Jon Glass, the 410th person I’ve met on my quest to have lunch with 500 strangers, works with clients who are often confused, low on confidence and unsure of their identity.

Jon is the owner of 64PLUS Retirement Coaching, which coaches people who are moving to, or have recently entered, retirement.

It’s common for strangers to ask each other what they do for a living – which seems harmless, until you realise that by asking and being asked that question thousands of times over decades, we often end up connecting our identity and self-worth to our job. So when we retire, it’s natural for people to wonder who they are and what value they have to offer.

Furthermore, once people stop hanging out with their work colleagues, they may be shocked to discover how small their social circle is – and daunted by the thought of having to make new friends.

So it’s understandable that many of Jon’s clients – who are often successful businesspeople – feel lost when they meet him.

As a coach, Jon doesn’t tell people what to do; instead, by actively listening to his clients and then asking thoughtful questions, he helps them solve their problems for themselves. Once clients have finished Jon’s coaching program, they have much more clarity about their life and purpose.

Jon isn’t just good with people; he’s also good with numbers. Jon spent his career in the investing industry, before founding 64PLUS Retirement Coaching in 2016, when he transitioned to part-time work. Despite now being 72 and financially independent, he’s eager to grow his business, because he loves his work and sees a great need for his service.

Unusually, Jon is not only good with people and numbers, he’s also good with words. He’s published several books and several plays; his latest production, ‘The Department of Family Values’, is debuting at the Hellenic Art Theatre in Sydney later this month.