Curse me Kilts!! What is the hell is point of any of it anyway?

[Jaygo]

For the first time in my life I have sold some investments and used the proceeds. The last couple years I have had pretty good returns and felt good financially so we sold about $120,000.00 Canadian worth of investments from our accounts and used the proceeds to put in a pool at our house.  

 

I really thought the feeling would be amazing, I even hoped to instill some investment wisdom in my kids that hard work and careful investments can bring great things. But honestly I look at the pool and my kids in it and it brings so much joy but looking at my lower account total has really put a damper on my mood. Its like my snowball got smaller and it really makes me wonder what the hell is the point of it anyway if I dont enjoy spending the money why bother?  Was the end goal just to have a big number and not actually use the proceeds?

 

Has anyone ever harvested a gain and had this same shitty feeling or am I just a greedy monster like Scrooge McDuck wishing the pool was full of money instead of happy kids?

[Sweet]

I’ve never harvested any gains, but I completely agree with you.  First priority is providing for my family and kids, second is ensuring the kids have a happy childhood, and lastly is I have enough away to help them out later in life.  It used to be about getting rich, now it’s all about them.  I’ve basically decided that I’m going to use all that money on them, because actually that’s what makes me happy.  I never got enjoyment on spending for myself.

 

The trouble, as you say, is you want to teach them the values you have.  Many kids who just get things are terrible with money when they are older.

 

Edited September 10, 2025 by Sweet

[Pauly]

I get it, but that negative feeling will fade as you adjust to the new reality. Meanwhile, the memories around the pool will only increase. And, more importantly, your kids' memories of growing up around a pool will last them a lifetime beyond you. They won't remember their dad having a larger account balance at one time. 

Selling because you have a bill to pay is much more painful. Then you really feel like you have nothing to show for it.

[schin]

1 hour ago, Pauly said:

I get it, but that negative feeling will fade as you adjust to the new reality. Meanwhile, the memories around the pool will only increase. And, more importantly, your kids' memories of growing up around a pool will last them a lifetime beyond you. They won't remember their dad having a larger account balance at one time. 

Selling because you have a bill to pay is much more painful. Then you really feel like you have nothing to show for it.

 

Or... remember kids when I bought the pool? Well, that was your college fund... Now you either have to get a full scholarship or enjoy community college! LOL

[gfp]

The feeling goes away when the $130k becomes a rounding error on your accounts.  At the end of the year when you are up $800k or 2m or whatever but it would have been $150k higher with no pool you will not care about the pool.  

 

If your kids get swimming scholarships you'll be psyched.  If someone drowns, you will regret the pool.  The money you will barely remember you spent.  

 

Even my UPS driver spent $80k (USD) this year putting in a nice pool.  UPS drivers make a ton of money at his age.  How do you put a price on getting to see your grandkids like 3x as often 'cause you're the house with the dope pool?

[thepupil]

I have the opposite feeling when i make big purchases. 

 

I generally am happy i did them and end up wondering why i didn't do them sooner (home down payment, home reno, big things). I think our lives are better for it.

 

I have the same feeling when i review the monthly annual spending on restaurants and travel. these are purchases that in totality are not "worth" it to me in hindsight...individually they seem fine, but collectively it's kind of like geez we spent how much on trips and restaurants...OMFG. 

[John Hjorth]

CofB&F - Book Forum : Morgan Housel - The Art of Spending Money.

[dwy000]

10 minutes ago, thepupil said:

I have the opposite feeling when i make big purchases. 

 

I generally am happy i did them and end up wondering why i didn't do them sooner (home down payment, home reno, big things). I think our lives are better for it.

 

I have the same feeling when i review the monthly annual spending on restaurants and travel. these are purchases that in totality are not "worth" it to me in hindsight...individually they seem fine, but collectively it's kind of like geez we spent how much on trips and restaurants...OMFG. 

Nobody ever lays on their death bed wishing they had worked more and went out to dinner less.  All the stuff is nice but its the experiences that are ultimately the most valuable.  

 

When people think back to their childhood they almost never wish the kitchen had been updated or the yard was bigger, they just think about the good times they had in that house regardless of what it looked like. 

