Guest Post: Round 2 – Confessions of an Ex-Perfectionist

Blog owner note: I’m definitely feeling this next edition of “Confessions of an Ex-Perfectionist.” And I love that I read it after jay-walking. But in all seriousness, I’m a staunch rule-follower, though, like Jenn, I’m trying to lighten up (hence the illegal road crossing). Enjoy! — LolaK

Guest Post by Jenn Ripley

If anyone who thinks I am borderline crazy could see inside of my head, their suspicions would be confirmed. And thanks to the ubiquitous power of the internet (and LolaK), now everyone will know. Hooray.

Following rules is part and parcel of escapading in this world as a perfectionist. I should know. I could probably count the number of rules that I’ve broken in my life on one hand and those were usually tied to some inherent injustice I knew would be trespassed by keeping those rules.

Rules are the comfort zone of a perfectionist. They make clear the difference between right and wrong and spell out what we are to do, how we are to act. Situations without rules, without a black and white option, tend to produce a lot of anxiety.

My goal now is to embrace the gray, to derail the anxiety that involuntarily rises up in my throat when rules are not clearly delineated.

I was reminded of this challenge on my journey to live in the gray recently when I slipped away for a weekend with several girlfriends.

Anticipating a weekend that would require me to keep my cool when things went awry, as they do in groups of 9 women, I was actually looking forward to a relaxing time with good friends.

We all met at my house and I managed to keep it together when we didn’t leave at the planned time because I had sneakily built in some extra travel time for just this situation.

I also remained fairly calm when we showed up to the spa 10 minutes late. The anxiety was there, of course, but I don’t think it showed.

All day long I met challenges of this kind and I slew them like a knight meeting a dragon. I emerged successful from a day with a flexible schedule, with mishaps left and right, with unexpectedly cold weather, with slow waiters, etc. I felt like a champion, “Victorious!”, my battle cry.

Toward the end of the day, high on life and gloating over my triumphs, I came face to face with a nemesis that caught me completely off guard—the crosswalk.

My group stood by the light post and waited for an extended period of time (at least 45 seconds) for the light to change and for the welcoming pedestrian light to bid us across the street.

Few cars were passing by, but it was becoming clearer and clearer that the light would still require 30 seconds of patient waiting.

To my horror, my bold friends began crossing the street willy-nilly as though they were allowed to do so.

I watched them gleefully cross the street into a world of new shops, restaurants and possibilities and I stood there. Paralyzed. My heart was saying, “Go!” and my mind was saying, “IT SAYS, ‘DON’T WALK!!’”

I rocked forward on my toes, as though I might dive in headfirst, careless and fancy-free, but I quickly rebalanced to my flatfooted stance. My heart was fluttering, I so wanted to follow my friends, yet the inner perfectionist inside of me was fighting to have its way.

When the light finally gave way, I hung my head and crossed the street (inside of the white lines of course).

The crosswalk won that day, but someday, I’ll be back. I’ll defeat it.

By the way, this gray thing? It’s exhausting.


Jenn Ripley is the writer, creator, and editor of The Trophy Generation (, a blog highlighting the fascinating people of generation Y, and their attempts to create success for themselves by following their passions and by using their unique gifts to stand out in an age of mass communication.  She hopes to inspire others in her generation to take risks to pursue their dreams and to dispel the negative characterizations of her generation including a supposedly inherent laziness and sense of self-entitlement.  Jenn also writes on occasion for and plans to continue to do so.

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