10 lessons I learnt from the rejection challenge

For the last year and a half I have been working on a rejection challenge where I am trying to get 100 rejections in my business. If you want to know more about what the actual challenge is then check out this blog post and also you can listen to this podcast chat I had with my friend and incredible illustrator-business-owner Katie Chappell. In this blog post we are going to dive into the lessons that I have learnt while doing this challenge.

1. You need to ask for what you want

Quite often in the past I have had the mindset that I have to wait for people to notice what I am doing and then they offer me opportunities. And even though this does happen, and has actually started happening more since I did the challenge (mainly because doing the challenge made me more visible), actually a lot of the time since there are so many people online that we are, I guess, ‘competing’ with it doesn’t work to just wait for people to notice you. So I do believe that often the best thing to do is ask for what you want. More often than not you will get a yes because the person you are asking didn’t know you wanted that, but actually you are a great fit, or it happened to be that you were asking at the right time for it to be a ‘yes’. Also it might be that people have noticed you but didn’t actually know that the thing you are pitching for is something you were interested in doing. People can’t read your mind. So I would really encourage you to ask for what you want, even though it’s scary because you might get a no! 

2. Know your goals

One of the things that I did when I first started the challenge was to make a long list of things I could pitch for. A lot of my goals at the time were around my podcast and so a lot of my pitches were approaching potential sponsors and guests. Knowing what your goals are means that you can be really targeted and strategic with your pitching rather than just a scatter gun approach. I did notice though that because of my mental shift of pitching for lots of opportunities, when other people asked me to do things outside of the challenge I was very quick to say yes because I was in the mindset of embracing all the opportunities that came my way. Much further in now I am aware that this isn’t particularly sustainable and so I am trying to be a lot more selective about what I say yes to so I don’t burn out. This allows me to invest time in activities that will actually move my branding business and my podcast forward.

3. The more I embraced rejection the quicker I recovered 

The aim of this challenge was never to get rid of the feelings that I felt when I was rejected, I am not sure that is even possible. I definitely hoped that I would get better at dealing with them and recovering from them and I really noticed that happen. There was one rejection in particular that I found quite hard, because I had told the person about the challenge and they were very much against the concept in general and didn’t hold back in letting me know that and so it felt quite personal. It sent me into a spiral and in the past I think it would have taken me quite a long time to get out of the spiral, but it actually only took me a couple of hours (and a few kind supportive messages from friends) to pull myself out of it and move on, which felt like a huge improvement. I think they key thing for me is taking a rejection, analysing the feelings and why they might have arisen and then learning what I can from it, but moving on quickly. The more I got rejected the easier it felt to recover. Of course some rejections are harder than others depending on what it is you have pitched or asked for.

4. Planning makes things easier 

Pitching for lots of things actually takes quite a lot of time. Before I started the challenge I wanted to make sure I had enough things to pitch for to make it a viable challenge to do. It turns out I had plenty that I wanted to pitch for but I needed to do it as efficiently as possible so I tried as much as I could to batch jobs together. Once I had my list of things to pitch for, I then spent a load of time trying to work out who the right person to contact would be. When I started the challenge, I had linkedin Premium, so I utilised that to find the relevant person at the company who I thought I should get in touch with. If their email wasn’t on their profile, I googled the naming convention of email at that company and usually could work out what their email address was. I then spent time writing pitches and came up with a bit of a structure and a template. I then had little sessions of sending out a flurry of pitches and waiting to see what happened. 

5. Sometimes it’s good to be spontaneous and grab an opportunity 

Even though my last point was about the importance of planning and batching tasks, sometimes spontaneity is the order of the day. For example, this looked like a dream podcast guest responding to me tagging them in a story and me taking the opportunity to reply right away and ask them if they would be willing to be on the podcast. Another example would be if you meet someone in person at an event and you want to suggest a collaboration idea with them. It could be anything really but sometimes the best thing is to not overthink it, don’t spend hours meticulously crafting the perfect pitch, just dive right in and ask. Quickly. 

