Designing a fulfilling retirement: Insights from coach Dr Jon Glass

When people think about retirement planning, most think about money. But what about your mindset? What about the sudden shift in identity, structure, and purpose?

In this interview, retirement coach Dr Jon Glass explores the psychological side of retirement – the parts that numbers alone can’t solve. Drawing on more than a decade of experience, Jon shares how retirees can navigate the emotional transition out of full-time work, and how planning for retirement should be about much more than finances.

Whether you’re approaching retirement or already in it, Jon’s practical insights and stories highlight how self-awareness, structure and curiosity can help you design a life that feels truly fulfilling.

Transcript

Robert Barnes

Today, we’re joined by Dr. Jon Glass, a retirement coach who helps Australians navigate one of life’s biggest transitions, leaving work and stepping into retirement with purpose and clarity. With a background in psychology and more than a decade of experience working with professionals from all walks of life, Jon focuses not on finances, but on the personal side of retirement –  identity, purpose, relationships, and daily structure.

Through one-on-one coaching, writing, and his 64 plus YouTube channel, he helps people design a life they actually want to live after leaving the workforce. If you’re preparing for retirement and wondering what’s next, this conversation is for you. Hi, Jon.

Dr Jon Glass

Welcome. Good morning. Thank you so much for that wonderful introduction. Could I add a few words about my background in addition to what you said, please, Rob? Please do. Absolutely. It’s that I work in the investment management investment industry for decades and decades. Ten years ago, I ceased full-time work in the investment industry. At that stage, I was wondering around, wondering what to do next. Should I go for another full-time job or not?

In the end, I decided my transition to retirement, because by then I was in my mid-60s. My transition to retirement would be through part-time work. I designed this business 64 plus based around exactly what as you said, finding the meaning and emotions for clients in their retired life, with a little bit of my own biography embedded in the way that I work with clients.

Because to be absolutely clear in terms of what I do, I don’t deal with financial planning. I assume the clients have their wealth all wrapped up. I don’t deal with their health because they have their doctor or doctors. I’m there to help people with their management of meaning and emotions in retired life because, frankly, you’re When you’re going to live for a long time when you retire.

I like to say retirement can last 10,000 days. That’s a large vacant room in which to feel fulfilled at one extreme or bored, rigid at the other extreme. My job is to help people to move towards the fulfil side of the room because I feel I’ve made that move myself to some extent and have the confidence to then help other people to make that same move.

Robert Barnes

Great. We’re going to start off thinking about the mindset and identity. I wonder, how can individuals redefine their identity after retirement, especially when their self-worth might be closely tied to their careers?

Dr Jon Glass

Yes, that’s a good question. I’ll begin with cite some research from Harvard University, which confirms that a positive attitude to ageing improves health outcomes. Now, if you take that as a given, it is research from Harvard University, then Where can that positive attitude come from in retired life becomes the question, the one that you posed.

At the centre of it all is meaning and purpose. What am I getting at there? Well, when you worked, and I’m assuming everybody listening to this podcast, watching this video has worked at some stage, your meaning and purpose inside work were very well defined. Otherwise, why did you bother turning up on Monday morning? You had that meaning and purpose. What will you replace that with when in my language, You’ve crossed that bridge into retired life. To locate that personal meaning and purpose is not straightforward, but some of the aspects of that are to be clear about your identity.

Who will you be in retirement? Do you want to be a retired person, or do you think there’s more that you have to offer yourself in the world? Do you want to be a grandparent? Do you want to be a volunteer? Do you want to ride a bicycle around Australia three times anticlockwise? Who knows? But having that identity is what gives you a chance to explain to other people what you’re doing in your life.

The canonical question is, Okay, Jon, you’re retired. What did you get up to yesterday? Wouldn’t you love to have a clear answer to that, even a story or two to tell. It all fits in with a broader sense of having an idea of your current and future life. When we work, it can often be very frantic, and we’re so busy either improving our status at work or working on behalf of clients, whatever that might be. But the beauty of retired life is you have time for self-reflection to think about who you’ve been, who you are, and who you want to be. You could almost call it design your life.

And finally, that could fit nicely into your routine because as a working person, surely you had a routine, whether it was Monday to Friday or something different, but you definitely had a routine. What routine do you want in your retired life? It’s up to I’m not sure you want to be waking up at midday and turning on Netflix. Maybe you do, but that’s not the work that I would be doing with you if you were one of my clients.

