Fancy spending your day cuddling a koala?
To be clear, this is not a metaphor or part of a bring your pet to work wellbeing scheme. The general counsel in question works at a zoo. She does do legal work. But she also has the more serious task of defending her shoe laces from a determined waddle of penguins.
Tom shares this, in the manner of a man who knows the effect this imagery has on its recipients. It is also, perhaps, the perfect entry point into this unusual story.
The accidental corporate lawyer
Tom has been a lawyer for 23 years. He began at Herbert Smith in 2003, part of what he describes as “the intake of the century.”
Sixty trainees and the kind of camaraderie that somehow survived the transition to marriage, children and everything in between—mostly via WhatsApp and occasional trips to the darts dressed as Star Wars characters.
It was, by all accounts, a proper legal upbringing: long hours (in the office) and just enough fun to make the exhaustion tolerable. Corporate law, however, was not the plan.
“I was terrified of it,” he admits, recalling ominous email chains about an infamous supervisor in the team. Litigation felt safer, somehow. More structured. More… legal.
And then, six weeks into an M&A seat, the light bulb moment happened. The fear evaporated, replaced by the realisation that corporate law was far more interesting and rather less sadistic than expected.
There is a lesson here: most early career decisions in law are made with very little information and an unhealthy amount of hearsay—tax lawyers, I'm sure, can relate.
Don’t specialise too soon (or at all, ideally)
If there is one theme Tom returns to, it is this: premature certainty is overrated.
Law students, he notes, have a habit of declaring lifelong devotion to niche practice areas—IP, competition, the occasional enthusiast for agricultural holdings rent review arbitration...
“I really just want to do corporate law,” is, in his view, about as persuasive as announcing you’ve decided on a life partner after a single date—possible but highly unlikely from an external examination.
His advice is simple: keep your options open. You have over 40 years of your career ahead of you; getting one year “wrong” is not, in the grand scheme of things, catastrophic.
Secondment to second home
Like many legal careers, Tom’s pivot arrived disguised as a temporary opportunity.
A secondment to Singapore—initially 12 months, then 18, which became three years, then a firm move and eventually 14.
This is how some of the most interesting careers tend to develop: not as carefully plotted trajectories, but as a series of slightly extended detours.
Singapore, he explains, is both exactly what you think it is and not at all. A city, yes. But also a highly sophisticated legal hub with its own system, its own rules and a gravitational pull stretching from the US to Australia.
It is also, crucially, a place where the law often intersects with business reality in a way that feels refreshingly direct. Less Halsbury, more “how do we actually get this deal done?”
The Myanmar chapter
If Singapore is a well-oiled machine, Myanmar—at least during Tom’s time there—was something closer to a prototype.
He helped open an office in Yangon, working on inbound investment at a time when the country briefly became the most exciting market in Southeast Asia. New laws were introduced. Foreign capital flowed in. And, in a familiar twist, very little guidance existed on how any of it should actually work or who would make sure it did.
“You’re doing it as you go,” he says, which is not a phrase traditionally associated with legal certainty.
It was here, early in his career, that Tom became aware of a niche emerging and the power that can have in turbocharging your career.
But for all that, I’d wager this isn’t the part that matters most to Tom.
Walk-To-Talk(.com)
Which brings us to the walking.
In recent years, Tom's been leading early-morning walks—12.2km loops—to raise money for dementia charities across the globe. After going through a tough period personally and then seeing the effects of dementia in his own family, he started walking.
It is, in its own way, a convenient counterpoint to the rest of the story: a reminder that careers and the lives they occupy, however impressive, however important they may seem at the time, ultimately need to provide fulfilment and make you happy.
Never take off your pads
“God, I’d have loved to have been a professional cricketer.” Perhaps the quote that resonates with me the most.
“There’s more to life than law,” he continues.
Whether it’s cricket, koalas or simply a life slightly less confined to the office, the point is a simple one: don’t lose sight of the things that make it all worthwhile.