[Eldad]

2 hours ago, Jaygo said:

For the first time in my life I have sold some investments and used the proceeds. The last couple years I have had pretty good returns and felt good financially so we sold about $120,000.00 Canadian worth of investments from our accounts and used the proceeds to put in a pool at our house.  

 

I really thought the feeling would be amazing, I even hoped to instill some investment wisdom in my kids that hard work and careful investments can bring great things. But honestly I look at the pool and my kids in it and it brings so much joy but looking at my lower account total has really put a damper on my mood. Its like my snowball got smaller and it really makes me wonder what the hell is the point of it anyway if I dont enjoy spending the money why bother?  Was the end goal just to have a big number and not actually use the proceeds?

 

Has anyone ever harvested a gain and had this same shitty feeling or am I just a greedy monster like Scrooge McDuck wishing the pool was full of money instead of happy kids?

Spending the principal is tough. Spending the interest and dividends instead of reinvesting is much easier. So I guess the goal for me is get the income big enough to use that later in life. Slowly transition from growth to income producing in 15 years or so. 
 

Had to sell a chunk last year to add on to my house. I have 3 kids that need their own room at this point, what are you going to do. It hurt. I have tapped dividends and interest to help with trips before and I have no problem with that. 
 

But yes part of this investing thing is just a game. 

Edited September 10, 2025 by Eldad

[73 Reds]

2 hours ago, Jaygo said:

For the first time in my life I have sold some investments and used the proceeds. The last couple years I have had pretty good returns and felt good financially so we sold about $120,000.00 Canadian worth of investments from our accounts and used the proceeds to put in a pool at our house.  

 

I really thought the feeling would be amazing, I even hoped to instill some investment wisdom in my kids that hard work and careful investments can bring great things. But honestly I look at the pool and my kids in it and it brings so much joy but looking at my lower account total has really put a damper on my mood. Its like my snowball got smaller and it really makes me wonder what the hell is the point of it anyway if I dont enjoy spending the money why bother?  Was the end goal just to have a big number and not actually use the proceeds?

 

Has anyone ever harvested a gain and had this same shitty feeling or am I just a greedy monster like Scrooge McDuck wishing the pool was full of money instead of happy kids?

Everything you do in life, including what you spend is about priorities.  Do what you enjoy the most, including a pool if that's your thing (its not mine but I live on the water and after last year would now prefer to be far away).  Balance your needs and wants.   Make sure you have enough to cover your needs so you don't feel guilty about spending on your wants.

[Eldad]

7 minutes ago, 73 Reds said:

Everything you do in life, including what you spend is about priorities.  Do what you enjoy the most, including a pool if that's your thing (its not mine but I live on the water and after last year would now prefer to be far away).  Balance your needs and wants.   Make sure you have enough to cover your needs so you don't feel guilty about spending on your wants.

Exactly. My thing is free time and low stress. I could probably sit under a tree and read library books the rest of my life and spend almost nothing. If I was a single man I might already be good to go. 
 

Now I also have in the back of mind I would like to someday be in a position to maybe buy or start a business that could potentially employ my children if they need that. 

[brobro777]

I set aside fun money and I use that for laffs, fun, or anything (even stuff that's Beavis and Butthead level stupid); I regularly contribute to it and when I have a real good year like this year, I put extra, sort of like a special dividend

 

Over the years I think I made better decisions spending more of this money than trying to be more strict - I think I came out ahead as a result, really

[Eldad]

Also, after the next 30-40% sell off you will probably be very proud of your pool LOL. 

[73 Reds]

21 minutes ago, Eldad said:

Exactly. My thing is free time and low stress. I could probably sit under a tree and read library books the rest of my life and spend almost nothing. If I was a single man I might already be good to go. 
 

Now I also have in the back of mind I would like to someday be in a position to maybe buy or start a business that could potentially employ my children if they need that. 

I had to laugh - I get a new book from the local library every week!  

[Milu]

57 minutes ago, Eldad said:

Spending the principal is tough. Spending the interest and dividends instead of reinvesting is much easier. So I guess the goal for me is get the income big enough to use that later in life. Slowly transition from growth to income producing in 15 years or so. 
 

