Rich Ruminates On The Benefits Of Being Uncomfortable. Can Imperfect Systems Help Build Resilience And Confidence?

I’d say he’s comfortable.

Hey Penny,

I appreciate your last post — it gave me a bunch of food for thought. This is exactly the sort of conversation we used to have over email, so I’m happy to reply on the blog. For those just catching up, here are the first 2 installments of this conversation:

If I could sum up the main emotional thrust of my initial post, it’d be something like: “My family is in the middle of a huge, tumultuous transition right now that involves money, work, life, school — is this really the good life??”

My answer to my own question, in that post, was The Good Life Is Not About Perfect Comfort.

Your answer, if I read your post correctly, is basically: Screw that! Get out of the rat race, ditch that prison school for a place your kids can thrive, and don’t knock Craigslist.

Again, this really made me think, so thank you. I’m going to try to unpack my original thought a bit more, with updated thinking based on the past week or so.


As I said, I understand the desire to retire as early as possible. The transition back to work in the US from overseas hasn’t been all high fives and pizza parties. So why don’t I try to retire earlier?

I won’t spend much time on the practical aspect of this, but the practical side is quite complicated. I’d need to shuffle accounts, reset priorities, move again, etc, etc. It’s all possible I’m sure, if we were really committed. Maybe I could retire at 50 instead of 55. Maybe. For 5 years of … what again?

The more important aspect of this is philosophical. As I’ve spelled out in several posts, especially my Philosophy Of Money and the Meaning of Life, personal growth and meeting my potential and the value of work are all real priorities for me.

Even though work has been a bit of a grind lately, I recently had some days that were fully engaging. There’s nothing quite like the feeling that I’m doing good work on interesting topics with other professional people I like and respect. There’s nothing quite like that feeling of FLOW: “the mental state of operation in which a person performing an activity is fully immersed in a feeling of energized focus, full involvement, and enjoyment in the process of the activity.” (Wikipedia)

What I’m getting at is that there’s a positive side to this, and sometimes the positive side only comes after a period of difficulty. I don’t want my career to be difficult all the time, but I also realize that very few things in life are achieved or enjoyed without effort. If we didn’t persevere through the difficulty, we wouldn’t enjoy the personal and professional gains on the other side. For me, the positive aspects of my career have far outweighed the negative.

Mrs. Rich and I want to meet our potential at work as much as possible. It stretches us, makes us grow, opens up new doors of opportunity. We have lived in different places around the country and around the world, and that scratches a special itch for us. We also live the lifestyle we want to live, and we feel lucky to be so lucky. Does that make sense?


One thing you mentioned that I don’t really understand: “And it seems to make more sense to me to Retire Earlier (if that’s what you’re planning on doing anyway) so you can watch your kids grow up ….”

Am I giving the impression that, as a busy professional, I don’t have much time with the kids to watch them grow up?

I can assure you, that’s not the case at all for me and Mrs. Rich. We chose to live close to school so we can walk them to and from every day, and we chose to live close to work so we can be with them rather than sitting in the car commuting. Mrs. R is a Kindergarten room parent, and I’m the soccer coach. There really aren’t many more hours in the day that we could spend with the kids even if we were retired right now.

Of course, we could be with them all day if we were homeschooling or something, which leads me to the education part of your note.


I don’t disagree with much of what you said about education. I’d probably prefer the Finnish way of doing things, or Montessori, or the little preschool we used to send our kids to.

That said, I’m not all doom and gloom about our local public school. It’s not much different from the schools I went to growing up. We were expected to sit down and we had homework and all that. I turned out ok, right?

Ha, don’t answer that.

I like your point about thriving: So, I don’t know, you say you’re boys are struggling in school, but, yeah, they’ll just have to adjust. Don’t you want something better than that? Don’t you want them to thrive?

I was open about the fact that my first, emotional, transitional reaction was to pull the kids right out of the new school and put them somewhere they’d be more comfortable. That’s a natural response for many parents. I also give a nod to the stages of development you highlighted in your post — I don’t feel as strongly as you do, but I see your points.

However, I also wonder, could there be some downside to pulling them out of uncomfortable situations? Conversely, is there some upside to giving them time to adjust to a different way of doing things?

I don’t have all the answers, but I should note that I’m already seeing some benefits from the new school. They are having better days, and starting to sing songs in Spanish at home. Did I mention it’s a Spanish / English immersion school? It’s cool. They are even better at sitting still. Not a big deal, but it’s been helpful at school and at home too. They are having happier days and I can see that they are proud of themselves for doing better. One of our boys got invited to a birthday party and was beaming. Our other boy got an award for being a good listener in P.E. and he was stoked. 