Robert Barnes

Are there any strategies that you recommend for maintaining a sense of purpose after leaving the workforce?

Dr Jon Glass

There are many components to that. I think one of the most powerful is to talk and listen, to have full discussions with your family, to talk to your friends, to find out what retirement other people have had, for example, your parents, and just get yourself into a mindset where you spend time contemplating these things. I like to draw the distinction between wingers and planners. What do I mean by that?

Well, wingers are people who wake up in the morning and think, What will I do today? Planners are people like me who have a longer term sense of what they’d like to achieve on a day by day, week by week basis. It’s that idea of planning that helps you to answer that very question because it’s in the act of planning that you give more thought and reflection to what life you want to have in the future.

Robert Barnes

Thinking about planners and wingers in retirement, how do you think that the companies differently approach retirement and how does that affect their satisfaction?

Dr Jon Glass

I think it’s very much personality-driven, of course. I suspect you’re one or the other, possibly a mix of the two. But in my experience, it’s the planners who are most amenable to thinking through and reflecting carefully on their future life and getting to that essential question I talked about earlier, which is finding their meaning and purpose. There’s a cute way of putting that in the Japanese language. The word is ikigai.

And ikigai translates roughly as the reason to get out of bed in the morning, which I did refer to before. I talked about the midday rising phenomenon. I’m not saying that in retirement, you need to get up at 5: 30 and go for a 200 km cycle, although that might suit some people. But it’s that sense of structure, routine, purpose, meaning, Ikigai that all fits together in a mould of having, I think, a fulfilling retired life that could last 10,000 days.

Robert Barnes

Can you talk about the concept of visibility in retirement and how that impacts self-esteem?

Dr Jon Glass

In your working life, and I have no idea what the viewers and listeners did in their working lives, but let’s take a generic worker, you did have visibility. Perhaps sometimes you wanted to go and hide somewhere, but you had visibility. People knew what you did. You had a clear idea. To come back to what I said before, if someone you’d never met before asked you during your working life, Well, tell me, what do you do? You’d have a clear answer. The answer may have drifted on for five hours until they left the table, but you had a clear answer. That visibility is something to do with your identity. It’s something to do with your meaning and purpose.

Of course, in retired life, you may want to literally retire. I believe the origin of that word is in medieval France, when people would retire to a monastery up the top of the hill somewhere and disappear. That’s a concept of invisibility. But I think for most people, you want to be visible in some way, particularly if you’re helping, if you’re giving back to the community in some voluntary capacity, you will that he want to be visible.

Robert Barnes

You’ve talked about routines in retirement that have the importance of creating a routine. Do you have tips for people who have a blank slate after having a work routine for so long?

Dr Jon Glass

It somehow comes back to this idea of self-reflection. It’s the idea of, what did routine mean to me when I worked? Not, I had to turn up at the desk at 9:00 AM on a Monday. Not that mundane sense routine. It’s, how did routine permeate my life? Did I enjoy the routine or not? Did I rebel against it? Did I seek a different routine? Did I want my life to be hectic or less busy? To that extent, I’ve invented my own acronym because I think everyone needs at least one acronym in their life, BINAM. Busy is not always meaningful.

I keep circling back to this concept of meaning and purpose. You could be busy in in your retired life. You can agree to pick up the grandkids from school seven days a week, et cetera, et cetera, take them to violin lessons and soccer practise. But is that the busy that you want? Again, you can Reflect on your routine as a working person and think through what you want your routine to look like in retired life, because let’s face it, you’re going to be, to some extent, your own boss, so you can chart your own course.

Robert Barnes

Structure is important, and relaxation is obviously important for a lot of people in retirement, and that’s the biggest change that they think is going to happen in retirement. How can retirees balance that need for structure and the need for relaxation?

Dr Jon Glass

I would circle around that a tagline I use, which is retirement, you won’t know what it’s like until you get there. So that balance between, as you said, perhaps pleasure at one extreme and tight routine at the other, should be negotiated in a flexible mindset. You should set yourself to experimenting with your retirement, in my opinion. The first year of your retirement is what is referred to in the retirement literature as the honeymoon period. It’s all wonderful. You spend a lot of time reordering the family photographs, going on that trip you couldn’t take for the last 10 years, perhaps catching up with friends and relatives. You do all that stuff. That’s what they call a honeymoon.

