A few years ago, if you had described my current life to my younger self, he would have thought he won the lottery.
A wife he loves. Kids. A growing business. A home. Meaningful work.
The things I spent years hoping for eventually became the things I woke up to every day.
So why, every once in a while, did I find myself missing a life I no longer wanted?
That question confused me for a long time.
Because gratitude and grief aren’t supposed to exist together, are they?
At least that’s what I told myself.
If your life is objectively good, what right do you have to miss the parts that came before it?
But the older I get, the more I realize that every meaningful gain involves some form of loss.
When I became a husband, I gained a partner. I also lost some independence.
When I became a father, I gained two incredible children. I also lost the freedom to make every decision based on what I wanted.
When I started a business, I gained purpose and ownership. I also gained responsibility, pressure, and countless sleepless nights.
None of those are bad trades.
I’d make them all again.
But they’re still trades.
I think many adults struggle because nobody prepares us for this reality.
We’re taught to focus on what we’re gaining.
Rarely do we talk about what we’re leaving behind.
The version of you that could spend an entire Sunday doing absolutely nothing.
The friendships that were effortless because everyone lived within ten minutes of each other.
The spontaneity that came from having fewer responsibilities.
The feeling that life was mostly ahead of you instead of already underway.
Sometimes I miss those things.
Not because I want my old life back.
But because those versions of me mattered too.
There’s a temptation to judge ourselves when these thoughts show up.
To think, “I should just be grateful.”
And gratitude is important.
But gratitude doesn’t erase loss.
I can love being a father and still miss sleeping through the night.
I can love my family and still miss the freedom that existed before they arrived.
I can be proud of my business and still miss the simplicity of clocking out and leaving work behind.
These truths don’t compete with each other.
They coexist.
In my work, I’ve noticed that many men have a difficult time acknowledging this.
They feel guilty whenever they experience sadness about something they willingly chose.
They believe that because they chose the path, they don’t get to struggle with the consequences.
But that’s not how being human works.
Every season closes a door.
Even the good ones.
Especially the good ones.
Maybe that’s why certain memories hit harder as we get older.
Not because the past was perfect, but because we’re remembering versions of ourselves we’ll never be again.
The young father becomes the experienced father.
The newlywed becomes the long-married spouse.
The dreamer becomes the person responsible for maintaining the dream.
Life moves forward whether we’re ready or not, and there is something beautiful and painful about that.
Lately, I’ve been trying to stop fighting this reality. Instead of asking why I feel grief, I’ve started asking what it’s trying to teach me. Often, it’s reminding me to appreciate the season I’m currently living. Because one day I’ll miss this version too. The chaotic mornings. The little thumping of footsteps. The toys scattered across the floor. The feeling of being needed every minute of the day. One day, these things will be memories.
If history is any guide, I’ll probably find myself missing pieces of this life while enjoying whatever comes next.
Maybe that’s the deal.
Maybe a meaningful life requires us to repeatedly let go of versions of ourselves that we once loved.
Not because we’ve failed.
But because we’ve grown.
And maybe the sadness we feel isn’t a sign that something is wrong.
Maybe it’s simply the cost of building a life that matters.
