Have a back-up plan, warns Oldcastle author as AI reshapes careers

For generations, it was presented as a guarantee. Study hard, get your degree and secure a graduate job. Climb steadily and retire comfortably.

It was a script repeated in classrooms and kitchens across Ireland, a quiet promise that stability would follow effort and loyalty.

But according to Oldcastle digital entrepreneur Conor P. Lynch, that promise is beginning to unravel, and artificial intelligence is exposing just how fragile it may have become.

“The career ladder story was simple,” says the Oldcastle author. “But the world of work is no longer simple.”

In his new book, Learn Earn Own, the digital strategist argues that the traditional career model of one employer, one income stream and one upward path is breaking down at both ends. Entry level roles are shrinking as automation absorbs routine tasks, while mid career workers report feeling stalled, exposed and increasingly uncertain about what lies ahead.

“The story we were told was linear,” Conor says. “Study hard, get a job, climb the ladder. But the world of work has changed dramatically and career advice hasn’t caught up.”

Since the release of ChatGPT in late 2022, graduate and junior job postings in parts of the UK and Ireland have fallen sharply. Many tasks once handled by entry level staff, including research, drafting, data analysis and administrative work, can now be completed in minutes using AI tools.

“In law firms, in marketing agencies, in tech companies, the kind of work that used to justify hiring a graduate can now be automated or heavily accelerated,” says the career strategist. “If fewer people are getting that first rung on the ladder, we have to ask what replaces it.”

While artificial intelligence has dominated headlines in recent months, the Oldcastle entrepreneur insists the underlying weaknesses in the ladder predate AI. Automation, outsourcing and digital transformation have been steadily reshaping the labour market for over a decade. AI, he argues, has simply accelerated what was already in motion.

“This didn’t start with ChatGPT,” he says. “AI has just made it visible. It has sped things up. The pressure that was creeping into graduate and mid level roles has suddenly become obvious.”

Any role built around repeatable tasks is vulnerable, particularly in sectors where efficiency and cost reduction are priorities. Customer service, administration, research and junior analytical roles are already being reshaped.

“That doesn’t mean there won’t be jobs,” Conor adds. “But the nature of those jobs is changing faster than the advice we’re giving young people.”

He believes the strain is not confined to graduates. Conor regularly speaks with Generation X professionals who followed the rules, built stable careers and now feel exposed to automation or restructuring.

“If entry level work disappears, the ladder breaks at the bottom,” he says. “But there’s also something happening at the top. I’m hearing from people in their 40s and 50s who feel opportunities are drying up. So the traditional ladder might only really serve a 20 year window in a lifetime. That’s not a long term strategy anymore.”

For the digital strategist, the conversation must widen beyond students and graduates.

“Most people are smart and work hard,” he says. “But their rewards don’t always match their efforts. They’re leaving money and opportunity on the table because they’ve relied on one income stream.”

His own career informs that view. After years working within traditional employment structures, Conor branched out around 2010 to build his own digital marketing agency, Connector. What began as a side project evolved into a seven figure business working with global brands before being acquired by Granite Digital in early 2020, just weeks before the pandemic upended the global economy.

Selling the company gave him unexpected space to reflect.

“I looked back at what we were told in school and compared it to what I’d actually done,” he says. “I realised most of the value in my career didn’t come from climbing a ladder. It came from building assets alongside it.”

What felt at the time like hobbies, building a website, developing a personal brand, speaking at events, were, in hindsight, compounding assets.

“Reputation compounds. Networks compound. Skills compound. Eventually, they create options.”

That insight underpins the central framework of Learn Earn Own, what the Athboy author calls the “Assets Ladder”.

Rather than focusing solely on progression within an organisation, the business owner encourages workers to build assets they themselves own, assets that generate leverage over time.

“Income follows assets,” he explains. “Employers own the office, the intellectual property and the systems. That’s why they capture most of the upside. But individuals can build their own assets too.”

Those assets need not be dramatic or risky. They can include a professional network, a personal brand, niche expertise, digital content, collaborative ventures or AI enabled skills. The aim is not necessarily to abandon employment, but to reduce total dependence on it.

“You don’t have to quit your job,” Conor stresses. “But your job shouldn’t be your only plan.”

He draws a clear distinction between entrepreneurs and what he calls “experimenters”.

“Not everyone wants to run a company,” he says. “There’s a big difference. An experimenter might start writing online, build a LinkedIn presence, create a small digital product or learn AI tools. It’s about testing and learning. Anyone can experiment.”

Artificial intelligence, in the view of the entrepreneur, is not purely a threat. It is also a leveller.

“Yes, AI is putting pressure on entry level roles. But it’s also creating opportunities. For the first time, someone with no formal coding background can build simple software by describing what they want. You can use AI to design, research and plan.”

He believes access to education is one of AI’s most underestimated benefits.

“For the first time in history, you can design your own personalised education,” he says. “AI can act as a tutor, a curriculum designer, even a career coach. You can learn almost anything, often for free and at your own pace.”

The digital strategist argues this could reshape who gets access to opportunity. In the past, proximity to institutions or financial resources often dictated educational access. Today, someone in a rural town can learn coding, marketing, design or financial literacy directly from global experts using online platforms and AI assisted study.

“That’s hugely empowering,” he says. “If someone is curious and disciplined, they can skill up in ways that weren’t possible before. That changes the playing field.”

At the same time, he cautions that tools alone are not enough.

“Curiosity matters. Adaptability matters. Nobody drifts into opportunity. You have to lean into it.”

The shift also raises difficult questions about higher education and return on investment.

“With the cost of higher education rising, families have to ask about value,” says the Athboy author. “Is a degree or Masters worth the money if entry level roles are shrinking?”

He does not dismiss universities outright, but suggests they may face increasing scrutiny as AI powered self learning tools become more sophisticated.

“There should be a public service announcement for parents,” he says. “The career paths they had may not exist when their children graduate. Families need informed conversations about careers, jobs and AI. Parents need to teach their kids to be learners and doers, not just passengers.”

He also rejects the suggestion that younger workers lack ambition.

“They’re not rejecting success,” Conor says. “They’re rejecting blind loyalty to a system that looks unstable and maybe doesn’t align with their values. They’ve grown up through financial crises, layoffs and now AI disruption. They’re looking for flexibility.”

The Athboy entrepreneur describes the future not as jobless, but as multi linear, a mix of employment, projects, collaborations and asset building that creates resilience.

“The future of work isn’t a job. It’s a portfolio,” he says. “Even small additional income streams or assets can reduce anxiety. If one stream disappears, you’re not starting from zero.”

Ultimately, the career strategist believes the deeper issue is psychological. Many workers still equate security with employment. In a volatile labour market, he argues, security increasingly comes from capability rather than contract.

“The safest position today isn’t loyalty to a company,” he says. “It’s having skills and assets that give you options.”

He is not alarmist about what lies ahead. There will be disruption, he acknowledges. Some roles will disappear. Others will emerge.

“Nobody knows exactly what the jobs market will look like in five or ten years,” he says. “There will be challenges. But the people who will have the best chance of success are curious, adaptable and building high value skills, especially with AI.”

For the Athboy author, the message is ultimately one of ownership. The traditional ladder may not vanish entirely, but relying on it alone is increasingly risky.

“Jobs are temporary,” he says. “Assets are what last.”

For more information visit www.conorlyn.ch