5 min read

A Month of Embracing Rejection Every Day

Collecting rejections

In May I decided it would be fun to do a little experiment: try and get out of my comfort zone every day.

I would be aiming to collect rejections, the idea being that by asking for something beyond the norm I become fine with getting a "no".

I'm already pretty good at reaching out to people but it never hurts to challenge yourself more! I managed to go out of my comfort zone (almost) every day in May. Here's what happened.

Some of the wins 👍

I sold my first annual plans for High Signal

I asked three members of my High Signal community to buy an annual membership of High Signal at $390 a year. Two of them, Val and Tom, said yes - thanks guys! This provided me with more cashflow as I don't have to wait 12 months for this money. I also got a new member Ruurtjan to join the Telegram group by reaching out on Twitter and I think another member might join soon from a DM I sent.  

So I made $799 from those asks and added $19 in MRR.

Some developers agreed to act as mentors

I asked some of my friends if they would do mentoring for my No CS Degree audience - a few said yes so that's great! I'll be adding mentorships soon.

I got another podcast guest

Lachlan Kirkwood agreed to do an AMA in High Signal on his success as a YouTuber making Bubble tutorials. This is a great value-add for the community and will be lots of fun for me as well! Every Thursday we do a Zoom chat but once a month we have a guest AMA and I release it as a podcast as well.

Testimonials for High Signal

I got testimonials from Corey, Kieran, CH Daniel, Phil and Lachlan for my High Signal newsletter for indie startup news


This social proof is great for growing email subscribers as I talk about in my Grow Your Newsletter course

I received free advice from a recruiter on job boards

I got a free call with a recruiter at a tech company on how they manage the recruitment process and work with job boards. As someone who has a job board for self-taught developers, this was very illuminating! I got the call by asking a friend for an intro.  

I learned more about customizing Ghost themes

I got some free advice from Dan Rowden on adding tags to a Ghost theme. Thanks Dan!

I got a £30 voucher from John Lewis

I had some really bad customer service at a department store - I decided to ask for a voucher as a result. I didn't get as much as I asked for but still, nice to get some compensation.

Email giving me a £30 voucher for bad service

I got a free coffee top-up

In the UK this never happens - unlike the US, we don't have a culture of free refills. I asked anyway and the barista agreed! They also now let me split a coffee over two cups, over different days. So this has effectively cut my coffee bill in half :)

In another cafe I also asked for and got a free hot chocolate.

Here's the full month of asking for rejections - I did miss a couple of days but hey ho.

Some of the fails 👎

Failed to get a free place on a coding bootcamp

I made a decent offer to a coding bootcamp - I would promote them for free on No CS Degree in return for a free place on their bootcamp. It never hurts to brush up on coding skills! I did not receive a reply...

Failed to sell art on a street stall

I did my very best to sell some of my friend's art at a community event. I may have had too much coffee at this stage LOL - I was unsuccessful but it was very funny and my friend saw me in selling mode for the first time.


Failed to get on some podcasts

I made a pretty good pitch to be on coding podcasts but they either said no or didn't reply.

A daily breakdown of rejections sought 👇

1st May

  • asked girl out

2nd May

  • asked Corey to add quote to High Signal website - he agreed
  • asked a Ghost developer for help with my theme
  • asked people's advice on adding a paywall

3rd May

  • asked Lachlan to do an AMA for High Signal - he agreed
  • asked Sabba and Kieran for testimonial
  • asked out girl
  • asked for a mentor call - no reply

4th May

  • asked to be on big podcast
  • asked out girl

5th May

  • pitched job board to company
  • asked Mubs to add Coding category to Podhunt - he replied
  • asked out girl

6th May

  • asked remaining free High Signal members to pay
  • asked for High Signal to be added to the IndieHackers podcast page
  • asked for a free hot chocolate
  • asked for a free coffee top-up
  • asked Anne-Laure to add reactions in the Newsletter Geeks Telegram group - she did it!
  • asked DHH to subscribe to High Signal

7th May

  • asked DHH for an AMA - he said too busy
  • asked Shaan Puri to check out HS newsletter - no reply

8th May

  • asked for a mentor call - no reply

9th May

  • asked to be on the Wes Bos podcast
  • asked a London dev to do an interview for No CS Degree

10th May

  • asked Courtland to add High Signal to the Indie Hackers podcast site
  • asked for a free place on a coding bootcamp
  • asked if people on Twitter want to buy Webflow directory theme

13th May

  • asked Val to buy an annual membership of High Signal - he said yes
  • asked Ruurtjan to join High Signal - he said yes

14th May

  • asked a passing cyclist for a bike pump - he said yes and it saved me a mile of walking

15th May

  • asked for a barista to put my coffee in two mugs so I can stay in the cafe longer

16th May

  • asked someone to do an inteview for No CS Degree

17th May

  • Asked someone to sponsor 4dayweek

18th May

  • asked a friend to meet an hour earlier than she suggested

20th May

  • asked someone to connect me to a recruiter to talk about job boards
  • pitched people on LinkedIn about my job board

22nd May

  • tried to sell a piece of art for my friend Jen at community event

23-24th May

  • asked developers to act as mentors for my audience - some agreed :)

25th May

  • asked for newsletter sponsors

26th May

  • asked for the second half of a cup of coffee that I didn't have a few days before in a cafe and they said yes
  • pitched an HR idea to three people
  • asked Tom to join annual High Signal plan - he agreed

29th May

  • asked some developers to act as mentors and they agreed

30th May

  • asked for and got 10% discount when buying running shoes by mentioning I was in a club, even though it's not registered with the shop

31st May

  • got a recruiter to agree to talk to me about job boards and their recruiting process


It never does any harm to ask! I found this month helped me continue to get out of the bounds of what society thinks is ok to ask for me. Most people just don't think they can ask for something and that's why they don't get what they want. Follow me on Twitter for more experiments like this :)