6. Get good at writing pitches 

A big part about asking for what you want is how you ask, and I think writing a good pitch is an art in itself. As someone who gets pitched to a lot by people asking to be on my podcast I have learnt over the years what I like and don’t like. I’ve then used this information to help with writing my own pitches. Since we are all different and like different things, a single pitch formart is never going to be perfect for everyone, but there will be some tips in there for most people when it comes to pitching. I will do a whole other blog post soon with my tips for pitching, but here are a few to get you started:

First up remember practice makes perfect, the more pitches you write the better you will become. Make sure your pitches are personal and that you have researched a little bit who you are writing to. If you know their instagram handle there is no harm in engaging with their content and leaving nice and supportive messages. It’s always going to help if they recognise your name (in a positive way) when it pops up in your inbox. Don’t make your pitch too long, but also give them enough information for them to work out if it is something they are actually interested in or not. Also don’t make it difficult for them to find out more about you. Share links to your website or social media accounts so they can easily do some research of their own. Don't be arrogant and write it as though you are assuming they are going to say yes (I have had this happen many times and it's almost always an immediate no from me). Ultimately I think it always helps to think how you would like to be spoken to.

7. How to deal with ghosting 

Some people really worry about being ghosted and honestly it probably will happen. There are so many potential reasons for this and quite often they aren’t bad. It might be that your email ended up in someone’s spam, or they saw it and got distracted by something and just forgot to reply. It could be that you aren’t the right fit for a project right now, but they filed it for possible future projects (I heard back from some of my pitches over 6 months later). Or it might even just be that they want to let you down gently and feel like not replying is the nicest way to do that (even if that’s not what you want). So if you do get ghosted, try not to take it to heart and just remember everyone is busy and has a lot on, and it doesn’t mean you are bad at what you do or they didn’t like your pitch. 

8. The importance of following up 

Leading on nicely from the previous point is the importance of following up. I didn’t do this all the time but again from receiving lots of pitches myself sometimes I really appreciate a follow up email. Often replying to an email is on my to do list, but I keep getting distracted by other things, or I know I want someone to be a guest on my podcast but I have a bit of a backlog of guests, and I actually really appreciate the nudge or reminder to reply. Again, there are so many reasons that people might not have replied and it could just be that they meant to be the email got lost in their busy inbox and it would actually help them out if it was bumped back up to the top again! You will need to work out what feels comfortable to you (and honestly for me there is nothing comfortable about this so I had to work through it) but I tended to wait about 2 weeks, sometimes a bit longer and I would only follow up once. 

9. Be patient - what you thought was a rejection might turn into an acceptance

This was a lesson that I enjoyed learning. There were quite a lot of pitches that after a few months got put in the rejected pile and then a few months after that again I heard back with a positive response. This was always a nice surprise and I think is another helpful reminder to not let something you thought was a rejection become a negative story you tell yourself about yourself, because so often it isn’t. There are two instances I remember clearly where it happened to me and both times it was because of a busy, out of control inbox and they eventually got through it and got back to me. It wasn’t because they didn’t like my pitch, or that they thought I wasn’t good enough or any of the reasons I used to convince myself of before starting this challenge. 

10. Be strategic

One thing I noticed when I started the challenge is that I got into the mindset of saying yes to all of the opportunities that came my way even if it wasn’t something I pitched for, and that was great and exciting but it did mean that at times last year I felt very overwhelmed and found myself slipping towards possible burnout. I realised that going forward I needed to be more strategic about what I was available for. It helps to be clear on what your goals are and then be more selective about what you pitch for and what you say yes to in order to make sure that you reach those goals. 

I hope these tips are helpful for you if you decide to embark on your own rejection challenge (or to be honest even if you don’t) and if you have any tips you have picked up along the way that you would add I’d love to hear them! 

I am planning to write more posts about this challenge but I am always interested to hear if there is anything you would be interested in me covering! Let me know!