One thing I do like about my job is the office. While most people ascribe to have penthouse-like river views, corner offices secluded and private, I don’t. In fact, that seems like a jail sentence to me. I’m more of a mid-90s dotcom boom giant warehouse open floorplan kinda guy. I’ll settle for my current setup though. With five designers in one room, you’re bound to talk about some engaging things.

This morning we got on the topic of graduate school, regrets, fears and the Ivy Leagues. As we mused and projected, I began to discover something about myself that I think has been lingering over my head for the past few months: I have a debilitating fear of failure. I’m paralyzed by the thought of failing.

As I tug on the first few strands of this unraveling string, I can see other threads come undone as well. I wonder if all along, my academic success was merely a cat and mouse game with my desire to do anything but fail. While I certainly did fail along the way (cough, honors physics and analysis, cough), it was never in a true sense of failing. It was a stumble for the normal student. A “C” is hardly an academic deathblow. Could this have been the only reason that I worked my ass off to get ahead, to get top marks?

While it is a distinct possibility, I think perhaps the more realistic determination is that it was merely a factor. I think I was afraid to fail, and perhaps that was the first line of ‘defense’ when I got down and wanted to quit. As if my psyche slapped me on the wrist and chastised me for even thinking of throwing in the towel. But even if it wasn’t the sole factor, what else could this fear have destroyed in my life?

My choice of college, for one. This is what I’ve realized today. Sure I could have been “meant” to end up at a small liberal arts school in the midwest. Yes it could have been the “best” place for me ultimately, but how would I know? When I was 18 and steering my future, I just wanted something small, something attainable. Why? Probably because the ring that you can see looks most plausible and within reach. I’m afraid that I settled.

Now, I don’t regret my choice. I met my soon-to-be wife here. I got my first (and current) job here. I made friends that I’ll have for life here. I negate nothing with these words, except the “what ifs” of my life. What if I had listened to my guidance counselor and applied Ivy League? What if I had ‘gone big’ and believed in myself? Where would I be now? Would I be working on my PhD in social theory, or education or design? Would I be teaching at a college somewhere, seeking tenure? I guess I’ll never know, but I ache to nonetheless.

I’m that person that hates the “what ifs” and everything that they stand for. I avoid those situations like the proverbial plague. The unchosen choice haunts me for everything that it could have flourished to be. This road not walked is far more romantic than the one that dusts my shoes today.

If I don’t believe in myself, I won’t believe in the choices I make. And if my choices aren’t purposeful, pointed and deliberate, the attractive mystique of the lost opportunity will continue to seduce me.

But I awake from my daydream, back to the world of voicemails and unfulfilled tasks. The alternate ending to my life (though not near completion in reality) can’t be dwelled upon for too long, for life will indeed pass me by.

But a guy can always wonder…