What will retired life feel like?

Entering a roomful of strangers

Ever had the experience of entering a room full of strangers, wondering how it will turn out? I think we all have. It can be scary, and so can retirement.

After a 40 year work life, retirement poses deep questions: who will you be, what will you do with your days? These are just two complex issues to grapple with in retirement. There are others.

I suppose you could decide to experience retired life as it comes. Careful, that may come with a price tag: wasting precious years as you flail about for a solution.

But wouldn’t it be better to anticipate some issues and think about them in advance?

Here another two of the common ones: 

·      boredom

·      not feeling valued

These four issues can all be addressed and discussed before you retire. You have the answers inside you. The trick is in locating them. 

Once you’ve found your answers, you can implement. For example taking on a volunteer role could provide a meaningful piece of your weekly routine. All of a sudden “Tuesday” may come alive again. 

A retirement coach can help you explore before retirement arrives. I happen to know one!

Do any of these issues concern you? Then text me on 0409 116 766 and we can set up a FREE 15 minute phone call in which we can discuss your retirement plans. Let’s see if I can help you.

Dr Jon Glass Retirement Specialist and Coach for more than 12 years.

The paradox of spending

Recently I've been reading a book about Italian fables and fairy tales. The feature that stands out in so many of them is money. But not simply money as we might understand it, rather it is extravagant amounts of gold, silver and jewellery. What's that got to do with retirement? First, let’s step into the real world of today.

When people think about superannuation in Australia they think that there is a two-part story: accumulation followed by pension. Or to put it differently, saving followed by spending.

It's commonly said that people in pension phase fear that they'll run out of money. In other words, they'll spend too much too soon. Funnily enough in my retirement coaching practice I meet many clients who are concerned about how to spend their time in retirement. How do they express that?

Questions come up such as:

·      Will I be bored?

·      Can I be useful?

·      What if I waste time?

The last one is particularly interesting as it comes up so often in coaching conversations. Can you hear the themes underneath: I want my retirement to be: 

·      Meaningful

·      Productive

·      Planful

which may not be so different from how people want to spend their money in retired life.

If this resonates and you’d like to discuss your feelings about how to spend TIME then email me: jon@64plus.com.au

Dr Jon Glass Retirement Specialist and Coach

64PLUS

Why retirement is not a problem you can fix simply.

For those who read last week's blog, but felt the talk about blocked toilets was too much, I'd like to develop the same idea but in another direction.

I will now make a distinction between solving a technical problem and dealing with its near opposite: an adaptive problem. Technical problems, such as fixing that blocked toilet, will typically have a solution that is clear, and usually with an effective outcome.

The non-financial aspects of retirement is an adaptive problem. Adaptive problems typically mask some deeper emotional issues that need to be uncovered, then addressed.

As a simple example: when you work you have an identity defined by your work, but what will your identity be when you retire? Nobody can simply hand you a new identity. You have to discover what will make you feel useful and engaged after work ends.

That is not a technical problem. It’s adaptive. Here are three common features of adaptive problems.

·       There can be values that are in conflict

·       Certain assumptions are held, but not questioned

·       Some relevant matters aren’t talked about

Let’s apply these to retirement in the order above:

Some people hold as a key value that retirement is a place to shuck off the stress of work so as to enjoy life. That's fine, but my point is that retirement can last for 30 years; and perhaps fun can only take you so far in that journey. You may value feeling useful; then fun and useful will be in conflict.

Retirement can also expose a conflict between freedom and structure. In particular, as an assumption, some people believe that retirement can be a period of time where you wake up each day and work out what to do. In other words, with no routine and no structure. Is that right for you? What if that freedom quickly morphs into a feeling of aimlessness and boredom?

There are also matters about retirement that we seldom question. One is that a satisfying life will naturally emerge once work ends. Perhaps it will. But is that something you want to leave entirely to chance? This leads to a subject we rarely discuss. We talk openly about how much money someone needs to retire. We talk far less about what will make their ordinary days feel worthwhile.

That silence exists partly because these questions expose uncertainty, which cannot be easily undone. A fulfilling retirement has to be worked out through honest conversation and practical experimentation.

If you recognise yourself in this article, email me at jon@64plus.com.au to arrange a chat about your situation.

Jon Glass
Retirement Specialist and Coach
64PLUS

Why do we often put off thinking about retirement?

Why do we put off preparing for retirement?

What is the difference between fixing a blocked toilet and thinking about the non-financial challenges of retirement? Does that sound like a strange comparison? Let me explain.

The answer to this question explains why people act immediately on some problems but postpone others for months or even years. How so?

A blocked toilet is concrete. You can see the problem and it needs to be fixed. You know what a plumber does, and you expect a result.

