The Day Your Kids Stop Asking

One of the quiet milestones of life is the day your kids stop asking for advice.

It sneaks up on you like a thief in the night.

For years, you were the designated problem solver. The one with the answers, or at least a valued (and sometimes unsolicited) opinion. The person who helped narrow down the decision on which college to attend. A trusted advisor on how to set up a monthly budget. The one they called when the faucet was leaking (in truth, that was never me). And the one they took with them to the dealership to negotiate for that first automobile.

Then time does what time always does. Your kids grow up.

Careers accelerate. Relationships deepen. Life becomes more complicated, more independent, and often, more remote. Slowly, without ceremony, the questions and the requests for counsel fade.

Not completely. But enough that you notice the difference.

For me, I didn’t grasp what was happening until I retired from my career. One day, I realized that the phone didn’t ring with questions about work from former colleagues. And come to think about it, my kids weren’t calling for advice any longer, either.

The shift doesn’t mean your kids love you less.

It simply means they no longer need you the same way.

And if I am honest with you, that recognition can feel a little disorienting.

Retirement Has a Companion on the Homefront

When I retired, I expected my professional identity to change. That is an essential element of retirement. You walk away from one identity and into a new one, or an open road, or a sunset. But you don’t walk away from purpose and value. You still have something to contribute. At least you think you do.

For a while, the phone still rang as I sat in my home office. Former colleagues would call with a quick question about a client or a process. Occasionally, someone needed my advice or perspective. Then those calls began to change.

“I need something” slowly turned into “Just checking in.”

Eventually, even those calls faded away.

Like a constantly flowing river, work moves forward on down the stream to new destinations. New people step into your role. The system adjusts. And you are standing on the riverbank watching it all flow by as if you were never there. That’s the natural rhythm of retirement from work and career.

What I didn’t fully anticipate was that something similar was happening in my role as a father.

My sons had grown into their own lives.

They no longer needed rides to practice or help with homework. They had navigated college applications, built careers, purchased cars and homes, and formed their own relationships.

My old version of fatherhood had also retired.

The difference is that I didn’t get to make the decision.

There was no paperwork to file. And definitely no retirement party.

Yes, the phone still rings. Or the text chimes. Or the FaceTime call lights up my day.

But the conversations are different now.

The Conversations That Never Happened

Thinking about this shift in my role and identity as a father brought back a set of difficult memories that have stayed with me for years.

During the final four years of my father’s life, he was bedridden in his home. A lifetime of work as a physician and healthcare leader had come to an abrupt, difficult end. The man who had spent decades leading institutions and caring for patients now depended on others for nearly everything.

I visited him regularly during those years.

I did my best to engage him in conversation. He did not want to talk much. Loss of purpose, value, and personal dignity had settled over him like a dark cloud. I can see it now as a form of depression.

We talked about familiar things. Family updates, sports, and occasional news stories.

Safe conversations, albeit ones without much meat on the bones.

But there was something I didn’t do.

I never really asked him how he was doing.

I don't mean the basic “How are you feeling today?” question.

I never asked the deeper ones.

What was it like for him to look back on his life? What did he believe mattered most now? What surprised him about getting older? What advice might he offer to someone who was still running through the middle of their career?

I had the opportunity to ask those questions.

But I didn’t.

Maybe I didn’t have the courage. Maybe I didn’t want to hear answers that would force me to confront my own future. Or maybe I simply didn’t realize how valuable those conversations could have been until it was too late. Or maybe, deep down, and this one stings now, I had mentally filed the retirement paperwork for him and figured he was “retired” from fatherly counsel, and I knew everything I needed from him.

Whatever the reason, those questions remain unasked. And I wish now, no, I see more clearly now, that he probably had a lot more to share with me if I had only summoned up the courage to ask.

The Advice That Didn’t Age Well

There was one moment I can recall when my role as the wise, experienced father took a fairly public hit. I should have realized it was time to take a knee, but I wasn’t ready to take off the uniform yet.

My oldest son was in his final year of college and beginning his job search. Like many parents who spent decades in the working world, I was more than ready to share my wisdom. Whether it was requested or not.

One evening, he asked my opinion about two opportunities he was considering.

The first was a traditional entry-level sales role with Xerox. I knew that world well. I lived it for over a decade. Xerox had built generations of sales professionals, me included. It was structured, disciplined, and a place where you could learn how to sell the right way.

The second opportunity was something very different. A small company that was trying to sell online menu services to local restaurants. At the time, the concept sounded a little speculative. Four years of college tuition, and he was going to knock on doors, carrying an iPad and selling menu services?

So, I gave him the kind of advice fathers have been giving their sons for generations.

Play it safe.

Go with the established company. Learn the fundamentals. Build a solid foundation.

You can probably guess where this story is going. He took my advice and joined Xerox.

The little company selling online menus?

A couple of years later, it was acquired by Yelp. Each employee who held early ownership stakes reportedly walked away with more than a million dollars.

My son still likes to remind me of that story from time to time.

Usually with a smile.

And also, with a question about the “wisdom” of my starting up a career coaching business.

Learning a New Kind of Fatherhood

That moment didn’t end my role as a father.

But it did quietly adjust, or solidify, my new position, lower on the organizational chart.

From that point forward, my advice was received with just a little more skepticism.

And honestly, that was probably healthy.

If we are fortunate enough, our children eventually reach the stage where their instincts, networks, and experiences are just as relevant as ours. Sometimes even more so.

Looking back, that story makes me smile.

Not because I gave perfect advice. Clearly, I didn’t.

But because it reminds me that one of the goals of parenting is raising children who are capable of making decisions on their own, even when their father might lean in a different direction.

These days, I try to approach our conversations a little differently.

Less instruction. More curiosity. Big ears and a little mouth.

The Opportunity in Front of Us

Looking back now, I sometimes think about those conversations I never had with my father.

I wish that they wouldn’t have been limited to only light, friendly, and safe topics.

They could have been about perspective.

About the long view of life.

About the things that matter once the scoreboard stops keeping score.

That understanding has stayed with me as I have moved further into retirement and into this new phase of fatherhood with my own sons. I want the conversations to be different now.

They could be deeper.

If we allow them to be.

One Final Thought

Yes, I wish I had asked my father more questions.

But time is a good teacher and retirement has a way of offering a second chance.

My sons may not need me the way they once did. The role of problem solver has faded, and the instinct to jump in with answers is one I’m still learning to quiet. What’s emerging in its place is something different.

Less about direction. More about presence.

Less about advice. More about listening.

I’m learning that being a father at this stage isn’t about being right.

It’s about being there.

Without judgment. Without urgency. Without needing to fix what doesn’t need fixing.

Just being there. Trusting that, when it matters, the conversation will find its way.

And maybe that’s enough for now.

This post is Part 2 of a three-part series on retirement and adult children. Part 1 reflects on how fatherhood quietly changes when the noise of youth sports, carpools, and busy schedules fades. You can read the Part 1 post here: When Fatherhood Quietly Changes.

Dan Troup is The Sunny Side of 57. He loves to reflect and write about life, family, career, and retirement. Check out more of his reflections on his blog site. Also, consider subscribing to The Sunny Side of 57. When not playing pickleball or hiking with Sue and Rigby, he aspires to write a new post at least once a month.