Then and Now (Jenny O'Connell)

So, to answer the question: Where are you today compared to where you thought you'd be upon graduation?

I've had three graduations in my life, high school, college and business school. For the most part I knew what would happen after high school (I was headed to Smith College) even if I didn't know what would happen during my four years there. And, I also knew what would happen after I graduated from business school - a job. But in between those two, upon my graduation from college, I had lots of unknowns (even if I tried like hell to convince myself I had it all under my control). I straddled thinking that I knew exactly how my life would work out and thinking how exciting it was that my future held so many possibilities!

Graduating from college was bittersweet:
First of all, I was leaving the best friends I'd ever had in my life. We were all going in separate directions - to cities and jobs and graduate schools where we'd be on our own. I was headed to a program at Radcliffe in Cambridge, MA for three months, but after that... well, I had no idea. Although obviously if I was jumping back into school so quickly, I thought I knew what I wanted to do (move to NYC, work for a big book publisher, become a fabulous uber editor of brilliant books). The second reason that graduation was bittersweet was that I loved college, had the best time of my life. Leaving a place I loved and people I couldn't imagine living without was a little depressing to say the least, even if I thought that a fabulous life was ahead of me.

So what did that fabulous life include? An amazing apartment in NYC (even though a starting salary in publishing would barely get me an apartment, no less something amazing); best friends to hang with; a thrilling social life that would include drinks after work at bars where they'd know my name and cheer when I walked through the door; a super fabulous work wardrobe (to this day I love wearing suits); and, of course, my college boyfriend (who happened to be the love of my life).

I'd still have awesome fabulous best friends from college that I'd see all the time, and my boyfriend and I would walk off into the sunset holding hands. Basically, the people I cared about the most would be close by and in my life forever.

And the reality? After leaving Radcliffe I moved out West - not exactly a mecca of publishing at the time and few industry jobs that would propel me into the stratosphere of uber book editor. I didn't know a soul until my boyfriend moved in with me. We had shitty jobs. We had no money. There was no local bar that I even remotely wanted to know my name. Other than the fact that I did make two new awesome friends, it sucked. He broke up with me. We broke our lease. Phase I of post-graduation life: over. In less than six months everything I'd imagined my life would be was not to be.

And that's when my crystal ball into the future totally shattered. The years that followed were nothing like what I would have predicted that day I wore a cap and gown. I moved to Boston and lived by myself for the first time, and then moved to Chicago without ever having even visited the city, went to business school, traded in dreams of being an editor for classes on economic theory and Black Shoals Options Pricing, and stayed in the Midwest for 15 years. My friends were all over the country, nowhere near me. And that boyfriend? We never talked again after moving out of the apartment we once shared.

But life has a funny way of working itself out. I ended up moving back to the Boston area and now one of my best friends from college lives 3 miles away from me and my other best friend is close enough to have lots of visits and late nights talks.(and frequent girls' trips in various locations). I had an idea and decided to write a book, which turned into ten books and a career as a writer...working with uber fabulous editors and big book publishers. And then last year I decided to get a divorce (another event I never would have predicted for myself upon graduation). And soon thereafter I was reconnected with... the ex-boyfriend from college. And we've been together ever since. So the very person I thought I'd spend my life with upon graduation is now the same person I see when I look next to me on the couch, and the best friends I used to share late night pizza with are so near by we could share a pizza every night if we wanted to. Not to mention that I did end up in the publishing industry, albeit as a writer rather than an editor (although I'd still love to be an editor).

It's amazing to me when I  look back and think that 25 years ago I thought I had it all figured out, only to have every preconceived notion about my life turned on its head. I discovered that the twisty, turny road of life has a way of getting us to the right destination, even if the routes we take seem to take us in the opposite direction. And if we're patient, in the end everything ends up the way it's supposed to be. Because I basically have exactly what I wanted when I was handed my college diploma 23 years ago, it just took me 23 years to get here.


  1. Love this post. So cool how our journeys unfold.

  2. The return of the college boyfriend is intriguing. It would make for an interesting plot in a novel.


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