What I liked most is the distinction between grit and ego. Sometimes choosing the hardest path is not courage, it is just refusing to admit that another path might fit us better. “The goal isn’t to break yourself. It’s to grow.” That feels like the heart of the piece.
I really understand this distinction between a challenge that stretches you and one that slowly starts to break you.
For years, my challenge was holding up the studio my husband and I had built and invested everything into. It was ours, it felt almost like a second home, and then COVID hit. We kept going because letting go felt impossible. At the time, that was the challenge in front of us, and we had to go through it.
But eventually that whole chapter pushed us toward something completely different. It took us almost two years to get here, and now we’re in Saudi Arabia facing a completely new set of challenges. The difference is that these feel like good challenges. They ask a lot from us, but they also feel like they are moving us forward rather than just asking us to survive.
So this really made me think about how not every hard season is the same. Some challenges are about endurance. Some are about knowing when to stop. And some are the kind that open the next chapter.
Oh wow! That sounds like quite the story! I’d love to do a call and hear more about it sometime.
Did you shut down the studio? I had to leave a company I helped build but it wasn’t my own company and I hadn’t built it from scratch. (I was employee #4 and ran it a few years though.) I can’t imagine how much harder it would be to leave something you built from scratch.
Yes, we did. We finally closed the studio in October 2025.
At first it was terrifying because we had built it from scratch and invested so much of ourselves into it. But very quickly, alongside the fear, there was also this huge sense of relief. We had been carrying it for so long that I honestly don’t think we could have gone on much longer the way we were.
Looking back, closing it wasn’t giving up. It was accepting that a chapter had ended before it completely broke us.
And yes, I’d really enjoy a call sometime. I think we probably have a lot to talk about around building something, attachment to it, and that strange moment when leaving becomes the healthier choice.
Yeah that sounds like a really tough transition but ultimately a good one. Let’s definitely connect in mid-October! The next week or two is going to be a bit crazy for me, but I’ll have some more time after that.
Colin, the line about the magic happening right on the border felt true to me. Your gym example made it click. There is a big difference between a hard lift that builds strength and one that tweaks a tendon. I have made the same mistake with work before, staying in roles that only made me smaller. Pushing yourself matters, but the setting matters too.
Really glad it resonated with you, Jeff! I think we all make that mistake sometimes. It’s just a matter of learning from it quickly! And obviously it’s taken me awhile!
I really relate to this because I’ve had to learn this the hard way more than once. I’ve always been someone who can push through a lot, and for years I almost treated that as a strength in itself — if something was hard, I could endure it, figure it out, carry more, keep going.
But there were also times in my life where that mindset kept me in things far too long. Businesses, roles, situations where I thought leaving would mean I had failed, so I kept trying to prove I could make it work. Looking back, some of those experiences absolutely grew me. Others just exhausted me. And now I am in a place where I don't have to push through anymore and my nervous system has to adapt to the sense of being enough.
Teresa, thanks so much for sharing! It’s a hard thing to wrestle with, especially if being able to endure anything is sort of a badge of honor for you. I definitely fall into that same trap all the time.
Do you have any advice for figuring out which things to stick with and which things to just move on from?
I think the thing worth sticking with is something that still has life in it, even when it’s hard. There’s still curiosity, meaning, growth, or a sense that the effort is taking you somewhere.
Rome and our business are probably the clearest example for me. For years, I convinced myself I had to keep going because it was our income and because leaving felt like failure. I was completely burned out, but I kept pushing because I thought I didn’t have another choice.
Eventually I had to learn that saying no, choosing differently, and walking away can also be forms of strength. It didn’t change overnight, but two years later my family and I relocated to Saudi Arabia and started again.
And for the first time in a very long time, I feel relaxed.
So now I ask myself less, “Can I endure this?” and more, “Is this still asking me to grow, or am I only staying because I’m scared of what leaving would mean?”
Yesss love your nuance around the right type of challenge and the distinction between grit and ego. It’s making sure we are running up the right mountain, versus just running up any mountain to prove we can get to the top. Thanks for sharing!
Really glad you liked it, Sam! Yeah… it’s not an easy lesson to learn. Picking the right mountain is a hard thing to do. Really like the way you put that. I hadn’t thought of it in quite those terms.
I related to this essay, more than I want to admit. I have spent my life chasing discomfort too. Canoeing the Boundary Waters, moving to a different country, changing careers, learning a new language and new culture. Reading your piece made me wonder how much of that isn't grit or ego at all, but something earlier: I grew up in a home that wasn't comfortable, and maybe some part of me just never learned to look for ease. Discomfort felt familiar, almost like home, long before it felt like growth.
I'm not sure "was it grit or was it ego" is even the right question for me. It might be closer to: was I reaching toward something, or running from stillness? Those can look identical from the outside and be completely different on the inside.
Thank you for writing this, it made me contemplate the concept of being in the discomfort.
Middle of the pack is a measurement you can only take afterward. You find out which side of the line you were on by which side you landed on.
The thesis story has the more usable version buried in it. One professor had already given you an A- on ancient history. The other had never given you above a B. Same amount of work either way, but the odds were different, and that's the part you can actually see before you commit.
Hmm yeah that’s a good point. Although with choosing a school or a team at work, I think we can sometimes guess how we’ll do, even if we don’t know for sure.
What I liked most is the distinction between grit and ego. Sometimes choosing the hardest path is not courage, it is just refusing to admit that another path might fit us better. “The goal isn’t to break yourself. It’s to grow.” That feels like the heart of the piece.
