1 Unpack What’s Behind Your Mess (Decluttering 101) Physical clutter is often a manifestation of mental clutter.
Whether you’re trying to figure out the next step in your career or trying to figure out how to solve the mess that is your kitchen cabinet, probing what got you into the mess is the first step of the tidying process. It’s difficult to make a path forward until you come to terms with what caused that mess in the first place.
Dean of Academics. What a fancy title, especially for a young former classroom teacher. It sounded impressive, particularly in NYC education circles, but don’t be fooled. My job title should have been Dean of Mess, because that’s really what I was. The “dean” title meant I was no longer a classroom teacher, no longer had summers off, and now had a lot of teacher management and student disciplinary responsibilities. That was difficult enough, but we’d also upsized our personal life. We had two kids under the age of two, and I was overwhelmed and exhausted.
So how did I get here?
Well, for years, everything moved along pretty much as I had planned. I checked off all the boxes on how I thought you’re supposed to transition from your twenties to your thirties. Years earlier Emily and I had announced in Frank Sinatra style, “If I can make it there, I’m gonna make it anywhere. It’s up to you, New York!” We’d made NYC our home, and now I was “successful.” But this was all a façade. The only thing I’d really become successful at was crying in secret.
It always started as a burning sensation behind my eyes. Then my breathing became labored. My chin started to quiver as I held back tears. I’d wait until I’d kissed Emily and the girls goodbye and made it a few blocks from home on my two-mile walk to school. Then, as the tears threatened to spill out, I’d start to repeat a mantra that I’d taught to my former students: “I am kind, I am smart, I am going to have a great day no matter what!” Trouble was, for nearly three school years my days weren’t that great. How bad? I’d characterize them as a dumpster fire.
Male elementary school teachers seem to have a shelf life of about five years in the classroom before people begin to ask questions, like “Why isn’t he more ambitious?” and “Shouldn’t he be an administrator by now?” My dad had been a teacher and followed an administrative track. He’d been an incredibly successful and well-respected elementary school principal and was able to balance his work with being a father to three kids. He was my role model. So, when I was offered a promotion to that fancy three-word title, I jumped at the opportunity.
Unfortunately, with my new position and two young children at home, my life had become like an overstuffed closet—with way too many things precariously teetering behind closed doors, waiting for me to sort through them. In addition to navigating early parenthood and
all the physical stuff that came with it, I’d also basically shoved all my stress, anxiety, and emotional baggage into the back of the closet (aka my mind) for that “someday” when I could process it all. Fatherhood had rewired my head and my heart, yet I felt like an impostor at work and at home. I would spend mornings, nights, and weekends trying to “catch up” on work, but could never seem to get ahead. I thought the logical way to solve problems at school was by working
more, but it was just taking time away from my family. I felt like I wasn’t good enough, strong enough, or competent enough to handle the stresses. But I dressed the part. While things may have looked tidy to others, I was experiencing a mental and emotional downward spiral.
One day, I stopped on the street on the way to school and had a complete breakdown. My chest tightened. My eyes darted from one side of the street to the other, watching the traffic pass. I could barely put one foot in front of the other. I took my phone from my pocket and called my wife. I told her I just couldn’t keep going. I couldn’t keep it all together anymore. I was honestly worried about what I might do to myself. I desperately needed help.
Confronting My Emotional Mess I’d started to build the doors of my overstuffed closet—the tidy façade—back in the late ’90s. I’d met Emily in eighth grade—her family had moved to Kentucky from Arkansas, and she had been assigned to sit next to me on the first day of school. That was one of the bright spots in an otherwise messy period of adolescence.
For starters, I was the target of schoolyard bullies. The Backstreet Boys shirt I’d worn on the first day of seventh grade had gotten things off on the wrong foot. I’d attended their concert with my sisters and best friend Jessie that summer, and apparently that wasn’t a cool thing for a middle school boy to do. Then I made the mistake of telling on a group of kids who had been smoking in the back of the bus. They got in trouble, and I became their number one target. They verbally and physically harassed me for most of the year, to the point that I was scared to even use the bathroom at school.
On the bus, they’d throw chewed-up pieces of candy at me, broken pieces of glass, even full bottles of Gatorade. One afternoon we had a substitute bus driver, which gave the bullies the opportunity to unleash a whole new level of harassment. Someone hurled a D-size battery at me, striking me in the face. Twenty-five years later I have a permanent indentation on the side of my nose from the attack.
Then came the new century. I was very worried about the Y2K bug, a potential computer error that was supposedly going to cause computer systems around the world to crash. People feared ATMs would stop functioning, airplane navigation systems would stop working, and the power grids would shut down. Those fears never actualized; systems didn’t implode. But what did implode in the new millennium was my parents’ marriage. I hadn’t seen that coming.
A “For Sale” sign went up in our front yard. The school bus driver noticed it and asked me excitedly where we were moving. I lowered my head and told him I didn’t know. He probably thought we were just moving into a bigger house—a time-honored marker of moving on up—but the truth was that
I did know what was happening: We were moving from one shared house into two.
Divorce may be commonplace now—and it wasn’t unusual back then either—but I didn’t have any friends whose parents were divorced, and I didn’t personally know any divorced people, apart from my aunt and uncle, who had both been divorced before marrying each other. And in our southern, conservative Christian community, it was frowned on. I felt like I had a scarlet letter embroidered on all my clothing (though not on the Backstreet Boys shirt; I’d already donated that one). I felt embarrassed and ashamed.
To compensate and divert everyone’s attention away from just being the “divorced kid,” I tried to present myself as the best, the brightest, and the funniest. I graduated from high school with honors, was on the dean’s list at college each semester, married Emily, became a teacher, and in my second year was named “Teacher of the Year” in my school and then in my entire district. I was accepted to a graduate school program at Columbia University, and Emily and I moved to New York City, where I planned to continue checking off the boxes of adulthood to prove that I was “successful.”
I taught full-time and took night classes, and graduated with my master’s degree in comparative and international education. Doesn’t that sound fancy? My grandpa, notoriously difficult to please, kept photos from my graduation in his wallet. He was impressed that I had attended an Ivy League school. For the first time in my life, I felt like I had made him proud. A few years later, accepting the promotion to Dean of Academics felt like more of the same—impressing others, making them proud, and presenting to the world the illusion that I had it all together.
If success meant working more hours, taking on more positional responsibility, and being “on call,” then success had found me. Part of my new professional responsibility was to monitor students in crisis in our school’s “recovery room,” a place where they could cool down if they’d been demonstrating unsafe behaviors or tantruming in the classroom. I worked in tandem with one of our school social workers, Kim, the mother of two elementary school–aged children.
The work was emotionally and physically exhausting. We had a lot of students in crisis at school, and Kim and I were in the hot seat to help make things better. Kim provided the counseling to students, and I provided the suspension papers and met with parents and teachers. After one particularly tough morning—I was slapped across the face by a kindergartner at a meeting with him and his mother!—my façade was starting to crack. We all have a personal threshold for how much we can handle, and I’d reached my limit.
Copyright © 2025 by Tyler Moore. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
