‘I Should Have Known Better’ Is the Most Dangerous Thought You Have, ‘Girls Gotta Eat’ Says

It seems the reeling of regret cranks itself up the older you get. Not because you’re doing worse—but because you’re doing more. More decisions with higher stakes. More people affected by your choices. More awareness of what you wish you’d done differently. And more pressure to act like you should’ve “known better by now.”

On a year-end episode of Girls Gotta Eat, hosts Ashley Hesseltine and Rayna Greenberg don’t treat regret like a character flaw or a motivational poster problem. They treat it like data: proof you’ve changed and outgrown an old version of yourself. They talk about the kind of regret that shows up as a constant mental replay—what the girls call a “micro-regret.” The photo you didn’t take. The thing you wish you said. The moment that felt too important to miss…and now you’re convinced you did.

‘Girls Gotta Eat’ Explains Why Regret Isn’t Failure—It’s Growth

But the point isn’t to pretend you don’t regret things. It’s to stop letting hindsight turn into self-attack. Because most regret isn’t evidence you failed—it’s evidence you have new information. 

Micro-regret vs. real regret

“I am plagued by what I would call micro regret,” Hesseltine explains. “This is the little stuff from, ‘I should have said this thing in our episode, or I should have made this joke on stage’ or little things that went wrong.” These aren’t mistakes anyone else notices. In fact, she’s clear that most of the moments she obsesses over are invisible to everyone but her. “Literally, there was not one thing that a guest would have thought went wrong,” she says about her wedding. “These are just things that I know and I beat myself up.”

What makes micro-regret so draining is that it disguises itself as responsibility or perfectionism. Hesseltine admits that being both “a perfectionist” and “really sentimental” makes it harder to let go—especially when the regret is tied to moments she believes she’ll “never get…again.” That sense of finality is what keeps the loop spinning.

The danger, she says, isn’t reflecting—it’s ruminating. “I feel like it was taking up space in my brain,” she admits, describing how these thoughts followed her even on her honeymoon. And that’s the key distinction the episode makes: real regret can guide future decisions. Micro-regret just consumes emotional bandwidth without offering anything useful in return.

The identity crash after success

“There was a point in 2025 where I was like, ‘if I really pull this off successfully…I will be so proud of myself and realize just what I’m capable of,’” Hesseltine says, referring to juggling a tour, shooting a special, planning her wedding, and running two companies at the same time. And she did pull it off. But the emotional aftermath surprised her.

“After the tour and the special and the wedding were over…I had this crash that I kind of thought, but I didn’t totally expect the magnitude of it,” she admits. What followed wasn’t burnout—it was disorientation. “It felt like a loss of identity because all I did for an entire year was plan the tour and shoot the special and plan the wedding. That was my focus…and then they both ended what felt like abruptly and I had this like, ‘who am I?”

The moment is important because it disrupts a common narrative: that achieving your biggest goals automatically brings peace. Instead, Hesseltine describes needing “about a month till [she] felt really back to normal,” even while feeling “pride” and “accomplished.” Both things existed at once.

What made the crash harder was how invisible it felt. On paper, nothing was wrong. But emotionally, the structure that had organized her days—and her sense of self—was suddenly gone. But the takeaway isn’t to avoid big goals. It’s to recognize that success can still leave emotional whiplash behind. And that needing time to recalibrate doesn’t mean you did anything wrong.

‘You didn’t make the wrong choice—you made the best choice with the info you had’

A recurring thread throughout the episode is the idea that regret often comes from judging past decisions with present-day awareness—a standard that no one could realistically meet. Greenberg returns to this again and again, especially when talking about career timing, relationships, and big life moves that didn’t unfold the way she once imagined.

Reflecting on why she didn’t pursue comedy sooner, she admits, “I beat myself up like, ‘Well, why didn’t you try doing comedy sooner? Why didn’t you try to get on stage before this?’” But instead of letting that spiral into self-blame, she reframes it. “Starting now is still starting,” she says plainly.

That same logic shows up when she talks about money and home ownership. Looking back on choices she’s now questioning, Greenberg doesn’t call them mistakes. She calls them decisions made in good faith. “You use the information that we had at the time to make those decisions,” she explains, adding that regret often just means “you’ve grown and you’ve got new information.”

“You can’t apply today’s literacy to yesterday’s version of yourself,” she explains. Use that as a reminder that hindsight isn’t wisdom—it’s context that simply didn’t exist yet.

Changing your mind is not instability

Changing your mind is not a personal failure. Repeat after us: Changing your mind is not a personal failure. Both hosts push back on the idea that consistency means sticking with every decision you’ve ever made—no matter how much you’ve changed. “It’s human,” Hesseltine states.

“I think of myself as a reliable, stable person,” Hesseltine says. “I really do, but I do be changing my mind.” She points out that she’s maintained long-term friendships, an eight-year business partnership, cancelling a major move, and a handling a demanding work schedule, all while still allowing herself to reassess major life choices.

Making a decision you later outgrow doesn’t mean you were reckless. You’re allowed to change cities. Change careers. Change goals. Change your mind. Doing so doesn’t erase your reliability—it proves you’re paying attention.

To listen to Hessletine and Greenberg’s full conversation, listen to Girls Gotta Eat wherever you get your podcasts.

Read More:

• Beyond the Mat’s Bryony Deery Has a January Reset Plan You Won’t Rage-Quit
• ‘Breaking Beauty’ Exposes the Everyday Habits That Are Quietly Sabotaging Your Skin
• Still Foggy? ‘The Skinny Confidential’ Says Your House Might Be the Problem