Last week I donated two items which had both been really important to me in the past.

The first was a pair of shoes. Not just any pair, my original "fancy" work heels.

I purchased them on a mid-day shopping trip to Neiman Marcus with my former boss/first real mentor. She had demanded that we take a shopping break in the midst of an all-consuming trial preparation month to "clear our minds." We'd been working 12 hour days for weeks. We deserve this, she insisted.

And to be fair, in 2009 I was all about shopping. 3% of my income was being directly diverted into my 401(k), almost half of each paycheck went to rent, and they rest went straight into my "entertainment fund." Said fund was emptied each month in the form of clothing, purses, iPods (I know, I'm really dating myself), and breakfast/coffee/lunch/happy hour/dinner/drinks out. All of which is to say she wasn't exactly twisting my arm.

She bought Manolos, I bought Cole Haans with Nike Air technology. They were more expensive than any clothing item I'd ever owned and were purchased with my own hard-earned money from my real-adult corporate job.

(Side note: I don't have a single photo of "Corporate Cary." Is this because our phones didn't yet function as cameras or because I've never felt less like myself than in a pantsuit?)

Fast forward to today.

Everything else from this time in my life is loooong gone -- all my suits, conservative silk tops, briefcases, tolerance for being yelled at by people who don't even know my name, etc.

But the shoes... After two years of them collecting dust at the top of my closet I knew I was never going to wear them, yet I was really struggling with the thought of letting them go. I felt like they represented this whole period in my life, a point of pride, an old mentorship.

These shoes symbolized to me that I was an independent, adult woman.

The second item was a kelly green Diane Von Furstenberg dress. I purchased this dress (using a Bloomingdale's credit card I signed up for to get 20% off -- oh how I've changed!) also in 2009 as a potential bridesmaid dress for my older sister's wedding.

To date, I've worn it to just shy of a dozen weddings and have celebrated the nuptials of some of my favorite people in the world while wearing it. I wore it in Montana, Tennessee, New Mexico, Chicago (twice), NorCal and SoCal. I wore it while I danced with my best friends, when I celebrated with my family.

So how on earth could I let these memories go?