Nearly two years after I left my profession to write full time, I finally got around to cleaning out my closet. My new boss—me—is a lot laxer on the dress code. So, I should have done it months ago. The experience reminded me of a couple of life lessons I clearly have not learned: If you do the small tasks you dislike, more often, then they won’t become daunting and abhorrent; Don’t buy fit and flare dresses with large flowers. It’s not a good look on you. Cleaning out my closet also taught me one new and profound lesson: The things I hold onto from the past tell me a lot about how I view the future. By that, I mean much more than the fact that there is no future in which I will look cute and feel confident wearing enormous red poppies. Here’s what I learned from some old suits, a stack of spine images, a half-hidden piece of art, and a couple briefcases.

You might be going back there.
Most of my closet was still filled with suits. I wore a suitcoat and skirt to work every day. I liked them. I blame my dad. He taught me to “dress like you care about what you’re doing”. I did care. I loved my career as a teacher, principal, and central office administrator. As I looked at the suits, I wondered why I kept them all though. There are women out there who cannot afford nice clothes for a job or an interview, and I have twenty suits I am never going to wear again hanging in a closet. I must have thought I would need them. I’m a writer now. Could keeping them be a sign I don’t have faith in the future of my new path? I might need to go back to work some day doing something that requires a suit. I will not. I have outgrown them. I don’t need them as a safety net for some hidden fear of future failure. Someone else needs them as a resource for their hopeful future.
Most of the suits and other clothing don’t fit me now anyway. I have a schedule now that is sane. I have the time to work out during the day, eat regular healthy meals, and practice mindfulness to relieve stress. These clothes no longer fit my body or my life. They show me how much I have grown but keeping them also suggests I don’t fully believe the changes will stick. I might gain the weight back.
I am donating those clothes. I can see the strength of the healthy choices I’ve made. I can let go of things that no longer fit me and will not serve me in the future.
Lesson? You are not going back there. Embrace the things that reflect your current and future self.
You might get hurt.
I’ve tucked away more than clothes in my closet. Hidden on a shelf in the back is a stack of myelogram images from 1990 (If you hate getting an MRI, be thankful you missed the myelogram era). Back in the day before MyChart and digital records, you had to carry your images to your surgeon. These were taken a few months before my first back surgery. The weekend before my first head coaching job was to begin, I ruptured three discs. I had to resign. Coaching was my dream, so this injury was both physically painful and personally devastating. I was determined to do whatever was necessary to recover and begin again. After I healed, I took the first coaching job available. Track and field. I coached shot, disc, and javelin. Though it had not been in my plan, it was one of the most powerful experiences of my career. Coaching track gave me the opportunity to work with athletes who still inspire me to this day.
I am keeping those images as a reminder that adversity is not permanent, and I am never powerless to change my situation. Sometimes amazing things appear just past a broken dream.
Lesson? You are strong and resilient. You can always forge a new path in the future.
You might have something to learn.
There are three briefcases in my closet: A modest portfolio my father gave me when I earned my bachelor’s degree. A messenger bag my father had made by the saddle maker in our hometown when I earned my master’s degree. A David King barrister case my father gave me when I earned my doctorate. I don’t need a briefcase for work anymore. I will never let these go. They remind me how far I’ve come, how much I’ve learned, and how hard I’ve worked. They remind me of the lessons my father taught me and the love of learning he instilled in me. They remind me he was proud of me.
I am keeping the things that remind me of my gifts and who helped me develop them.
Lesson? You are a learner. No matter what the future holds, you will be successful or you will learn (which is success in itself).
You might forget what that feels like.
At the end of the rack is a long dress protected in plastic that I have only worn once, to my daughter’s wedding. As with the suits, it’s too big now. Certainly, it’s too fancy for most of my activities. Every time I look at it, I think of that day. Standing in the sun holding my husband’s hand as we watched our daughter take the hand of the man she loves. Just seeing the dress makes my heart clench and tears swell. I am so grateful that she has a partner to live her best life with.
I don’t need to keep the dress. But I am going to, for now. I like the warm and joyful feelings I get seeing it.
Lesson? In the future, there will be many more moments to fill your heart. Still, you get to keep all the ones already living there.

You might lose someone.
On the shelf is a block print of a bird. My best friend in college made it years before I met her. She was so proud when it placed in her high school art show, I’m told. Her mother gave it to me when we buried her. It’s not on my wall because it is still too painful to look at forty-one years later. I glimpse it every day, though, as I pick out an outfit. I miss her still. That’s the problem with loving people; some will leave you behind forever. I still remember the first day we met and all the fun we had. Those memories swirl around the pain like a blanket and make me so grateful I knew her. Her joyful spirit still touches me all these years later.
I will keep this piece of art forever. I would not wish away one second of that pain, because I know the only way to miss the pain would have been to miss out on the big love of her friendship.
Lesson? In the future, you will lose people you love, but you must never miss the chance for love and friendship because you fear the pain of that loss.
You might grow apart.
In a beach bag tucked into the corner of the closet is a collection of swimsuits. Since I live in Washington, I rarely need one. I’ve worn each of these over the years though, when my closest friends and I visit one of our pack who has moved away. She lives in the sun and has a pool. Our day-to-day lives are so busy. We don’t always have the space and time to connect. The weekend we spend together, floating and laughing and catching up, draws us back and it is as if we are never apart.
I am tossing most of the swimsuits and buying a new one. Things change. Strong connections endure, even thrive, in change.
Lesson? You may move apart physically from the people you love and care about. In the future, your best friends will always be there. Nothing, not distance, time, work, or life events, will ever change what really matters between you.
The past has passed. Let it go, unless it brightens the future.
I probably could have cleared out my old clothes in an hour. It took me most of the day. Though I feel a bit silly getting sentimental about the glitter encrusted stilettos my daughter just had to have for the prom but only wore for an hour as I predicted, I loved every minute I spent in that closet.
You don’t have to let go of the past. I gave away some things that don’t fit me, and the fear that they would someday again. I threw away some things that don’t serve me anymore, and the need to cling to them in the future. I tossed some things I don’t need because I realize what they represent will remain forever in my mind and heart. But I kept some things. A few just make my heart happy. It’s that simple. A few—the most joyous and the most painful—remind me that I am strong, resilient, and brave, and I will be all of those things in the future, too. I might need those reminders from the past so that I can see that future more clearly.
Catherine, I enjoyed reading this! When I left my crazy, 70 hour a week administrative job in 2015, I donated a car full of “professional” clothes (but not my shoes) to a place here in Philly called the “Clothes Closet”–as you describe, a place where women just entering or reentering the job market can pick up an interview outfit and some “starter” suits, blouses, etc. In 2018 when I dislocated a tendon in my ankle, the first thing my (female) doctor told me with sorrow was that I had to give up my “cute” shoes–no heels, no platforms, no strappy sandals, no mules…Yikes. I loved my shoes. But I’ve adjusted just fine to athleisure and sneakers. I just don’t understand why my closets and bins all need sorting and cleaning out again!
Thanks for the note! I hated giving up my heels but now I can’t imagine why I ever wore them!