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ESSAY

No Longer Part of the Club

The right decision can still carry real loss.

Chris Herring
Chris Herring
Entrepreneur • Husband • Father • Med Spouse
Co-Founder, Other Side Med
Caregiving

Six months ago, I walked away from a career I spent more than a decade building.

In the last few years of my career, I served on senior and executive leadership teams. I was leading, building, creating, traveling, speaking, and solving complex problems alongside incredibly talented people. My work challenged me. People knew what I was capable of and valued my contributions.

Then I left everything to become a stay-at-home dad.

It was the right decision for our family. I believe that as much today as I did when I made it.

But six months into this transition, I’m beginning to understand what it cost me.

When things are hard, my natural instinct is to grit my teeth, do whatever needs to be done, not complain, and keep moving forward. But internally, I knew this would be hard, even if I didn’t yet have the words to explain why.

However, I think I’m starting to put my finger on it….

I miss being part of the club.

The Club

For more than a decade, I belonged to a world of high achievers, entrepreneurs, executives, innovators, and talented leaders.

I was surrounded by people building things, taking risks, solving difficult problems, and pushing one another to think bigger. Some of my closest friends are wildly successful entrepreneurs. And when I see what they are creating, I feel inspired by them. I’m proud of them. I know how hard it is to do what they’re doing.

But what I’m feeling isn’t jealousy…. It’s more like watching people you love play a game you used to be really good at and realizing you’re no longer on the field…or even in the dugout.

And that’s when it hit me… Damn. I’m out of the clubhouse, and I really miss that.

I miss being challenged at that level. I miss the energy of building something. I miss traveling and speaking. I miss the adult friendships and professional relationships. I miss being recognized for what I could do. I miss being known.

When I left my career, it felt like the club shut its doors behind me. And that’s been harder to accept than I expected.

The decision I would make again

I want to be very clear about something: I am not bitter towards Hannah.

I don’t resent that she still gets to work. I don’t wish she had stayed home so I could keep pursuing my career. I don’t believe caregiving is inherently a woman’s responsibility or that our roles should be reversed simply because I’m the husband and she’s the wife.

Hannah spent 13 years training to become the physician she is today. She’s exceptionally good at what she does, and she’s making a meaningful difference in the lives of women in our community. I love watching her succeed, and I will always cheer her on.

She’s also a wonderful mom.

So hear me when I say this… I don’t want anything I share about the weight of being home to diminish how present, loving, and engaged she is with our boys. She acknowledges what I do, celebrates it, and regularly reminds me that my work at home matters.

So this is not a story about a husband carrying everything while his wife pursues her career. It’s a story about two parents making the best decision they can for their family, and one of those parents feeling that the right decision still comes with a sense of loss.

The right decision can still come with a sense of loss.

The work matters

Since I came home, our boys have been thriving.

Emmett is learning, growing, and developing into an incredible little boy. I get more time with him than most dads ever will. I know his routines, his imagination, his questions, his fears, and the funny little things he says throughout the day. I’m helping shape his character, not only during the significant moments but through thousands of ordinary ones.

Oliver is getting stronger. He makes it to his appointments and therapies. His medications are given, his feeds are managed, and his needs are met. His growth may happen little by little, but little by little matters enormously in his life.

I know that what I’m doing is important. There may be no work I ever do that matters more than this.

People say these years are short and that time is fleeting. They say that one day, I’ll miss hearing their feet in the hallway and being needed for every snack, every diaper, every toy, every problem, and every reassurance. But knowing something is important doesn’t automatically make it easy.

Meaningful work can still be exhausting. Sacred work can still feel invisible. And being grateful for this time doesn’t eliminate every other part of who I am.

The invisible work of being home

At work, achievement was visible.

There were goals, numbers, titles, promotions, financial incentives, conversations, recognition, and results. I could point to something and say, “I built that. I solved that. I made that happen.”

At home, the work resets every morning.

The kitchen gets cleaned and then becomes dirty again. The toys get put away and then pulled back out. Everyone gets fed, dressed, transported, comforted, entertained, and kept alive, and then we wake up and do it again.

There is no applause when both boys make it through the day with their needs met. No promotion arrives because I handled multiple therapy appointments, a feeding complication, a toddler meltdown, and dinner without everything falling apart.

