Eeyore in a World of Pooh

I should do that.

I should be like them.

I should get a normal job and move to suburbia instead of working two jobs while living in a major city.

I should be that.

I should be a happier person instead of an Eeyore in a world of Piglets and Pooh….(The Winnie, not the other).

The dreaded “should” being the operative, safe, “road well traveled” way that is expected as adults.

This is what I should do now.

This is who should be now.

I’ve been thinking about this lately. The laundry list of “should(s)” that I can’t bare to face, much like the actual laundry that I can’t bare to face, and it got me thinking about how our relationships with the “should(s)” not only change as we get older, but how we often find ourselves trading in our freedom of thought, imagination and fearlessness for a list of obligations that keep us away from the actual freedom that we as adults now have.

Freedom of thought that we have as children versus actual freedom that we have as adults.

What happens to us? Fear? Judgement?


I experienced this recently, now that I’ve been thinking seriously about my next pivot. What am I going to do next that could potentially put food in my mouth and clothes (though most would argue that with me that comes way before food) on my back.

What is the next thing that will challenge and excite me in ways where my current situation falls short?

And as I’ve been researching ways where I could jet off on my own instead of working and building someone else’s empire, I couldn’t help but think of the people that I know.

What will they think when I tell them I’m doing something else?

What will they think when I tell them that I’m temporarily abandoning my idea of a book, because I don’t think I’ve lived enough to tell the full story, or that I want the story to have another ending that I haven’t lived yet?

What will they say?

What will they think if I try something else?

Maybe more importantly, Why do I care?

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J is a happily single 30-something currently documenting her stories of love and loss. Her blog, “I Quit Dating” features excerpts of her journey as she reflects on the lessons learned from the men she loved. A complete collection of essays detailing her walk away from finding Mr. Right in order to pursue a more fulfilled life will be self-published next year. She recently moved from Los Angeles to New York. Contact: iquitdating (@)

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