When was the last time you intentionally tried to screw something up?
For someone like me—a resolute perfectionist and overthinker—the answer would be never.
Not once in my life have I deliberately set out to do something, fully aware there was no hope of it going well. In fact, I do the exact opposite. I plan and plan and plan some more, meticulously preparing for the task at hand, clinging to the hope that I might—if everything aligns perfectly—succeed gracefully.
Perfectionism is often about control, and control is often about fear.
But let’s be honest: this is no way to live, right?
Let me tell you a story:
This past weekend, I was invited to a dinner party. I was excited for the party's theme: everyone had to bring a dish from a cookbook written by a Philly chef. But as much as I was looking forward to the gathering, I couldn’t help feeling a bit apprehensive. I’m not used to cooking for other people.
Just a few weeks ago, I found myself eating tuna straight out of the can like some spoiled house cat, wondering how on earth my life had declined to the point where I, at 28 years old, lacked even the willpower to dump the tuna into a bowl first. And now, against my better judgment, I was expected to cook a dish for ten people. Lord help me.
I decided to choose Dinner at the Club by Joey Baldino and Adam Erace—a cookbook featuring Italian recipes from the 100-year-old Palizzi Social Club in South Philly. There was no way I could screw up Italian food, right? Right?
Two days later, the cookbook arrived. I eagerly opened it, only to realize I was in way over my head. Every recipe seemed to include a food that I had never attempted to make before. Tomato and cinnamon-braised tripe. Spaghetti and crabs. Braised rabbit. Chinotto ribs. Whole roasted suckling pig.
As I flipped through the pages, a sense of mounting panic crept in. I slammed the book shut. What the hell is tripe, anyway?
After some deliberation, I settled on one of the simpler recipes in the book: stuffed peppers. It seemed straightforward enough. But after reading through the recipe, I realized it was going to be a two-day process. The first day would involve making the meat ragu, and the second day would be all about assembling and baking the peppers.
I prepared accordingly. On Friday evening, I diligently gathered the ingredients and made the ragu. So far, so good. But Saturday was shaping up to be a whirlwind. I had plans in the morning, and then I’d need to race home, run to the supermarket, and somehow cook the stuffed peppers in time for the dinner party that night.
To keep this story concise, here’s a timeline of how Saturday afternoon unfolded:
2:30 PM – I’m making great time. Off to the supermarket! Woohoo!
3:30 PM – Back from the store. Let’s get cooking!
4:00 PM – Is this pot big enough for all the rice I need to make?
4:30 PM – Dang, this rice is taking forever to cook…
5:00 PM – I’m behind schedule, but it’s fine. Don’t panic. Don’t panic.
5:15 PM – Where the hell is my cheese grater?!
5:30 PM – Why is this cheese so impossible to grate?!
5:40 PM – SHIT. I forgot to core the peppers.
5:50 PM – Get stuffed, peppers!
5:55 PM – Oh no. These peppers are too fat for the pan. I can’t fit them in the oven!
5:56 PM – WAIT—where’s my ceramic baking dish? That’ll work!
5:58 PM – FOUND IT!!!! A MIRACLE!!!! GO, GO, GO, GO, GO!!!!
6:00 PM – YOU EVIL, EVIL PEPPERS—GET IN THE OVEN NOW!
The recipe called for the peppers to bake for an hour and 15 minutes, but I only had 40 minutes before I had to leave. So, I cranked up the oven and hoped for the best.
If you had tracked my heart rate and blood pressure during that final hour, you might have assumed I was in some kind of hostage situation.
And, in a way, I was. The perfectionist in me had taken my entire nervous system hostage, demanding that I produce a flawless dish. But the moment things started to go awry, hysteria set in, and I almost threw in the towel altogether. Honestly, if I hadn’t found that ceramic baking dish, I’m not sure what I would’ve done.
But it’s all so ridiculous, isn’t it? To get so worked up over something that’s supposed to be fun?
Which brings me back to my original question.
When was the last time you did something hoping to mess it up—hoping to fail—just for the sake of trying something new and different and exciting?
For some people, I imagine this might come easily. We all have those friends who seem to float through life effortlessly, without putting too much pressure on themselves, without letting their insecurities or inner voices hold them back from whatever they set out to do.
But if you’re like me—someone who struggles to make everything perfect—it can actually be helpful to do the opposite: to fail on purpose. When your default definition of success is perfection, you’re setting yourself up for failure anyway. It becomes inevitable. So why not lean into it?
Put another way: if I had approached this process with the goal of making stuffed peppers, rather than perfect stuffed peppers, I might have been able to enjoy myself a lot more.
What’s interesting is that, during this two-day ordeal of making these peppers, I happened to be reading The Old Man and the Sea by Ernest Hemingway. For those unfamiliar, it’s about a man alone at sea in a small boat, struggling to haul in a massive marlin he’s caught. I won’t spoil the ending, but the story is really about perseverance—about seeing a task through to the end, no matter how many challenges arise along the way.
It’s almost absurd to admit, but I think that if I hadn’t been reading that book earlier in the day, I might have completely given up when I realized the peppers weren’t going to turn out the way I’d envisioned.
I arrived at the party on Saturday evening, peppers in hand, and ended up having an amazing time with wonderful company. Everyone told me the peppers were great—which, honestly, was hard for me to believe. But what I believe isn’t the point. The point is that I showed up with my dumb stuffed peppers in the first place.
So now, when I set out to do something new or unfamiliar, I won’t ask myself how I can make it perfect—or even good. Instead, I’ll ask myself how I can take the pressure off, how I can fail on purpose, with all the delight and freedom that imperfection brings.
It’s not about taking a perfect step in the right direction. It’s about taking any step at all.
