Back in Spring 2023 I started sending out pitching emails to a range of clients I wanted to work with as an illustrator. I had invested in the AOI Directories and was approaching a range of Publishing, Editorial and Advertising clients that I thought aligned with my illustration style.

Not all of the pitch emails I sent had a response, but some of them were really positive, and although they didn’t have opportunities at the time, they were happy for me to add them to my mailing list to keep them up to date with future projects.

However, I had one reply from a publication that I had sent a pitch email to that was extremely negative in their response. They took the time to explain exactly why they didn’t think I had talent as an illustrator and that I needed to ‘go back to art school’, amongst many other things they framed as ‘helpful’ feedback.

At the time I was quite new to sending pitching emails and in building my illustration portfolio. I found their email really hurtful and really struggled not to take it to heart. It stopped me from sending more pitching emails at the time, and also from building my illustration portfolio.

However, after discussing the rejection, and how it made me feel, with friends and family, I decided that the best response was to simply prove this person wrong and continue putting myself out there.

A few months later I heard about the ‘100 No Thank You’s Challenge’ from Katie Chappell and also Liz Mosely, and I felt inspired to start a challenge of my own.

The idea is that you aim for 100 ‘No Thank You’s’ by sending out lots of pitches to people and companies that you would like to work with. It gamifies the rejection process because if you receive a ‘No’ response, you just add it to your list of ‘100 No Thank You’s’.

And, spoiler alert, you actually receive a lot more ‘Yes Please’ responses! I’ve now been doing this challenge for 10 months and I’ve only had a handful of outright ‘No’ responses. The rest have either been Yes, or Yes but not yet, or just no response, which is fine too as you can’t expect everyone to reply.

Anyone I know that has done this challenge, generally has to stop doing it as they get so busy with all the work and opportunities that come their way!

So I thought I would share a few of the things I have learnt from doing this challenge so far…

Photo by Faye Hedges

Do Your Research

Before you start pitching to companies, make sure you have researched them to be sure that you will be a good fit. Also, make sure you have found the best contact in the company for the opportunity you’re interested in. You can do this on Linked In, and can also check email address formats on websites like Hunter.io and Rocket Reach.

Also - do take the time to write a personalised pitch email explaining why you love the organisation and why you think you would be a good fit for them.

Photo by Faye Hedges

Pitch For Anything and Everything

When I started the challenge I thought I would just be sending pitch emails to possible publishing, editorial and advertising clients I would like to be commissioned by. However, as my business has evolved into being more focused on live illustration and hosting workshops and retreats, I have now been pitching to work with lots of different brands and live event companies, as well as for press and PR opportunities.

I also have pitched to work with local businesses and had the opportunity to work with Midrib Plants creating plant portraits of their customers for their 1st Anniversary last year, as well as hosting workshops at Nood Stores in Reading.

I also started pitching for guest spots on Podcasts I liked and now I’ve been a guest on the Makings and Musings Podcast, and The Business Nest Natters Podcast.

You can also pitch for press opportunities in magazines, newspapers and local radio and more.

And you can also pitch to collaborate with other small businesses you’d like to work with. This is the reason I started the Flow and Flourish Retreat with Jodie Rose Calligraphy. You can read more about how we planned the retreat here.

Think outside the box, and doing be afraid to pitch for something that may be out of your comfort zone - you’ll be amazed at how many people will be super excited to hear from you.

Photo by Faye Hedges

The Magical Power of Following Up

The number one rule of pitching is ALWAYS follow up! I have very rarely had a response from the first pitch email that I send. I get far more success from sending a polite follow up email a couple of weeks later. Never assume that someone hasn’t replied because they’re not interested. They may have been on holiday, your email might have gone to junk, or they may just be super busy.

Also - sometimes if you really really want to do somthing, just being super persistent can pay off. I love this story of Radio 1 DJ Edith Bowman being so determined to get work experience at her local radio station that she kept pestering them until they gave in and she got 2 weeks work experience.

I also love this interview with actress Margot Robbie where she reveals that she got her big break in Neighbours at age 17, simply from cold calling their casting agent over and over again until she got through and they happened to have a role available that she was a great fit for.

Also, if you get a response from a possible client / company and they don’t have an opportunity right now, put them down as a ‘not yet’ and make sure to send a follow up email 3-6 months later. You can also ask if they would like to join your mailing list, so they can keep up to date with your latest projects and events.

Networking

Attending Networking and in person events is a great way to find out about opportunities for people and companies to pitch to. I often hear about other markets and events I can apply for when I chat to other stall holders at an event.

And I’ve started attending more Networking events in my local area (including The Business Nest events) and I’ve met lots of other small business owners I can work with, or who have suggestions on companies that I can approach.

But remember - don’t let the other person contact you if they say they will, always send them an email after the event to follow up on the opportunity.

Photo by Faye Hedges

Get Organised

Finally, make sure you get organised with your challenge. I track mine on a simple Google docs spreadsheet, but you can also use Trello, Notion, Airtasker or similar to track your pitches.

I also have set up a series of template emails that I can send (and personalise) for each type of pitch, as well as a follow up email template.

If you’re pitching for press opportunities I highly recommend setting up a 'Press Pack’ of a short bio about you, professional headshot photos, photos of your products / services, and your press release (if relevant).

I hope I’ve given you some inspiration to get started on your own 100 No Thank You Challenge. Let me know if you start one!