Midlife Memoirs – Setting Yourself Up for the Second Half – By Chris Andersen
Prelude
All my life, I've been looking for guides and mentors. First it's your parents, then teachers, friend's parents, religious figures, colleagues, friends and friends of friends.
This is all very local. The people you speak with can only guide you through their own experience and what they've learned from others.
I don't want to get stuck in the weeds in debating whether lived experience is more important than lessons learned from others, apart from to say the lessons learned mean very little if you don't pass them on to help someone else learn.
Once you develop the ability to read, you're able to look more broadly, although it may take a while to find books worth reading and authors worth following.
I've decided to write this collection of talks to allow me to distill the work of two authors - Carl Jung & James Hollis. I've discovered them both over the last three years and have read mainly their books during this time.
Now, both of these people have written over 20 books each and I'm yet to read them all, however Hollis' books are a distillation of Jung's teachings and I aim to simplify both into a talk that can be consumed in less than 30 minutes, total.
Both Jung & Hollis are psychoanalysts and Hollis trained through the Jungian school when he decided that was his next stage of development in midlife. I won't be speaking about dream analysis here but more the framework that Jung created to explain the midlife process of individuation or becoming yourself.
I've split the 3 talks into:
Act 1 - The first 35-40yrs
Intermission - The Midlife Process
The Finale - The Downhill Run
Like a play, the first act is character development. The midlife process is intermission rather than the second act to allow just enough time for a costume change and a bite to eat. The finale is where the wheels have been greased, tension released and the main character can settle more into their role in the world.
Now, it's the midlife process in intermission which allows for the second half of life to become easier. Just because it's shorter, doesn't mean it's less important. It's just intended take 1-10 years rather than the approximately 40 years in each half of life.
Speaking of years, Carl Jung died at 85. James Hollis is currently 85 and continues to write and appear on podcasts. It's only since the 1950s that average global life expectancy rose above 50 years old so it's certainly a luxury of modern times to be able to think and learn about middle age.
But that's enough of a prelude, let's get on with the first act.
First Act
There are many books out there that talk about how the first 5 years in a child's life can guide their development towards a secure attachment style.
If you don't do it early, developing a secure attachment style can take a lifetime through both therapy and interpersonal relationships.
I don't intend to talk about that much here apart from to say, the child learns to interact with the world, trust people, read facial expressions, body language and tone of voice then goes on to talk and walk, not necessarily in that order.
They learn to interact with parents, peers and teachers. They learn all that's required of them at kindergarten and school. They learn to fit in. They're scolded if they're overly competitive or aggressive and their chided if they're overly meek. This level of conditioning often depends on gender but also on the values of the people surrounding them.
Someone growing up surrounded by Navy Seals will most likely be different than someone growing up surrounded by peace loving hippies.
Neither is right or wrong, the two opposite ends of the spectrum will just shape values differently.
The key point here from a Jungian perspective is that you learn both who you are and how to fit in. You may also get a chance to learn how you may be different from others early in life but that may come a while down the road.
Some say it's important to go with the flow, others say it's key to fit in with the herd. Either way, socialisation is an important part of the early stages of life and making friends is key so you can develop a healthy ego.
You may learn you can do well at school, you may learn you can make friends easily, you may realise that you're good at mental challenges, you may see that physical endeavours are more your style.
Most likely, you'll learn that society currently has a preference for one of these styles and you may be shaped accordingly.
My parents played hockey, I eventually played rugby, soccer has now become a lot more popular as people learn the long term effects of head knocks and concussions.
My dad used to hunt, ride his bike and fish. I rode my bike, skateboarded and played Sega. Kids these days ride e-bikes and scooters and play on their tablets or phone.
Apparently, many 10 year old kids would prefer to be a professional gamer or a YouTube creator than become a sports star, doctor, lawyer, banker or teacher.
The fact that kids have more access to information these days allows society to shape them sooner through relationships outside their parents, teachers and wider home.
No matter which way they're shaped, it's key they learn to do something well. We'd like to think that society is not competitive but people learn who they are based on where they sit in comparison with everyone else.
They could be struggling in multiple different areas but finding that one single area where they can excel will allow their ego to develop and for them to feel a sense of self-esteem.
They may struggle all day in the classroom but excel during sports at lunch.
They may love the classroom and decide they'd prefer to read a book at lunch than play sports or socialise.