When was the last time you intentionally tried to screw something up?
For someone like me—a resolute perfectionist and overthinker—the answer would be never.
Not once in my life have I deliberately set out to do something, fully aware there was no hope of it going well. In fact, I do the exact opposite. I plan and plan and plan some more, meticulously preparing for the task at hand, clinging to the hope that I might—if everything aligns perfectly—succeed gracefully.
Perfectionism is often about control, and control is often about fear.
But let’s be honest: this is no way to live, right?
Let me tell you a story:
This past weekend, I was invited to a dinner party. I was excited for the party's theme: everyone had to bring a dish from a cookbook written by a Philly chef. But as much as I was looking forward to the gathering, I couldn’t help feeling a bit apprehensive. I’m not used to cooking for other people.
Just a few weeks ago, I found myself eating tuna straight out of the can like some spoiled house cat, wondering how on earth my life had declined to the point where I, at 28 years old, lacked even the willpower to dump the tuna into a bowl first. And now, against my better judgment, I was expected to cook a dish for ten people. Lord help me.
I decided to choose Dinner at the Club by Joey Baldino and Adam Erace—a cookbook featuring Italian recipes from the 100-year-old Palizzi Social Club in South Philly. There was no way I could screw up Italian food, right? Right?
Two days later, the cookbook arrived. I eagerly opened it, only to realize I was in way over my head. Every recipe seemed to include a food that I had never attempted to make before. Tomato and cinnamon-braised tripe. Spaghetti and crabs. Braised rabbit. Chinotto ribs. Whole roasted suckling pig.
As I flipped through the pages, a sense of mounting panic crept in. I slammed the book shut. What the hell is tripe, anyway?
After some deliberation, I settled on one of the simpler recipes in the book: stuffed peppers. It seemed straightforward enough. But after reading through the recipe, I realized it was going to be a two-day process. The first day would involve making the meat ragu, and the second day would be all about assembling and baking the peppers.
I prepared accordingly. On Friday evening, I diligently gathered the ingredients and made the ragu. So far, so good. But Saturday was shaping up to be a whirlwind. I had plans in the morning, and then I’d need to race home, run to the supermarket, and somehow cook the stuffed peppers in time for the dinner party that night.
To keep this story concise, here’s a timeline of how Saturday afternoon unfolded:
2:30 PM – I’m making great time. Off to the supermarket! Woohoo!
3:30 PM – Back from the store. Let’s get cooking!
4:00 PM – Is this pot big enough for all the rice I need to make?
4:30 PM – Dang, this rice is taking forever to cook…
5:00 PM – I’m behind schedule, but it’s fine. Don’t panic. Don’t panic.
5:15 PM – Where the hell is my cheese grater?!
5:30 PM – Why is this cheese so impossible to grate?!
5:40 PM – SHIT. I forgot to core the peppers.
5:50 PM – Get stuffed, peppers!
5:55 PM – Oh no. These peppers are too fat for the pan. I can’t fit them in the oven!
5:56 PM – WAIT—where’s my ceramic baking dish? That’ll work!
5:58 PM – FOUND IT!!!! A MIRACLE!!!! GO, GO, GO, GO, GO!!!!
6:00 PM – YOU EVIL, EVIL PEPPERS—GET IN THE OVEN NOW!
The recipe called for the peppers to bake for an hour and 15 minutes, but I only had 40 minutes before I had to leave. So, I cranked up the oven and hoped for the best.
If you had tracked my heart rate and blood pressure during that final hour, you might have assumed I was in some kind of hostage situation.
And, in a way, I was. The perfectionist in me had taken my entire nervous system hostage, demanding that I produce a flawless dish. But the moment things started to go awry, hysteria set in, and I almost threw in the towel altogether. Honestly, if I hadn’t found that ceramic baking dish, I’m not sure what I would’ve done.
But it’s all so ridiculous, isn’t it? To get so worked up over something that’s supposed to be fun?
Which brings me back to my original question.
When was the last time you did something hoping to mess it up—hoping to fail—just for the sake of trying something new and different and exciting?
For some people, I imagine this might come easily. We all have those friends who seem to float through life effortlessly, without putting too much pressure on themselves, without letting their insecurities or inner voices hold them back from whatever they set out to do.
But if you’re like me—someone who struggles to make everything perfect—it can actually be helpful to do the opposite: to fail on purpose. When your default definition of success is perfection, you’re setting yourself up for failure anyway. It becomes inevitable. So why not lean into it?
Put another way: if I had approached this process with the goal of making stuffed peppers, rather than perfect stuffed peppers, I might have been able to enjoy myself a lot more.
What’s interesting is that, during this two-day ordeal of making these peppers, I happened to be reading The Old Man and the Sea by Ernest Hemingway. For those unfamiliar, it’s about a man alone at sea in a small boat, struggling to haul in a massive marlin he’s caught. I won’t spoil the ending, but the story is really about perseverance—about seeing a task through to the end, no matter how many challenges arise along the way.
It’s almost absurd to admit, but I think that if I hadn’t been reading that book earlier in the day, I might have completely given up when I realized the peppers weren’t going to turn out the way I’d envisioned.
I arrived at the party on Saturday evening, peppers in hand, and ended up having an amazing time with wonderful company. Everyone told me the peppers were great—which, honestly, was hard for me to believe. But what I believe isn’t the point. The point is that I showed up with my dumb stuffed peppers in the first place.
So now, when I set out to do something new or unfamiliar, I won’t ask myself how I can make it perfect—or even good. Instead, I’ll ask myself how I can take the pressure off, how I can fail on purpose, with all the delight and freedom that imperfection brings.
It’s not about taking a perfect step in the right direction. It’s about taking any step at all.
