The Most Important Question I Ask My Aging Parents: When Are You Happiest?

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Last Updated on September 6, 2026 by Michelle

Yesterday, I had one of the best conversations I have had in a while.

It lasted about seven minutes.

My father-in-law was in hospital, and I had gone to visit him with my son. The hospital has a two-visitors-per-slot policy, so for that little window of time, it was just the three of us.

Before I went, I had already decided I wanted to ask him something.

Not about his test results.

Not about when he might be discharged.

Not even really about how he was feeling.

I wanted to ask him what I have come to think might be one of the most important questions we can ask the people we love:

When are you the happiest?

And then the slightly more uncomfortable second question:

How much time are you actually spending on the thing that makes you happiest?

I have asked versions of this question before.

A few years ago, I asked my own mother what made her happy. She answered almost immediately: volunteering.

Last year, when I visited my best friend’s mother because she wasn’t feeling well, I found myself asking her something similar.

And when I heard that my father-in-law was in hospital, I somehow knew I wanted to ask him too.

I like my father-in-law very much. He has always been an exceptionally kind and generous father-in-law to me.

So I asked.

What surprised me was how little time he needed to think.

He knew.

There was no long pause. No searching for a socially acceptable answer. He simply answered.

And that one question opened the door to a seven-minute conversation that I haven’t stopped thinking about since.

We Talked About Happiness, Then Somehow About Everything Else

Once he told me what made him happiest, I became curious about what his ordinary life actually looked like.

We talked about his days.

Was he sleeping enough? Was his sleep comfortable?

Was he eating well? Was he getting enough nutrition from his meals?

What did work mean to him?

What did money mean?

What about his friends?

It wasn’t an interview. I wasn’t working through a checklist.

One question simply led to another.

And then he told me something I didn’t know.

He has seven good friends from school.

For years, the seven of them met once a year.

Then around three years ago, the meetings stopped.

Not because they had fallen out.

They had started falling ill.

I felt strangely sad when he said that.

Perhaps because it was such a simple description of aging.

Seven boys become seven young men.

Then seven middle-aged men.

Then seven older men who still meet once a year because they have known each other for most of their lives.

And eventually the group becomes harder to assemble because bodies begin to fail.

I asked him why the meetings had to stop completely.

What if all seven couldn’t come?

Couldn’t three meet?

Or four?

Or even two?

It didn’t need to be the same annual gathering they had always had.

Perhaps the tradition could change instead of disappearing.

He agreed.

So now I know one thing I want to ask him the next time I see him.

Have you contacted your seven friends?

We Often Ask Older People About Their Health. Maybe We Should Ask More About Their Lives.

After coming home from the hospital, I told my own father about the conversation.

My dad smiled and said something along the lines of:

Your father-in-law must have had such a good time having that conversation with his eldest daughter-in-law.

That comment stayed with me.

Then I told my mother.

Her reaction was slightly different.

She said communication is so important, especially for elderly people.

And suddenly I found myself wondering:

When was the last time someone asked my father-in-law a question like that?

Not, Did you take your medication?

Not, What did the doctor say?

Not, Are you eating?

Not, Does anything hurt?

But:

When are you happiest?

What are you enjoying these days?

Who do you miss?

What do you look forward to?

What still excites you?

What do you want more of?

As our parents get older, I think it is incredibly easy for our conversations with them to become increasingly practical.

Doctors.

Medication.

Blood-test results.

Meals.

Insurance.

Mobility.

Appointments.

Whether they should be driving.

Whether somebody needs to accompany them somewhere.

All of those things matter.

But somewhere along the way, the person can become the patient.

And I don’t want that to happen.

Don’t Only Prepare for Their Decline. Design for the Life That Is Still Here.

I’ve been thinking quite a lot about aging parents recently, especially as my own mother approaches 80.

And I keep coming back to this idea.

When someone we love gets older, our instinct is often to protect them.

We think about what might go wrong.

Falls.

Illness.

Finances.

Dementia.

Care arrangements.

What happens if they can no longer live independently.

These are responsible questions.

But they are almost entirely about preventing bad things from happening.

What about helping good things continue to happen?

There is still a life being lived.

There are friendships.

There are things they enjoy.

There may be places they still want to visit.

People they still want to see.

Things they want to learn.

Food they want to eat.

People they want to help.

Stories they want to tell.

Things they are still looking forward to.

Maybe one of the kindest things we can do for aging parents isn’t merely to make their lives safer.

Maybe it is to remain interested in the life that is still ahead of them.

The Seven Friends Changed the Conversation for Me

I keep coming back to my father-in-law’s seven school friends.