They may not excel in the classroom or sports but may have worked out a way to develop a business on the side so they can't wait to get home to develop systems or interact with clients.
No matter where their natural talents lie, having the opportunity to grow and develop in areas where they can enjoy the satisfaction of achieving at a high level will allow them to develop confidence.
As they progress through school, they may have opportunities to continue to expand on their areas of competence or they may be funnelled into an area with a potential for high income, high status or some combination of both.
Plenty of creative, outgoing kids decide to become accountants. The kids who are good at drama, music or arts may become artists, actors or musicians or they may see more opportunities to utilise their talents and abilities to make a living through social media in 2025.
The intelligent, analytical types who were traditionally expected to become scientists or engineers also have multiple different options. Over the last few decades, it's become popular for engineers to study MBAs then shift into business. This was how management consulting originated.
Many of these same people could have instead opted to work in IT or technology or explore the world of entrepreneurship, much like Elon Musk.
For those that may have struggled at school, many go on to be successful in entrepreneurship, trades or sales. Richard Branson is a famous dyslexic who has employed smart people to bring his visions to life, to the tune of many billions of dollars.
Now, just because you’re good at school, doesn’t mean you’re smart. It just means, according the IQ tests of the world, you have a highly functioning left brain. The right brain, global thinking, people oriented crew are often the ones who run the businesses, much like Sir Richard Branson.
Often, the traditionally intelligent, engineering/accounting types are more risk averse so they excel with all the technical details while working for someone else.
What some people lack in traditional intelligence, they make up for with courage, determination and creativity.
No matter your natural abilities or the path you choose, it's likely that your initial choices will have been shaped by your surroundings.
Your parents and teachers may have been your main guides or it may have been your peers and social expectations.
As you're making all these decisions about career, you're also exploring the world of dating and relationships.
With so many opportunities and avenues to explore, it's highly probable that we may start in an area or with a partner that no longer fits for us 10, 20 or 30 years down the road.
But before we come to that realisation, we first need to learn to fit in with our peers at school, TAFE, College or University then we need to learn to fit in with the older people around us when we start at work.
Somewhere along the line, the chances are that you learn it's not really safe to just be you.
This is when you craft your persona or the mask or many masks you wear in the world.
The masks help you fit in, but they may also lead to you forgetting who you really are.
You could be like Batman and find yourself playing that role more and more. If you never take the mask off, who is Bruce Wayne?
We'll cover that in the next episode.
Intermission
Sometimes, we can wear a mask so long we forget we're wearing it.
It starts to feel like the mask has become us.
But you can always take it off.
The issue is, you put the mask on to help you fit in, please people, make friends, to appear harmless, friendly, nice, safe.
If you decide to take off the mask, you risk displeasing people, losing friends, being seen as too much, too strong, too difficult.
This is when you realize the importance of the first act.
Everything you went through in the first act, in your first 40 years, is important in helping you build your self esteem, your confidence, your ability to withstand criticism.
Your healthy ego is important to help you stand alone.
To be yourself and let the chips fall where they may.
It's likely that you've already achieved some measure of success in a field that was important to you during your development.
You're now in a position to change paths to suit the real you. You're allowed to dress different, look different, be different.
You're allowed to just be you.
Jung called this process individuation.
This is the time when you shift from focusing on what the people around you want to start focusing on what you really want.
It's a time when you can start listening to the call of the unconscious.
Both Carl Jung & James Hollis work with people through psychoanalysis and a large part of this process is dream analysis because dreams tap into the unconscious.
You can think, process, analyse, hypothesise all you want but all this comes from the conscious brain.
Letting the unconscious speak means allowing yourself to listen to the calling of your soul.
To go inward rather than looking outwards.
The other side of this is that you will have certain parts of your personality that you've tried to tone down or switch off entirely.
It's likely that these parts have been deemed unacceptable at sometime throughout your life.
This may be the anger that slips out when you're tired, the harsh critic when you're trying to be positive or your soft side when you're trying to appear tough.
You learned to tone those parts down to fit in, to get along, to succeed.
But you can't turn them off entirely.
These are what Jung called your shadow and in the second half of your life, you can learn to integrate your shadow side into your whole being.
That feeling of anger you try to hide from those around you, is it possible you've forgotten to protect your boundaries?
Do you find it only seeps out when you're at home with your loved ones?
Do they really deserve that?
