Matt, I loved the point you brought up about "Do I really want this?"
I had the same feeling when I quit my corporate job and moved to Europe. Once I was cut off from my income every purchase felt like it held so much more weight. Whenever I "splurged" I felt a sense of guilt, so many of your words in this essay resonated with me. Thank you.
Thanks, Brian. Yeah the fluctuations of whether it feels guilty vs. worth it vs. unsure is something interesting. A month in with the new money coming in, I've been finding myself trying to recalibrate what "worth it" means. For example, I've caught myself buying things at the grocery store that don't actually feel worth it or necessary. But yesterday I took a $97 Uber back home from the airport after a red eye which was 100% worth it because the alternative would be spending 2.5 hours in public transit while super exhausted. So still figuring it out!
Wow, the depth of thought presented here is uncanny. Hands down the best writing I have read today (big compliment, I read ALOT). Thanks for sharing, Matt. Learned alot!!
Thanks Rick, yeah the same core ideas keep circling in my periphery - one of which is how valuable time is. It just keeps getting more and more valuable to me!
About to jump in the hole and this was a great reminder to set some intentions around money.
Weighing every little purchase at the grocery store is so real. I'm trying to remember to not sweat the small stuff and not feel bad about spending money on the things that will give me the ease and bandwidth I'm looking for with the time off
Excited for your hole-jumping or cave-entering depending on you see it :) There'll be things that emerge too. For instance, something that I know you can relate to: the sweet satisfaction of being able to align your hobbies and activities to the weather & environment down to the hour. There is something beautiful about being able to ski when it's dumping, or whatever the activity calls for in weather, and then spending time resting and doing stuff indoors when it's not the best weather. That sort of stuff can't be priced, and it can't even really be understood over reading about it, it has to be experienced.
This is great Matt. It's good to see you talk about the uncertainty & psycholigically managing the change in financial position. Something I'm navigating too.
Thanks for reading Ryan, yeah the uncertainty was a big aspect. It truly did feel like I was in a hole at some point. Once the I could "see the light" at the end of the tunnel, I finally could tell that I was in a cave that I could walk out of just as easily as it was to enter.
Thanks for writing, Matt. I love the contrast of buying omakase vs. taking the time to source ingredients and teach yourself. A really good example of how money replaces time and vice versa.
Also, had the same experience with quarterlife and thinking I was a meaning type originally but realizing I was a stability type…makes sense that we’re friends
Haha, yeah it's interesting that the author has two distinct buckets. I'm not actually sure if I buy that we can categorize people so neatly. But it's useful and simple frame. There's something I didn't touch on which is the difference between having stability and the skill of knowing you can find stability if you want it. I think those are two different things. If someone was super confident they could just go and find stability quickly and easily then I think way more people would take breaks/creative pursuits/sabbaticals, etc. But unfortunately it's not always so clear at the beginning. At least it wasn't for me.
The sushi thing has been a fun occasional thing I do also with my friend from Hawaii. It's fun to collab and make dinner for friends. We did a couple when I was living in Hawaii. Such a nice experience because usually when you go to sushi you have to sacrifice portion size for quality. But when we buy it ourselves, we can get a huge amount of fish and it ends up coming out to only like $30pp for all the ingredients :O
Interesting story, similar in many ways to one I’m on … with the exception that I’m never going back to the kind of job I held before. I wrote this nearly a year ago, and I’m thinking about updating it to reflect what I’ve learned after being without an income for another year. I’m getting much more comfortable with it, for sure. https://tompendergast.substack.com/p/retirement-reflections
"Intellectually, I knew I could return to working full-time in tech, but I had a visceral reaction to this idea. Turning back felt like lying to myself by not fully expressing my skills and interests outside product management. It would also betray my future self, the one that would recognize being in the hole as an essential chapter in my journey. Exiting the hole just to go back to how it used to be, felt like a regression, bringing along with it old patterns, stories, and core beliefs that no longer serve me. I truly believed that climbing out of the hole prematurely would be setting myself up for failure."
I'm actually experiencing this right now - the only thing keeping it at bay is how free and happy I feel in the current moment re-exploring my creative self. Would you say that the most powerful learning you had here was facing that uncertainty and discomfort head on and just marinating in it?
It feels much like another newsletter I read about retiring early (https://tompendergast.substack.com/p/retirement-reflections) and how stepping out of that continuous paycheck mentality is a skill in itself and in some way, it's beautiful and privileged to have this practice before the REAL thing later on.
Matt, I loved the point you brought up about "Do I really want this?"
I had the same feeling when I quit my corporate job and moved to Europe. Once I was cut off from my income every purchase felt like it held so much more weight. Whenever I "splurged" I felt a sense of guilt, so many of your words in this essay resonated with me. Thank you.
