Author Topic: Your biggest shoulda/coulda's  (Read 8478 times)

MMMdude

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Your biggest shoulda/coulda's
« on: November 26, 2017, 05:38:32 PM »
Just curious what others biggest investment mistake has been in terms of missing out on an opportunity.  I'm Canadian so for me it has to be Dollarama.  I recall being in one around 2011 thinking man this place is super popular I should invest.  However I thought, nah they will be killed if the Cdn $ weakens as all their stuff is pretty much from China or overseas. 

Currently their stock is around $160 while in 2011 it was $17ish when I was looking at it.  I've never had even close to a 'ten bagger' but this would have been it.  My typical purchase back then was around $3500 so pretty much $30K+ in profits out the door.  I have no idea what I invested that money in at the time...probably an index fund so I guess I can take solace in the fact I had some gains out of that money.


JLee

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Re: Your biggest shoulda/coulda's
« Reply #1 on: November 26, 2017, 05:39:55 PM »
Buying/mining bitcoin in 2009.

Retire-Canada

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Re: Your biggest shoulda/coulda's
« Reply #2 on: November 26, 2017, 06:32:19 PM »
Investing more in my late 20's and early 30's when the money really started rolling in.

Mighty-Dollar

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Re: Your biggest shoulda/coulda's
« Reply #3 on: November 26, 2017, 07:03:08 PM »
Not using simple bond/stock diversification leading up to 2008. Also not rebalancing out of a natural resources fund that I was way over-allocated into because it had made a huge run up in value.

Putting my trust in investment advisors when I was younger, thinking that they had magical stock or fund picking powers. Now I know to stick with index funds on my own and that no advisor should ever attempt to beat the indexes.

fattest_foot

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Re: Your biggest shoulda/coulda's
« Reply #4 on: November 26, 2017, 07:16:04 PM »
Buying/mining bitcoin in 2009.

My brother-in-law tried to convince me to start mining in 2009, but I didn't. He did and mined quite a few, but apparently lost them (not sure if he doesn't know where he stored them or can't access). I'd imagine he would've had a few hundred thousand dollars right now if he had them still.

But that's all assuming I didn't sell them many thousands of dollars ago, too.

Ms.BecomingFI

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Re: Your biggest shoulda/coulda's
« Reply #5 on: November 26, 2017, 07:22:18 PM »
Wish I would have been maxing out my 401k's and IRAs all along.  Instead I had no idea and just had money sitting in savings accounts for years... deflating.  Of course that gave me the freedom to do (mostly) what I wanted, so it's not bad to have some FU money up your sleeve! =)

jleo

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Re: Your biggest shoulda/coulda's
« Reply #6 on: November 26, 2017, 07:26:05 PM »
Thinking I knew what way a stock was going and I did get lucky a few times, I ended up giving it all back and ended up watching AAPL climb from 110 to 175 as I held it for over 3 years before that and sold right before the run up!

Or listening to Cramer on stock recommendations when I first started out and both stocks went to the penny sheets within 3 years, I learned whatever he says do the opposite and your better off.

They hurt but I have learned a lot from these mistakes.

Bicycle_B

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Re: Your biggest shoulda/coulda's
« Reply #7 on: November 26, 2017, 07:33:32 PM »
In 2010, thinking stocks had bounced back and were unduly supported by TARP, bought a new car because "dealers must be desperate, if I'm ever going to buy new, it's now."  Pre-Mustache obviously.  Bad enough to spend $20,000 more than needed on a car.  Worse to realize that the money spent would be $45,000 or more today just by staying in the stock market. 

2Birds1Stone

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Re: Your biggest shoulda/coulda's
« Reply #8 on: November 26, 2017, 08:00:15 PM »
I invested all of my portfolio into gold and silver back in 2010-2011, wish it had been Vanguard Total Stock Market Index instead.

markbike528CBX

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Re: Your biggest shoulda/coulda's
« Reply #9 on: November 26, 2017, 10:39:53 PM »
If you have to think that "this stock can't possibly go lower" it will.  COHN/IFMI /COHN
Shoulda passed.