That feeling of kindness, that empathy...
Do you feel you're too strong to show it?
Or are you just afraid it will somehow make you look weak?
What would happen if you took off that armour and became whole?
What if you just started exploring that unloved part of you moment by moment.
How would your children feel if you suddenly gave them some positive feedback?
How would your partner feel?
Your employees?
Initially, people may feel amazed that you can actually be caring.
They may be amazed that you're actually standing up for yourself.
You may be amazed that this unexplored side of yourself can actually have some positive impact.
If you're used to filling in all the gaps in conversation, what happens if you just start exploring the silence?
You may learn the power of the pause.
You may learn there's no need to explain yourself.
You may realise you actually just want to leave this conversation entirely.
You may realize you'd prefer to hang out on your own.
During this midlife process, you get to play with what happens if you don't live up to the outside expectations.
You get to ask yourself, what do I really want?
And if you do the work, you can let go of all the baggage and focus only on the necessities.
You can focus only on what you need to just be you.
Now, if you look at both Jung & Hollis as examples, they both achieved success in the first half of life.
But it left them feeling hollow.
They'd gone after all the things that were expected of them by their parents, their friends and their society.
They went to university, achieved their doctorates, married, had children and achieved some success but it seems they felt it was not THEIR success.
Jung found a mentor in Freud and he had the courage to let him down, to disagree with him, to think differently so he setup his own school of Analytical Psychology, now known as Jungian Psychology.
Hollis left his academic career behind to move to Switzerland, undertake extensive psychoanalysis then learn the skills to lead others through the same process from the Jungian School.
Hollis focused mainly on sports at College until he was told he had a degenerative bone disease and he could no longer play.
Only then did he really start to focus on becoming a good student
Hollis did his initial writing to publish for his doctorate, he then wrote a book as he felt like it was a necessity for his career.
He then proceeded to protest against writing for more than 10 years afterwards.
He's written over 20 books since then but that's because he's started writing the books he really wanted to write.
These examples make it all sound easy. Achieve success, realise it's unfulfilling then take steps to move in the right direction.
The issue is, this period of unfulfilment is likely accompanied by a season of depression.
If I've done everything right, why does it feel so wrong?
Well, we get caught up in the race.
We're too busy competing to consider what we're actually doing it for.
In my life, I first studied finance and economics then I moved into wealth management.
If I'm honest, the market downturn in 2008 spooked me in seeing that I could potentially give good advice that could still lead to people losing money.
I remember one of the stockbrokers saying to me, in this business, you may end up in a position where you've just lost someone a million dollars.
You may even lose it yourself.
But all this talk of wealth management was mainly focused on helping people retire.
I realised that retirement became more important for people as their work became increasingly unfulfilling.
That's when I started helping people buy properties. The fact that I struggled to find enough clients to support me was a big part of my first depression.
But I also bought a property with my ex-gf that year, and I realized achieving this big goal didn't fulfill me.
The "success" didn't click.
Now, if you love architecture and design and properties, that first property purchase may really light you up and you may decide that you need to do more of this to make you happy.
For me, I felt more satisfaction and excitement when my mechanic and I supercharged my first car to make it go faster. An ugly Volvo nonetheless… but that was even better for me… who would suspect an hatchback Volvo to be fast, right? It was the classic wolf in sheep’s clothing and I loved it.
If you get to midlife, feel unfulfilled then just stick it out for the next 20 years to enjoy the pot of gold at the end of the rainbow then it's possible you may need to endure a couple of decades of bitterness and resentment while you toil away at something that really isn't right for you.
It may not actually be that easy to just suddenly feel happy and free when you're financially able at 65 and over.
Our emotional state can settle in over time like a new coat and like a big woollen coat, it can hang heavy.
That bitterness and resentment can start to feel normal.
To fix this, some decide to make more money sooner.
I decided it was more important to find what I love then give myself the freedom to do it for longer.
But you still need to pay the bills.
And in 2025, the cost of living has made it difficult to allow yourself the flexibility to experiment in midlife.
That's when you need to take a look at all your expenses and realise how many of those also exist for other people.
Just to keep up with other people.
Just to help you fit in.
Do you really need the fancy car?
Do you really need the big house?
Is it those things that will make you happy?
Or does happiness come from what you get to do with your time?
Does happiness actually come from fulfilment?
Both Jung and Hollis speak about the importance of living a life of meaning.