Thanks, Brian. Yeah the fluctuations of whether it feels guilty vs. worth it vs. unsure is something interesting. A month in with the new money coming in, I've been finding myself trying to recalibrate what "worth it" means. For example, I've caught myself buying things at the grocery store that don't actually feel worth it or necessary. But yesterday I took a $97 Uber back home from the airport after a red eye which was 100% worth it because the alternative would be spending 2.5 hours in public transit while super exhausted. So still figuring it out!
Wow, the depth of thought presented here is uncanny. Hands down the best writing I have read today (big compliment, I read ALOT). Thanks for sharing, Matt. Learned alot!!
Wow! Thanks for the big compliment haha. I appreciate you for reading and for taking the time to let me know :)
Love your writing and insights, Matt. Wishing you a new chapter full of exploration and enoughness😊
Thanks Hagai, appreciate you for reading and commenting! The exploration continues
You call yourself frugal, but you also splurged on one of the most expensive purchases: buying time.
I think one of your powers is understanding trade-offs to ultimately pursue your highest aims. You let go of lower level ambitions for a greater one.
Most people are incapable of doing that… they are not in control.
Thanks Rick, yeah the same core ideas keep circling in my periphery - one of which is how valuable time is. It just keeps getting more and more valuable to me!
About to jump in the hole and this was a great reminder to set some intentions around money.
Weighing every little purchase at the grocery store is so real. I'm trying to remember to not sweat the small stuff and not feel bad about spending money on the things that will give me the ease and bandwidth I'm looking for with the time off
Excited for your hole-jumping or cave-entering depending on you see it :) There'll be things that emerge too. For instance, something that I know you can relate to: the sweet satisfaction of being able to align your hobbies and activities to the weather & environment down to the hour. There is something beautiful about being able to ski when it's dumping, or whatever the activity calls for in weather, and then spending time resting and doing stuff indoors when it's not the best weather. That sort of stuff can't be priced, and it can't even really be understood over reading about it, it has to be experienced.
Great piece Matt! slowly coming out of the hole myself now and life feels substantially different than it did 7 months ago.
Thanks for reading Kiran!
This is great Matt. It's good to see you talk about the uncertainty & psycholigically managing the change in financial position. Something I'm navigating too.
Thanks for reading Ryan, yeah the uncertainty was a big aspect. It truly did feel like I was in a hole at some point. Once the I could "see the light" at the end of the tunnel, I finally could tell that I was in a cave that I could walk out of just as easily as it was to enter.
Thanks for writing, Matt. I love the contrast of buying omakase vs. taking the time to source ingredients and teach yourself. A really good example of how money replaces time and vice versa.
Also, had the same experience with quarterlife and thinking I was a meaning type originally but realizing I was a stability type…makes sense that we’re friends
Haha, yeah it's interesting that the author has two distinct buckets. I'm not actually sure if I buy that we can categorize people so neatly. But it's useful and simple frame. There's something I didn't touch on which is the difference between having stability and the skill of knowing you can find stability if you want it. I think those are two different things. If someone was super confident they could just go and find stability quickly and easily then I think way more people would take breaks/creative pursuits/sabbaticals, etc. But unfortunately it's not always so clear at the beginning. At least it wasn't for me.
The sushi thing has been a fun occasional thing I do also with my friend from Hawaii. It's fun to collab and make dinner for friends. We did a couple when I was living in Hawaii. Such a nice experience because usually when you go to sushi you have to sacrifice portion size for quality. But when we buy it ourselves, we can get a huge amount of fish and it ends up coming out to only like $30pp for all the ingredients :O
Interesting story, similar in many ways to one I’m on … with the exception that I’m never going back to the kind of job I held before. I wrote this nearly a year ago, and I’m thinking about updating it to reflect what I’ve learned after being without an income for another year. I’m getting much more comfortable with it, for sure. https://tompendergast.substack.com/p/retirement-reflections
"Intellectually, I knew I could return to working full-time in tech, but I had a visceral reaction to this idea. Turning back felt like lying to myself by not fully expressing my skills and interests outside product management. It would also betray my future self, the one that would recognize being in the hole as an essential chapter in my journey. Exiting the hole just to go back to how it used to be, felt like a regression, bringing along with it old patterns, stories, and core beliefs that no longer serve me. I truly believed that climbing out of the hole prematurely would be setting myself up for failure."
I'm actually experiencing this right now - the only thing keeping it at bay is how free and happy I feel in the current moment re-exploring my creative self. Would you say that the most powerful learning you had here was facing that uncertainty and discomfort head on and just marinating in it?
It feels much like another newsletter I read about retiring early (https://tompendergast.substack.com/p/retirement-reflections) and how stepping out of that continuous paycheck mentality is a skill in itself and in some way, it's beautiful and privileged to have this practice before the REAL thing later on.