Had to sell a chunk last year to add on to my house. I have 3 kids that need their own room at this point, what are you going to do. It hurt. I have tapped dividends and interest to help with trips before and I have no problem with that. 
 

But yes part of this investing thing is just a game. 

I think this is one of the mental accounting issues that many people struggle with. Return is return whether it’s from capital appreciation or dividend income. Many investors seem delighted when a company pays out some large special dividend, but look confused when you explain you can just create your own ‘special dividend’ by selling some stock and realising capital gain, typically more tax efficient too as income tax is typically higher rate.

Edited September 10, 2025 by Milu

[LC]

For me it was always freedom and relieving a burden of needing to work, needing to live in a high-income area.

 

Then once the investment account grew to the point where I could retire and never think about the harsh realities of life, I don't really know what to do with the money. I feel like quitting my job won't really change my life for the better, it will just make me a little more bored in the middle of the day.  I travel as much as my girlfriend wants, but that's her passion and not really mine. I was debating getting a place in Chile to ski year round  but that just seems excessive. Plus most of my friends are still working so it would be a more solo adventure, not as fun. 

 

I think Munger or Buffett was right when they said that ultimately the money doesn't change your lifestyle.

[Castanza]

3 hours ago, Jaygo said:

For the first time in my life I have sold some investments and used the proceeds. The last couple years I have had pretty good returns and felt good financially so we sold about $120,000.00 Canadian worth of investments from our accounts and used the proceeds to put in a pool at our house.  

 

I really thought the feeling would be amazing, I even hoped to instill some investment wisdom in my kids that hard work and careful investments can bring great things. But honestly I look at the pool and my kids in it and it brings so much joy but looking at my lower account total has really put a damper on my mood. Its like my snowball got smaller and it really makes me wonder what the hell is the point of it anyway if I dont enjoy spending the money why bother?  Was the end goal just to have a big number and not actually use the proceeds?

 

Has anyone ever harvested a gain and had this same shitty feeling or am I just a greedy monster like Scrooge McDuck wishing the pool was full of money instead of happy kids?

 

If money is the goal you'll always be disappointed....There is a difference between being rational and reasonable. It might not be financially rational to spend principal on a pool interrupting your snowball. However, it's reasonable because your gaining something money can't buy...time and experiences with your family. Isn't that the purpose of money? Freedom of choice and experience along with time. 

 

I paid my house of early in my early 30's...definitely not a financially savvy move! That's a lot of $$$ I'm passing on during my retirement.....but I'd argue it's reasonable because it means my wife has to work 1/5th as much and gets to mainly be the stay at home mom she wanted to be. My kids and wife will have far more experiences together over the years and once they are in school she can work more if she chooses and not miss out on time that could have been spent with the kids. It also means I don't have to work 80 hours a week to make additional money and miss out on after work family experiences.  

 

 

[Eldad]

20 minutes ago, Milu said:

I think this is one of the mental accounting issues that many people struggle with. Return is return whether it’s from capital appreciation or dividend income. Many investors seem delighted when a company pays out some large special dividend, but look confused when you explain you can just create your own ‘special dividend’ by selling some stock and realising capital gain, typically more tax efficient too as income tax is typically higher rate.

True but the interest and dividends don’t involve any sell decisions and harvesting them rather than selling will typically mean more cashflow in the future. 
 

There is a reason many trust documents only let the gold digger 2nd wife spend the income and save the principal for the kids haha.

[SharperDingaan]

You are the master, money is the servant. Money is to be used; either as capital to build something lasting, or as ongoing dividend/interest money towards day to day experiences. The casino is also fickle; so take chips out while you're a hero, 'cause tomorrow you will be a bum. It is the only drug addicts and pushers who cannot leave. 

 

Just be mindful that withdrawals cumulatively corrupt, hence proactively manage. When everybody leaves university debt free, has no mortgage, etc, etc ...... it is not how the real world lives, and screwed up families are a common result. Enjoy the pool, and take dividend/interest money to pay someone to maintain it. 

 

Our nephews are older; when they were younger, capital repatriation would often pay for 'once-in-a-lifetime' trips, plane tickets/spending to visit, grub stakes in various enterprises , and concert tickets to see the world's best .... when they were at their best. Experiences they would not otherwise have had. 

