In Focus: Why so many say ‘I fell into’ insurance – and why that’s changing

Every insurance professional has been asked the same question at some point – how did you get into the industry?

All too often, the answer is a sheepish “I actually fell into it”.

The phrase is almost universal, repeated across underwriting, broking, claims and actuarial. But it reveals a deeper truth about how the sector is perceived – both by those outside it and those within.

Few people grow up aspiring to become an underwriter. Careers fairs rarely highlight insurance as an attractive route for ambitious graduates.

The Chartered Insurance Institute (CII) described the sector in its Talent Shortage Crisis report, published in 2024, as “stale, pale and male” – an industry that has long struggled to attract new entrants.

The consequences are now acute. The CII estimates that 25% of the workforce is due to retire within the next decade, while only 4% of young people view insurance as an appealing career choice.

Against this backdrop, the industry can no longer afford to present itself as the sector people simply “fall into”.

A reputation problem

For Caroline Wagstaff, chief executive officer at the London Market Group, the phrase itself is part of the problem.

She said: “We use this phrase because we haven’t deconstructed the problem and tried to do anything about it.

“So, we fall back rather lazily on this ‘Oh well, everybody just falls into insurance’ and we should be doing something about that.

“Historically, we have not told a strong story about why this is a great place to work. Actually, you could be more pejorative and say we haven’t told any story at all.

”We’re a global leader. We contribute 2% to the UK’s gross domestic product (GDP). We employ 60,000 people and nobody’s bothered to tell anybody that this thing exists.”

That silence has fuelled stereotypes. Richard Coleman, managing director at Ecclesiastical, is blunt about the public image of the sector.

He said: “It is boring. Insurance? It’s grey suits and boringness. It’s monochrome. But it’s not – it’s full of colour, it’s full of dynamism, it’s full of loads of different people doing loads of different things. So yeah, ban the boring.”

For those already in the industry, the reality is clear – insurance is complex, rewarding and essential. But for many potential recruits, that message is rarely heard.

Chance encounters

Career psychology offers one explanation for the prevalence of “falling in” stories. Krumboltz’s Planned Happenstance Theory, developed in the late 1990s, argued that career paths are often shaped less by deliberate planning and more by unplanned opportunities.

Insurance careers frequently bear this out. Lee Mooney, managing director at Markel, recalled his own unconventional entry when speaking to Insurance Times editor Katie Scott recently.

Mooney explained: “I fell into it. It was in Manchester, 1999. My friend was working in [a] call centre type environment and there was just a job that came up.

“I was previously doing sound engineering, like putting speakers into football stadiums. Then a friend said ’they’re recruiting at this insurance company’. I went in, spent about a year and a bit thinking, what’s insurance? And then I thought, actually, this is quite interesting. I could get a career here. The rest is history.”

Charles Bush, head of large and complex and commercial insurance claims at Zurich, by contrast, made a deliberate choice – spurred by his father’s advice to stand out from the crowd.

He explained: “I donned my best suit, complemented by a very trendy red stripy shirt, and off I went into the big smoke. 

“I spoke to multiple senior leaders that day, ending up in Chaucer’s reception, having a conversation with their chief executive at the time, Ewan Gilmore.

”He generously took the time to listen to the reasons why I wanted to work in the industry and why he should hire me. He put me through the application process and Chaucer offered me my first job.”

Bush was clear about why more people don’t make that kind of conscious choice.

He noted: “I feel there’s a misconception that it’s dull and fuelled with bad intent – although that is changing for the better, in my opinion. Nothing could be further from the truth – the world couldn’t evolve without insurance.”

The sticky factor

Once people do enter the industry, however, they rarely leave.

Rachel Flynn, chief risk officer at Westfield Specialty International, explained: “We’re great at keeping hold of people – once you’re in, you’re in – because it’s often only when you’re in the industry that you understand it.”

Adrian Browne, portfolio manager at QBE Europe, agreed: “Once people are in the industry or in QBE, they do like to stay because there’s so much opportunity.”

For Caroline Wagstaff, that stickiness stems from a sense of belonging.

She said: “One of the things that makes it really sticky as a career is because it has a real sense of community that other bits of financial services have lost.

“The fact that we are physically co-located in a single postcode, that we are a village, has a lot of charm about it.”

Telling that story matters. As Wagstaff put it: “When I deal with Westminster, I’ve spent five years saying it’s not about cars and homes, it’s about rock stars and rockets. That’s where the action is.”

Indeed, as Flynn emphasised: “Insurance touches everything. Without it, doctors couldn’t operate, planes couldn’t fly and banks wouldn’t open. In insurance, every day you contribute to making sure the world keeps on turning.”

That message is slowly cutting through. An Axa trainee underwriter recently told researchers that their first awareness of insurance as a career came from “a TikTok”.

She continued: ”It was about insurance in London and how they said you can have the Big Banking lifestyle and wages but not have those working hours and stresses.”

Wagstaff believes the sector must embrace new platforms. 

She added: “Now you could be on TikTok and reach a million people. You couldn’t have done that before the advent of social media and that’s a huge change that we really need to embrace.”

Examples of proactive outreach are emerging. Like Bush, graduate Alexander Mani also took a self-starting attitude to entering the industry, securing himself an internship at Howden after advertising his interest in broking on a sandwich board in the City. The bold move caught the attention of brokers and underwriters, with many encouraging him that he had “picked the exact right industry to do this in”.

Mani said the experience had cemented his ambition: “In five years’ time, I can still definitely imagine myself in insurance. I can’t really see myself anywhere else, to be honest.”

Walking in with purpose

Part of the challenge is ensuring the industry matches the expectations of new entrants.

Coleman said: “If I just came out of university and I was used to using elements of automation and really strong tools to drive business forward, if we don’t find ways to harness those in working lives, then that’s not going to feel like a step forward. We have a great obligation to make sure that working experience for people feels good.”

Diversity and inclusion also play a central role. Coleman acknowledged: “There can be an image of insurance as pale, male and the rest.

“We’re changing that. Diversity feels really important in terms of thought, but also to keep challenging us and moving us on.”

Flynn agreed: “The aim has to be for insurance to rival some of the more traditionally sought-after industries in the financial services as a career destination of choice. This is ambitious, but reflective of the undeniable benefits that anyone who works in insurance knows that the industry offers.”

Insurance remains one of the most intellectually demanding, internationally mobile and socially useful careers available – even if that truth is often hidden beneath a reputation for dullness.

For many, serendipity will always play a role in career choices. But as Adrian Browne at QBE noted: “More people are choosing it consciously. It used to be a case of you fell into it because you didn’t know about the industry and now people are more actively choosing it.”

That shift matters. New generations are not falling into the industry by accident – they are opting in for the opportunities, stability and challenge it offers.

The sector should stop apologising for being a second choice. Instead, it should celebrate those who are walking in with purpose.