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Shelly Whitehead

Shelly Whitehead

From Closet Bossy Girl to Boundary-Setting Entrepreneur - How Kay Fittes Got Me on the Right Track

True confessions: I was a bossy little girl.

In my defense, I had to be to organize events like annual neighborhood carnivals when I was 8, fully produced plays at 10, and other stuff that no little kid should probably ever have taken on.  But, with the help of a pack of willing worker-bee friends, I did, and, in the process, we had a lot of fun and made a little cash.

But, all that “bossiness” drove my genteel, Southern Belle-ish mother crazy, and all I ever heard her say was “stop being so bossy – you’ll never have any friends!  No one will like you.”  And later, “Boys, don’t like girls who are bossy, Shelly.”  So, being the good little girl I was, I internalized that message.  And internalized it and internalized it all the way until Grown-up Shelly became afraid to ever set boundaries or lead anybody anywhere for fear they wouldn’t like me and I’d end up a grumpy, lonely old maid.

Funny thing is, that didn’t work either.  In fact, it downright backfired on me time and again throughout my career when I’d push down my ideas and needs and go along with the prevailing winds in the hopes that everyone would “like me.” Problem was, it never lasted and finally, I’d have to let it all out – often with disastrous consequences.

I tried to find answers via an assortment of gurus, but finally just figured there was just something terribly wrong with me.  Then, I asked Kay Fittes for her take on an emerging workplace problem and -- amazingly –- in one quick evaluation, she hit the problematic nail square on the head.  With her quick, to-the-point observations of a few of my interactions with an associate, Kay opened my eyes to the fact that even fairly convincing, pretend-pushover/closet-bossy gals like me, can’t keep up the act forever.  At some point, you have to stand up for yourself and, as Kay suggested, wouldn’t it be better to set boundaries at the outset instead of continually being pushed around until you explode?

Wait.  What?!  …  That actually makes sense.

A Sorcerer’s Gift for Seeing your Personal Stumbling Blocks

Honestly, I don’t know how she does it, but I truly wish Kay Fittes would clone and bottle herself for distribution to every young woman at the start of their careers.  The particular problem I took to her revolved around an increasingly unproductive relationship that was developing with a well-meaning associate.  In short, emotions for both of us were elevating, while productivity was plummeting.  And, through it all, clueless me had no idea that anything I was or wasn’t doing was provoking the situation.

But as ever-diplomatic Kay put it, “Perhaps you need to set some boundaries?”  Of course, at first, I balked.  “What?!” I thought. “That would be kind of bossy, wouldn’t it?” I said as my mother sat firmly planted on one shoulder.

“No,” Kay explained, “it’s establishing your needs to get the job done.”  “Oh!” said clueless Shelly.  “Not bitchy?  Not bossy?”  “No,” explained ever-patient Kay again.  “Standing up for yourself and your needs to do a good job.”

It was eye-opening.  It was a breakthrough.  It was the kind of guidance we all need and I was lucky enough to get.  I’ve left a lot of career damage in the wake of my “friend-pleasing, un-bossy” behavior over the years.  But hopefully, I will have the chance to work with a new empowered attitude from here on out that sacrifices neither me, nor my career, nor my true friends.

Thank you Kay Fittes, for helping me get started on that path.

Shelly A. Whitehead is a producer/reporter of the monthly regional KET TV show, Inside Northern Kentucky.  She creates custom marketing content as well as fun and funky personalized footwear.  For more info or a link to her website launching February 14, either call or text 513.478.4485 or go online to