Regarding both work and school, I’ve been thinking about resilience. It’s currently an overused term, I know, but it’s the best word I can think of.

My spin on it is that life is full of imperfect systems. That’s life. How do we as humans learn to survive — or even thrive — in imperfect systems? I’m not going to claim that it’s all settled in Kindergarten; that said, I do think kids can benefit from sticking with something they don’t enjoy right away.

They also do swimming and soccer. A couple years ago, they weren’t always enthused about swimming and soccer, but now they love these activities. It reminds me of two quotes from Amy Chua, the Tiger Mom:

“Everything I’ve ever done that’s valuable is something I was afraid to try.” 

“Nothing is fun until you’re good at it.”

There’s some truth to those quotes, at least for my kids.

Don’t get me wrong, I’m not saying we should force ourselves or our kids into all sorts of scary situations. It can get extreme. But could it also get extreme on the other end, if we don’t nudge them to do anything they’re a bit afraid of at first?

To this day, I still have occasional experiences at work that make me nervous or uncomfortable. At first, it’s tough. But I have a bunch of similar experiences to draw on, and it helps me to get past that mental reservation and to a place where I can approach a new challenge with confidence. Maybe I’ll thrive, and if I don’t thrive, I know how to adjust, or even fail, and try again.

I’m curious what you think of all this. We are very different in this respect, I think. I often seek out new, challenging, even uncomfortable situations. You tend to stick with routines, with what you know. How do you think this relates to your perspective on careers, on confidence, or on anything else you think is related?

Finally, Penny, I want you to know I don’t see this as a debate — I really do agree with a lot of what you said in your last post. Public school is an imperfect system. Modern, professional living is one of many imperfect situations. I’d say there’s no perfect way of approaching the good life.

We’ve talked a lot over the years about different systems in life — education, student loans, careers, retirement. I often say I enjoy learning how to succeed in these systems, to play “the game” as it were, while you tend to avoid the game because the game can be stupid. What are the pros and cons of these approaches, and what drives us to these ways of living?

Sometimes I do wonder what it’d be like if I were more content with less change / challenge / adventure, as you are. Is there anything you wonder about in that way? Any experiences or ways of living that you’d like to try out, if you could have an out of body experience and do something that normally makes you uncomfortable?

By the way, I just turned 42. Halfway to 84!



2 Replies to “Rich Ruminates On The Benefits Of Being Uncomfortable. Can Imperfect Systems Help Build Resilience And Confidence?”

  1. I’ll answer all of your questions in a post, but I wanted to address this statement briefly:

    “Your answer, if I read your post correctly, is basically: Screw that! Get out of the rat race, ditch that prison school for a place your kids can thrive, and don’t knock Craigslist.”

    Actually, I wasn’t answering to anything. I didn’t read your post and was judging you for it or giving you advice on what to do. I was going to write a post on my Educational Philosophy anyway, and that just happened to coincide with your newfound experiences of having your boys in kindergarten, so that might have seemed like I was addressing that directly, but I was not.

    And the other thing, about the rat race… that was just a thought that occurred to me after hearing you kind of knock all the FIRE people over the year. It occurred to me that you ARE actually a FIRE person yourself, since you plan on retiring early, just not as early as them, so why you be knocking them?
    Penny @ recently posted…Rich Ruminates On The Benefits Of Being Uncomfortable. Can Imperfect Systems Help Build Resilience And Confidence?My Profile

  2. Hey cousin — don’t worry, I didn’t take your post as judgment — I was going for more of a funny tone with the “screw that” paraphrase. Sorry if it came across the wrong way.

    My perception is that whether answering my post directly or not, you think I should try to retire earlier and that public schools are not very awesome … or else why would you ask (rhetorically, perhaps) if I wouldn’t want my kids to thrive rather than adjust? That was a direct response to my statement they would adjust, right?
    Anyway, correcting for the tone, am I incorrect in these perceptions? I’m not in debate mode, I really want to know.

    Regarding the FIRE people, I think I’ve always described why I am not personally a FIRE person, for reasons that are well known. I don’t remember knocking anyone for being a FIRE person. Have I done that? Probably I have, jokingly. Mostly I think, more power to them.

    Most FIRE people shoot for much earlier retirements than 55. I do wonder about it philosophically, with regard to the value of work and personal growth and lifestyle and so on. Then again, if I had $5 Million in the bank maybe I’d think differently …
    Rich @ recently posted…Monthly Money Check: Rich Increased Net Worth By $200K in 2 Years And Bought A Car Online — August 2017My Profile

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