And it doesn't need to have meaning for anyone else, your life has to have meaning for you.
That's the beauty of the second half of life.
You've learned plenty, you've learned to compete in someone else's race, now you get to run yours.
The first half of life is looking outwards, focusing on others, during intermission you learn to look inwards, you learn to focus on yourself.
Psychoanalysis and dream analysis can help you listen more to your unconscious, but you can also learn the practice of listening to yourself.
How do you feel?
How do the people you're with throughout the day make you feel?
What did you notice when you first walked into the room?
What is it you're doing when you notice you're feeling different, more alive?
How could you start doing more of that?
What is it you're doing when you notice you feel less alive?
How could you start doing less of that?
How could you start listening less to the expectations of the people around you and more to what your own body is telling you?
How could you start focusing more on what YOU actually want?
When was the last time you made something just for the fun of it?
It could be a painting, a poem, a piece of furniture, a story, an essay, a dish to eat from, some food to eat.
These periods of time where we allow time to fly by while we're fully absorbed in the moment are the periods where we remember what it feels like to be ourselves.
To be alive.
It could be that you've done something before in your life that was very close to this ideal, what changes would you need to make to move it closer to perfect?
There will most likely be an answer that jumps out at you.
Learn to listen to that answer and you will start moving closer to your true path.
Maybe you feel most yourself with people, maybe it's more while you're on your own.
It doesn't really matter either way, it only matters that you learn what works best for you.
And if you already know and you're not allowing yourself to move in that direction, you can understand why you're not feeling your best.
The upside of looking at it early, is you have the rest of your life to adjust.
And if you manage to make the changes, if you manage to shift into the mode of being that's true for you, then you set yourself up for the next chapter, The Downhill Run.
The Downhill Run
"May the wind always be at your back and the sun upon your face. And may the wings of destiny carry you aloft to dance with the stars."
That's a quote from another Jung, George Jung, from the movie, Blow.
You might remember it.
And I think you get it.
When you run downhill, the wind is at your back, there's no road that rises up to meet you as your journey is without resistance.
In other words, if we take the right path, life can be easy.
Once you've climbed the mountains in the first half of life, once you've learned what you needed to learn and tested yourself, it's now your opportunity to carry the treasure downhill.
And while you may be running, it's not necessarily a race.
But if it is, it's your race.
And when you run your own race, there can only be one winner.
You.
So, walk, don't run, to the beat of your own drum and remember the sound of the rhythm.
That's all you.
Listen to the rhythm, move to the beat and may the world be at your feet.
It's up to you to tell your own story from here.
But if you’d like a hand with better telling your story or even just for a chance to reflect further, feel free to reach out to me on 04 2468 ANDO (2636). In the format where you usually see it, that’s 0424 682 636.
If you’d like some more individual assistance, below is a quick outline of the Cultivated Confidence Program. This program will also include membership in The Sunday Sessions monthly coaching calls, as shown on the Coaching Page.
The weekly training will help you develop your sales skills while the individual work will help strengthen your self knowledge so you can show up as powerfully as possible.
Session 1 - We walk through the warts and all story of everything that’s happened up til now so that it exists in reality, not just in your own head. Once we have that sorted, we do some personality testing to learn more about you to work on next week.
Session 2 - We do an in depth review of your strengths and weaknesses, as you see them, to assess exactly what you bring to the table. We also work through the results of the personality testing so you can learn more about how someone like you usually shows up in the world and the strengths and weaknesses associated with your personality type.
Session 3 - This is where we take stock of all the work we’ve done so far, reassess all the weaknesses and strengths then record a more positive story that you can use to play back to yourself at times when you may be feeling less confident or less accomplished. Effectively, we’re rewriting the story that plays in your head so you can tell a better one in all future encounters.
Session 4 - This is where the rubber hits the road. We’ve worked on the story, we’ve worked on understanding your strengths and weaknesses and now we build a plan of attack to make it happen to help you achieve your goals.
Monthly Coaching - Each month, I’ll bring along a new topic to consider over a few coffees or non alcoholic beers on a Sunday morning.
If you’d like to do some additional one on work to improve how you show up in the world and ensure you set yourself up for success in al future sales encounters, click the below link to buy the program.
If any of your questions are yet to be addressed, feel free to shoot me a message or give me a call on 0424 682 636. I look forward to speaking with you soon. Bye :)