The 5 Biggest Challenges Men Face in Midlife—and How to Handle Them
One of the toughest things any man can face is the breakdown of a relationship.
Divorce. Separation.
The collapse of something you thought would last forever.
It’s brutal. It’s messy. And it hits hard.
Several of you have shared your stories of heartbreak with me.
I get it—I’ve been there too.
But let’s be honest: that’s just one of the many shitstorms we men face in midlife.
During a podcast interview recently, I was asked a big question:
What are the biggest challenges men are dealing with today?
It got me thinking.
After years of coaching and speaking with men in the 35-50 age group, these are the Top 5 Battles I see most men fighting right now.
1) Career and Work-Life Balance
If you’re a man in your late 30s or 40s, chances are you’re at a critical point in your career.
The pressure to climb the ladder or hit the next milestone professionally can feel overwhelming.
But it doesn’t stop there.
You’re probably juggling those work demands with family commitments. Being present for your kids. Supporting your partner.
It’s fucking hard to find the balance.
When you’re trying to keep everyone happy, the cracks can start to show.
And if you’re not careful, before you know it, you’ve knobbed it.
Stress builds. Burnout looms.
Relationships feel the strain.
Sound familiar?
2) Money Worries
Finances can be another heavyweight on your shoulders.
Crippling Mortgage Repayments. High Interest Loans. Car payments. School fees.
A lot of it’s a scam anyway.
It’s a constant balancing act.
And let’s not ignore the clowns running the economy—the lizards are not exactly helping us, are they?
Economic uncertainty can add to the stress.
You might feel like you’re treading water financially, trying to stay afloat in a system that’s stacked against you.
Although some would say the system is deliberately trying to enslave you in lifelong debt.
3) Health Concerns
Midlife has a way of shining a light on health—physical and mental.
You hit 40, and suddenly things start to feel... different.
Weight creeps on. Stress piles up. Sleep takes a hit. Hair gets thinner.
And yet, nose hair gets longer, WTF!
And let’s not even mention the health issues most men don’t want to talk about.
Living a healthy lifestyle sounds simple in theory—exercise, eat right, manage stress—but in reality? It’s tough.
But ignoring it only makes things worse.
4) Relationships and Family Dynamics
In midlife, we wear a lot of hats:
Husband
Father
Son
Brother
Stepdad
And every single one comes with its own set of demands.
You’re trying to keep everyone happy while dealing with the complexities of relationships, family life, and, for some, custody battles or co-parenting struggles.
These challenges can test even the strongest man.
I know, because I’ve talked to so many.
It’s no wonder that shitloads of us feel stretched to breaking point.
5) Isolation and Mental Health
Men aren’t great at talking about their struggles.
And that silence can breed isolation.
We let the pressure build up and it will come out one way or another.
Lockdowns only amplified this problem, but even now, many men in midlife feel a growing sense of disconnection.
You question your choices. You wonder if this is really what life was meant to look like.
Here’s the truth:
We’re social creatures.
We need connection.
Brotherhood.
A space to talk openly without judgement.
When that’s missing, it takes a toll on your mental health.
What Would You Add?
These are the 5 challenges I see men wrestling with most often:
Career and work-life balance
Money worries
Health issues
Relationships and family struggles
Isolation and mental health
But this isn’t just about listing problems.
It’s about recognising them, facing them, and finding a way to navigate through.
If any of these resonate with you—or if there’s something else you think should be on the list—let me know in the comments.
Let’s get the conversation started.
Because these struggles?
They don’t define us.
But how we handle them does.
Cheers
Anthony
Whole Man Academy
Struggling to figure out where you stand right now?