Most days, no one even sees it.

I love my boys more than I could ever put into words. But I’m also tired.

Where do I belong now?

The isolation has surprised me.

I have no real group of local friends to spend time with during the day. I can go for hours and even days without meaningful adult interaction. Most of my conversations take place at a three-year-old’s level.

Going to the park as the only dad among a group of moms can feel awkward. No one is doing anything wrong, but I’m aware that I don’t fit the traditional norm. I’m not naturally part of that community, yet I’m no longer part of the professional community that shaped my adult life either.

I’m out of my club, remember? And I don’t belong to Hannah’s club either.

Medicine has its own language, culture, hierarchy, and shared experiences. Hannah earned her place in that world through years of sacrifice. Her peers are physicians who have done the same. And yes, whether they realize it or not, they have their own club.

Previously, I entered those rooms with my own professional identity. My work was different from theirs, but it was still understood as significant. People were interested in what I was building. There was a sense that we were equals, just in different fields.

Now, I’m the stay-at-home dad.

That title should carry enormous dignity. I believe that intellectually, but society doesn’t really treat it that way, and if I’m honest, I don’t always feel proud of it either.

When someone meets me today, they have no idea of my past life. They don’t know what I built, how much responsibility I carried, or the level at which I operated. They just hear that I’m a stay-at-home dad, and their responses are all the same: “Oh, interesting, that’s different.”

I’d like to say I don’t care what anyone thinks. Most of the time, I don’t. But being misunderstood does seem to affect me after a while.

And I think the subtle judgments hit Hannah and me simultaneously. Hannah gets judged for continuing to work. I get judged for being the one who doesn’t. She can be made to feel like she isn’t sacrificing enough for our children, and I can be made to feel like I’m not contributing enough to our family.

It’s a lose-lose situation built on expectations neither of us chose.

When your contributions change

This isn’t about money.

We are incredibly grateful that we can make this decision and still provide for our family. We know that many families need two incomes and don’t have the option for either parent to step away.

But we also live in a world where professional success and high incomes are normal. For years, I contributed meaningfully to that part of our lives. Not doing so anymore has been harder on me than I expected.

“Money isn’t the measure of a person’s value.” I believe that completely. But income was one visible expression of my ability to build, lead, and contribute. Losing it didn’t just change our bank account; it changed how I experience my place within our family and the world around me.

And there is a professional fear beneath all of this that I can’t ignore.

Leaving tech at this moment may have been career suicide.

AI is transforming the industry at an astonishing pace. Six months outside of that world can feel like years. If the day comes when I’m ready or able to return, I don’t know what opportunities will be there because of how fast things have changed at the executive level, and whether people will view the time I spent caring for my sons as meaningful or merely as a gap on my CV.

Truthfully, I may have walked away from a door that will be impossible to reopen and a club I’ll never be able to rejoin.

That thought scares me.

Not because I regret choosing my family, but because I still believe I have a lot to contribute outside our home.

I don’t have the lesson yet

I would love to end this with a clean resolution.

I’d love to say I’ve completely surrendered my ego, embraced this season, and stopped caring whether anyone recognizes what I do.

But that wouldn’t be true.

I’m only six months in, and I’m still learning how to receive my sons’ growth as evidence of meaningful work. I’m still learning how to value contributions that no one else sees. I’m still trying to separate my identity from my title, income, accomplishments, and proximity to other successful people.

And I’m asking God to show me where this struggle is about legitimate loss and where it’s about pride.

I don’t want to spend these fleeting years obsessing over the room I’m no longer in. I want to become more present in the one I’ve been given.

I don’t want to spend these fleeting years obsessing over the room I’m no longer in. I want to become more present in the one I’ve been given.

That doesn’t mean I have to stop missing my career. It doesn’t mean my ambition has disappeared or that I’ll never build something again. It doesn’t require me to pretend every day at home is fulfilling.

It simply means I’m trying to hold all of this honestly.

I love Hannah, and I’m proud of the physician, mother, and wife she is.

I love my boys, and I know the time I’m giving them matters.

I believe we made the right decision.

I miss my old life, but I’m trying to be content in the here and now.

I don’t know what the future will bring.

And six months into this transition, all of those things remain true.

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