Here's What I Learned When I Went Back To College At 36

Never too old to succeed.

I would never have gone back to school had it not been for one thing: I was laid-off.

In 2009, I was one of thousands of Americans who got caught in a downsizing slaughter as companies quietly laid off employees in an attempt to stay out of the red. I was working in "luxury" retail. Unfortunately, as the economy began falling to pieces, not many people were interested in buying luxury anything.

I was called into a short meeting one morning, handed a severance package, and unceremoniously laid off by an H.R. manager on a conference call. 


I had spent my 20s and early 30s doing various jobs that ranged from cutting pizza to tending bar to armed security occasionally going to community college to study acting and, later, police science. 

I just never finished.

So, in the late summer of 2010, I applied to Columbia University's School of General Studies, the Ivy's undergraduate college for non-traditional students. I was accepted at Columbia for the Spring 2011 semester and moved to New York City in January of that year. 

I was 36: twice the age of most and older than some of my professors.

Yeah, I was about to be the old guy in class.

As it turns out, that didn't really matter. Because I would learn that there are many ways to define success. 

Despite my age, most of my friends were traditional undergraduates.

They took me in — strangely enough — and treated me like one of their own.

They introduced me to their friends. They invited me to their events. They told me about their lives. We crashed parties together, stumbled home at 4am together, drank bottomless mimosas together. 

We even occasionally studied together. 

When two girls, about 21, sat next to me at Campo, a bar near campus, on the Saturday morning before the first day of classes, I didn't think twice about drunkenly posing a two-word question...

"Shots, ladies?"

And that's how I made my first friends at Columbia.  

Some graduated before me. Others would graduate later. All of them, however, taught me something. 

While many of the lessons I learned at Columbia came from its rigorous academic environment and extracting wisdom from literature and analysis, many came from being allowed into the lives of the millennials that were — and are — my classmates and friends.

Here's what I learned.

1. The fears and insecurities that 20-somethings have aren't limited to 20-somethings.

No matter where you go to school or what you study, you will always have a fear of disappointing the people who support you. I had friends for whom coming home with anything less than an A was as bad as coming home and saying that they had dropped out. No matter how confident anyone appeared – and much of college life, I realized, teaches the importance of keeping up appearances – they all suffered anxieties about failing. There was a general feeling of competition and stress that never let up. I don't know anyone who slept on anything remotely resembling a normal schedule.

That started the first day I was there and, quite frankly, it persists to this day. 

But plenty of good came out of those fears and insecurities. Firstly, they taught me that I was capable of doing more than I ever thought possible. Secondly, but no less importantly, they brought my friends and me closer together.

2. The difference between college at 18 and college at 36 is that at 36, I was used to all kinds of stress.

By 36, I had lost plenty of friends, been robbed at gunpoint twice, been laid-off, endured the loss of my mother to cancer, seen plenty of break-ups, and had moved more times than anyone ever should. I was used to stress: I was used to pressure. My only two thoughts when it came to something as relatively benign as homework and demanding professors came from my life experience: 

        -I don't have to like it, I just have to do it and

        -Well, they're not allowed to kill me. 

Don't get me wrong, it was plenty stressful... But I knew that I had it in me. And I knew that my friends had it in them, too. 

3. You can learn something from everyone.

The variety of personalities, political leanings, and life experiences that I came into contact with when I went back to school was vast, to say the least. I didn't always agree with the people I met or the ideas I encountered, but I found that if I was willing to hear them out, I would walk away with a better understanding of not just them, but myself. 

" Success comes in many forms—and sometimes the challenge is its own reward."

I found that some of my long-held opinions changed. I gained a greater insight into parts of the world that I never understood. I came to see connections that I had never noticed. I came to become friends with people I might never have met otherwise. 

In short, I learned. And I learned that I loved learning, loved discovering things, loved things outside of my intellectual comfort zone and that even if I didn't completely understand them at first, those things all helped me learn more about myself and the world around me. 

Success comes in many forms — and sometimes the challenge is its own reward.

4. You need to have a "why," because at some point, everyone asks, "is this really worth it?"

I graduated at 39 with a degree in English and Latin honors: my first job out of college? A start-up conceived by Ashton Kutcher called A Plus. 

Within a few days of graduating, I was sitting in Ashton Kutcher's dining room in the Hollywood Hills. I hadn't even gotten my diploma yet. We grew from 5 people in a dining room to a team of talented writers, sales pros, engineers, and strategists.

I arrived in New York in the dead of winter. It was covered in snow: the quantity of which you just don't see in the south, let alone Hawaii, where I grew up. I was profoundly lonely in my tiny studio and towards the end of my first semester, I began to wonder if the loans and the stress and the solitude were really worth this degree. I began to ask myself why, exactly, I was doing it and I didn't have a real answer. I wanted to make my family proud. I wanted to show other people that I could do it. I wanted to be able to find more secure work. Those things were all answers to the question "why," but none of them were enough to keep me from dropping out: they certainly never worked before. 

My friends, though sympathetic, left it to me to decide.

They only told me to make sure that I wouldn't regret whatever decision I made.

That was key for me: make sure that I wouldn't regret whatever decision I made. 

Your "why" has to be about you. It's your education. It's your brain. It's your time. Other people may be proud of you, may cheer for you, may support you... but you're the one who's gotta do the work, take the time, and get it done. It can't just be about pleasing other people. You've gotta want it for you. 

When I took other people out of it, my "why" became much simpler: because I deserve the best education I can possibly get and because I am willing to work to get it. 

In the end, it wasn't about a preconceived notion of what it means to "succeed" — money, say, or status — but about enriching myself and doing what I felt like my life needed. 

I took a leap of faith in going back to school. A Plus took a leap of faith in hiring me. 

I hope they have no regrets. I certainly don't. 

Neither will you. 

Join Strayer University in the Readdress Success Movement to change Merriam-Webster's definition of success! For every signature, Strayer University will donate 50 cents to Dress For Success!

To learn more about Strayer, visit


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