When Nikolai from Russia vanished into the Matrix.
Systems that support our work are crucial to shepherding us through disruption.
Before starting Vale, I built a product called Clarity. It was a command-line tool that filled Word documents using data from an Excel spreadsheet. It supported conditional logic. Stuff like inserting “her” instead of “his”, or a maintenance clause to a will if minor beneficiaries could be inheriting. Simple stuff, but time-saving stuff designed to free up my own internal CPU and clear the clutter.
I built it over a few weekends, and it worked well enough. For me.
Then I tried to roll it out to the rest of the firm at O’Neill Solicitors.
Chaos.
The tool didn’t launch properly on half the computers because of operating system issues. The only developer I’d worked with, Nikolai from Russia, who I’d found on Upwork for $3 an hour, had long since vanished into the Matrix.
Apple soon rolled out a security update that broke it for good. I forked out thousands of dollars to fix it, driven as much by a sunk cost fallacy as I was a serious determination to make our work easier.
I eventually hired another developer just to get it running again. It never quite worked the way I needed it to. Especially for those at the firm who weren’t me.
The first real lesson I learned about building software reminds me of a friend who bought a gorgeous MV Augusta F4 (a very cool motorcycle). Fast. Elegant. Classic. Every square inch machined by hand, most likely a weathered elderly Italian master craftsman.
I think it made him feel like Bruce Wayne. He was the envy of every other motorcyclist in Sydney. But it spent half its life at the mechanic before he bought a Honda.
Faster doesn’t matter if you can’t reliably get from A to B. Especially when B is within walking distance. Most of my colleagues were happy enough walking, and I was designing roller-skates that didn’t work.
But what happens when the world starts moving faster around us?
Like I covered a couple weeks ago I’ve got a degree in mechatronic engineering and have always enjoyed taking things apart to figure out how they work, what happens when they don’t, and what I can do about it. I like building things. Systems. Logic flows. Repeatable solutions.
So when I joined the firm, I naturally started poking holes in the tools we were using.
In 2018 we were still running on Corel WordPerfect. It worked better for the staff than the “modern” tools, but clients hated getting files they couldn’t open. The truth was that stone age software was fitting our firm’s needs better than anything else on offer.
We were paying for Leap at $200 to $300 per license but only really using the trust accounting feature. The rest sat idle. Document automation was too slow. Precedents weren’t flexible. There was no way to add logic or reduce manual editing. I wanted more.
So I tried. First with Clarity. Then with a conveyancing intake form built in Microsoft Forms. The idea was to cut down the meeting time and let the client fill out a long questionnaire in advance, then I’d just confirm details on a quick call. Smart, right?
Ugh. Not quite.
I tested it on a young, tech-savvy couple. They came back a few days later and told me (very politely) that it was awful. It took them over two hours. The questions were confusing. They didn’t know what half of it meant and left them anxious.
Awesome, I had officially contributed to the young couple’s anxiety market. I had caused localised disruption. The bad kind.
And they were right. I’d taken my own domain knowledge for granted. When I ask questions in person, I can read body language. I can sense hesitation. I can ask a follow-up or soften the tone. A static form doesn’t do that.
The mistake I made wasn’t technical. It was directional. I’d optimised for speed. My speed, not theirs. I’d ignored our clients’ need for support along the way.
Probate can be tedious, delicate, and messy. There I was, in my 20s, seeing the world through a prism of potential life-hacks and engineering for speed.
At the time, I was also going through that break up I regaled you all with last week. I threw myself into fitness. I did a six-month SAS prep program. I was running hills with 40kg on my back. Training six days a week. Working full-time. Building Clarity on the side. In hindsight, I was trying to outrun personal discomfort by doing as much as possible, as fast as possible. I reckon I mirrored this in the workplace.
Eventually, I crashed. The software I built broke. The systems I tried to implement didn’t stick. And I realised: you can’t optimise your way out of a problem without building solid support structures first.
Building support. For us all.
What I’ve come to understand (slowly) is that the most meaningful kind of progress isn’t the kind that rushes. It’s not about hacking the process to move faster. It’s about building tools that give us the space to operate well. Tools that support us. Probate taught me that.
When we built Clarity, I treated speed-focused tools like silver bullets. I wasn’t wrong about our need for new tools, but I missed the mark on their overall purpose. Hundreds of hours of surveying lawyers, thousands of hours of practise, and uncountable hours spent developing and using probate-sector-specific digital tools have shown me that what we actually need is the ability to be technically supported in the hard parts, instead of treating tools like self-driving motorbikes, hopping on the back, and expecting to be zipped to the end of a process.
Probate can be tedious, delicate, and messy. There I was, in my 20s, seeing the world through a prism of potential life-hacks and engineering for speed.
Software, internal processes, and practice management systems should strive for speed, sure. But focusing on speed and efficiency at the expense of user support is an inefficient way of achieving much at all.
I’ll explain:
It took years in wills and estates of putting the cart before the horse. I engineered the way I’d tried to recover from a breakup.
The kind of tools we need are those that support the work we already know how to do, not speed-run us through it. Tools that stop you from passive-aggressively emailing your assistant about the missing title (again) are tools that bring support to your workflow. Tools that let you remember where a matter is up to without scanning three folders and six emails can change a lawyer’s day. Tools that make it easier to be a good lawyer, not just a busy one, are tools that see efficiency as a by-product of support.
Building Vale hasn’t been fast.
I’ve had to learn a new domain every few months. Product design, fundraising, legal structuring, team leadership, marketing…
I’ve made mistakes. Some I’m still paying for. But I’m glad it’s taken time. Because each detour has reminded me what I’m actually trying to build.
Not a shortcut. Not a hack.
But a system that respects the work. A product that enables slowness and care. A support system.
A platform that helps lawyers do this job with more confidence, more consistency, and more clarity.
Because when the work is heavy, faster isn’t always better. It’s support that we need.
You can’t ride roller-skates in the rain. But with a little support—a little calm before the storm—you won’t need to.