Retirement is often depicted as a time when as we move away from the world of the stresses and strains of full time work all our worries disappear. 

You’ve seen the unrealistic but stereotypical images. A worry-free retired couple smiling on a bench or deckchairs on a beach, or even a man enjoying a nice cup of tea! 

Now whilst I can argue that the majority of images, we see which seem to reflect retirement (or the third chapter of our life) are often a little patronising, I’d also suggest that a lot of these images reflect a worry free life. 

But here’s the thing… 

My experience from working with many retirees in my 20 odd year career as a financial planner is that worries don’t go away… they simply change. 

But, there’s a big question. How do these worries change… and what can we do about them? 

So, in this blog I want to talk about the 5 underdiscussed worries we need to consider when we’re thinking about retirement (or the next chapter of our lives) and more importantly what we can practically do to overcome these worries. 

I’m going to look at both ancient philosophy and modern research and talk about the worries you face and the practical actions you can take to mitigate these worries in an achievable way. 

All to ensure that, whilst you’re clearly going to worry about stuff in retirement, you’ll be equipped with 9 mental tools in order to thrive in the next chapter of your life… 

Retirement and the run up to retirement is often depicted as a time where life has never been better…and that’s true in a lot of ways. 

However, my experience having worked with clients in this period of their lives over the past couple of decades is that whilst the challenges we face in the third chapter of our lives do evolve, they certainly don’t disappear. 

So, here’s the 5 challenges we specifically face whilst approaching retirement and the one small action we can take to  

1. Living in the Sandwich Generation 

It’s interesting. A relatively modern challenge, we face when we hit our 50’s, 60’s and beyond is the fact that we’re more likely to have older parents who we’re continuing to care for but also adult children who potentially need continued support for longer. 

This can lead to some interesting challenges. Some of the challenges of living in the Sandwich generation are financial, however a lot of the challenges I find many people in the sandwich generation face are about both time and emotional challenges of supporting both kids and parents. 

The one thing we can do here is think a bit more about self care and the importance of ‘being kind to ourselves first’. 

In the book I wrote about kindness, a few years ago, I thought a lot about, after telling the strange story of how a financial planner finds himself writing about kindness, I didn’t start talking about how we can be kinder to charities, or our friends and family. 

I wanted to start with the important subject of being kinder to ourselves and talk about the book why in Airplane safety briefings they always talk about putting your own oxygen mask on first before helping others. 

It’s clear why they recommend you do this. Looking after yourself provides you with the opportunity to help others. 

Now I know this is easily said and not so easily done. I also know that we don’t live in an idealised world but instead in a world where emotions, relationships and demands on our time are complex. 

However, focusing on and thinking about investing a bit more time in self care when both the older people and younger people in your family have demands on your time is worth thinking about. 

2. Reduced earnings and the worry of enough 

In my work as a chartered financial planner, many of my clients work with me to answer one clear question… 

Have I got to the stage where I’ve achieved enough wealth to be financially independent? 

Often, the conversation about ‘enough’ happens when we start to seriously consider life after our current careers. 

Now, we can have a debate about whether this is too late because the reality is that the best time to think about enough and plan and prepare for financial independence. 

However, and you know how much I love a bit of ancient wisdom, there is a Chinese proverb which talks about the fact that “The best time to plan a tree was 20 years ago. The second-best time is now.” and that principle applies to your journey towards financial independence. 

My experience is that taking ownership of your journey towards financial independence, even though you might not want to hear that you’re not there yet, is the first step you need to take. 

Secondly you need a plan to help you achieve financial independence. 

And 

Lastly, take incremental action to help you get there.  

I’ve recorded a video recently which should help you do this in a way which might help and you can find this video here… 

In this video I’ve used a super broad framework called the ‘4% rule’ which whilst might give you a starting point to understand where you are in your journey to financial independence there’s another question. 

What happens when you want a more detailed, more nuanced plan. I suppose there’s a couple of things here worth considering. Firstly, it might be worth you considering getting a bit of help from someone like me who can build you a nuanced plan, highlight elements you might want to consider when thinking about how much is enough and work with you on a consistent basis to support you on this journey. 

However there are also some independent tools available designed for you to build your own plan which are worth researching too.  

3. Loss of Identity and Purpose 

In the 1985 film, Mad Max beyond Thunderdome the protaganist, Aunty Entity (played fantastically by the brilliant Tina Turner) uses the following phrase… 

“One day you’re cock of the walk. Next a feather Duster.” 

