It was a very good meal. Our server brought out a birthday dessert. And sometime between my next sip of my cocktail inside of a real coconut, three-year-old River celebrated by sticking his finger directly in the candle flame.

This is, more or less, what it looks like when our family goes out to eat.

Will and I were in Chicago for spring break with our three kids, ages 11, 6, and 3. We ate together at Crying Tiger, Duck Duck Goat, and Monteverde — so three James Beard-nominated chefs in three days. We are opening a restaurant of our own back in Metro Detroit, so Crying Tiger and Duck Duck Goat technically qualified as research. Monteverde happened because I wanted to eat there forever and stalked OpenTable all week until a reservation opened up. Somehow, we made it through all three meals without handing any child an iPad, even despite River singeing his pointer finger.

This is not a flex. This is a learned skill. And the learning had less to do with logistics (the sticker books, the weird reservation times) and more to do with me unlearning what I thought I wanted from being a mom.

I grew up in a suburb outside of Detroit called Waterford, where Chili’s and Don Pablo’s made up the bulk of cultural dining experiences available to me. We ate a normal amount of dinners that came packaged in cardboard, though my dad wouldn’t ever let us go to the White Castle on the corner of our street. My mom said “raymond noodles” for years, and I don’t think anybody knew well enough to correct her. Nobody was taking me to interesting restaurants as a kid, partly because upscale restaurants didn’t really exist for families in the ‘90s like they do now, and partly because we just weren’t that kind of family.

I don’t say this with resentment. My parents gave me everything they had, and we ate well. But I noticed the gap. I read constantly and I dreamed about other places and other foods and just experiencing a different way of being. My mom worked on the suite level of our local stadium, so I regularly came in contact with people who, like, stayed at the Four Seasons and chartered private planes. I envied them so much. I think a lot of people who grew up middle class in the ‘90s in America know this feeling — the sense that there was a more interesting version of life happening somewhere else, and if you just worked hard enough, maybe you could get to it.

I don’t think I did it deliberately. But I did marry a chef. Will is Michelin-trained, and food became central to our lives in a way I never could have imagined as a kid. I married a good, kind, intelligent man who ALSO wanted to eat three separate dinners on our first real date out, who asked me to marry him and then took me to Au Cheval for burgers and bone marrow when I said yes. We understood each other, and we hungered for the same things. And it felt like a correction, or an opening, for how I wanted to live my life.

Our oldest, Amelia, my stepdaughter, grew up wandering around kitchens while Will was doing sales calls for his sausage company. Amelia has always been around restaurants. She eats almost everything. She’s 11 now and has opinions about service flow and table spacing. Even at 5, she was a great dining companion.

It was somewhere in between our wedding, with Amelia roaring like a lion in her little white bridesmaid dress and desserts by a James Beard-winning chef, and my first pregnancy, that I began to detail the fantasy. Not just that my kids would eat well, but that we would become a certain kind of family. I saw us at a table in Montmartre, my children in matching linen and chambray, the toddler eating cassoulet with a tiny spoon while Amelia commented on the umami notes of the amuse bouche. The baby’s first word might be fromage. We wouldn’t be rich, but we would be cultured. I would smugly tell other parents that “it’s just about the choices you make at home.”

Was I wrong to want it? Wanting better for your kids than what your parents could give you is about as American as it gets. But I can see now that what I was building wasn’t just a food life for my family. It was a food performance, starring the curated version of me.

Instagram and TikTok have made these fantasies more immersive, more commercial than ever. We’ve been conditioned to believe that if we live the fantasy beautifully enough, it will eventually pay out. But for me, the performance wasn’t about a revenue strategy. It was about social currency. A kindergartener eating uni isn’t just a child with a sophisticated palate; they are high-signal proof that the parent has Taste.

