A story most leaders tell themselves

“I have no idea what I’m doing.”

It doesn’t matter how senior they are, whether they’re at a Fortune 500 company or Founded a successful Not-For-Profit. All leaders are making it up as they go and will experience moments of doubt, insecurity and, yes, feeling like an imposter.

Knowing this, what would it look like for you to remove that backpack full of perfectionism bricks and impossible expectation textbooks?

A question on rules

What rules have you created for yourself that are no longer serving you?

Because having a rule to always wake up at 5am can be great, until you start going to bed later and it’s the reason you’re so exhausted and moody at work.

We’re all operating in accordance with rules we’ve set for ourselves, but how often do we stop to question them?

Two hundred

The brilliant Jen Waldman and I just released Episode 200 of our podcast.

It marks 200 consecutive weeks of showing up, sharing stories and asking questions about creativity, leadership and entrepreneurship.

It’s 200 weeks of laughter, learning and height jokes (she’s 5’1″ and I’m 6’7″ for those who don’t know… you’re welcome).

It’s also 200 weeks of delightful self doubt and swirling stories like:

“I have no ideas”

“Why would anyone listen to a word we say?”

“Was that even an episode?”

200 is a great round number and a milestone we’re proud of. It’s also a reminder that the milestones and achievements we see in others often sit atop a pile of self doubt, bad ideas and then the occasional moment of clarity.

Thanks to anyone who has tuned in over the journey and here’s to 200 more weeks of learning, laughter and, well, mini-existential crisis.

Recent reads and listens – July edition

Hey legend,

Here’s a small collection of books and podcasts I ate up in July and recommend you do too.

If you’re fascinated by humans and our quirky, irrational behaviours:

The Laws of Human Nature by Robert Green.

If you love learning languages (or, let’s be honest, the idea of learning languages):

Checkout this interview with founder of Duolingo, Luis von Ahn.

If you’re interested in nerding out on emotional intelligence:

This episode of The Imperfects podcast with Lael Stone should do the trick.

In case you missed it:

We released Episode 200 of The Long and The Short Of It this week.

What was your favourite thing you read/listened to last month? Let me know by replying to this email and in the meantime, keep being awesome.

Mistakes vs failures

Why do mistakes feel light, funny, and recoverable while failures feel heavy, serious, and permanent? Are these two sides of the same coin or something different altogether? Can a creative process, which often encourages mistakes, also make room for failure?

Last week I wanted to find out so I asked my most creative friend, Jen Waldman, in this week’s episode of The Long and The Short Of It. You can tune in wherever you get your pods or, you know, by clicking the link above.

The coffee ordering personality test

If you order a coffee in a cafe and they mistakenly give you the wrong one, do you:

a) let them know about the mistake and request the right coffee because that’s what you ordered? or;

b) suck it up and drink the wrong coffee (while resentfully promising to never come to this stupid cafe ever again) because you don’t want to “cause a fuss?”

Regardless of your answer, you can learn a lot about your personality by answering this questions and listening to this episode of The Imperfects podcast.

As for me? I’m in camp B, attempting to convince myself there’s no difference between a weak, soy, extra hot mocha and the long black that I ordered.

Tennis practice

The brilliant Michelle Florendo recently pointed out that the opportunities presented to us through work and life are a bit like tennis practice.

On one side of the net sits a ball machine, firing ball after ball to the other side of the net. These balls represent opportunities.

Some we capitalise on perfectly having enough time and composure to hit a satisfying forehand back across the net. Others might come a little too fast or a little too slow, causing us to mishit, shank off the frame or swing and miss entirely.

Then there are the balls that hit us square in the face when we’re not ready. The ones that cause our eyes to water and an emotional outburst to occur where we throw the racket, look up to the sky and scream “I don’t even like tennis, especially when used as a metaphor!”.

The thing about a ball machine, though, is that there’s always another ball coming. The machine doesn’t care whether you hit the ball or the ball hit you. It certainly doesn’t care how you feel about it.

In life too, there is a constant stream of opportunities. We can view this stream as overwhelming and frustrating or we can view it as an opportunity to practice, improve and get better… Especially when we get hit in the face.

What diet coke and red wine can teach us about mistakes

When in Paris recently my wife ordered a diet coke and received a glass of red wine. It was an insight into how ‘good’ our basic French was (it was terrible) as well as a fascinating example of how to respond to mistakes.

In this case we explained to the waiter (in even worse French) about the mishap, apologised for our terrible French and she proceeded to laugh and swap the drinks, without fuss. It was funny, a little bit awkward and easily fixed.

It got me thinking about all those times when we don’t laugh off a mistake. When we choose to avoid the awkward and get angry or frustrated at a miscommunication at work. When we take a mistake personally and create a story that someone is out to sabotage us rather than pausing to laugh at what might have transpired.

No-one wakes up in the morning hoping to make a bunch of mistakes. No-one hopes to miscommunicate and cause frustration. No-one wants to serve someone a red wine when they ordered a diet coke.

So what might it look like if we acted as such?

Recent reads and listens – June edition

Hey legend,

Here’s a small collection of books and podcasts that I consumed in June, while eating my bodyweight in pasta, pizza, gelato and assorted pastries in France and Italy.

… well this is awkward.

Turns out I didn’t consume anything but aforementioned food groups.

Instead, I switched to using a different part of my brain (the part that decides “what will I eat next?”) and took some time out to rest.

For more on this novel concept, see this recent podcast. You didn’t think I’d leave you without at least ONE resource, did you?

Shorts in a job interview

Have you ever had the experience of hearing someone share an embarrassing, vulnerable story, and immediately feeling more connected to them? Like the time I wore shorts to a job interview with an Executive in a very formal government department.

It’s because our imperfections connect us.

So what if we lead with them? (See The Imperfects and Armchair Experts podcasts for great examples of how to do this).

PS. By some miracle, I still got the job.

Same same, but different

“The tone is wrong, the characters ring false and the humour is strained and simply awful. Don’t waste your time and money.

I loved every minute reading it. It had a whole new feel to it.

These are two seperate reviews of the exact same book. Two humans having a completely different experience when faced with the same thing.

It’s baffling, hilarious and really quite reassuring.

Another moment of Sonder. Another reminder that no-one knows exactly what you know, believes exactly what you believe or cares for exactly what you care for. Another reason to lead with curiosity and empathy and ask: what might be happening for this person to make them feel this way?

The book in question? One from the Harry Potter series.

Showing up is a skill

There’s a story in the book Atomic Habits about a weightlifting coach who works with some of the world’s top athletes. When asked what separates the best from the others (ie people like me with obnoxiously long limbs and poor flexibility) he shares that beyond genetics and muscle mass he believes it boils down to ones ability to deal with the boredom of doing the same exercises over and over, session after session, year after year.

Three things I take from this:

  1. Those who are world class at what they do aren’t always motivated and inspired. They get bored and feel like giving up just like the rest of us and;
  2. While they might feel like skipping a session, those at the top of their game choose to show up anyway. They realise that the act of showing up is a skill.
  3. At 6″7′ with 2 dinky hips and poor hamstring flexibility, I’ll never be a world class weightlifter.