The safest way to become a mediocre lawyer is to avoid doing anything that might make you look like a bad one.
Darren's career was shaped by the opposite instinct.
Again and again, he found himself in situations where responsibility arrived before confidence. He moved from a structured training environment into a smaller, faster-growing team where a newly qualified lawyer was suddenly expected to help run matters.
He was put in front of clients. He negotiated. He made mistakes. Later, as a senior associate, he had to decide whether to follow a departing group or stay and defend important relationships himself.
None of it was particularly comfortable.
That's the point.
Early in his career, Darren spent six months in a highly structured team after qualifying in London. Then his supervising partner moved firms and took four associates with him.
Darren was one of them.
The move meant going from a large organisation where work was more readily fed down to a smaller team where there was considerably more expectation to take ownership. He was still carefully supervised but he was also allowed to run with things, make decisions and push transactions forward.
He was, in other words, given opportunities that most junior lawyers would quite reasonably regard as slightly terrifying.
It's tempting to think confidence comes first.
It doesn't.
Often the responsibility arrives first and confidence is what you build afterwards, usually through a combination of necessity, repetition and a few harrowing experiences you'd rather not relive.
Darren remembers being encouraged to pick up the phone and negotiate rather than hiding behind beautifully constructed emails. You might lose a couple of points in a negotiation. Someone might make you feel as though you don't quite know what you're doing.
Good.
Those experiences stay with you.
The carefully drafted email proves that you can draft a carefully drafted email. Getting something wrong in a live conversation teaches you how to handle the next one.
There's a difference between knowing the law and knowing what to do when another human being disagrees with you.
The second one is harder to learn from a textbook.
The same principle appeared later when Darren had to make a more consequential decision.
A significant part of his team was leaving for another firm. He could have gone with them. It would've been the obvious, comfortable option.
Instead, he stayed and backed himself to retain important client relationships while building a team around them.
He was relatively junior compared with some of the partners he was effectively competing with for those relationships.
That didn't make the decision easier.
The experience taught him something about partnership that's difficult to understand from the junior end of the profession. Being a partner isn't simply about knowing more law.
It's about taking responsibility, persuading people to follow you and being willing to discover whether your judgement was actually as good as you thought it was.
Confidence becomes much less theoretical when other people are relying on it.
The same instinct later influenced his move to Fried Frank. Darren believed the London market was moving towards greater US influence and saw an opportunity to be part of that shift early. He didn't know with certainty that the prediction would prove right.
He backed himself anyway.
Looking at London now, it was undoubtedly a good call.
But the more interesting lesson isn't that he predicted the market correctly.
It's that he was willing to make a decision before the outcome was obvious.
That attitude also explains Darren's emphasis on personal relationships and personal brand.
Lawyers have a convenient hiding place: the firm.
The firm has the reputation. The firm has the clients. The firm has the website explaining that everyone is a trusted adviser.
The junior lawyer can therefore spend several years being very good without becoming particularly known.
Darren thinks that's a mistake.
He encourages lawyers to build their own relationships and their own reputation alongside the firm's. The client contact who appears relatively junior today may eventually become a decision-maker tomorrow. The relationship you build when nobody notices can become the network you rely on years later.
It's also why he puts such emphasis on authenticity.
If lawyers spend their careers performing what they think a lawyer is supposed to look like, they eventually start to resemble a tinpot imitation of something nobody asked them to be.
The better approach is to develop judgement, relationships and a reputation for being someone people actually want to deal with.
Clients can choose from hundreds of firms.
They'll assume you're competent.
The interesting question is whether they like working with you.
There's a broader lesson in Darren's career that applies well beyond real estate.
Junior lawyers are often told to develop confidence, build relationships and take ownership.
All sensible advice.
But none of those things can be acquired entirely through preparation.
At some point someone has to let you make the call.
You have to pick up the phone. You have to negotiate. You have to speak to the client. You have to use your judgement. You have to discover that sometimes you were wrong and then work out what to do about it.
The danger for lawyers is that the profession is exceptionally good at rewarding the appearance of competence.
Everything can be polished. Every email can be checked. Every sentence can be qualified until nobody could possibly object to it.
But a career isn't built from sentences nobody can object to.
It's built from decisions.
Darren's career suggests that the lawyers who progress fastest aren't necessarily the ones who make the fewest mistakes. They're the ones prepared to make mistakes early enough that they can learn from them.
Sometimes becoming a better lawyer requires doing something that feels remarkably like becoming a worse one.
You have to risk being seen before you're ready.
Then, eventually, you become the lawyer you were pretending to be.