But we all know honeymoons don’t last forever. It’s after that period that you could give some consideration to how flexible you want to be. Of course, you should have fun in your retirement. Why wouldn’t you? But in terms of what you set yourself as your routine to fulfil your meaning and purpose, well, how dedicated do you want to be? Do you want to do it flat out or do you want to take a month off and do you want to travel, blah, blah, blah? That’s a very personal decision. But I would say the mantra should be flexible, flexible, flexible.

Robert Barnes

Switching to relationships and social life, how do you advise retirees that want to maintain or build social connexions after leaving the workplace?

Dr Jon Glass

I’ll often pose to clients a really cheeky, rude question, which is this, When did you last make a new friend? People retreat into themselves and find that a difficult question to answer. Why so? Because Because making new friends, which we all found to be automatic in our school years, perhaps we went to university in the years of our work life, maybe, wasn’t so hard because we were together with people.

But in retired life, where there you are, you might have a family, of course, a partner, et cetera, et cetera, children living at home, blah, blah, blah. Your friendship circle perhaps fell away and deteriorated during your work years because you just didn’t have enough time to dedicate to your social circle. Well, guess what? A little bit like your health. When you’re retired, you no longer have the excuse, I can’t go see the doctor, I’m busy. Now that you’re retired, you no longer have the excuse, I’m too busy to see my friends. That’s why I tease with that question, When did you last make a new friend? Now, practically speaking, how might you go about doing that, I think is the number of your question.

It’s not as hard as it looks. For example, join a course somewhere at a university or a college or, I don’t know, take up cooking, you’re going to meet people naturally. Find a hobby, you’re probably going to meet people naturally. There are things called men’s sheds. Probably the technique that will not work because I think those techniques have a high chance of success.

The technique that won’t work is to sit at home waiting for the front doorbell to ring. The technique that won’t work is to sit in the local coffee shop with your iPhone facing upwards, hoping at the third cappuccino that someone rings you. I think the essential message is, get out there, build your social life, rebuild your social life, connect with people. I like to say that, and I don’t mean this to be cynical, but in terms of friendship, it’s a gift. When you connect with a friend, you’re saying to them, I’m giving you my time. I know that sounds cynical and mercenary. It’s not meant to be quite the opposite. It’s a lovely idea. It’s the gift of time. Most people appreciate that.

Robert Barnes

You touched on hobbies there. What role do they play in community involvement or volunteering? What role do they play in helping social engagement?

Dr Jon Glass

I think hobbies are a very obvious in this case, because whether it’s woodworking, you’re making chairs or what else could be playing in an orchestra, you are going to be with other people. Let’s use that as our definition, invigorating your social is all about being with other people. Most of us want to do that a lot of the time. I know some people are a bit introverted, but I do believe having a vigorous social life, and what do you mean by vigorous? That’s a very individual choice, is critical to that psychological well-being that I mentioned before. Social life is everywhere in the literature about happiness in life.

But how you make those friends, you talked about volunteering. I think that’s a great way to make contacts. Let’s have a definition of friendship that we don’t need to get too up tight about. I’m not talking about close, close, close friends. They could be people who are referred to as weak ties. That’s a lovely term from the literature. They’re people you bump into and you can have a conversation about whatever you want, about the footie or something like that. They aren’t necessarily your friends, but there’s a spectrum from weak ties to very close friends.

I’m saying friendship circle should be somewhere in the middle at a place that you want it to be. And so volunteering is clearly a great way to populate your life with people who sit on that spectrum from weak ties to close friends. And there are many, many, many ways to volunteer. For example, I volunteer as a primary ethics teacher, which is all about helping children to learn how to have sensible debates about topics of interest that they might find, should I be a vegetarian? How much money should I give in charity? Primary ethics teaching is a nice way to build a circle of friends because the other teachers are amenable to chatting after the class, et cetera.

Robert Barnes

I bet that keeps you young as well.

Dr Jon Glass

Yes, that’s right.

Robert Barnes

How can one navigate the changes in family dynamics as well, such as becoming a grandparent, dealing with adult children, or even the fact that a couple who are separated by work are spending all data together again.

Dr Jon Glass

That’s where I often will talk to people about managing time and space in retirement. Let’s take space as the first topic. Imagine there’s a couple living together in the same house or apartment. I’m strongly of the belief that the management of that space in the apartment or house needs to be managed. Ideally, each person would have their own room. That may not be, I don’t mean bedroom, I mean study. In their own place to retire to on their own. Ideally, it may not be practical for some relationships, but that’s ideal because then you have that sense of privacy as well as communality.

