program with the graduate literature studies department of Charles University in Prague, Czech Republic hosted by a literature professor at my school.

My tuition was paid with student loans that were accumulating interest at an alarming rate that I was painfully unaware of at the time, but as I write this now I somewhat painfully recognize that I was finally in a position of growing into a person that I was more proud of than I had ever been in my life to that point. I was of adult age, picking my own path, putting in the work and taking advantage of opportunities that were good for me, rather than just passively passing through the social conveyor belt of life doing what was easiest and most expected of me. For the first time in my life I felt a sense of self-confidence that I had yearned for my entire life. I had grown into something better and I believed good things would continue to come to me if I tried to do the right thing and work hard.

I took the opportunity to go to Prague and study at one of the oldest universities in Europe. I did wind up in a dorm room there, which had its pitfalls associated with my previous time at UMass Dartmouth, however that didn’t define my trip. While I certainly partied too much, I also was able to break away from the people I lived with and delve deep into the art, culture, people and places of the Czech Republic and make friends outside of the cohort of 5 students I came to Prague with. The classes were far more challenging, but also more enjoyable than anything I’d taken before. Studying at the graduate school I felt pride in being able to keep up and achieve good grades among international students who were elite in their own right from all over Europe. Before coming to Prague I couldn’t have found it on a map or told you anything about its history, yet the experience of living and studying there blew apart the walls enclosing my mind as a city kid who’s world started and ended within a 50 mile radius save for some vacations prior.

While in Prague I became close with one of my fellow students from the cohort who was also managing editor of the student newspaper. While we had somewhat of an antagonistic relationship on an intellectual level, given we were from different backgrounds, her from the South and myself a New Englander, she had seen my writing through the courses we did together, my ability to edit others work and she offered me the Managing Editor position at the school newspaper after we got back as she had planned to become Editor in Chief. I was honored and a bit nervous about the opportunity but took it and wound up loving the experience. I enjoyed the staff writers who became a close group of peers up until graduation.

As the two years at Suffolk drew to a close I had started to feel like a child at home who didn’t want to leave the home I’d made for myself. I had proven myself capable of doing good work through my internship, journalism, academics and the prospect of going into the real world felt like a step function change I wasn’t prepared for. In fact, I was not financially prepared for it at all as the student loan loomed large and I was banking on getting a good job after graduation to start paying down my debt so I could have the bigger and better life I had dreamed of and promised myself.

After graduating in 2006 the reality of the jobs I was qualified to take, the salary I required to pay my loans and pay for my expenses as well, did not match. I had developed enough skills and references to get a job in journalism, which I badly wanted. But the starting salaries which were well under $30,000 a year were nowhere near to make ends meet. This started the slow creep away from the dream of writing for a living to doing something that used my skills in the private sector that could pay me more. I wasn’t aware of it at the time but the battle to bridge the gap between what I loved to do and what I had to do was just getting started and I had no idea how hard it would be and how much it would define my life for decades to come.

Working temp job after temp job, not getting any long term employment despite submitting over a thousand resumes to jobs I wanted and seeing my bank account get close to $0 month after month was demoralizing. Not just because I didn’t have any money to do fun things, but also the rejection leading to self doubt about my work done to that point put me in a position that felt desperate. I couldn’t afford to live anywhere close to the city so I kept finding shorter term rentals further and further away from downtown Boston until I gave up the dream of living in the city I’d grown to love. I always said to myself that Boston, like many other places in America, was great if you had money to enjoy it. In college I felt comfortable and soaked it all in because I was living off money I borrowed for my student loan. Now that reality had set in and I was not able to generate the income needed to sustain even a basic productive existence within a reasonable commute, I figured it was maybe time to try to move back to Worcester where it was much cheaper and maybe find a job there and see if I could make a life where I’d grown up.

To my surprise and disappointment the big city skills and experience I had didn’t even translate to being especially in demand in a smaller pond of a city. It was beyond frustrating. I’d eventually get a job offer at a senior housing development in the Newton area, outside of Boston. Even though it was outside of Boston, commuting there from Worcester was still 90 minutes minimum in traffic. It was an easy job, managing fun activities for the seniors living there like outings and cultural programming. My internship for the state was my in there. I was only employed for about six months there and worked for a group of women who, while not sure about my rough edges as a city kid with a journalism degree, were kind and supportive of me. My boss there pulled me aside one day about 6 months in and told me in so many words that she thought this was a dead end job for me and that I should either try to get a social work masters degree and move up the human services ladder there or probably look elsewhere. I wasn’t making much money there, of course, but I knew she was right.

