What were the three most important decisions of your life?

A recent Quora question asked, “What were the three most important decisions of your life?”

I’ve been debating this question for almost a month, and I have finally settled on three. While many decisions could have occupied these three spots, I decided to favor the toughest and most unlikely decisions of my life rather than the ones that were easy and obvious.

For example, deciding to marry Elysha is probably the most important decision of my life, but it was barely a decision. Who wouldn’t want to marry Elysha if given the chance? It was a no-brainer.

Instead, I found three extremely important decisions in my life that could have gone either way and changed the course of my life forever.

1. Maintaining my innocence when charged with grand larceny and embezzlement.

While being questioned about a crime that I did not commit, the police almost had me convinced to confess to the crime rather than risk a lengthy prison sentence. I spent a minute in a mop closet pondering that decision and ultimately decided to stick to the truth, but it was a close call. The police can apply a great deal of pressure in these moments, particularly when you are a 19 year-old kid without any parents, any money or an attorney.

The result was a brief period of homelessness, 18 months spent working 80 hours a week at two different jobs in order to pay a $25,000 attorney’s bill, a permanent case of post traumatic stress disorder as a result of an armed robbery, and a trial where I was found not guilty.

Had I confessed and accepted their plea deal, I could not have become a teacher. 

2. Choosing West Hartford Public Schools over Newington Public Schools.

In the summer of 1999, my hometown of Newington, CT had offered me a permanent position as third grade teacher in one of their elementary schools. I was asked for a day to consider their offer, but the wait time was merely perfunctory. I was taking the job.

During that 24 hour period, I received a call from a principal in West Hartford requesting an interview. Out of curiosity more than anything else, I agreed to speak to him that day. Three hours later, he had offered me a one year position covering a second grade teacher on maternity leave.

The permanent position in Newington would have been the wise and sensible choice. It was in my hometown and would provide me with long-term stability in a time when teaching jobs were hard to find. But I was impressed by the principal, his commitment to children, and his support for the arts. After much debate, I decided upon the one year position in West Hartford, and 16 years later, I am still teaching in the same school.


That decision changed my life. I met my wife while teaching at that school school. I met five of my closest friends while teaching, including the principal, who has since retired but remains one of my closest friends today. I met my son’s and daughter’s god parents while teaching at that school. Many of my former students are my children’s favorite babysitters, and one of my first students is our primary babysitter and like a member of the family.

I was given the freedom to create a classroom environment that placed reading, writing, and theater at its core, and I have developed a teaching philosophy that has led to much success in my field. I was named Teacher of the Year in West Hartford and was a finalist for Connecticut Teacher of the Year.

I started playing golf, a game that I love beyond all others, thanks to the friends I met at that school, and ultimately wrote a book about it. 

The school’s community, teachers, students, and parents, have become a second family to me. When my job and my future were threatened several years ago, they rallied around me in ways I could have never expected.

3. Saying yes when my best friend asked me to start a wedding DJ company with him.

In 1997, I was attending Trinity College and Saint Joseph's University fulltime, working on degrees in both English and elementary education. I was also managing a McDonald’s restaurant fulltime and tutoring students part-time at the college’s writing center. I was writing for the college’s newspaper. I was the Treasurer of the Student Senate.

I was busier than I had ever been in my life.

Then Bengi called and asked if I wanted to be a wedding DJ, even though we had no experience or equipment or knowledge of the industry, and I said yes.

Seventeen years later, we remain in business. I have entertained at more than 400 weddings in that time. The DJ company has provided me with much needed income through the lean times of my life.


I met one of my best friends while working as the DJ at his wedding, and that friendship has led to me becoming a Patriots season ticket holder. That same friend led me back into writing when I had given up hope on ever becoming a novelist and professional writer.

I would not have a writing career today had it not been for him. 

I unknowingly gained 17 years of public speaking experience, which allowed me to step into the world of storytelling and public speaking three years ago with unexpected ease and success. I won my first Moth StorySLAM in large part to the experience I gained as a DJ.


I have since competed in 24 Moth StorySLAMs in New York and Boston and won 12 of them. I’ve told stories for Main Stage shows and GrandSLAM championships and many other storytelling organizations in New York, Boston and Hartford. I would not be the storyteller and speaker I am today had I not worked for almost two decades as a wedding DJ.

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Telling stories for The Moth led to the founding of Speak Up, the Hartford-based storytelling organization that my wife and I founded last year. In a little over a year, we have produced eight sell out shows, launched a series of storytelling workshops, and have now been approached by outside venues, asking us to take our show on the road.


The DJ business also led to me becoming ordained as a minister. I have presided over almost 20 weddings, one baptism, and three baby naming ceremonies in that time.

I’d love to hear your three most important decisions if you’re willing to share. Post in the comment sections. Send me an email. Contact me through social media.

