How to Cry at Work: An Excerpt From Justin Kerr's New Book

How to Cry at Work: An Excerpt From Justin Kerr's New Book

7 true stories.

With the disruption brought by the pandemic, people are experiencing grief, anger, frustration, loneliness and confusion in more ways than ever before. Whether because of illness, layoffs, social upheaval or video chat exhaustion, we are all having to learn how to say goodbye to old ways of work — and life. Justin Kerr, Staples Worklife magazine columnist, talks about how people express these feelings in his new book, How to Cry at Work. Here’s an exclusive excerpt.


7 Stories About Crying at Work #icried

Trading stories about other people crying at work is a workplace tradition, but I wanted to try something different. I asked people to share stories about when they cried at work as a way of de-stigmatizing and de-gendering crying, moving it from something we make fun of or gossip about into something we acknowledge, share and gain insight from. It’s not about celebrating crying, it’s about acknowledging it as a natural part of being human at work. 

These are real stories from real people. Some wished to remain anonymous.

How about crying during a job interview? 

I had been let go from one job at age 47 and I had never felt so depressed. I was desperate for work and to pay my bills. During an interview for a job that I didn't want, the managers asked me who my hero was. I thought of my teenage daughter, who is so sunny and has her whole life ahead of her. I said her name, and I burst out into uncontrollable tears. Just thinking about her optimism made me realize how low I had sunk. The managers shifted in their seats. I finally rebounded with a joke. "Damn, I should have just said Michelle Obama." Everyone laughed uncomfortably. Needless to say, I didn't get the job. - Anonymous

You’re leaving me?

My first employee at my startup told me she was resigning and as she kept talking, tears started to well up in my eyes. I had worked with her for three years through thick and thin, good and bad and here she was, giving me a full three months notice. She was so graceful in that moment, I was crying at just how kind she was. We both knew she would be leaving me all alone with a growing/failing startup. I took a few deep breaths (so as not to cry too much) and told her how much I appreciated her—and that’s when the tears really started coming! I was 43 at the time, and the CEO of the company. - Daniel  

I cry when I fire people

I took over running a small creative studio when I was 27 years old and part of my responsibilities was having to lay people off when money got tight. I was coached to be decisive and unafraid to make hard choices. I was told that “hire slow, fire fast” was a winning formula. But when you look someone in the eye and tell them this will be their last day at the company and their whole world seems to come crashing down in front of them, that false sense of BS masculine pride completely falls away. I was crushed. 

In most occasions, I couldn't help but start crying right there in that moment, if not immediately afterwards. The humanity of the situation hit me like a ton of bricks. It took me months to recover. Every time. But, what I've learned is that being the "boss" means your responsibility for empathy and care for individuals in those moments is not a nice-to-have, but a duty. It was a very difficult lesson, but one I'm glad I learned. - Matt 

Mean girls

I felt like I was living in a bad movie. Everyone had a bad attitude, everyone was mean to each other, complained about everything and I didn’t trust my boss. I felt like a shell of a person and when we had team meetings I wouldn’t say a word. I’d just sit there silently and hold back everything I wanted to yell at my coworkers. I confided all of this to my mentor and much to my surprise, she must have told my boss because at the next team meeting my boss stopped the meeting and said: “Team, Alexis has the floor, let’s hear what she has to say to us…” I froze. I told her I didn’t have anything to add and then I quickly excused myself to run outside and cry on the phone to my mom, or boyfriend—I don’t remember which. - Alexis

The day Elliot Smith died

It was late afternoon on October 21, 2003, when I learned that musician Elliott Smith had committed suicide. At the time, I was working as the Director of New Media for a multinational magazine, reporting to the CEO and publisher. 

Given his struggles with substances and mental illness, I wasn't shocked to hear that Elliott Smith had taken his own life, but I was suddenly and deeply saddened. When I heard the news, I remember wanting to connect with somebody who could understand the magnitude of the loss for the independent music community, so I walked outside to call a musician friend. But when I got outside, I didn't call anyone—I just broke down crying and stood there for ten minutes on the outer edge of the parking lot where no one could see me. When I was done, I wiped my eyes and walked back inside and started working.

For a long time, I wasn't even sure why I cried. I loved Elliott Smith's music, had seen him play several times and had even been introduced to him by mutual friends, but I didn't know him. In retrospect, I realized his songs were the soundtrack to a period in my life that had ended a few years prior to his death—a phase that included the end of a positive long term relationship and the death of my father—so when I heard the news, it triggered something intensely personal. It's now clear that I was crying for myself and mourning my own loss.

I still can't listen to Elliott Smith without some of those feelings coming back. - Brent

I’m getting a divorce

When I told my boss I was getting a divorce, I cried. In response, she stopped everything she was doing and took me to lunch. I told her I would be going to therapy and I would need to leave early once a week. She didn’t blink. She told me she would support me any way she could. 

When I told the team I managed I was getting divorced, I cried again. When I told my peers and immediate co-workers, I also cried. I told everyone I was going to have good days and bad days and that I would be transparent with them if I was going through a particularly bad day (so they didn’t take it personally). I was also open with them about therapy and the steps I was taking for self-care to get through this tough time. 

The way my boss, my team and my co-workers showed up for me in that moment was incredible. I realized that by engaging in vulnerable conversation with coworkers about myself, I gave them permission to be open about things going on in their own lives as well. Since that moment nine months ago, I have had more real, honest conversations than I experienced in the previous 15 years of my working career. The relationships that were built from this shared moment of vulnerability provided me with an unexpected support system and friendships that I will have for the rest of my life. 

It doesn’t always have to be about crying, but now I know that removing the stigma of mental health and self-care in the work environment is something I will prioritize for the rest of my life for myself and my teams. - Kelly

Getting back to work

I’ve only cried at work one time. It was my first day back from maternity leave and I was in a closet (literally a closet) pumping breast milk. Every bone in my body told me that I needed to be home with my four month old son James but instead here I was doing extremely trivial things like resetting my logins and passwords. I cried a few tears and went back to work. - Amy

No matter where you work, you’ll experience ups and downs, and crying and emotions are part of your worklife. Read more stories, and learn about how to navigate workplace emotions, in How to Cry at Work.