 

SD

 

 

[Parsad]

6 hours ago, Pauly said:

I get it, but that negative feeling will fade as you adjust to the new reality. Meanwhile, the memories around the pool will only increase. And, more importantly, your kids' memories of growing up around a pool will last them a lifetime beyond you. They won't remember their dad having a larger account balance at one time. 

Selling because you have a bill to pay is much more painful. Then you really feel like you have nothing to show for it.

 

100%!  My Dad died young...I'd give up my entire bank account for just one more hug from him.  

 

I have a pool in my condo complex and my niece and nephew use it somewhat regularly...those memories are worth a fortune!

 

But now that you have a pool, if you ever feel like such a splurge again...maybe do something smaller together.  Also, at least you didn't waste it on a sports car!

 

Cheers!

[nsx5200]

I ran across Die With Zero that talks about the trade off between life experience with accumulation of wealth, and agree with @SharperDingaan that money/wealth is there to serve you and not the other way around.  A lot of us are conditioned to think the other way, and that's wrong.

 

Something that really helps is to really deliberately consider all the impulse/unnecessary spending that, most of the time, doesn't really improve our long-term happiness but instead increase the chance of an unhappy experience in old age.  You'll make mistakes with those decisions and trade-offs, as we can not fully predict the future, but with any skill, I believe as you make more deliberate choices and reflect on past choices, you'll make better choices.

 

Now that it's spent, it's already done.  You've already paid it, so why 'cry over spilt milk' by aggravating yourself.  That's unnecessarily mentally paying for it again.  The best thing you can do now is to try to maximize it by enjoying it.  Try to find ways to increase the usage in order to minimize your per usage cost.  That's how a logical business would think about some capital asset.  Be a decisive business leader: make a decision, wrong or right, and make the best of it.

 

p.s.  not saying your decision is wrong.  That's for you to decide in a few years as you reflect, but IMHO, it's a bit irrational to mentally pay for for it again, so you should really enjoy it, worry free.  HTH.

[Red Lion]

6 hours ago, gfp said:

The feeling goes away when the $130k becomes a rounding error on your accounts.  At the end of the year when you are up $800k or 2m or whatever but it would have been $150k higher with no pool you will not care about the pool.  

 

If your kids get swimming scholarships you'll be psyched.  If someone drowns, you will regret the pool.  The money you will barely remember you spent.  

 

Even my UPS driver spent $80k (USD) this year putting in a nice pool.  UPS drivers make a ton of money at his age.  How do you put a price on getting to see your grandkids like 3x as often 'cause you're the house with the dope pool?

I just put in a pool and wonder why I didn’t do it sooner. 

[Jaygo]

2 hours ago, Parsad said:

Also, at least you didn't waste it on a sports car!

Lol, yes thankfully. The ultimate dweeb move. Not that I havent been tempted though!

 

Thanks for everyone responses. The mind is funny. Our perception of what's important can be really odd. I'm sure its some sort of evolutionary thing where we feel money is associated with survival just like the caveman who had the biggest pile of marrow bones in his cave.

 

 

[Jaygo]

2 hours ago, nsx5200 said:

Now that it's spent, it's already done.  You've already paid it, so why 'cry over spilt milk' by aggravating yourself.  That's unnecessarily mentally paying for it again.  The best thing you can do now is to try to maximize it by enjoying it.  Try to find ways to increase the usage in order to minimize your per usage cost.  That's how a logical business would think about some capital asset.  Be a decisive business leader: make a decision, wrong or right, and make the best of it.

 

I definitely dont regret building the pool. But the effect of my investment account balance going down is what has been the mood killer. Since I started investing with real interest I have only ever added to the account and with ups and downs in the market I was always contributing. Now that I took a big chunk out its a odd feeling. 

[ICUMD]

Budget.  Try to set aside a proportion of your income/ funds annually for home improvement and travel, experiences etc.

 

As your investment portfolio grows, you can allocate more to these annual endeavors.  

 

Large expenditures may need several yrs contribution.

 

The fun part is making yourself spend all of it.