Uncertainty about retirement is different. Why so; what appears on the horizon of retirement?

Several issues. You may be financially secure and still wonder what will occupy your days. You may be concerned about losing the structure and identity that work has provided.

But these concerns are difficult to see and describe. Retirement may also seem far enough away that nothing needs to be done today.

There is another difference. A plumber does most of the work for you. If you engage a retirement coach then the coach will ask you to participate.

With retired life you may need to admit that you do not yet know what shape it will take. You may have to examine questions about boredom or family relationships in a new environment. You may encounter feelings that are easier to avoid than confront.

This does not mean that you are failing. It means that preparing emotionally for retirement is more complicated than solving a practical problem.

There may also be little external pressure to act. Other people in your house will insist that you call a plumber. Few will insist that you examine what you need from the next stage of your life. You can remain busy, tell yourself that everything will work out.

But here’s the thing: postponement is still a decision.

Retirement coaching does not provide an instant repair. It provides a structured opportunity to identify what is troubling you and decide how you want YOUR retired life to feel.

If you recognise yourself in this article, text me on 0409 116 766 to arrange a chat about your situation.

Jon Glass
Retirement specialist and coach
64PLUS

The question pre-retirees don’t ask | the challenge of retirement | 64PLUS

How can you build shape into your retired life in a way that has meaning for YOU? In this article 64PLUS founder Dr Jon Glass discusses why having challenges in retired life can help answer that question.

I have a retired friend, roughly the same age as me, who has a passion for learning languages.

He is already fluent in German, Spanish and Italian. Today he told me that he plans to study Portuguese.

Why would someone who is retired choose to take on another language?

Part of his answer is simple: he loves learning them. He has an ear for languages and sometimes travels overseas to take an intensive course.

He also hopes that continuing to exercise his brain may help protect him against dementia. I cannot tell you whether the medical evidence supports that belief, and I make no claim to expertise in that area.

But perhaps there is another benefit that can matter just as much.

Learning a language gives him something to work towards. It demands regular effort. It also provides a sense of achievement, which can become harder to find in retirement.

It does not have to be a language. It might be music, gardening, painting or learning how to use unfamiliar technology. The particular topic matters less than having something that gives you the satisfaction of making progress.

Having goals in retired life will generate that wonderful feeling of satisfaction that comes with effort and progress. You experienced that when you worked didn’t you? On the other hand, to not have goals of this kind may lead to you feeling stuck in retirement. The answer won’t emerge from a checklist, as it’s a decision that will engage your feelings and emotions. What do you think might work for you?

If any of this sounds familar, you don’t have to work it out alone. Book an obligation-free 15 minute call below:

No pressure, just an honest conversation about your circumstances.

Dr Jon Glass founder of 64PLUS and author of the book Finding Joy in Retirement.
Retirement Specialist and Coach with 12 years experience based in Sydney, Australia.

Why the decision to downsize may be more complex than it appears.

For many couples, retirement is also the time they decide to downsize. It sounds like a practical decision. In reality, it can be one of the first emotional challenges of retirement. Why?

The decision isn't just about moving house. It can feel like closing the door on one chapter of your life together, but before you're ready. After all, the family home is a place of memories, of identity, of security and of achievement.

What are the issues that may arise for a couple about to downsize?

·      Are they in complete agreement about this move? One partner may want simplicity, while the other may feel they're giving up part of their life.

·      Will they miss their friends from the old neighbourhood?

·      Which possessions to keep, and which to let go?

Downsizing isn't simply a property decision. For many people, it's one of the first emotional transitions of retirement.

If you're finding your downsizing decision harder than you expected, let's talk.

Please text me on 0409 116 766 for a 15 minute obligation free chat about your circumstances. Let’s see if I can help you.

Jon Glass Retirement Specialist and Coach

You can afford to retire. So why can't you bring yourself to do it?

Most people judge retirement by one question: "Can I afford it?" That's an important question. But it's only half the picture. The other half is emotional.

Here is an example. Many people hold off retirement by continuing to work longer than they need to financially. Often they will rationalise their inaction by stating that no-one can replace them at work. What’s wrong with that?

It's easy to tell yourself you're indispensable. Sometimes that's true. More often, it hides a deeper anxiety: stepping into a life you've never experienced before.

So how will you know if you’re emotionally ready to retire?

If you've spent thirty or forty years working, it's perfectly normal to hesitate. That is natural because the transition to retirement is a major life change.

Here are four questions worth asking yourself:

• Am I retiring towards something, or simply away from work?

• Can I picture how I'll spend a typical Tuesday six months after I retire?

• Apart from my job, what gives me a reason to get out of bed in the morning?

• What will give shape and structure to my week once work has gone?

You don't need to have all the answers today. But these are questions worth thinking about before you retire, not afterwards.

