Are You Actually Retiring Toward the Same Life?
Most couples don’t fight about retirement.
They assume they’re aligned.
They assume they want the same kind of retirement.
They assume the details will work themselves out.
And sometimes… they do.
But often, what I see isn’t conflict—it’s quiet drift.
Two people heading toward retirement together, but picturing slightly different lives once they get there.
One imagines slow mornings and nowhere-to-be days.
The other imagines travel, projects, and a full calendar.
Neither is wrong.
They’re just unspoken.
Alignment isn’t automatic
If you’ve been married a long time, it’s easy to assume alignment means agreement.
“We’ve made it this far—we must be on the same page.”
But retirement changes the rhythm of everything:
- How you spend your time
- How much time you spend together
- How you define purpose, usefulness, and rest
And if you don’t talk about those shifts out loud, money becomes the stand-in for the real conversation.
“We can’t afford that.”
“We should wait.”
“That’s not responsible.”
Sometimes those statements are about dollars.
Often, they’re about expectations.
The conversation most couples skip
Here’s the conversation I wish more couples had before they retired:
“What does a good life actually look like for you—day to day?”
Not the big, glossy stuff.
The ordinary stuff.
- What does a perfect Tuesday look like?
- How much structure do you want… and how much freedom?
- What are you excited about doing together?
- What do you hope you still get to do on your own?
These aren’t financial questions.
But they are planning questions.
Because money can’t support a life you haven’t described.
The “grandkids” conversation most couples think they’ve had
This is one of the most common places I see quiet misalignment.
A couple will tell me,
“We want to be more involved in our grandkids’ lives.”
And both spouses genuinely agree.
But what they’re picturing isn’t always the same thing.
One spouse is imagining:
- Being at every game, recital, and school event
- Babysitting regularly—sometimes at the drop of a hat
- Structuring their week around the grandkids’ schedules
The other spouse is imagining:
- Being present and involved—but with flexibility
- Saying yes often, but not always
- Still protecting time for travel, rest, and spontaneity
Both love their grandkids deeply.
Both have good intentions.
But if those expectations aren’t talked about before retirement, money and calendars start carrying emotional weight they were never meant to hold.
Suddenly it’s not:
“Do we want to help?”
It’s:
“Who gets to decide how our time is used?”
And that can quietly erode joy in a season that was supposed to feel expansive.
Why this feels harder than it should
These conversations feel awkward because they brush up against identity.
Work has quietly answered a lot of questions for us:
- Who needs me
- Where I’m supposed to be
- What a “productive” day looks like
When that structure disappears, it can feel unsettling to admit:
- “I don’t really know what I want yet.”
- “I’m worried we’ll want different things.”
Those worries don’t mean something is wrong.
They mean you’re standing at a meaningful transition.
A few questions worth asking—gently
You don’t need a grand sit-down or a perfectly worded plan.
You just need curiosity.
Try starting with one or two of these:
- “What are you most looking forward to about this next season?”
- “What are you nervous about—even if it feels silly?”
- “What does being ‘involved’ with our grandkids actually look like to you?”
- “How much flexibility do we want to protect—for ourselves and for each other?”
- “What would you love to say yes to more often?”
Listen without fixing.
Resist the urge to reassure too quickly.
Let the answers surprise you.
This isn’t about agreement—it’s about awareness
You don’t need identical visions.
You need shared awareness.
When couples understand what matters to each other, financial decisions get easier:
- Trade-offs make more sense
- Compromises feel intentional
- Money becomes a tool instead of a tension point
That’s when planning works best—not because the math is perfect, but because it’s supporting a life you’re building together.
One last thought
If you and your spouse haven’t talked about retirement in this way yet, you’re not behind.
You’re right on time.
And this conversation doesn’t end in one sitting.
It unfolds—over walks, car rides, quiet evenings, and honest moments.
That’s what Money Talks is really about.
Starting the conversations that make everything else clearer.
Coming next in the Money Talks series
Loving Your Grandkids Without Losing Your Own Life
Because being deeply involved—and staying deeply connected to each other—both matter.