My daughter graduated from high school this week.
I know this is supposed to be one of those cleanly celebratory moments. Caps in the air. Proud parents. Big smiles in awkward family photos. And yes, there was all of that too.
But underneath the celebration was something else entirely: grief. Not catastrophic grief. More like the quiet ache that comes when a version of your life dies before you’re ready to let it go.
My wife and I are suddenly staring down the barrel of becoming empty nesters. And even though we knew this day was coming for eighteen years, it still feels disorienting. Which got me thinking about transitions and how profoundly bad humans are at understanding them.
That became the basis for this week’s “10 Things” episode of Earn & Invest.
Even the transitions you desperately want can feel awful at first.
Marriage. Retirement. Moving to a new city. Selling your business. Having kids. Sending them off to college.
We assume difficulty only belongs to tragedy. But often the hardest moments arrive wrapped in joy because every transition—even a beautiful one—demands the death of an old identity. And identity deaths are messy.
At the same time, some of the transitions we fear most end up becoming unexpected gifts.
When my wife was essentially pushed out of her professional role, it felt unfair and abrupt. But in hindsight, it became the exact catalyst she needed to finally embrace retirement. Left to her own devices, she probably would’ve kept grinding for years.
Sometimes life drags us toward the thing we secretly need most.
One of the biggest mistakes we make during periods of transition is assuming the first year tells us anything meaningful. It usually doesn’t.
The first year after any major life change is often confusing, emotional, and profoundly incomplete. We are terrible judges of our lives while actively living through upheaval. The real benefits of change frequently don’t reveal themselves for three to five years.
That’s hard for our optimization-obsessed brains to tolerate.
We want immediate certainty. Immediate meaning. Immediate proof we made the right decision.
Life rarely works that way.
So how do we survive these in-between seasons?
For me, the answer increasingly comes down to acceptance. Not passive resignation. Not toxic positivity. Acceptance.
The Stoics talked about viewing life as happening for us instead of to us. Buddhism teaches us to accept reality exactly as it is rather than exhausting ourselves fighting against what already exists.
I’ve spent enough time with dying patients to know this much is true: resistance compounds suffering.
The people who navigate transition best aren’t the ones with the easiest circumstances. They’re the ones who stop demanding reality be different before they allow themselves to move forward.
And maybe that’s where agency comes in.
I’ve become convinced that agency—the belief that your choices still matter—is the closest thing we have to a superpower. It’s the antidote to burnout. To despair. To helplessness.
Not because you control outcomes.
You don’t.
But you always retain some ability to decide who you want to be inside the circumstances you’ve been given.
That’s intention.
That’s identity.
That’s freedom.
Toward the end of the episode
I also answered a listener question about generational wealth and what my wife and I are currently doing with our own kids.
Right now, we gift each of them $5,000 every quarter. They immediately invest it into Vanguard index funds.
Some people hear that and think it’s excessive. Maybe it is.
But after spending decades talking to the dying, I’ve become less interested in maximizing inheritance after death and more interested in creating possibility while people are alive enough to use it.
If compound interest works mathematically, why not emotionally too?
Why not help your kids build a runway early enough that they can actually use freedom to design meaningful lives instead of spending thirty years digging themselves out?
The truth is, I don’t care if my kids become fabulously wealthy.
I care if they become independent enough to ask deeper questions than “How do I survive?” I want them to experience what abundance actually gives you: the ability to become yourself.
That’s what this entire episode is really about.
Transitions are uncomfortable because they force us to confront the gap between who we were and who we might become.
Most of us spend our lives trying to avoid that gap.
But maybe the gap is where everything important lives.