Because there is something larger hidden in that small story.

When we’re younger, friendships happen almost automatically.

School gives us friends.

University gives us friends.

Work gives us colleagues.

Our children give us other parents.

Life keeps putting people in front of us.

As we get older, that infrastructure starts disappearing.

We retire.

Children grow up.

Mobility changes.

Friends become ill.

Someone’s spouse dies.

Driving becomes difficult.

Suddenly maintaining relationships requires much more intention.

And perhaps that’s exactly when they matter even more.

Longevity isn’t very meaningful if it is accompanied by increasing isolation.

Which is why next time I see my father-in-law, I don’t particularly want to ask only about his health.

I want to ask about the seven friends.

Maybe I will even encourage him again to organize something.

Not all seven.

Whoever can come.

Because perhaps aging well sometimes looks surprisingly ordinary.

Coffee with three old friends.

A familiar restaurant.

Talking about stories everybody else has heard a hundred times.

Laughing.

Going home.

Looking forward to the next one.

Work Came Up Too

There was another part of our conversation that made me think.

My father-in-law places a lot of importance on work.

To some extent, my own father does too.

And I see traces of this in my husband.

I will admit I don’t always like it.

I sometimes look at men of their generation — and occasionally the next generation too — and wonder whether work has occupied more of life than it deserves.

But perhaps that judgment is too simple.

Because work can mean very different things to different people.

It can mean money.

But it can also mean usefulness.

Identity.

Routine.

Respect.

Competence.

Social connection.

Being needed.

Purpose.

Perhaps the better question isn’t:

Why are you still working so much?

Perhaps it is:

What does work give you?

And then:

Could you get more of that somewhere else too?

I suspect this is a conversation I will continue having with the people I love — including my husband.

Not because work is bad.

I have spent more than two decades in a career that has given me enormous intellectual stimulation, opportunities and relationships.

But I increasingly believe work should serve a life.

The life should not quietly disappear in service of the work.

When Are You Happiest?

I’ve now asked some version of this question to my mother, my best friend’s mother and my father-in-law.

And I’ve noticed something.

People seem to know the answer much more quickly than I expect.

Maybe happiness is less mysterious than we make it.

Maybe somewhere inside us, most of us already know.

The harder question may actually be:

If you know what makes you happiest, why aren’t you doing more of it?

My mother’s answer years ago was volunteering.

I remember being struck by how quickly she answered.

It made me think about how much value human beings derive from being useful to others.

Now my father-in-law has given me another answer and another glimpse into what matters to him.

These conversations have started changing the way I think about aging.

I used to think about well aging mainly from the perspective of my own future.

How do I remain healthy?

How much money do I need?

What work will I do?

How do I keep learning?

What relationships do I want?

Who am I becoming?

Increasingly, I realise well aging is also relational.

It includes how we help the people we love continue to age as themselves.

Not simply keeping them alive.

Not simply keeping them safe.

Keeping them connected to the things that make them feel alive.

A Question That Belongs in BYORM

The BYORM Method has evolved as I’ve lived it.

Physical Vitality.

Financial Freedom.

Intellectual Growth.

Meaningful Connections.

Purposeful Reinvention.

And most recently, Anticipation.

The conversation with my father-in-law made me see Meaningful Connections and Anticipation slightly differently.

Maybe anticipation isn’t just something we should deliberately create for ourselves.

Perhaps we can help create it for the people we love too.

Something as small as:

Let’s meet your friends next month.

Let’s have lunch there again.

Let’s ask the grandchildren to come over.

Let’s plan that little trip.

Something ahead.

A reason to say:

I’m looking forward to that.

I’ve come to believe that a well-designed life has purpose behind you and anticipation ahead of you.

I don’t think that stops being true because someone turns 70 or 80 or 90.

Perhaps it becomes more important.

It Was Only Seven Minutes

Nothing dramatic happened in that hospital room.

I didn’t give my father-in-law profound advice.

We didn’t solve aging.

I asked him a question.

He answered.

And for seven minutes, we talked about his life.

Not his illness.

His life.

I am so glad I did.

Because one day there will be questions we wish we had asked the people we love.

Things we wish we had known.

Stories we wish we had heard.

And perhaps there will also be ordinary conversations that, for reasons we can’t know at the time, turn out to have been precious.

Yesterday’s seven minutes felt like that to me.

So there is one question I now find myself wanting to ask more often.

Not just of aging parents.

Of my husband.

My children.

My friends.

And myself.

When are you happiest?

Then perhaps the more important question:

How much of your life are you actually spending there?

And if the answer is not enough

maybe that tells us something worth listening to.

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