I was never going to start an Instagram account where my kids ate their way photogenically through Europe. But my fantasy came from the same place. I did want my children’s relationship to food to be nurtured and curated into a story that reflected back onto me, even if I never admitted it out loud. And their sophistication would be the evidence that I, that girl from Waterford, had finally made it.

And then we had Desi, and reality surfaced.

Desi is 6 now. His dinner menus pretty much consist of fruit, chicken fingers and pizza. When he came along, suddenly we were staring down a future of endless Sedona Taphouses. I wanted to scream. We’d built this whole identity as a food family, and here was this kid who wanted no part of it.

We blamed ourselves. He was born in January 2020. Once the pandemic hit, we were scrambling to pay the mortgage, to keep our businesses going. Will regretted not offering the baby enough vegetable purees. Des had eaten congee as a baby. Now he was terrified of rice. Amelia was such a good eater, so curious, that I figured I was the villain. Will had gotten things right with her, but I had failed Desmond. This trended nicely with my own postpartum depression.

As a mom who has now had two kids and a part in raising a third, my views on nature vs. nurture have shifted considerably. I have two kids who will happily gorge themselves on Peking duck and a third who eats exactly one kind of red meat — the microwaved hamburger patties in his daycare lunch.

The fantasy was always a lie.

Not because it was wrong to want it. But because no amount of curating was going to turn my beautiful, silly, stubborn, chicken-finger-loving Desi into a child who eats branzino.

I also want to be honest about the screens. When the kids were younger, I let them watch stuff on my phone at restaurants. A lot. I was overwhelmed, neither Will or I were sleeping, and sometimes I just needed to be a human and not a mom. I worried we’d created a demon spell we could never undo. Then at Monteverde the other week, we told the kids they could watch Creature Cases during the meal. They got distracted by crayons and forgot. That felt like a long way from where we came.

A big part of that, honestly, is just that they got older. That’s the part no one tells you when you’re in the middle of a screen-time shame spiral: sometimes the solution isn’t a better parenting strategy, it’s just more birthdays.

But I still remember the years when the phone felt like a life raft. Except every time I handed it over, I felt a familiar, heavy disappointment. I wasn’t disappointed in the kids — I was disappointed in myself, and in Will. I couldn’t see past the fantasy of the family I thought we were supposed to be, and I couldn’t stop tallying up all the ways we were coming up short. I was so busy mourning that “smug mom” version of us that I couldn’t see we were just a normal, tired family doing our best.

Once I finally looked past the fantasy, I realized my kids weren’t failing a test; they were just a toddler and a preschooler. And eventually, they simply grew into the kind of small people who, sometimes, prefer the crayons.

And I grew up too. Once I let go of the fantasy, I didn’t stop caring about restaurants. I stopped caring about what our family looked like in them.

And what was left, underneath all the aspiration and the curating, was the thing that was real all along: good restaurants are miraculous.

A great restaurant is the sum total of an entire team’s imagination and craft and perseverance, brought to life reservation by reservation, night after night. Eating at a great restaurant is like sitting courtside watching Jordan and Pippen run the triangle. You are watching people from all different walks of life operate together at the peak of what is possible. That wonder hasn’t changed just because my kid showed up in Paw Patrol shoes.

So we go. Not as the linen-clad fantasy family. As the actual one. And it turns out the actual one is delightful.

I know a lovely mom with kids, and she has never once taken her family to a restaurant nicer than pizza. They would never make it through a meal, she explained apologetically.

And I get it. I do. Taking small children to a good restaurant requires planning and patience and a willingness to leave early if it’s not working. It’s not relaxing, not in the way dining out used to be, and many (most?) moms already feel like they’re doing more than their share and life is hard enough. But I think there’s something underneath that statement that’s worth examining: a resignation that kids don’t have the capacity to appreciate vibe and quality. That once you become a parent, you’ve traded in good restaurants for Hot & Readys until they’re 12.

I disagree. Not because I’m a better parent (I’m not, and we eat a lot of Hot & Readys), but because I’ve seen how my kids respond as we keep choosing places that take food seriously.