Are you reading this and thinking:

"That's exactly where I am. I could retire, so why haven't I?"

Then let's talk. A 15-minute, obligation-free conversation may help you see the next step more clearly. My details are below.

Here is a final thought. No-one taught us how to leave work. We spend decades learning how to build a career, but very little time learning how to let it go.

Tel: 0409 116 766

Email: jon@64plus.com.au

Doctor Jon Glass Retirement Specialist and Coach

Why friendship at work is hard to replace in Retirement part 2: or why we don’t all live in the same time zone.

In a previous article (see link below) we wrote that: you can leave work, but it can be hard to leave behind the network of social connections that work provided. Many people cross the bridge into retirement with a vague sense that something is missing. Not dramatic. Just… an itch they can’t quite locate.

Then it becomes clear: Work gave social connection, without you having to think about it.

Today I was reminded of this when I visited a dear friend who owns a café. We often enjoy good conversations between customers. That's always been our unspoken arrangement.

Today, however, she was exceptionally busy. As I sat there, it occurred to me that we no longer live in the same time zone. She works, whereas I am almost fully retired (I still work part-time as a retirement coach).

One of the hidden errors of retirement is assuming that everyone else's timetable has changed as well. It hasn't. Many of your friends are still working and so are in a different “time zone”.

Conclusion

Perhaps one of the skills of retirement is learning how to maintain friendships across different time zones. Some friends still live by the rhythm of work. Others don't. Successful retirement often means finding ways to bridge that difference.

Do most of your friends still work? If so, how have you adapted your friendships to different time zones? You’re welcome to start a conversation about this topic here:
https://www.64plus.com.au/contact

Link: https://www.64plus.com.au/blog/2026/7/1/why-friendship-at-work-is-hard-to-replace-in-retirement

Dr Jon Glass
Retirement Specialist and Retirement Coach

Why friendship at work is hard to replace in Retirement

You can leave work, but it can be hard to leave behind the network of social connections that work provided.

Many people cross the bridge into retirement with a vague sense that something is missing. Not dramatic. Not urgent. Just… an itch they can’t quite locate.

Then it becomes clear: Work gave social connection, without you having to think about it.

For many people, work provided a steady stream of human interaction:

• Conversation

• Shared purpose

• And the simple pleasure of banter.

That banter matters more than it seems. It’s not just light conversation. It’s a signal:

·       that you belong

·       that you are seen

·       that you matter

Most of us need this. (Lighthouse keepers may be the exception).

If social connection mattered in your working life, it will matter just as much, if not more, in retirement.

If you’re finding it difficult to rebuild that sense of connection, working with a retirement coach can help you manage this.

Conclusion

Retirement is a time to rethink social connections, where they come from, and how to maintain them.

You’re welcome to start a conversation about this topic here:https://www.64plus.com.au/contact

You may also find this related article helpful:https://www.64plus.com.au/blog/2026/3/28/why-you-can-feel-lonely-after-retirement-even-when-youre-busy

Dr Jon Glass
Retirement Specialist and Retirement Coach

Why high achievers can feel lost in retirement, part 5

In four previous blogs, we discussed issues that high achievers may face in retirement (links are below).

I would like to add a thought. But first a lovely quote from a friend “life is like the phases of the moon, if you’re not growing you’re shrinking.”

In my coaching practice I distinguish between two broad styles of retirement:

• Growth – exploring new possibilities and continuing to develop.

• Defensive – preserving the status quo and avoiding unnecessary challenges.

Neither approach is inherently right or wrong. But one of them is right for YOU.

High achievers typically spent their working life pursuing a growth strategy. They enjoyed solving problems and taking on new challenges. That way of thinking became part of their identity, or probably was their identity.

Retirement presents a choice to a high achiever.

You may discover that growth is fundamental to your personality.

Or you may decide that this is the time to slow down and place fewer demands on yourself.

If that is the case, a quiet retirement with few commitments may leave you feeling restless or dissatisfied. What then?

What kind of person do you want to become in retirement?

If these ideas resonate with you, why not let me know about a retirement question that is on your mind? Text me on 0409 116 766 and I will personally reply within 24 hours.

Dr Jon Glass
Retirement Specialist and Coach

Part 1:
https://www.64plus.com.au/blog/2026/6/1/why-high-achievers-can-feel-lost-in-retirement

Part 2:
https://www.64plus.com.au/blog/2026/6/8/why-high-achievers-can-feel-lost-in-retirement-part-2

Part 3:
https://www.64plus.com.au/blog/2026/6/17/why-high-achievers-can-feel-lost-in-retirement-part-3

Part 4:
https://www.64plus.com.au/blog/2026/6/18/why-high-achievers-can-feel-lost-in-retirement-part-4