Awkward conversations at Pizza Express

“I have to be honest… being with you all day made me feel a bit shit.”

It’s not an easy thing to say, especially to one of your best friends.

I debated long and hard about whether say it, but decided that I needed to own it, because it was true. When I had got home the previous day, I felt bloody awful about myself.

Let me explain…

It was the first day of a magic convention and I’d spent the day with my good friend Steve, which was fabulous…

…until it was shit.

Before you think me the world’s worst mate, it’s not Steve that made me feel shit. It’s what he’s done with his life.

Hang on, that sounds even worse.

Let me try that again…

About two years ago, Steve created a magic review show on YouTube. Magic dealers peddle a lot of magic tat (and that’s putting it nicely), so on the show, Steve reviews magic tricks, tests them in the “real world” (whatever the hell that is) and gives his honest opinions on them, so other magicians know what they’re buying.

He stops magicians from getting burned.

As a result, he’s built a bit of a following in the magic community.

Spending an entire day with Steve at a magic convention was like shadowing Ariana Grande at the Smash Hits Poll Winners Party (oh my god – how old am I?).

He was besieged by people, thanking him for his reviews, with magic dealers thrusting free tricks into his arms in the hope of a favourable review and endless women thrusting their undergarments into his pockets.

(OK, so I might be exaggerating, just a little…)

The first time this happened, I was absolutely delighted for him. 

The second time? I was happy for him.

Third time? I was happy…ish.

Fourth? Jealousy rising…

By the fifth time, I was Googling “what is the best way to dispose of a corpse with 47 stab wounds?”

(I’m going to be needing someone to delete my browsing history when I die!)

I felt inadequate and inferior.

“I’m the same age as him. I should have people giving ME free magic tricks and thanking ME!”

I was being a whiny little [insert your preferred derogatory term here].

So I decided to tell him over a pedana pizza at Pizza Express (where all the difficult conversations are had).

“I have to be honest… it was great to see you yesterday, but, being with you all day made me feel a bit shit. Everyone that thanked you or gave you some free stuff made me a little bit angrier. I kept thinking ‘why haven’t I created something that makes people give me free stuff?'”

For most people, awkwardness would follow, but he let out a massive laugh.

Even though he knew I was being serious, he could tell from my tone what was REALLY going on – I was taking the mickey out of myself.

Which brings me to the point of this email, and one of the main benefits of using humour:

Humour makes conversations easier – even the difficult ones.

Once you realise that you can be lighthearted and fun – about even the most serious of topics – they become easier to deal with.

When things are easier to deal with, they’re less stressful.

For most people, telling their best mate that being with them made you feel terrible would be a Jeremy Kyle moment, but when you realise you can be light-hearted without sacrificing any of authenticity (darn, I hate that word), it takes a lot of stress out of your life.

You can have the difficult conversation…

…without any of the difficulty.

Think of all the stressful situations that can crop up in your business. The ones that you’re struggling to face:

  • The client who’s late paying
  • The prospect who you can’t quite pin down for a meeting
  • The supplier you forgot to get back to…8 years ago.

How can you use humour to make an awkward conversation easier?

“Hey! I don’t know if you’ve been getting my invoices or whether you’ve been distracted by endless proposals from Russian wives or Nigerian millionaires, so I thought I’d send you another…”

“Hi. I know we’ve tried a few times to get together and it’s not happened. I would love to meet you, so I’ve enclosed a voucher for some drinks and nibbles at that trendy new eaterie for this week. I’ll be there all day Monday… what do you say?”

“Dave! I’m so sorry. I got kidnapped by aliens last week and transported to the planet Veruci 7, where I had to pass a series of rigorous tests to save humanity. OK, so not all that is true, but it’s a lot better than ‘sorry, I completely forgot to reply to your email’, isn’t it? Forgive me…?”

Sure, humour won’t save your bacon in every situation, but it’s an easy way to make difficult conversations a bit less stressful – for you AND for them.

If you’re struggling with a difficult conversation, or have an unopened email in your inbox that makes you wince, try and think of a way you can use humour to make it a bit easier and see how it works.

Have a great Thursday!


P.S. Don’t forget, as a subscriber, you can use the discount code “FIERCEANDLOYAL” to get 25% off “Smack My Pitch Up!” – the simple guide to creating a clear and compelling networking pitch (released on the 8th March). More details can be found here.