Playing It Safe Is Costing You More Than You Think
Why playing it safe in midlife is quietly costing men purpose, health, and leadership.
There have been many times in my life where I’ve played small. Not because I lacked ambition. Not because I wasn’t capable. But because I settled for comfort and slowly lost touch with my purpose. It didn’t look like failure. It looked like success.
When Success Is Comfortable but Empty
Early in my corporate career, about five years in, I did what many men do.
I secured a solid corporate role. Climbed the ladder. Became a manager. Moved overseas chasing money and adventure. Contracted. Earned well. Built security.
From the outside, it all made sense.
But inside, work was just work. There was no fulfilment. No meaning. No sense that what I was doing actually mattered.
I was working in large corporate environments where the primary goal was increasing shareholder profits. I’d leave work with a decent pay-check, but no real sense of value.
I was playing it small, not because the job was beneath me, but because it wasn’t aligned with the man I wanted to become.
One day, sitting in the office, I looked around at my colleagues.
Stressed. Tired. Overweight. Unhealthy.
And I asked myself a question I couldn’t ignore:
👉 “If I stay in this corporate job, is this me in the next 3-5 years?”
The answer was clear.
I valued my health, my energy, and my life more than money, status, or material things.
So I quit.
The Two Fears That Quietly Shape a Man’s Life
Since then, I’ve come to see something clearly. Men aren’t held back by a lack of discipline or ambition.They’re held back by two fears:
• Fear of failure
• Fear of success
I’ve felt both.
Climbing the corporate ladder brought a fear of success. The higher you go, the greater the responsibility, pressure, and expectations. And while the rewards can increase, so do the costs.
Health. Relationships. Purpose. Fulfilment. Meaning.
I understand why men chase that version of success. But it wasn’t the life I wanted.
At the same time, fear of failure has been just as real. Quitting a corporate job to become a personal trainer. Investing a large chunk of my life savings into opening a gym. Selling that gym. Moving my business 100% online.
I’ve attempted to build multiple businesses that failed.
Now there’s Midlife Mavericks. Will it succeed? I honestly don’t know. But I keep going. I keep experimenting. I keep moving toward work that inspires me and aligns with what I care about.
I’ve learned that if there’s no fear, you’re probably not growing. And if you’re not growing, you’re drifting.
Comfort feels safe. But it comes at a cost.
How Safety Quietly Shows Up
For me, safety has often looked like staying busy. I’ve always been a hard worker. Switching off, sitting in silence, or being fully present hasn’t come naturally. That’s something I’ve had to confront, especially after becoming a father.
Busyness looks productive. But it can quietly erode relationships, health, and quality of life.
Training has also been a place I’ve hidden.
Work and training are measurable.
To-do lists. Skills. Weights on the bar. The scales.
They give a sense of accomplishment and control. But they can also become a distraction from the uncertainty and discomfort in other areas of life, a way to feel successful without asking harder questions.
For a long time, I didn’t want to admit that.
If This Feels Familiar, Read This Slowly
If you’re reading this and thinking:
"My life looks good on paper but feels flat.” “I stay busy so I don’t have to slow down.” “I don’t hate my work, but I don’t feel alive in it.” “I’m providing, but I’m not really leading.”
You’re likely out of alignment.
Noticing that, without rushing to fix it, is often the first real shift. That’s where change actually starts for a lot of men in midlife.
The Wake-Up Call I Didn’t Expect
The real wake-up moment for me came through The Warrior to King Framework.
Both building the framework and doing the work myself forced me to slow down and ask questions I’d never really asked before:
Why do I train like this? Why is this important to me? Who is the man I want to become? What am I actually doing to move toward that identity? What is living out of alignment really costing me?
The realisation was uncomfortable. I was hiding in work and training, feeling successful, while avoiding the bigger picture of my life.
From Autopilot to Intention
That shift changed everything. Life became less about doing more and more about intention.
Cutting out the fluff. Focusing on what truly matters. Planning my weeks with purpose. Showing up more fully for the people who matter. Saying no to things that don’t align.
The result wasn’t instant success.
It was calm. More moments of flow. A deeper sense of alignment. Excitement about the work I’m doing now.
What surprised me most was how long I’d lived on autopilot, chasing a version of success that wasn’t aligned with my values or strengths.
I pushed hard for something I thought I wanted, only to realise it wasn’t true.
The Lie We Don’t Question Enough
The lie I believed for too long was that money or status would make me happy. No one told me that playing it safe would cost me more than it would save me.
We’re told safety equals security. That it gives us an easier life. That it’s the responsible thing to do.
But does it really?
Does safety give you deeper connection with your family and friends? Does safety give you adventure, purpose, and growth? Does safety give you legacy?
Or does it quietly keep you smaller than your potential?
I understand the need for financial security and providing for your family. That matters. But at what cost to everything else?
Playing it safe isn’t leadership. Avoiding risk isn’t responsibility. Staying small to keep everyone comfortable isn’t protection.
Leadership means being willing to grow. To stretch. To model what it looks like to live with intention, courage, and alignment.
Your family doesn’t need a man who stays safe.They need a man who leads himself first.
What I Wish I Knew Earlier
What I wish someone had told me earlier is this:
Slow down. Ask better questions. Look at the big picture, not just short-term gains.
For most of my life, I chased measurable goals.
The weight on the bar. The number in the bank account. The title. The material thing.
Things you can track. Things you can point to and say, “I’m winning.”
And for a long time, I never questioned how hollow that pursuit actually was. None of those things come with you when you’re lying on your deathbed. What you’re left with are moments. The days that felt alive. The conversations that mattered. The laughter. The warmth. The love. The sense that your life meant something beyond achievement.
Money and material things can create certain feelings; security, relief, status, comfort. But what if the emotions we’re chasing through money, status, and success could be experienced more often, and more fully, by choosing differently?
Instead of grinding our lives away at a desk job, waiting for permission to feel joy once the bank balance hits a certain number…
Instead of sacrificing health, relationships, and presence now for a future that keeps moving further away…
What if we designed life around the emotions that actually matter?
More connection. More meaning. More adventure. More presence. More alignment.
Not someday.
Now.
That doesn’t mean abandoning responsibility or ambition. It means asking a harder question:
👉 What is this version of success costing me?
👉 And is the price worth paying?
Because leadership isn’t about accumulating more. Its about choosing what matters, and living it, daily.
An Invitation, Not a Prescription
If any of this feels uncomfortable, that’s the point.
Discomfort isn’t a sign you’re doing something wrong. It’s often a signal you’re telling yourself the truth.
If nothing changed in your life for the next 3-5 years, would you be proud of the man you’re becoming?
Inside the Midlife Mavericks Brotherhood, this is exactly the work we do. Not hustling. Not chasing more. But restoring direction, rhythm, and self-trust across life, health, and work.
In January, we’ll be working deeply with these themes, moving off autopilot and into intentional leadership.
If this question lingers, the Brotherhood exists for a reason.
You’re welcome to join us. Not to chase more.
But to live more aligned and on purpose.
