100 Rejections Challenge

After about 60, it really does hurt less

I Like to Draw All Day Long…

In the last year, I’ve learned to deal with the painful idea of outreach. Putting myself out there. Being my own 🤢 cheerleader. But standing outside an art director’s office with a boombox over my head seemed like a terrifying strategy. I’m hilarious at parties, but overly (perhaps unnecessarily) frightened about my career. A few months after first building my portfolio, I still equated myself to Simon in the Bathtub showing people drawrings of my summer vacation.

My friends over at the Inkygoodness Collective put together an interesting challenge, though. While we shared our fears and worries about the future, it dawned on a lot of us that it didn’t matter if you were a budding illustrator or an established artist. Many of us sat in solitude (or in my case, a bathtub), paralyzed and convinced that our work was never going to be good enough.

Then somebody had shared this lovely TedTalk by Jia Jiang, and it immediately resonated with a lot of folks. From there, it seemed like a fun idea to test out this exercise. Not just on illustration-related inquiries, but on our everyday lives to help us feel more confident in general. We decided to try and get 100 rejections in 100 days, ranging from a cold email, to a LinkedIn invitation, to simply asking someone to meet up for coffee. 100 seemed like a nice round number. Like walking 10,000 steps. To make it a little less stressful, we agreed that anything sent out was an immediate rejection until it was answered.

It felt awful at first, but slowly my brain started to understand the assignment. Most importantly, because of the 100 Rejections Challenge, I built an understanding of how the industry worked.

It’s Not A Rom-Com, It’s A Business

While it was nice to imagine some unsuspecting art director bumping into us at a coffee shop and seeing our drawings on the floor and offering us jobs, we felt like we had to be more realistic. My friends and I decided to pool our ideas together and talk about strategies that could work best.

For a lot of us, we started with a simple spreadsheet of contacts. It wasn’t a lot, but I slowly built mine out to include interesting people and organizations that I would like to work with. I looked at illustration directories, magazine mastheads, website credits, LinkedIn profiles. From 10, it grew to over 70 potential contacts. I guess that was the easy part.

Next, creating the draft for the cold email. The first few were really awkward. I tried different tactics: overwhelming flattery (don’t), exaggerated praise for their publication (don’t), simple one-line emails (50/50), and somewhat personal tidbits to share about myself (50/50).

We even talked about social media etiquette, as many of us wondered the most polite but effective way to expand our online presence. Did folks just impulsively add people on LinkedIn? Was including a small note better, or was it more efficient to simply click the blue button and hope for the best? What about the randos?

Because I had a support group with Inkygoodness, we all started to compare our experiences and talk through it together. Turns out, nobody thought I was stupid for writing a shitty email. Even better, as our collective numbers grew, we began to share our own insight into our inquiries.

On more than one occassion, a friend’s experience would deepen my impression about a certain company or agency. It helped to feel that we were taking some kind of power back, rather than feeling like we were on an endless cycle of American Idol auditions.

Most of all, I didn’t have to be my own cheerleader, thank goodness. Other people encouraged me to keep going, even when things felt really bleak.

Remarkably, a couple of months into it, a whole bunch of us started getting somewhere. One friend somehow was able to send out over 500 emails, resulting in work for several magazines and editorial pieces. Another friend had scored a workshop/talk at a pretty big conference because he simply applied for it. A couple of people also ended up getting agency representation.

The wonderful thing was, as soon as these good things happened, we found out that we also had a place to share our excitement. What a powerful feeling to know that our space for rejections could also be a space for joy and celebration.

In my case, I ended up with a few art directors and agents following me on Instagram and connecting with me on LinkedIn. From there, the algorithm admittedly worked in my favour, showing me more recommedations and suggestions. I was able to add more to my little spreadsheet.

Expanding my contact list also encouraged me to seek out even more companies and people, none of whom I would have ever discovered if I didn’t take that initial step.

I didn’t contact them right away, because I swear I’m not a psycho. I simply dug deeper and tried to get to know their online presence before deciding if it was worth reaching out.

Later on, I also realized that this is what art directors were doing on the other side of the wall too. Because, you know, we’re not all psychos.

It was “6 Degrees of Kevin Bacon” and I ultimately made it a goal to actually reach Kevin Bacon somehow.