I had continued to submit applications and got another offer from a company in Watertown, a town next to Newton that paid about $10,000 more a year than I was making at the senior housing job. It was a software company that sold marketing insights to big companies and while I knew nothing of software at the time, I took the opportunity to just do basic support for customers and learn the job. What would become known as the Great Recession was not in full swing, though I wasn’t really aware of it at the time. I spent about a year and a half in that job getting good at the day to day activities, making myself more valuable while not really wanting to get promoted as the corporate structure seemed absolutely miserable. I’d started reading blogs online about people who were stuck in their careers and trying to cut a path to something better. The messages really resonated with me as I felt I had no special Ivy League background to propel me into the circles of power and wealth and I even started my own blog to share my own story.

The feeling of others discovering my writing was euphoric for me. I felt like I was being seen for the first time in my life and started developing friendships with other people going through the same stuff I was. My blog would eventually get picked up for syndication by a blogging community out of Madison, Wisconsin founded by an author of a book about my generation, Millennials, taking the roundabout route to build a life outside of the normal corporate ladder. There was no shame in job hopping and taking lateral promotions strategically if it meant more money and opportunity. As I had always had a raw spot in my heart towards shirking authority I really embraced the idea that if I was going to succeed in any meaningful way that I’d have to be aggressive about it and do it for myself rather than wait for others to do it for me.

This blog community eventually hired me to manage the community as I’d developed relationships with many of the other bloggers who joined. They offered me a small relocation package to move to Madison, Wisconsin which was incredibly exciting and scary at the same time. Even though I’d studied abroad in Prague, I had never really lived so far away from home truly on my own. As I drove a Uhaul away from my home in Worcester waving goodbye to my mom and sister with tears in my eyes, I was totally unsure about what lay ahead of me.

Though this job was short lived, as I got laid off 9 months later due to lack of revenue at the company, it ultimately set the tone for how I’d approach my career for my adult life to come. I’d manage to conjure an UNcommon role at an uncommon company not because I had some specific degree from a prestigious college, but because I had a vision and I was willing to put myself out there. I couldn’t find any jobs in Madison after the layoff and after licking my wounds for a brief moment in shame for not succeeding I decided to move to Boulder, Colorado, which was a growing tech hub with lots of startup opportunities.

From 2006-2014 I had managed to keep myself barely afloat financially by taking jobs using my community building and writing skills at startup after startup. Most of my jobs didn’t last more than a year. I wasn’t a bad employee that couldn’t hold a job, but I rarely worked at companies that could sustain me in the long term. I was hoping that I’d join some early stage team with equity and have that life changing financial payout you’d hear about from Silicon Valley employees who were early at Facebook, Google, etc. That never happened. However, to my own sense of self-worth, I did grow relationships through this string of short jobs. I never left on bad terms and despite the discomfort of explaining why most of my jobs were short lived, I always had references that said I was a good guy, but just let go for financial reasons. A small consolation.

New beginning after new beginning. As I write this I recall that the self talk and story telling I had been doing up until recently was that my 20’s were mostly just a shit show of financial duress, tough breakups with girlfriends who couldn’t appreciate that I was a work in progress and being a victim to my own circumstances. It’s easy to paint the picture that you’re a victim of your own life when going through hardships, but in hindsight it’s utterly clear that many of the small decisions I made along the way amounted to where I had found myself in life and I was responsible for most of what happened.

I think for the first time maybe ever while writing this, that this period in my life was not “the dark years” or a “lost decade” as I’d flippantly described them before. But rather the time of my life that I shed the cloak of limiting self beliefs that lead me to believe that I wasn’t worthy to share my gifts with the world, take in beauty of serendipity and be who I was at the moment and be okay with it.

I wish I had been kinder to myself back then. If there was one major plot device that held me back from actually creating an easier life for myself, it was the student loan that I took for college. Then again, dealing with it as I created my life post-college and the opportunities I was able to experience during college also created the life I have now, which I am endlessly grateful for. I didn’t know it at the time, but when I moved to South Korea to teach English after losing my job in Colorado and breaking up with my then girlfriend, I’d find a new beginning once more. However the difference this time for me was that I was granted the opportunity to put many of the lessons learned consciously or subconsciously into action to start to grow into the man I wanted to be.

New beginnings don’t always have to mean wiping the slate clean and starting from scratch. How I got to the pivotal point in my life in South Korea was just as unexpected to me as the path I’d find myself going forward. From meeting my wife, to having a child, to learning to invest and use my money in a wiser and more conservation-minded manner are just a few examples of how I had to let life show me the path and being faithful to the process while I put in the work to make each new initiative take hold.

As I find myself in “middle age” territory post 40 years old, I’m enamored with the fact that life’s path doesn’t amount to a clearly marked google maps guide to an end destination. I’m starting to enjoy the feeling of being ushered down the current of life’s rivers and tributaries, appreciating my family and friends as they’ve accompanied me and nodding in thanks to the people from my past who also graciously gave of their time and love who may not be a part of my day-to-day life anymore.