Recording a podcast recently, one of my hosts, the media lawyer and writer David Allen Green, argued that City law is intellectually humdrum. The gist was that much commercial practice is vapid and repetitive and that City law is a club that sucks up the academically solid and socially acceptable but not those with independent intellects. This leaves more agile and questioning minds to gravitate towards mid-tier practice or the Bar.

It's a line I've heard a lot over the years, and it's not my personal view. The idea that the magic circle is stuffed with dullards in comparison to the polymaths and renaissance men of the mid-tier is a big stretch. There's a lot more price-sensitive, bog-standard lawyering done in the mid-tier than cutting-edge practice in funky boutiques.

Yet there is surely a big fat lump of truth in Green's comments. Plenty of City veterans would concede that many areas of document-heavy banking law are as much a test of stamina and resistance to boredom as of brainpower, and that hyper-specialisation can play havoc with the critical faculties; I have on occasion seen a specialist partner go 'rabbit in the headlights' when asked a question one centimetre outside their patch.

And in many transactional areas, the real skills are often more about client handling, project management, industry nous and the ability to apply well-established law pragmatically rather than any creative mastery of your black letters. It is also patently obvious that the tight restrictions of the City law firm model squeezes out some of the most stimulating areas of practice. Meanwhile the independent Bar still punches well above its intellectual weight against the City, though it's debatable whether long-term trends will sustain that advantage.

Let's face it, this issue underpins much of the angst about commercial law. When there is discussion about whether aspiring lawyers still want to be partners, about work/life balance and long hours, about the prestige and value of commercial law – what is often really being debated is whether the legal industry, having gone from profession to business, still reaches hearts and minds. In short, does it provide personal and intellectual fulfilment?

Here's one way to answer that. A while back, I read Malcolm Gladwell's Outliers (for the few who need an introduction, the book is a study of why some individuals are highly successful; it's also well-known in legal circles for the chapter on Skadden's Joe Flom and the rise of Jewish lawyers in Manhattan from the 1960s onwards)

Gladwell (pictured above) puts forward a simple test for what makes work fulfilling or meaningful:

• Autonomy – does the job allow the individual to work under their own direction? Can you become a boss or get to define your own direction?

• Complexity – does the work take real effort to improve at or master? It is intellectually demanding?

• Effort leading to reward – is there a close link between personal effort and reward in terms of opportunity, career development and money?

The author uses this yardstick in the context of the European immigrants who moved to New York in the early part of the 20th century and became successful via the application of skills in the textile trade, married with a phenomenal work ethic. Gladwell's argument is that these immigrants were able to apply themselves with huge success to back-breakingly hard graft because their work passed these three tests; giving them intellectual stimulation, a chance to improve their lot and control of their lives. Their work had meaning. As he writes: "Hard work is only a prison sentence if it does not have meaning."

It still strikes me as one of the best descriptions I have seen of the qualities that make a job fulfilling.

But how would City law stand up to that test? You can make a good case for complexity, though it varies hugely among disciplines. But autonomy and effort/reward – well, you can see the challenge law firms face in managing their intake up the ranks.

There is a link between effort at the start of a legal career, when trainees and junior lawyers are paid high salaries in reward for academic sweat. But after that they face a rigid lockstep for eight to 10 years. And then up or out. Of course, once lawyers get near partner level, they get much more freedom, control and a far stronger link between performance and reward (partnership itself being the motherlode of deferred payoff). But at the earlier stages, when that reward is so distant, it's not hard to see why large law firms have a struggle on their hands.

It's also interesting that two words often used to describe City law are 'factory' and 'club' – images that are poles apart. While one conjures visions of hard toil, servitude and repetition, the other implies a relaxed social gathering of like-minded people. What they have in common is that both denote conformity and an organising institution and neither suggests a means of achieving fulfilment or personal meaning. And I don't think I've ever heard commercial law called a vocation.

Of course, the business of law will continue to be successful – or it will as long as high-quality candidates keep flocking to it. But, even in hard-nosed business terms, you can get something altogether more valuable out of your staff if you can give them a little more meaning.

Food for thought, perhaps, both for partners pondering how to connect with the troops and the aspiring lawyers wondering if the City is really for them.

Anyway, if you're looking for more meaning in law, I recommend you listen to the podcast that kicked off this blog – Without Prejudice. Hosted by Green and the well-regarded legal bloggers Mike Semple Piggot and Carl Gardner, the latest edition features Financial Times general counsel Tim Bratton as a guest.