The challenge we face as we approach retirement is the fact that, for many of us, we’ve built our businesses, our reputations and our identity around what we do. 

I think the most pertinent conversation I had about this was with a client who looked me dead in the eye when he was talking about leaving the job he’d built his professional and personal reputation in and told me… 

“What am I if I’m not that?” 

So, what are we if we aren’t the managing director, or expert in our field, or relied on in our occupation and how do we navigate this really important challenge. 

This is a complex subject and one worth further exploration, which I intend to do in a future video, but there’s a few positive practical actions you can consider and take to make this transition a lot easier. 

First, take a look a the Japanese model of Ikigai, and work out what (in this upcoming chapter of your life) means that you’re spending time doing what you love, doing what you’re good at, doing what the world needs and (if you still need to worry about this) doing what you can be paid for. 

This might be one thing. This might be a combination of things. But thinking about this model as you move into this chapter of your life is definitely worth thinking about. 

Secondly start to plan early for Wellbeing in every aspect of your life. A lot of people approaching retirement plan for the fun elements of retirement. That’s a vital thing to do. 

However, what may people don’t do is plan to take action in the areas of their lives which will provide continued purpose. 

So, there’s an important question here I’d suggest you ask way before you intend to stop work, which is… 

How, after I sell my business or stop my current job, maintain a sense of purpose in my life? 

Thirdly, think about doing something in this upcoming chapter of our lives which can help others. 

Often in our businesses or careers we’ve ‘done well’ (however you define that) by supporting others. It’s likely throughout your career you’ve helped your clients, supported your teams and taught a wide range of subjects to a wide range of people throughout your career. 

So, the big question here is… 

“If I’ve decided to take action and leave my current career, how do I continue to help other people?” 

The good news now, is that in this chapter of your life, the support you give and the help you provide can be 100% on your terms. 

4. The change of social relationships 

Whilst for a bunch of us the social engagement we get from work has changed since more flexible working, for most of us we still get a lot of spending time with people we like working together on something you care about. 

However, if you’ve decided to retire and leave the current job, the reality is that your social relationships you hold at work are likely to change. 

I’ve written a lot about the negative impact on loneliness in our lives. In fact I recorded this video on this particular subject and we know the evidence points to the fact that feeling socially isolated can have a negative impact on our physical health too. 

So, if a lot of your friendships are at work, but you feel the need to either retire or move to the next chapter of your life, leaving your current role there’s a bit question… 

What can we do to ward off the challenge of social isolation… 

There’s a bunch of things you can do but I think the most powerful one I’ve seen work time and time again is typified by three simple words. 

Join. A. Club. 

Now you may be asking what sort of club might work for you and I’d suggest there’s three questions you might want to ask yourself… 

Firstly, what do you love to do?  

Secondly, what do you care about? 

Thirdly, what would you like to get better at? 

You might choose a sports club, or a social club, or a club which has a positive impact in the world. Even better, there might be a club which combines all three elements! 

However, spending time with other people who share what you love, share what you care about and share your desire to improve a specific skill might be a great place to start. 

5. The Balance between life and legacy 

There’s a question I think about a lot… 

“What’s the right balance between living (and enjoying my life) and doing meaningful work?”  

The challenge you, I and everyone reading this article we face is getting the right balance between the various roles we have and will continue to have in the third chapter of our lives. 

For many of us, including you if you’re in your 50’s, 60’s, 70’s and beyond, work in whatever form it takes (be it volunteering, mentoring, employment, business ownership) or a combination of all of these is likely to be a factor in your life. 

It’s a question I often think about in my own life too. However my experience, both in my own life and in my clients life, tells me this… 

Perfect Balance is a falacy. The important thing is self-awareness and continuous recalibration. 

So my tip here is to simply being aware of how you feel about the current balance in your life, and what you need to do to recalibrate how you spend your time in incremental ways. 

If you’re still working but considering retirement, consider a flight path (where instead of moving from full time work to no work, look at reducing the amount of employed work you do gradually.) 

And If you’re already retired, look at how you spend your time and how you might want to change this to better suit what you want to do in this chapter of your life. 

So, that’s it, the 5 challenges we often face when we retire and the actions we might want to consider. 

However I’m curious, what of these challenges resonated?  

What challenges did I miss?  

If you’ve retired, or are approaching retirement, what challenges are you most worried about? 

I’d love to know…