MAKING HEADWAYBY RICH FARRELLY
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Welcome to issue #17 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.
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Dear Open Tabs, My Dad’s been on a weird little hot streak lately - I’ll be dining out on those meat tray wins from two months ago for a while yet - so I’ve decided to try and draft on his luck. I’ve started entering a few “25 words or less” competitions. It’s become a mini-sport. I'm being given a tiny box and being asked to build something elegant inside it. It reminds me of the fast fiction I was writing about this time last year - the particular joy (and pain) of working with a hard edge. Turns out there’s a whole cottage industry of advice
for these comps, but the real lesson is simple: constraints don’t shrink creativity… they concentrate it. It’s a specific kind of creative architecture, and it’s made me look at the opposite end of the scale with fresh eyes.
Which is why I’m fascinated by friends who are writing books - the opposite experience. All runway, no guardrails, and a real risk of missing the off-ramp. Beautiful for exploration; dangerous
for deadlines. I can’t wait to read what they’ve made, but for now, I’m sticking to the "short and sharp." Speaking of new rhythms and different scales: I’ve started an actual J-O-B. I’m now a casual coffee bean delivery driver. I have a van. I have a Toby’s Estate T-shirt. I look… alarmingly
legitimate. It started as a practical way to fill the gaps between coaching and facilitation gigs. But as the application rolled on, I got unexpectedly excited about the "anthropology" of it all. It’s a chance to get out of my own head, meet people I’d never normally cross paths with, and see the real-world (not theorised) challenges leaders are dealing with - the ones you only witness when you’re actually in the flow of their day. Once I stopped thinking of it as a
side gig and started seeing it as a weekly social study with caffeine, it just clicked. It’s a different lens - a way to stay grounded in how work actually happens when nobody has time for the perfect process. Case in point: my own digital 'ecosystem' decided to go rogue this month. Of course, life has its own way of imposing unwanted constraints: my website got hacked this month. I suspect it was an online
gambling outfit from Cambodia (let’s add an “allegedly” here for legal-ish reasons). It’s fixed now, but it resulted in one of those weeks where you don’t do the work - you do the work around the work. The good news: your personal details are safe. They’re stored elsewhere, entirely separate from the site. The reboot did knock a few background systems out of alignment, though - so if anything looks a bit wonky while you're browsing, that’ll be
why.
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Photo Credit: The New Yorker/YouTube The Woman in the Candy StoreI
fell into a short documentary the other day and came out thinking about one person: Ann. The setting is a former candy factory in Brooklyn — a building with “great cheekbones” that now houses a community of artists. But the film is really a portrait of
Ann Ballentine, the woman at the centre of it all. She bought the place back in 1979 and, over time, became far more than a landlord. People struggle to name what she is: fairy godmother, benevolent mayor, the OG — the person who somehow keeps the whole organism alive. What struck me most is the way she seems to notice people. Not in a performative, networking-event way. In a steady, practical, human way. Artists talk about how
she’s there when you need her. How she connects people. How she creates the conditions for them to stay long enough to make real work — not just scramble for the next studio as rents rise and neighbourhoods change. There are moments in the film that made me laugh out loud, and a few that caught me in the throat. One artist talks about being able to keep showing up to his creative process during a brutal stretch of illness —
because he had a place to go. Another tells the story of donating a kidney to a fellow artist and joking he “traded a kidney for this space.” That’s not a standard lease arrangement. That’s what happens when someone quietly holds the centre. And Ann’s “screening process” says everything. She’ll talk to you for hours, ask your star sign… and she wants one thing: that you walk in and say the words — I love this. Because
for Ann, it’s never just been about renting space. It’s about choosing people who will add to the culture, and then looking after them once they’re in. If you can find a spare 18 minutes, watch the film. It’s a small, beautiful reminder of what one person
can make possible. (Have a tissue handy.)
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Photo credit: Me Why This Story MattersWhat Ann is doing isn’t “being nice.” It’s a masterclass in a set of leadership skills we often overlook. In emotional intelligence — specifically the RocheMartin framework — we call this Other Focus. Other Focus is the capacity to tune in outward: to read what’s really going on for the people around you, and adjust your impact so they feel safe, seen, and able to do
their best work. It’s turning down the volume on your internal dashboard (to-do lists, stress, rehearsed responses) so you can pick up the frequency of the room. In the RocheMartin model, Other Focus shows up in three competencies: Empathy — the social radar Not “being nice.” Being accurate and kind. Ann doesn’t default
to spreadsheets and screening forms — she pays attention to people. She listens for what matters: curiosity, care, intent… and that unmistakable “I love this” energy. In day-to-day work, empathy is noticing the work around the work someone is carrying before you pile on the agenda. Straightforwardness — the clear mirror Direct and honest in a way that helps, not harms. In the film, Ann isn’t vague
about the culture: you’re either adding to it, or you’re not. Straightforwardness is the opposite of corporate fog — it’s the clean line that lets everyone relax because they know where they stand. It’s the same hard edge that makes 25 words work: clarity creates momentum. Relationship Skills — the connector The quiet craft of building trust over time. Ann connects people, holds continuity, and
creates enough safety that people stay for decades. That’s not a transaction. That’s a community with a centre. In leadership terms, relationships are the infrastructure you don’t notice… until they’re missing.
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Photo by charlesdeluvio on Unsplash The InterplayIt is worth noting that none of these competencies operate in a silo. They function as an interlocking system—a
three-legged stool where each leg depends on the others to keep you upright. Empathy without Straightforwardness is how you end up stuck in the hole with someone. It’s "nice" leadership that avoids hard truths, which usually leaves people feeling supported but ultimately stuck. Straightforwardness without Empathy is just blunt
force. It’s the "short and sharp" edge without the human context, which tends to leave people feeling bruised rather than briefed. Relationship Skills without either is just shallow networking. It’s "performative" rather than "anthropological"—you’re making connections, but they lack the trust or clarity needed to actually get things done. Ann
Ballentine is the "OG" precisely because she balances all three. She has the Radar to sense the need, the Mirror to be direct about the culture, and the Connector skills to hold the whole organism together. When they work in tandem, you move from just managing people to truly cultivating them.
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Refining Your Approach: Three Actions for the week aheadIf all this has sparked a bit of curiosity about how you’re showing up for others, try these this week: 1) Put on the “Toby’s Estate” T-shirt (Empathy) You don’t need to borrow my
van to be an anthropologist. Try this: In one meeting, choose observation over performance. Watch the flow: Who goes quiet? Who is pushing hard? Who looks like they’re carrying extra weight that isn’t on the slide deck? 2) Screen for the “I love this” (Straightforwardness) We spend a lot of time checking “credit scores” (outputs and competence) and not enough
time naming what really matters. This week: Ask someone, “What part of this are you actually enjoying right now?” Then share yours. Clear is kind. Unclear is unkind. 3) Acknowledge the “wonky” (Relationship Skills) Most people have an “online gambling outfit” running in the background of their week — the invisible friction that makes everything
harder. Action: Don’t lead with the deadline. Lead human: “I can see there’s a lot of work around the work happening. How are you holding up?”
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Need help tuning out the noise to tune into your people?Send me a message or hit reply, and let’s start with finding your benchmark.
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Guest PostOur regular good friend of this letter, Paul Edwards, has had a lot on his plate lately—including buying and selling a house—so he’ll be back with us next month.
Expecting more?There is so much more to write on each letter I send, but I appreciate limited attention spans and other commitments. I know you would like more, so get in touch and I am happy to chat.
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
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