Thanks @Antonio Castellaneta! I didn’t even figure out that until I finished writing the essay and realized it was kind of a story about ego.
‘The magic happens on the border’, well said. Enough to challenge you, enough to give the satisfying feeling of progress!
Really glad it resonated with you!
I really understand this distinction between a challenge that stretches you and one that slowly starts to break you.
For years, my challenge was holding up the studio my husband and I had built and invested everything into. It was ours, it felt almost like a second home, and then COVID hit. We kept going because letting go felt impossible. At the time, that was the challenge in front of us, and we had to go through it.
But eventually that whole chapter pushed us toward something completely different. It took us almost two years to get here, and now we’re in Saudi Arabia facing a completely new set of challenges. The difference is that these feel like good challenges. They ask a lot from us, but they also feel like they are moving us forward rather than just asking us to survive.
So this really made me think about how not every hard season is the same. Some challenges are about endurance. Some are about knowing when to stop. And some are the kind that open the next chapter.
Oh wow! That sounds like quite the story! I’d love to do a call and hear more about it sometime.
Did you shut down the studio? I had to leave a company I helped build but it wasn’t my own company and I hadn’t built it from scratch. (I was employee #4 and ran it a few years though.) I can’t imagine how much harder it would be to leave something you built from scratch.
Yes, we did. We finally closed the studio in October 2025.
At first it was terrifying because we had built it from scratch and invested so much of ourselves into it. But very quickly, alongside the fear, there was also this huge sense of relief. We had been carrying it for so long that I honestly don’t think we could have gone on much longer the way we were.
Looking back, closing it wasn’t giving up. It was accepting that a chapter had ended before it completely broke us.
And yes, I’d really enjoy a call sometime. I think we probably have a lot to talk about around building something, attachment to it, and that strange moment when leaving becomes the healthier choice.
Yeah that sounds like a really tough transition but ultimately a good one. Let’s definitely connect in mid-October! The next week or two is going to be a bit crazy for me, but I’ll have some more time after that.
Colin, the line about the magic happening right on the border felt true to me. Your gym example made it click. There is a big difference between a hard lift that builds strength and one that tweaks a tendon. I have made the same mistake with work before, staying in roles that only made me smaller. Pushing yourself matters, but the setting matters too.
Really glad it resonated with you, Jeff! I think we all make that mistake sometimes. It’s just a matter of learning from it quickly! And obviously it’s taken me awhile!
I really relate to this because I’ve had to learn this the hard way more than once. I’ve always been someone who can push through a lot, and for years I almost treated that as a strength in itself — if something was hard, I could endure it, figure it out, carry more, keep going.
But there were also times in my life where that mindset kept me in things far too long. Businesses, roles, situations where I thought leaving would mean I had failed, so I kept trying to prove I could make it work. Looking back, some of those experiences absolutely grew me. Others just exhausted me. And now I am in a place where I don't have to push through anymore and my nervous system has to adapt to the sense of being enough.
Teresa, thanks so much for sharing! It’s a hard thing to wrestle with, especially if being able to endure anything is sort of a badge of honor for you. I definitely fall into that same trap all the time.
Do you have any advice for figuring out which things to stick with and which things to just move on from?
I think the thing worth sticking with is something that still has life in it, even when it’s hard. There’s still curiosity, meaning, growth, or a sense that the effort is taking you somewhere.
Rome and our business are probably the clearest example for me. For years, I convinced myself I had to keep going because it was our income and because leaving felt like failure. I was completely burned out, but I kept pushing because I thought I didn’t have another choice.
Eventually I had to learn that saying no, choosing differently, and walking away can also be forms of strength. It didn’t change overnight, but two years later my family and I relocated to Saudi Arabia and started again.
And for the first time in a very long time, I feel relaxed.
So now I ask myself less, “Can I endure this?” and more, “Is this still asking me to grow, or am I only staying because I’m scared of what leaving would mean?”
Yesss love your nuance around the right type of challenge and the distinction between grit and ego. It’s making sure we are running up the right mountain, versus just running up any mountain to prove we can get to the top. Thanks for sharing!
Really glad you liked it, Sam! Yeah… it’s not an easy lesson to learn. Picking the right mountain is a hard thing to do. Really like the way you put that. I hadn’t thought of it in quite those terms.
Good perspective Colin. And great you’ve learned it at a relatively young age. 🏆
Thanks so much, Bob! I’m really glad it resonated so much with you. And yes… still trying to learn the lesson, but hopefully I’m almost there!
I related to this essay, more than I want to admit. I have spent my life chasing discomfort too. Canoeing the Boundary Waters, moving to a different country, changing careers, learning a new language and new culture. Reading your piece made me wonder how much of that isn't grit or ego at all, but something earlier: I grew up in a home that wasn't comfortable, and maybe some part of me just never learned to look for ease. Discomfort felt familiar, almost like home, long before it felt like growth.
I'm not sure "was it grit or was it ego" is even the right question for me. It might be closer to: was I reaching toward something, or running from stillness? Those can look identical from the outside and be completely different on the inside.
Thank you for writing this, it made me contemplate the concept of being in the discomfort.
Middle of the pack is a measurement you can only take afterward. You find out which side of the line you were on by which side you landed on.
The thesis story has the more usable version buried in it. One professor had already given you an A- on ancient history. The other had never given you above a B. Same amount of work either way, but the odds were different, and that's the part you can actually see before you commit.
Hmm yeah that’s a good point. Although with choosing a school or a team at work, I think we can sometimes guess how we’ll do, even if we don’t know for sure.