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MAKING HEADWAY

BY RICH FARRELLY

Welcome to issue #10 of Making Headway, a monthly letter to you, with a focus on doing your best leadership work and hopefully, making some tweaks to your life. I love that you are here. If this was forwarded to you, subscribe here.

Sunday, August 3rd, 2025 

Hello Wildcard,

I love that we're at double digits in this little letter thing we have going. There will be mistakes along the way.

I'm coming to you from the Sunshine Coast of sunny Queensland. We came here to escape the depths of the cold Melbourne winter and warm our bones. Some of the reasons we drive the 2000km (1200 miles) to Caloundra are:

• Our hearts can't bear putting the two boys, Skipper and Rocket through the trauma of a flight

Cue cute photo of Skipper (L) & Rocket (R) in the back seat (Photo credit: Me)

• We get to support the little country towns on the way up. 
• We love looking at farmland and the changing landscape that you don't get from 30,000 feet in the air.

* * *

I forgot to mention last month that in June I was a contestant on a game show called Tipping Point. There is a UK version, the Australian one is waaaay better. 

It was a redemption episode. I had been on it once before in 2024, but took a gamble on 'Jackpot Temptation', and failed. I lost a fist full of cash, but won a 75 inch TV. Given the size, I had to buy a new TV cabinet to sit it on. All up, that appearance cost me 500 bucks. You can see me lose a little piece of my dignity right here. (you'll probably need a VPN if you're outside Australia, and use the postcode from the footer of this letter if it asks for one)

About a year later I was invited back for another crack at the title. This time was a little more successful - I won a coffee machine (my life is now complete) and the jackpot. We are thinking of remodelling the kitchen to fit the coffee machine.

If you haven't seen the episode, do yourself a favour and tune in. There is some serious tension and a few thrills. The classic viewing is right here. 

Me losing   

Me winning   

Whatever your thoughts on game shows, they are a fun experience I can highly recommend.

This letter takes a few forms over the month I write it. I often suffer from what author George Saunders calls "the tyranny of the first draft". When I first start to write, I expect things to be perfect the first time and this often stops me from starting or continuing. 

Many of us suffer from the self-defeating assumption or expectation that our first try - whether at writing a book, launching a business, playing a sport, or choosing a career - should be great or right or perfect. 

In reality, Saunders notes, "before anything worthwhile can be good, most of the ways it is bad must be tried first." 

I remember when I first started thinking about writing these letters to you and taking the leap of faith. So, I tapped away with the words of George Saunders in my ear, “The first draft doesn’t need to be good, it just needs to be, so you can revise it and make it good.”

Failure was on my mind. I think failure is worthwhile for many reasons, but mainly because failure is relatable.

So, let's talk about failure.

(I know, alot of failure in there)

Photo credit: Photo by Jon Tyson on Unsplash

What looks like failure might just be the wrong audience

Before Kermit, before Cookie Monster, before Count von Count, before Jim Henson became Jim Henson - he failed.

Not in the way people usually talk about failure. There were no box office flops, no lawsuits, no network cancellations.

His first big failure was internal.

He gave up.

In 1954, a young Jim Henson discovered puppetry at his local library. He was hooked - crafting puppets, creating voices, imagining worlds. And then, as happens so often in the early stages of something vulnerable and beautiful, someone came along and squashed it.

A teacher walked past, saw him holding a puppet, and casually said, “You’re wasting your time with those puppets.”

That’s all it took.

Henson internalised the comment, folded his ambition into shame, and abandoned the dream. “It didn’t seem to be the sort of thing a grown man works at for a living,” he later said. “I decided to chuck it all.”

That was his first failure: he stopped believing in what lit him up.

But then came the redemption arc - not through effort, but through exposure.

In Europe, wandering aimlessly, he found something extraordinary: puppeteers who took their craft seriously. Artists. Innovators. Adults.
Suddenly, what had once been “a silly hobby” became a calling.
A legitimate, expressive, joyful artform.

That shift - seeing what looked like failure through a different cultural lens - brought Henson back to life. He returned from Europe “fired up to do wonderful puppetry,” and the rest is fuzzy, felt-covered history.

Sometimes failure isn’t loud or dramatic - it’s subtle.
It’s believing someone else’s low expectations.
It’s abandoning what you love before it has the chance to bloom.

But failure doesn’t have to be the end. It can be a pause.
A detour.
A reminder that where you are isn’t the same as who you are.

Henson didn’t just succeed in spite of that early doubt - he succeeded because he saw a different version of what was possible.
That’s what we all need sometimes: a new environment where the thing we were told was a waste of time… is celebrated.

* * *

Photo Credit: Me

Five Smarter Ways to Look at Failure

We talk a lot about success - how to chase it, shape it, scale it.
But failure? That’s the bit we whisper about. Tidy up. Keep in the drawer marked “lessons learned” and only open when HR insists.

And yet… failure is often where the real stuff lives.

