How a 100 Rejections Challenge Prepared Me for Life’s Biggest Rejection

Today’s post is by writer, editor, and educator Libby James.

As soon as I left my marriage, I called everyone I knew. That’s not an exaggeration. By the end of the first month, probably more like the first week, everyone was aware that my husband was having an affair and that I, having been freelancing for the last six years, was desperately in need of a reliable full-time job.

When people asked what I was looking for (in a job, not a new partner), I said anything. I was open to full-time work that would allow me to afford a tiny studio in the Twin Cities, and that was my only big stipulation. I was leaving behind me, along with my husband, the creative world I had built my life around.

I was at a loss for what to look for in a new career. I didn’t feel I had the luxury or time to shop around. The first week, I focused on government jobs and jobs with pensions. When I received no interviews for those, I moved on to university jobs with good health care and free bus passes. Next were jobs in connection to communities I had been a part of in the past—the military, LGBTQIA+ services, and nonprofits that supported unhoused populations (the latter I could have found myself a part of if not for the kindness of my friends and family). I then expanded outside the metropolitan area, then outside Minnesota, then anywhere.

I had been out of the traditional workforce for many years and simply could not have imagined how hard it would be to even land an interview these days. I applied for 134 jobs before I received my first offer three months later, which, although not ideal, I knew I had to take no matter what at that point.

The rejection from 100 jobs might have been annoying. It surely was humbling, as I’d never had such a hard time getting a job before—the last time I found myself unemployed and seeking was in 2008, and even then, I found it way easier. Was the six-year gap in my resume really the problem, or was it the job market? Regardless of the reason, I never let the rejection touch me deeply. I wasn’t stalled in my quest, and I know exactly why.

Several years ago, I read an essay in Literary Hub by Kim Liao called Why You Should Aim for 100 Rejections a Year, about how striving for rejections can lead to more publications and opportunities. I started to implement this technique in my own creative life. I submitted to literary journals, artist grants, and contests all year round with different projects, obsessively. Rejections started coming in quickly, but with them also came acceptances—more than I had seen in the many years I had been in the writing world. I began to build up my stamina for rejection. Within the first year, I stopped being fazed by a rejection in my inbox. There would be a beat or two of sadness for the ones I wanted badly, but little energy was spent on those passing on my work. This is a hard business with a lot of writers and limited page space, limited grants. This challenge helped me take this business less personally.

Years later, during my time of grief over the loss of my marriage, the job rejection was just annoying instead of devastating to my psyche. When I would get interviewed and then rejected, it was annoying. When I received a form rejection, it was annoying. When I received no response, it was annoying. But nothing stalled me for one minute. I wallowed very little over the job rejections; I did wallow over the life I had before and the fact I was married to a liar, for sure, but because I had already built up a strong tolerance to rejection, the job rejection did not faze me. I was able to return to the computer day after day because rejection was something I was used to by now. I could sit through an interview for jobs I wasn’t qualified for and handle the awkward pauses with a smile on my face because I had been in hundreds of workshops and listened to writers discuss in front of my face what was wrong with my short stories and poems. I could easily revise a cover letter over and over because I had rewritten so many drafts of an entire novel I lost count. I have had creative works that my heart was in rejected again and again, so a job application rejection has nothing on what an artist needs to be able to withstand that act of creative endurance.

The job I took seeking stability didn’t last long. I returned to the creative world because I love creating something that wasn’t there before, and helping others do the same, and that feeling that comes from a yes after a hundred nos. I will forever be grateful to that essay, its author, and to the challenge. It built me up in ways I never realized could be applied outside the creative world. It taught me rejection needn’t be regarded as “You are a failure,” but instead met with “Thank you, what’s next?”

Libby James

Libby James is an author, editor, educator, and rebel. She publishes Letters from Libby James, a newsletter for adults who want to strengthen their writing, navigate the publishing world, and turn their art into activism. Her work has appeared in Hanging Loose, Hobart, Matter, and The Blue Mountain Review. She also teaches young writers through Ms. Libby’s Lab, a space for early imaginations to explore language and story. Learn more about her writing, teaching, and editorial work at www.Libby-James.com.