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MAKING HEADWAY

BY RICH FARRELLY

Credit: Austin Kleon

Welcome to issue #13 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, November 2nd, 2025 

Hello Braveheart,

What a hectic month. Plenty of family activities (including a brother's 60th birthday), amazing clients, incredible program participants, and 'work-work' - the bits where I bang my head against a wall. I love what I do (I don't call it a J-O-B), but there are bits that I really need to stretch myself into. Also, in a bit where I try and persuade you to go to it, I refreshed the Head to Head website.

One thing I did to slow it down was watch this YouTube video that recently popped into my feed - algorithms are a blessing and a curse all at once. There is a bit going on it, and I try to follow a different person each time. It then followed onto this one. The dancing in both of them brings me joy in different ways. Even though I took swing dance classes for the best part of a decade, I only ended up less bad than when I started, so the skill of everyone in these (and people who can dance generally) is remarkable to me.

If you are following closely - or even at a distance - there has been no news on my stolen electric scooter. If you have just tuned in, you can read about it here. I’ve accepted the scooter isn’t coming home. That’s okay as I’ve fallen back in love with my old bike. Here it is:

Credit: Bikeradar

Who wouldn't love this bike?

To me, the funny part is when I unintentionally match it. A bit of orange on me, a lot of orange on the frame. It's the same with one of our dogs, Skipper. He wears very cool boots on his paws since he stepped on glass a few years back, and somehow I often end up colour-coordinated with him too.

Credit: Me (That's Skipper in the purple tartan with the purple boots)

It makes me feel a bit daggy when I notice it, but I love it. The scooter didn't have such quirks. It was slick, but a little soulless.

Go On, Have a Crack

As a city cop for a good chunk of my career, I spent a lot of time helping tourists with directions, and posing for photos. I’m probably in hundreds of family photo albums around the world.

Many didn’t speak much English. They’d come up with a paper map, or just a scrap with a place name, ask in their best English, and I’d give simple directions, often sketching a quick diagram in my police notebook and tearing the page out (technically a policy breach… I lived on the edge).

I didn’t think much of it until a 2004 trip to Europe. I’d studied a bit of Italian, enough for a friendly chat, but once I left England, far out, it was hard. That’s when it hit me: how much effort those tourists made to approach me, ask a question, then decode my Aussie twang, complete with the odd “yeah, nah, dunno.” and really listen.

Asking for directions in a foreign country, in a new culture, means putting your ego aside and having a crack, all to make the experience richer. It sounds small, “Where’s Flinders Street Station?”, but stepping into that awkward, slightly thrilling and slightly daunting space takes courage. I love that they did that.

So, let’s talk about courage.

Courage as a Style Guide

When I’m working with an individual or a group, I’ll often ask them to describe the attributes of their best leader. The list changes; one word never does: brave (or courageous). We talk about brave leaders as if courage is loud. Often it’s quiet, a clear choice and a clean “no.”

Giorgio Armani put it simply: “Lo stile è il coraggio delle proprie scelte e il coraggio di dire di no.”

Translation: “Style is having the courage of one’s choices and the courage to say no.”

He said it about fashion; it maps beautifully to leadership and life.

Courage, in other words, is choosing the identity you’ll stand for and protecting it with a clear no.

It reminds me of a story a friend told me. He was in an upmarket watch store in Melbourne. A couple were talking with a salesperson; the husband was eyeing a particular watch they were keen on and said it was very expensive. The salesperson paused, leant forward, and said softly, “Sir, it’s not about how much it costs, it’s about how it makes you feel.” The credit card came out immediately.

If a watch can sell a feeling of who you might be, leadership can create a shared feeling of who we are. The buyer wasn’t in the store for a watch; he was lining up for identity. Fashion says, “Here’s who you might become.”

Leadership does the same: we invite people into a future state of the work, the team, the way we treat each other, and then we make the gutsy choices that keep us true to it.

Lead the circle, not the chart

When Frances Hesselbein became CEO of the Girl Scouts (USA) in 1976, she didn’t tweak the org chart. She redrew it as circles, with herself in the centre looking across, not down. Her lunch-table demo said it all: a glass in the middle, plates radiating out. “I’m here,” she’d say. “I’m not on top of anything.” 
 

She led that way for fourteen years, through to 1990. It wasn’t theatre. It was courage. She pushed leadership to the edges and designed inclusion into how the organisation worked. Minority membership tripled. Overall membership grew to about 2.25 million girls, supported by around 780,000 adults, mostly volunteers. 
 

Peter Drucker called her one of the greatest leaders he’d met. But the point for us isn’t the structure or the praise. It’s the nerve it takes to bet on shared leadership before there’s a dashboard to prove it. 

How courage works (in 10 seconds)

Comfort: low risk, low learning. Feels safe, stays same.

Growth: sweaty-palms, stretch, learning happens.

Panic: overwhelm; thinking narrows, learning stalls.

Leader’s job: spend most of the week in Growth, dip into Comfort to recover, avoid Panic (or shorten it fast).

Also the leader's job: Support others to spend most of the week in Growth, encourage them to dip into Comfort to recover, help them navigate or avoid Panic (tip: shorten it, fast)

Here's a version of the comfort and growth zone I prepared earlier - I miscalculated the space for the panic zone. When you ask what it is like being in your comfort zone, someone usually says 'Comfortable' - just give them that one off the bat.

Guest Post

This month we have our regular, and good friend of this letter, Paul Edwards. 

Expecting more?

There is so much more to write on each letter I send, but I appreciate people's attention spans and other commitments. I know you would like more, so get in touch and I am happy to chat. 

Thanks to the many people who wrote to me after my last letter about Expectations. I did not expect it to resonate with so many. 

On that, 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

P.S. If you like this newsletter and want to support it, there are a few ways you can do this! PICK ONE, right now before you forget.

Because whether it’s this newsletter, a keynote, or a workshop, my whole thing is helping leaders tackle complex challenges in practical, human ways....and maybe even building the answer out of LEGO.

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