At breakfast at Manny’s Deli in Chicago, the staff brought over steaming bowls of broth with matzo balls as big as River’s fists. Amelia loved the noodle kugel, and when we told her that Grandma makes it too, because she grew up in a Manhattan neighborhood that was half Chinese and half Jewish, Amelia wanted to know how that happened.

We started talking about how the Chinatowns where her great-grandparents lived were formed; how families were shut out of wealthier neighborhoods and restricted in where they could live or work. Amelia was flipping through the Reader, but when I told her the word “ghetto” came from the neighborhood in Venice where Jewish people were once forced to live, she looked up.

“I know that word,” she said. “I didn’t know that was where it came from.”

Then Will explained that places like Manny’s started as gathering spots for Jewish people, but they served everybody — how food brought people together who wouldn’t normally be in the same room. As we were finishing, the fourth-generation owner, Dan Raskin, came over to say hi. Will calls Dan a “real operator,” his highest compliment in the food business. When food benefits were frozen during last fall's shutdown, Dan fed anybody who came in with a SNAP card, for free.

That’s what a restaurant can be. And that’s a big part of why we haul our kids to these places. Because that conversation doesn’t unfold the same way over a Happy Meal.

At the table, we talk a lot about how restaurants work — the flow, the service, the wallpaper. The kids have things to say. River, who is always the three-est, points to things and shouts that they are “BOOTIFUL!” Amelia is motivated by design. She swooned over the giant tiger portrait at Crying Tiger and pouted at Duck Duck Goat because there was wood paneling on the bathroom walls — “why does it look like a sauna in here?” Desmond, when asked what kind of restaurant he would open, says “pizza dinosaur fire restaurant.” It’s a winning concept.

Does it always work out? Nope. We built an entire trip to Charleston last summer around a visit to a famous chef’s restaurant, but the dining room was hotter than hell and we couldn’t beat back the flies. The kids were grossed out. We left half the food on the table and walked out before dessert. I was crushed. We had road-tripped 12 hours each way for inspiration, not flies and 90% humidity.

But then we drove to Savannah to a restaurant called Brochu’s Family Tradition. We ate grilled oysters with a half-dozen dressings and chicken livers on toast, but also incredible fried chicken. It’s the kind of place where the person who wants to spend $30 and the person who wants to spend $300 both get what they need. It’s hard to thread that needle, to build a place that’s welcoming to its neighbors and still ambitious about what they want to do. Brochu’s did it.

We met Andrew Brochu, who came out of Alinea in Chicago but settled in Savannah with his wife, Sophie. They opened the restaurant and they have a young daughter and they are making it work. The staff has mostly been there since day one. You could feel how happy they were to be a part of it. It was a perfect meal. And after dinner, while Andrew took Will on a tour of the kitchen, I sat at the table and let the kids watch a little Moana.

So we didn’t end up being the stylish, globe-trotting family of my dreams. I have spent the last month trying to convince Desi that if he can just manage to eat one tortilla, I will take him to Mexico to swim in a cave full of bats. He loves bats. He is currently weighing the culinary risk of trying a new food against the reward of a cavernous mammal encounter. It’s a stalemate.

There are a lot of good reasons I can invent to take my kids to nice restaurants. But I also don’t mind saying that I am selfish. I do a lot for my kids, and it is okay to ask them to do something for their dad and for me. And this is what I chose. The second glass of Ligurian white wine that tastes like lemon oil and sunshine lapping on the waves. This is my extravagance, over the bags, the Botox, and everything else I am supposed to want.

Because at the end of the day, I am still that girl in Waterford, sleeping in a bed full of her books, dreaming about the places she’d never been and plotting how to get to them.

She got that life. It just doesn’t look exactly the way she pictured. It looks like a three-year-old in Paw Patrol shoes, preparing to stick his chubby little finger in a candle at one of the best restaurants in Chicago, while his mother sips a cocktail from a coconut and thinks: this is better than the fantasy. This is real.