Not the fluffy quote kind of failure. The real, messy, inconvenient kind. The stuff that stings before it sings.

Clear your cache. Here are five reboots on failure that might just make you see it differently:

1. Fail First, Learn Fast
Failure isn’t the opposite of success. It’s a crucial co-conspirator.

Behind most breakthroughs are bellyflops, false starts, and “well, that didn’t go how we planned”, and  "How fascinating!" moments.

The question isn’t “Did it work?” but “What did we learn that we wouldn’t have otherwise?”

2. Find the Hidden Gold
Some mistakes are avoidable. Some are noble. Some are just weird and oddly helpful.

The smart move? Pause long enough to notice the type of failure and the truth it’s offering.

There’s always a message buried in the mess, if we’re brave enough to look.

3. Perfection Is Overrated
Perfectionism is just fear wearing a shiny name tag.
The people who get things done don’t wait until it’s flawless. They ship the rough cut. They test the prototype. They press send.
Done, flawed, and in the world will always beat perfect and imaginary.

4. Make Failure Part of the Plan
Failure shouldn't be a surprise - it should be part of the plan.
When teams feel safe to say “I stuffed up,” without fear of being side-eyed or sidelined, magic happens.
Build spaces where reflection beats blame, curiosity beats cover-ups, and no one has to fake perfection.

5. Lead Like You’ve Failed Before
A leader who says “That’s on me” changes the entire vibe of a room.
Mistake-tolerant teams don’t just survive - they adapt, grow, and keep moving when others stall.
Resilience isn’t about always getting it right. It’s about bouncing forward, not just back.

Failure isn't a detour. I want to say it is part of the map, but it’s really more part of the territory.

If we can stop hiding it, fearing it, or over-analysing it into oblivion, we might just find that failure is the best teacher we never asked for.

Next time something doesn’t go to plan, try this:
Instead of asking, “How do I fix this?”
Ask, “What’s this here to teach me?”

That shift alone might be the most successful thing you do all of this week.

Guest Post

This month I have another chat to my good friend, Paul Edwards about failure and he had an interesting story.

PE: You know, this month's theme on failure reminds me of something I saw happen almost 20 years ago.

RF: Oh! Tell me about it.

PE: I was working for a company, and there was a project manager there - let's call him Klaus. Klaus was a solid project manager, and when the Head of Professional Services role opened up, he was encouraged to apply. He did, and got the job.

RF: Good for Klaus! But I'm guessing there's a twist?

PE: Spot on. A few months into the new role, things weren't going well. Klaus was struggling, unhappy, and his team wasn't thriving under his leadership.

RF: The scent of failure is starting to emerge.

PE: Exactly. But what Klaus did next is what fascinated me. He approached management openly, admitted it wasn't working, and requested to return to his previous role, even accepting a pay cut.

RF: That's impressive humility. Did he get his old role back?

PE: He did, but here's the kicker - he only stayed a few months. Management started giving him difficult, low-value projects, effectively pushing him out. They couldn't accept Klaus stepping back as anything other than failure, and it made them look bad too.

RF: Sounds like a classic example of the Peter Principle.

PE: Tell me more.

RF: It's the idea that people get promoted to their level of incompetence - they succeed in one role, but those skills don't necessarily transfer to a higher role.

PE: Exactly! Klaus realised it and tried to correct it, but ironically, management's pride prevented them from seeing the wisdom in his choice.

RF: Perhaps they had reached their own level of incompetence.

PE: Ha! Quite possibly. But it highlights something deeper: the unwillingness to accept failure often stems from an inability or refusal to be vulnerable.

RF: Vulnerability - interesting. It’s a paradox, isn't it? We avoid vulnerability, yet embracing it often leads to greater strength and growth.

PE: Absolutely. Vulnerability isn't weakness; it's a powerful form of strength. It allows us to own our failures openly, learn from them, and move forward more effectively. In fact, being vulnerable is a cornerstone of emotional intelligence - it requires self-awareness to recognise and admit our limitations, and empathy to understand and support others in theirs.

RF: So, the real lesson here might be that true success requires vulnerability - and that failing honestly is far better than pretending to succeed.

PE: That's exactly it, Rich. So perhaps the question isn't whether we're going to fail - it's how courageously we're prepared to respond when we inevitably do.

RF: Well said, Paul. A perfect lesson in embracing failure.

And, Just something different for you
A few things have come across the Head to Head desk in the last month. One of them was a very possible reason for why the Great Wall of China was built - https://youtu.be/2yckqyg75oE?si=H9NstPW1MyweJMx0

I like to think we are all little cheer squads for each other in this world and our default position is that we all want each other to succeed in business and in life, so feedback and ideas are always welcome. I know it is coming from a good place. I am even open to a ‘letter to the editor’, if you are inspired to write.

Thanks for reading this far. 

Write back and let me know what breakthrough you have had after reading this letter. What thoughts you had. Just a sentence (or longer, if you like).

Write to you next month.

Rich

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