I use this example – What are you going to talk about at the dinner table now that you’re not working? That really comes to life when one in the partnership is still working and the other has fully retired. Then all of a sudden, there’s the issue of, I went to work today and all these things happen to me, what have you been doing all day in the house? Tell me more about your contribution to the family, the house, et cetera. That conversation could get quite difficult and strained at times.

I’m talking about two things here. One is managing the relationship as people move to retirement, but an aspect of that is managing the space of the house or the apartment. But then the second dimension I referred to as time. How much time do you spend together? If you do have a partner? When you both retire, do you want to be together 24 hours a day? Maybe not.

Again, going back to Japan, such a cultural inspiration because it’s such a different country from ours. They have something called the wet leaf syndrome. The wet leaf syndrome concerns the Japanese salary man who finally retires after 40 years of commuting to and from central Tokyo. His wife has been the homemaker all that time. In his retirement, day number one, he says to her, What are we doing today? She says, I’m going to the supermarket. Guess what? He’s trailing behind her, a bit like a wet leaf on the back of her shoe. That can lead to tension. This idea of not only managing time and space, but managing separate identities in a relationship, and that extends to children and grandchildren as well.

Robert Barnes

Retirement arrives in different ways for different people. Could you talk a little bit about that?

Dr Jon Glass

Yeah, because retirement does arrive in many ways. You could be made redundant. You could be dreamy about retirement from the age of 45. You can phase your retirement through part-time work, which was my approach, and transition to a portfolio of activities, which has been my approach. Sadly, you could be ill or incapacitated, or you could reach that age where you could access your pension and you go, Now’s the time.

There’s an interesting group, the last one to talk about, called the Never Retire Brigade. They’re often self-employed. If I asked them, some of my friends are like this, When are you going to retire? Their answer seems to come back uniformly, I could never retire. I get all my intellectual stimulation for work, so I’ll be there, as they say, till they carry me out in a pine box. This thing about work, and I’ll close with this final comment, another matter for the viewers and listeners to think about.

As you untie yourself from your work identity and cross the bridge into retirement, what will you miss from work? This is critical because it gives you some self-understanding. A lot of people miss the Monday morning banter around the water-cooler. They miss that. They miss a sense of mission and purpose with their work, which I’ve referred to before. Here’s an odd one that you might not think about. They miss the chance to mix with younger people because at 60 or so, you might find yourself engulfed in a population of 60-year-olds. Nothing wrong with 60-year-olds. Some of my best friends are 60, but we get ideas from younger people, and that probably happened in your workplace.

But of course, the flip side, and this is also worth thinking about is, what won’t you miss from work? What are you going to be glad to give up? Well, most people will say the four-hour commute. I won’t miss that. Another one, a bit darker, is I won’t miss having to fix up other people’s messes that they create because you don’t really do that so much in retirement. Then all my clients will say, I won’t miss the bureaucracy, which probably confirms the fact that I’ve never had a bureaucrat as a client.

Robert Barnes

Jon, are there some common fears that you see many retirees having?

Dr Jon Glass

Yes. I’d like to highlight one because we’ve touched on most of the others, I think. No, two. Relevance deprivation syndrome. I think that’s a big one. It’s not my phrase. It’s been around for a long time. People with jobs where they felt they were relevant, important, central, etc. Might suddenly find the week after they retire that the phone doesn’t ring, the emails have gone silent, and they might feel deprived of that relevance. The response I give to that is, Okay, how can you rebuild relevance outside of a work life? It can be done.

Then the other big one is boredom. Ten thousand days, I’ve referred to before, that opens up a very large yarning space in which to be bored. Guess what? You don’t need to be bored. There’s a myriad of ways in which you can fill your retired life with meaning, purpose, and Ikigai, and boredom doesn’t need to come along at all. Although a bit of boredom from time to time can be quite a boost to creativity, you certainly don’t want to have long days and weeks of boredom.

Robert Barnes

So thank you so much, Jon. There’s some great insights there and some great things to think about. How can people get in touch with you or learn a little bit more about how you work?

Dr Jon Glass

Thank you very much. I did enjoy the interview. On this last slide here is my website and my email address. Please reach out. Let’s have a chat on the phone to see if you want to know answers to any questions you might have, some individual questions that you might have. Everyone experiences retirement differently. I’d love to hear from you.

Robert Barnes

Fantastic. Thanks, Jon.

Dr Jon Glass

Thank you. Goodbye.