Cost effective way of attending college

The New York Times recently ran a piece on the soaring cost of college:

For all borrowers, the average debt in 2011 was $23,300, with 10 percent owing more than $54,000 and 3 percent more than $100,000, the Federal Reserve Bank of New York reports. Average debt for bachelor degree graduates who took out loans ranges from under $10,000 at elite schools like Princeton and Williams College, which have plenty of wealthy students and enormous endowments, to nearly $50,000 at some private colleges with less affluent students and less financial aid.

NPR offered this visual of the increasing costs of higher education:


With justifiable concern over the high cost of a college degree, I find myself constantly reminding people that there are alternatives to the traditional accumulation of debt in pursuit of a college diploma, including the slightly unorthodox path that I took to college.

I began my college career at Manchester Community College in Manchester, CT at the age of twenty-three. I stated college later than most, primarily because the path to secondary education had never been made apparent to me.  Throughout my childhood and during my entire high school career, the word college was never once uttered to me. Not by parents, not by teachers, and not by guidance counselors. For reasons that I will never understand, it was universally determined at an early age that I was not college material. 

So even though I graduated in the top 5% of my high school class, I found myself rudderless and lost after graduation with no plan for the future. I quickly moved out of my childhood home, a process that had begun two years earlier when my parents gave me bath towels, flatware and a microwave oven for my birthday (making it clear what they expected of me), and embarked on a five year journey of difficulty and heartache that ultimately led me back to school.

I attended Manchester Community College for two years, earning an Associates degree in liberal arts. I have attended three other colleges and universities since my days in Manchester, earning degrees at each one, but the best education I ever received was at MCC.   

After graduating from MCC, I enrolled at Trinity College in Hartford, CT. Trinity accepted all but one of my community college credits, meaning that I effectively received two years of Trinity College credit at a community college price.

At the time, tuition at Trinity was about $38,000 per year.

The cost of my two years of community college? Less than $5,000.

A savings of more than $70,000 for the two years.

As a result of my academic performance (top 5% of the class again) and involvement in the MCC community (President of the Honor Society, member of student council, a Truman Scholarship finalist), I was offered immediate acceptance and a sizable scholarships at a number of outstanding schools in the area, including Yale University, but I opted for Trinity College for a number of reasons.

Most important, Trinity was only about fifteen minutes away from home and work. While attending MCC and Trinity, I worked about 50 hours a week managing a McDonald’s restaurant, launching my DJ business and tutoring in the writing center on campus, so proximity to home and work was critical if I was going to succeed.

Trinity also had a program that specifically catered to non-traditional students. Though it did not change my course work in any way, Trinity’s IDP program was designed to help integrate the non-traditional student into campus life as much as possible, and the program made me feel more welcomed and accepted than any of the other colleges I was considering.

Trinity was also a member of the Greater Hartford Consortium of Colleges, affording me access to a number of colleges in the greater Hartford area. This allowed me to earn a degree in English from Trinity while simultaneously earning a teaching degree at St. Joseph’s College, an all-women’s school in neighboring West Hartford that had a solid reputation for turning out excellent teachers. Thus I earned two degrees at two different institutions for the price of one.

Enormous savings.

I attended Trinity College (and St. Joseph’s College) for a total of three years, meaning that I spent a total of five years in college while most traditional students spent four. But I graduated with two degrees (three if you count my Associates degree from MCC), making the extra year well worth it.

I received a number of scholarships from Trinity based upon my academic performance at MCC (another enormous benefit of attending community college first), but I was still responsible for well over half the cost of tuition during those three years of school. I paid for this with student loans, Pell grants, and personal savings, graduating with about $16,000 in debt.

Don’t get me wrong. $16,000 is a lot of money, but it’s not an overwhelming amount of money when paid off over time. Six months after graduating, my loan payments amounted to less than $300 a month.

Absent any parental support or college savings, the cost of a college education could have been astronomical for me. Paying the full cost of four years at Trinity College without the benefit of scholarships would have left me with a debt exceeding $100,000. Though I certainly had to make sacrifices in order to earn my college degree, I did so without crippling my financial future.

While it would have been wonderful to attend college immediately after high school and live on campus for four years, this was simply not a possibility for me after high school. I did things a little differently, and though it set me back by at least five years in comparison to my peers, I also feel like I was much better prepared for college when I finally made my dream a reality. I had spent the previous five years before college struggling immeasurably. I had been homeless, jobless, penniless and had experienced the crushing sadness that comes with the belief that you have no way of making your dreams a reality. When I entered my first college classroom in the fall of 1994, I was ready to work and prepared to excel.

There are many roads to college. Some are easier than others. Some are costlier than others. The crippling debt that so many students graduate with today is not required in order to be successful. It is a choice that is made by students who do not want to compromise on their road to higher education. I respect their decision. I sometimes wish I had made the same decision. But the crushing debt that follows graduation should not come as a surprise. A college education has a cost attached to it, and that cost is made clear before a person ever signs a student loan agreement.  

I remind my students almost every day that anyone can find a way to pay for college, regardless of their family’s financial means. All they need is the desire to succeed and the willingness to work.

Don’t let anyone tell you otherwise.