Starting Over at 50 Was the Best Thing That Ever Happened to Me
Dec 17, 2025
I spent most of my life believing that if I worked hard enough, sacrificed enough, and pushed long enough…
one day I’d finally be free.
Free financially.
Free from stress.
Free to relax.
I told myself, “Just get through this season.”
And then another season came.
And then another.
By the time I hit my early 50s, I thought I had done everything right.
I had worked relentlessly.
I had saved.
I had built.
And then… it all unraveled.
In just a few short years, I burned through my RRSPs.
I pulled equity out of my home.
And the part no one talks about?
I was burning through my relationships too.
My marriage was strained.
My daughters didn’t like the man I was becoming.
And I didn’t recognize myself anymore.
On the outside, it looked like success.
On the inside, I felt lost.
I realized something terrifying:
The way I was chasing freedom was about to cost me everything that actually mattered.
There was a moment quiet, uncomfortable, undeniable when I understood this truth:
If I kept going the way I was going,
I wasn’t heading toward freedom.
I was heading toward divorce.
Toward distance from my kids.
Toward waking up one day with money… and no one left to share it with.
That was my wake-up call.
Not a motivational quote.
Not a book.
Not a podcast.
A mirror.
And the man staring back at me was exhausted, disconnected, and scared.
So at 50 something years old, I did the thing I never thought I’d have to do.
I started over.
Starting over didn’t mean quitting life.
It meant rebuilding it on different rules.
I started two new businesses from alignment instead of desperation.
One of them was JP Smitty Sauce a family brand built around time together, legacy, and shared effort.
My daughters help. My wife helps.
It’s not just a business it’s a table we all sit at.
The other was JG Fleet Services, where I help people navigate car buying without pressure, manipulation, or bullshit because I know what it feels like to be overwhelmed and taken advantage of.
But the most important thing I rebuilt?
My mornings.
Because I realized if I couldn’t lead myself first thing in the day, I couldn’t lead anyone else.
Every morning, no matter what
I step into cold water.
Today was day 715 straight.
Not because it makes me special.
But because it reminds me of something simple:
I can do hard things calmly.
That one habit became my anchor.
Cold immersion.
Movement.
Stillness.
Intentional starts.
That’s how I rebuilt my mind before I rebuilt anything else.
Here’s what I know now and what I wish someone had told me earlier:
Starting over doesn’t mean you failed.
It means you woke up.
Sometimes losing the version of life you planned
is the only way to find the life you were meant to live.
If you’re in your 40s or 50s
and feeling behind, confused, or like you’re rebuilding instead of retiring…
You’re not broken.
You’re not alone.
And you’re not late.
You’re early to the version of yourself that actually gets it.
So if you take one thing from this, let it be this:
Don’t wait for everything to collapse to change direction.
Don’t sacrifice the people you love for a finish line that keeps moving.
And don’t confuse money with meaning.
Because the best thing that ever happened to me
wasn’t success.
It was the moment I realized success nearly cost me my family
and I chose differently.
I didn’t lose everything.
I finally woke up.
If you want to keep following this journey the rebuild, the habits, the businesses, the real conversations
I’m sharing it openly.
Not because I have it all figured out,
but because none of us are meant to do this alone.
one day I’d finally be free.
Free financially.
Free from stress.
Free to relax.
I told myself, “Just get through this season.”
And then another season came.
And then another.
By the time I hit my early 50s, I thought I had done everything right.
I had worked relentlessly.
I had saved.
I had built.
And then… it all unraveled.
In just a few short years, I burned through my RRSPs.
I pulled equity out of my home.
And the part no one talks about?
I was burning through my relationships too.
My marriage was strained.
My daughters didn’t like the man I was becoming.
And I didn’t recognize myself anymore.
On the outside, it looked like success.
On the inside, I felt lost.
I realized something terrifying:
The way I was chasing freedom was about to cost me everything that actually mattered.
There was a moment quiet, uncomfortable, undeniable when I understood this truth:
If I kept going the way I was going,
I wasn’t heading toward freedom.
I was heading toward divorce.
Toward distance from my kids.
Toward waking up one day with money… and no one left to share it with.
That was my wake-up call.
Not a motivational quote.
Not a book.
Not a podcast.
A mirror.
And the man staring back at me was exhausted, disconnected, and scared.
So at 50 something years old, I did the thing I never thought I’d have to do.
I started over.
Starting over didn’t mean quitting life.
It meant rebuilding it on different rules.
I started two new businesses from alignment instead of desperation.
One of them was JP Smitty Sauce a family brand built around time together, legacy, and shared effort.
My daughters help. My wife helps.
It’s not just a business it’s a table we all sit at.
The other was JG Fleet Services, where I help people navigate car buying without pressure, manipulation, or bullshit because I know what it feels like to be overwhelmed and taken advantage of.
But the most important thing I rebuilt?
My mornings.
Because I realized if I couldn’t lead myself first thing in the day, I couldn’t lead anyone else.
Every morning, no matter what
I step into cold water.
Today was day 715 straight.
Not because it makes me special.
But because it reminds me of something simple:
I can do hard things calmly.
That one habit became my anchor.
Cold immersion.
Movement.
Stillness.
Intentional starts.
That’s how I rebuilt my mind before I rebuilt anything else.
Here’s what I know now and what I wish someone had told me earlier:
Starting over doesn’t mean you failed.
It means you woke up.
Sometimes losing the version of life you planned
is the only way to find the life you were meant to live.
If you’re in your 40s or 50s
and feeling behind, confused, or like you’re rebuilding instead of retiring…
You’re not broken.
You’re not alone.
And you’re not late.
You’re early to the version of yourself that actually gets it.
So if you take one thing from this, let it be this:
Don’t wait for everything to collapse to change direction.
Don’t sacrifice the people you love for a finish line that keeps moving.
And don’t confuse money with meaning.
Because the best thing that ever happened to me
wasn’t success.
It was the moment I realized success nearly cost me my family
and I chose differently.
I didn’t lose everything.
I finally woke up.
If you want to keep following this journey the rebuild, the habits, the businesses, the real conversations
I’m sharing it openly.
Not because I have it all figured out,
but because none of us are meant to do this alone.