All black. Eyeliner. Cheetah print fake fur coat. The kind of outfit I would have worn in 2006 without thinking twice. Ready for a cigarette, some loud guitars and a night at Comet Bar or the Old Miami. And you know what? I still looked fucking fabulous, even at 41.

It made me think about who I was when I used to wear that coat. Much younger, bolder, more reckless. And it made me think about everything that’s happened between then and now. Specifically, the startup I built, the one I lost, and everything it taught me.

Detour Detroit was a community-first digital news organization I founded in 2017. I left a big corporate job at one of the most respected newsrooms in Michigan to do it. People thought I was an idiot. Honestly, they were mostly right. But I did it anyway, because I believed there was a better way to do local journalism—one that actually listened to people. And I also don’t like being told what to do.

Both Detour Detroit and I failed to survive in our original form. Detour merged with the fine folks at Outlier Media. A year later, I stepped away. I became a mom. I stopped wearing cheetah print anything. And for a long time, I lived in the space between pride and grief, trying to figure out what went wrong, what went right, and what any of it meant.

Here’s what I’ve landed on.

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What I Got Wrong

1. I thought I had to build alone before I could ask for help.

There’s this mythology in startup culture that you should be building in your garage, heads down, humble, grinding away until someone notices. I believed it. I kept thinking: I’ll build it bigger, I’ll build it better, and then I’ll figure out what to do with it.

But if you’re doing something big, you can’t spend a long time being small and then suddenly change. I built community. I built a team. Those were real. But I didn’t cultivate people who could truly support me — people with the means and experience and knowledge to help build something different.

I didn’t know I could ask. I figured if someone had something to offer, they’d come to me. The reality is that people are extremely busy and nobody is ever going to do that. You have to ask, and ask again. And I was afraid to ask. It was easier to put my head down and grind than to put my head up, look them in the eye, and tell them I was worth their investment.

I’m not as afraid anymore. Or rather, I’m not afraid of being afraid. That’s one of the gifts that came out of this. More below.

2. My business plan didn’t account for the fact that I was a human being.

My business plan for Detour Detroit could have been boiled down into one sentence:

I can work myself into the ground!

That was what I’d always done. So I built around that assumption.

I didn’t fundraise. I didn’t have savings. I worked on Detour and consulted on the side, and once I had a kid, daycare cost as much as I was paying myself, so I was essentially working for free. The math only worked if I never stopped.

And then, frustratingly, I couldn’t stop being a person. Postpartum depression. A child’s developmental challenges. Moving to the suburbs to live near my stepdaughter’s school and feeling like I’d lost my authority to engage with the city I built for.

None of that should have been fatal. But I’d built something that required me to be superhuman every single day, and when I wasn’t, there was nothing underneath to catch it. I could have gone slower. I could have found partners earlier. I could have built a structure that didn’t collapse the moment I needed to be a person and not just a founder.

3. The people who celebrated me on stage wouldn’t fund me or invite me into the room.

This one burns, and it’s not unique to me. Many organizations and funders will put you on a panel. They’ll invite you to speak about how you’re changing journalism. They’ll use your story to show the world that innovation is happening.

But when it’s time to actually invest? They fund scale and institutions, not risk-takers. Not experiments. Not you.

If I could go back, I would have spent less time performing innovation and writing proposals for people who were never going to back me, and more time finding and engaging the people who actually would. Don’t waste your energy or pin your strategy on people who will co-opt your narrative to suit their own needs but won’t stand with you when you actually need them.

I could go on for a lot longer about this, but you are readers, not therapists.

4. I didn’t understand that business knowledge is creative power.

When I was younger, I thought business and creativity were opposing forces. I was an English major. Capitalistic values were, in a word, garbage. And I didn’t see how understanding equity structures, compensation models, or organizational design could possibly serve my values.

