AI and the Retirement Horizon: Career Lifeline or Final Straw?

AI and the Retirement Horizon: Career Lifeline or Final Straw?

At Futurum Group we’ve been working with lawyers approaching retirement for over five years. Through our one-to-one Encore Coaching™, we have identified several common challenges that most people face at retirement stage, but there’s a new one that is surfacing more and more frequently: The implementation of AI in law firms.

While the headlines often focus on how AI is shaping the careers of younger workers, there’s a quieter conversation happening among those approaching retirement. After decades of technology changes and adapting to the next new platform, some lawyers are asking themselves if they really have the desire to stay around to learn how to use AI. Mastering AI tools can seem overwhelming, especially if training is geared towards digital natives. There’s also the risk that employees who don’t — or can’t — adapt to AI, might feel pressured to step away earlier than they would have planned.

The Opportunity: Extending Careers Through AI

For some, however, AI represents an unexpected career lifeline. One of AI’s most powerful promises is its ability to automate repetitive, time-consuming work. For experienced professionals, that can mean less admin, fewer late nights, and more time to focus on the strategic thinking and relationship-building that only decades of experience can deliver.

​​Gus Neate, Co-Founder and CEO of WilsonAI, an AI-driven platform designed to streamline legal operations, sees the opportunities for older workers: “While historically legal tech tools might have been niche and hard to adopt, we're seeing senior lawyers jumping in and finding they are given superpowers by working with AI.”

Many lawyers believe this is an opportunity not a threat and that AI has the potential to extend lawyers’ careers in ways that were not possible before. They  can take on more intellectually stimulating work while letting the technology handle the grind.

A Question of Support

The real issue may be less about AI itself and more about how it’s introduced. Is there dedicated training that recognises the needs of later-career professionals? Are leaders clear about how AI complements, rather than replaces, human judgement? And is there space for employees to voice concerns without being dismissed as “resistant to change”?

Gus Neate agrees that dedicated training is essential: “We run workshops where we show lawyers how to create great prompts, use AI for making a playbook for contract review, and how to quickly verify that AI's outputs are accurate.”

Retiring with AI

Moving on from the workplace, people approaching retirement need to consider what role AI is going to play in the next stage of their lives, the stage we call the Encore.

Orrin Onken, who retired from law in the USA in 2020, recently shared with Business Insider how AI shapes his everyday life in retirement: “I'm experimenting with AI in my 70s. I've had to adapt to new technologies my entire career – those who embrace change survive. I retired after 30 years of working in law, so I was comfortably out of the workforce when ChatGPT was released in 2022. At the time, some people were aghast and predicted an imminent robot uprising. Meanwhile, I was eager to start experimenting with it. I now use AI nearly every day as my assistant and advisor, but I don't have to integrate it into a workplace. Some professionals are nervous that this latest technological revolution will upend their careers, but my years in the workforce taught me that those who embrace change survive. I've seen many waves of new technology, and I'm not worried about this one. I spent a career writing briefs that AI could now write as well as most recent law school graduates. It summarizes material well, but I'm not sure it's sophisticated enough to appeal to the emotions of a judge.

Which Side Are You On?

Through our Encore Coaching™ we help people challenge their own ideas about the next exciting stage of their lives; helping them to live in alignment with their values and what truly matters to them. If people tell us they ‘want out before AI arrives’, our job is to challenge their feelings around that decision and explore what lies behind it. Some may want to hear more about how they can move forward, embracing the technology: be that in or out of the workplace.

Wherever you land, one thing is certain: the conversation about AI and retirement is just getting started.

©Futurum Group Ltd

Gus Neate, Co-Founder and CEO of WilsonAI