I’m a great fan of cheeky letters. Some of the best things I’ve ever done – and some of the most significant, have come about because I dared myself to write a cheeky letter.

I am a big advocate of boldness. I always encourage the people I work with to be bold, aim high, and write cheeky letters. What do I mean by cheeky? I guess I mean the sort of letters that stand out for their boldness, enthusiasm and desire to do what it takes to get on in life. Letters that are not shy of asking for help, targeted at those who are in the best place to provide a timely ‘leg up’.

It was a cheeky email to craft&design magazine that got me writing for them and led to me being their business editor. And a cheeky letter in the mid 80′s got me a long lasting working friendship with some lovely people in New York – and I ended up going back and forth to work with them over  a 7 year period. More recently, a cheeky request landed me a writing gig with the Cape Craft & Design Institute’s monthly online magazine – a valuable overseas assignment.  Oh, and a cheeky request got me the chance to do my TED talk.

Somewhere in the recesses of your mind, you’ll have list of people you’d love to talk to about your work – but something is holding you back from sending them the info.  Maybe the fear of rejection or ridicule. Maybe the simple fear that they’ll ignore you. Maybe the fear that they’ll get in touch and you’ll have to do something about it   ;)

Just Do It! On average 7 out of 10 people you contact will be willing to talk to you – yes, you’ll get some rejections and zero responses. But remember this – most successful people have a had a leg-up from someone more experienced along the way. And they remember, and they like to pass on the love.

Follow these rules:

  • Ask the right person: Do they have the power to help you?
  • Is the context right? Do they have the resources to help you with your idea?
  • Ask the right question: Have you thought this through – is your request relevant and complementary to their work and values?
  • Is your timing right? Is your request timely – will it fit with their calendar and workflow? Research this.
  • Ask the right way: Have you thought about the best way to approach them? How do you imagine they might like to be asked?
  • Avoid cold-calling – follow them on social media, like and share their posts. Make yourself known and then ask if it’s OK to write to them or schedule a call.

If you can say yes to all of these questions, then go for it. What’s the worst thing that can happen?

Remember that the process – working towards the goal, can be more important than the goal. The goal is an indicator of future performance. As you learn, the goalposts might move. Don’t wait until you have defined your ‘perfect’ goal. You know that is a trap. Avoid the traps.

Above all – be yourself. That’s the hardest thing on earth for someone else to copy.

Good luck, but above all, just do it!


You can find lots more ideas like this – and some great thinking around the thorny question of self-promotion – in The Art of Shouting Quietly