I was wrong.

I never made Detour Detroit a nonprofit. I said I didn’t want to give up control. In reality, I didn’t understand governance. I didn’t know what a board was for or how it could help me. That left me isolated. It signaled to funders I wasn’t serious. And it meant I forked over a percentage of crucial revenue to fiscal sponsors who were only there to collect checks, not help me grow. I thought taking the time to build a professional structure would slow me down. In reality, it hobbled my growth potential.

Business can be profoundly creative. When you understand how things work, you can build structures, teams and systems that reflect your values and your vision instead of just hoping those feelings will be enough to get you through the hard times. It also builds trust with your team — you’re not talking the talk, you’re walking the walk.

Your values are the compass. Business knowledge is how you build the path forward.

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What I’d Do Again

1. I built community before the field had language for why it mattered.

In 2017, building a community-first news organization was a radical idea. We wrote stories, we made product decisions, we tried things — all because we listened to the people we served. We made them feel like they mattered. We involved them.

I talked to a publisher in Louisiana recently who told me Detour was a blueprint for what they built. It’s a fact I’m finally allowing myself to own. I have gone back and forth on cutting this section like three times, which shows you HOW HARD it still is for me to do this.

The lesson anyone can take: find your true believers. Build for them. Listen to them. If you do it that way, no matter what happens to the company, you’ll be at peace with the work. It’s slower going, but it’s the right way. And it leaves you whole.

(For another post: why have I internalized that arrogance is the worst thing for a woman to demonstrate?)

2. I became someone who experiments.

Detour wasn’t just one thing we tried. It was dozens of experiments, hundreds of small bets, a constant practice of surfacing ideas, investigating risk and acting anyway. And that practice changed who I am.

Now, when my husband and I tell people we’re opening a restaurant, they say it’s risky. (Yes, we are aware that restaurants fail, thank you for your advice!) Then they talk to us and they see the calculations, the plans behind the dream.

Risk doesn’t have to be as scary once you’ve developed the muscle and the practice to work within it. Risk doesn’t have to be terrifying if you build with intention. It’s actually addicting.

3. I chose my family when I needed to, and now I get to try again.

When I started Detour, I had a little gold necklace that said #girlboss. I wore it like armor. The girlboss narrative says you push through everything, you never stop, you sacrifice everything for the vision and that’s what makes you strong. And when I began falling apart, I thought I wasn’t good enough instead of realizing how incomplete and false it all was.

The #girlboss narrative has no room for ambiguity. It only celebrates the grind. It doesn’t make space for the woman who walks away from the thing she built because her kids need her and she’s crumbling.

When I decided to walk away from Detour, that’s exactly who I was. I needed to focus on my kids. I needed to stop keeping an organization alive and start keeping myself alive. That was the right call. But I was terrified that people would think I was a failure.

I don't need to be a girlboss anymore. I don't want my kids growing up believing their worth is tied to how hard they work or what they produce. I want them to see that it’s okay to listen to their own needs, that their overall happiness matters more than what other people think, more than living up to some narrative, more than what their LinkedIn bio will say.

And now, my kids are older. I’m stronger. More durable. More ready. And I get to show them something I couldn’t show them before: that it’s a back and forth. Your identity, your needs, your future — none of it is fixed. Sometimes you withdraw and protect yourself. And sometimes you step back out into the ring for another shot.

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The Cheetah Coat

Here’s what nobody tells you about the worst-case scenario: once you’ve actually lived through it, once you know what real loss feels like, you understand something that changes everything.

It’s just not that bad.

The failure of my first company was not the end of my story. It was the beginning of knowing who I am.

And that cheetah coat? It still fits. And that coat is why I'm writing. Because to write and publish out loud is to rebuild the muscles of courage and ownership and out-loud experimentation that I let atrophy these past years.

I want to be Cheetah Print Ashley again, not Dead Mommy Ashley withering away in silence.

Let’s go.