I spent a year trying to get rejected…

This piece was originally commissioned by Toggl in 2020, written to commemorate my first anniversary as a freelance writer. Having recently celebrated my 3rd anniversary (this month!) I simultaneously discovered it was no longer published on their website. This is advice I actively give out to fellow freelancers; not as a silver bullet for success – it is not and I am far from being able to boast about my earnings as a freelancer – but as an exercise which has helped me tremendously in tackling my fears of rejection and their associations with self worth. I sincerely hope it helps whomever might be reading this, in some way. I’d also like to add, because I think it’s pretty awesome, that my oldest daughter came up with the last line of this essay. She was paid £3.00 and 1 ice cream cone for her work. x

A vicious circle of rejections

As a relatively new freelance writer, the idea of rejection once stung to the point where it almost derailed me from pursuing this career. At one point, rejections were often followed by an overwhelming sense of self-doubt, anxious and rapid-fire negative self-talk. This was often followed by desperate grasps for any opportunity or feeling of productivity, no matter their importance or even relevance to my work or goals. All that then left me feeling drained and out of time to develop real depth of thought for the next project or pitch I was actually interested in, resulting in further rejections. 

I had gotten myself into an unsustainable loop, and I knew if I wanted to continue down this career path, I would have to do something to change it. 

Embracing rejection and taking control

Then I heard stand-up comedian Emily Winter on the podcast Work Life with Adam Grant. Winter wanted to break into comedy writing and had challenged herself to get rejected 100 times in the course of a year. I decided to follow suit, at least until I had a better plan. 

I created a spreadsheet called Top Rejections 2019 and began my journey towards rejection. I logged each pitch, along with the publication, title, and editor’s information into my spreadsheet along the way. I automatically assumed that each new one I sent belonged in the rejected category, rather than waiting for a confirmation from the editor. 

As I soon learned, oftentimes the rejection comes in the form of silence. I had to learn to accept the lack of control I had over the outcome of my pitch. But at the same time, I also didn’t want to feel helpless and stuck, spending my time waiting around for someone else to make a decision. 

I had decided to go into freelance writing in the first place partly to have a sense of control over my own work. By assuming each pitch automatically went into the “no” pile I was able to progress on my own terms. Of course I still wanted the “yes.” But by tracking each pitch I was able to see progress no matter the outcome. 

Pitch-by-pitch, the process of multiple rejections began to shift my perspective. 

Process and outcomes

During the course of the year of rejections I threw myself into ideas and outlets that frankly felt like a stretch, some surprisingly wonderful, others that in the end weren’t really worth the effort. I probably wouldn’t have been so bold ordinarily, were it not for my goal. I began to take rejection less seriously. I knew I was allowed to try again, and each time I did, I got to add it to my precious spreadsheet: a sign of progress. 

I became invested in improving the pitch, the writing, and the process rather than spending that energy wringing my hands over the outcome. 

My first commission, a personal essay, came in June, two months and seventeen rejections into my freelance career. My second, a reported story from my hometown of Cleveland came later over the summer. Slowly the commissions began to trickle in.  

My latest acceptance, a career milestone, was based upon a collection of work I had been building, developing and chipping away at for the previous two years. Various forms of the work had already acquired at least ten rejections. Had it not been for my newly-acquired resilience throughout this rejection process, I’m not sure if I would have had the guts to continue to back it, especially after first being challenged by the same editor that later accepted it. Admittedly, that ‘yes’ actually brought me to tears as a sense of accomplishment mixed with relief washed over me. Someone else had finally seen the value in the work I loved so much. 

Nothing about this process felt easy. But there was incremental progress, because I worked with a process that allowed me to see it.

Better rejections

Perfectionism is something so many women, in particular, spend their lives feeling pressured or programmed to strive for. As a recovering perfectionist, this year of rejections was the ultimate test. It was a means of unlearning beliefs, including disconnecting the link between perfection and self worth. 

By embracing this process I also, in a way, moved up to the next level of rejection, a concept that I frankly wasn’t aware even existed. I was able to notice that I was getting better rejections. Rather than the silence or flat “I’ll pass” I received at the beginning of my journey (though I still receive a lot of those too) I’d also begun receiving positive feedback, even if it came with a rejection. I encountered editors who, though passing on the pitch itself, had found merit in its concept, and had taken the time to tell me so. There were editors who encouraged me to pitch to them again. Some even suggested other places to pitch, where the article might sit well. I am beginning to collect these editors as colleagues, through shared ideas and perspectives (even the rejected ones!) rather than through the convenience of a shared location. These meaningful connections have been a surprising byproduct of my willingness to make mistakes and take risks.  It has done wonders to buoy my trust in this process by unveiling benefits I hadn’t even considered when starting.

I recently celebrated reaching my 100th rejection, albeit slightly later than I had originally planned, having passed the 1-year mark by two months. I practically limped over the finish line; I’d also unexpectedly ended up becoming a homeschool teacher to my two daughters, and I’d woken up at 5:30 a.m. for months on end in order to reach 100 rejections.

I still have some works in progress that I believe deserve good homes. But I’m able to accept that this might not be right away. After spending a year (and two months!) trying to get rejected 100 times, I have developed resilience, determination and a healthy sense of self-worth outside of success (or failure) along the way. To quote Emily Winter, “Failing doesn’t make you a failure.” I haven’t failed, I’ve just found 100 ways that don’t work yet. 

About The Author


Eat. Drink. Wander. Think. Write.


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