Spoiler alert: I have yet to get to contact Kevin Bacon.

Another spoiler alert: I didn’t actually reach 100.

Turning The Automaton Off

It’s easy these days to try and automate everything, and to test out theories until the fire burns out. But what I learned from the 100 Rejections Challenge was to also pay attention to the short-run feedback. Sometimes I was better to call it halfway through, especially if patterns and outcomes were becoming blatantly obvious.

To give you an idea, here’s a snapshot of my portfolio from Oct 2023:

As I sent out my work, I became very aware of the context of which it would be viewed.

• Would a fashion/art magazine think this was relevant?

• Why am I sending mock-ups of drinks cans to book designers?

• Why am I sending mock-ups of books to brand agencies?

You see where I’m going with this?

None of this outreach was happening in a vacuum either, as I was still continuing my daily practice and learning from past illustration challenges. As each arm of this endeavour started punching windmills into the air, I started paying attention to where the gaps in my work were.

• My portfolio was not targeted enough for a specific industry or category, which probably confused art directors. Or at the very least, I didn’t give them the confidence to trust me in completing a specific kind of project.

• My outreach net was cast too wide, making it feel like I was trying to be 100 different things. I was contacting fashion magazines along with business magazines and art licensing agencies and kids magazines. I had to tell myself that I was not Jennifer Lopez.

• There was no intention or focus to my strategy, and trying to reach 100 this way felt like I was just doing this for the sake of doing it.

• I realized that I actually did not know what I wanted yet, and was blindly shooting where there was noise. This didn’t seem like a sustainable approach.

While the challenge was supposed to run for 100 days, I took some time away from it as I revisited my portfolio. Every few batches of inquiries gave me something to think about, and I would adjust my direction accordingly. Instead of condensing it all into 100 days, it’s become an integrated part of my practice to send out inquiries once in a while over the course of the year. I broke the rules. Sorry, girls. 😎

Over time, my decisions became stronger, and the illustration career I wanted started to take shape. Like a molting seal covered in bird shit and matted fur, I began to envision the future I wanted and shimmy my flabby way towards that.

Sometimes I’d get responses months later, where the initial work I had presented no longer resembled the new work I was putting out. This gave me an idea of how busy people were, and how little attention my one email would get in the vast sea of daily notifications and conversations.

I actually felt relieved to think that I just ended up in some wastebasket—because I knew my work right now was stronger than it was a year ago. Each interaction gave me a reason to reflect on my work and make it better. The rejection was not of me as a person, but of the quality of work that I was capable of showing at that time.

Without those signposts in the form of rejections, I’d still be guessing and flailing and shooting in the dark.

Here is a snapshot of my website today September 2024, with a specific category for book covers:

A Party for Dreamers

The 100 Rejections Challenge was a framework for me and my buddies to get together and to make the illustration world a little less scary. It was never meant to be a full-on strategy to success. We weren’t all just sitting around complaining about the state of the world eating sad lady cake. We were actively engaging and sharing and discussing, allowing ourselves to grow as a group.

In the end, I think I got to about 60-70 inquiries of varied efforts and varied outcomes. The most important part for me was the chance to learn from my friends as they shared their own experiences. For those 100 days, I really did feel a lot stronger, less alone. The hardest part for me is trying to figure out things by myself. Surprisingly, I am not afraid to reach out anymore, but of course it’s always more fun when you bring a friend along.

I did the 100 Rejections Challenge over a year ago now. Since then, I’ve been able to really define and refine my work. I’m more decisive about who I want to contact, and the types of jobs I want to take on.

Knowing that I have more lines out in the water makes me feel less desperate. It keeps me from obsessing about a single inquiry and building a shrine around some person I’ve never met. If anything, I feel more optimistic. I’m familiar with the advice of diversifying your income. I think it’s also smart to diversify your prospects.

There is another round of 100 Rejections Challenge with Inkygoodness happening this year. I’ve joined as a buddy with some battle scars, looking to learn from those in my position a year and a half ago, and those who have now become more established in their chosen fields. I don’t think I’ll reach 100 again this time, but maybe this is the year I cross paths with Kevin Bacon. Fingers crossed.