IF I had waited 5 weeks in late 2008 to go all in to stocks, I'd have even more than I do now(enough).
But that is what my investment plan said and I'm glad I had it to ensure that I got into a heavy stock allocation near the bottom of the market. 

maizefolk

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Re: Your biggest shoulda/coulda's
« Reply #10 on: November 27, 2017, 05:41:41 AM »
Buying/mining bitcoin in 2009.

My brother-in-law tried to convince me to start mining in 2009, but I didn't. He did and mined quite a few, but apparently lost them (not sure if he doesn't know where he stored them or can't access). I'd imagine he would've had a few hundred thousand dollars right now if he had them still.

But that's all assuming I didn't sell them many thousands of dollars ago, too.

My coulda/shoulda for bitcoin is in 2012 when it was already at ~$100. I know I wouldn't have lost the private key because I did buy and I still have it. Unfortunately I bought ~$40 worth. If I'd bought a few thousand worth instead I'd be FI right now. *shrug*

NoStacheOhio

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Re: Your biggest shoulda/coulda's
« Reply #11 on: November 27, 2017, 08:37:30 AM »
Buying/mining bitcoin in 2009.

My brother-in-law tried to convince me to start mining in 2009, but I didn't. He did and mined quite a few, but apparently lost them (not sure if he doesn't know where he stored them or can't access). I'd imagine he would've had a few hundred thousand dollars right now if he had them still.

But that's all assuming I didn't sell them many thousands of dollars ago, too.

My coulda/shoulda for bitcoin is in 2012 when it was already at ~$100. I know I wouldn't have lost the private key because I did buy and I still have it. Unfortunately I bought ~$40 worth. If I'd bought a few thousand worth instead I'd be FI right now. *shrug*

Ditto. 2011-2012 was around the time I actually looked into Bitcoin. I tried mining, but didn't really get anything. I may have ended up with some fraction of a coin, but long since lost the wallet/key/whatever. I never bought any because I was like "this is just gambling/speculation," plus I was just out of grad school with no job and minimal money. So yeah, I could've converted it to serious money by now (probably would've cashed out in 2015 when we bought our house), but it could've just as easily gone to zero, or been stolen in one of the several capers/shenanigans that have happened over the years.

Timodeus

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Re: Your biggest shoulda/coulda's
« Reply #12 on: November 27, 2017, 02:11:23 PM »
Buying/mining bitcoin in 2009.

This is mine too. I remember graduating in 2010 and first reading about bitcoin while couch surfing looking for work. I knew then it was (or more precisely something like it was) the wave of the future. I had maybe $20 I was thinking about putting into bitcoin, at that time, it would have bought me 20 BTC, roughly $200,000 at today's rates. I recall exactly why I didn't do that, I saw a chart showing it spiking up then plummeting down to around. Too risky I thought, man I missed the boat on that one. I did end up buying that $20 worth of BTC in 2013, riding it up into the triple digits then down again, then exchanging it for one ounce of silver. That silver is worth $17 now, that BTC is now $20,000. I can only laugh otherwise I'd cry. What I keep thinking about, if I had put $100 into BTC when I first saw it in 2010, I could retire now.

Travis

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Re: Your biggest shoulda/coulda's
« Reply #13 on: November 27, 2017, 02:16:27 PM »
Learning investing fundamentals.  I was nearly all-cash until age 30 (I'm 37 now) except for some money in TSP bonds and an outrageously high-fee large-cap mutual fund.  If I simply knew how to invest back then and changed nothing else about my past (didn't become Mustachian until 2013) I'd be at my FIRE point today.

I toyed with the idea of going into real estate around that time since I was sitting on a pile of cash and figured that buying property near a soon-to-be-crowded military base would be a smart move, but alas I didn't know where to start. 

ILikeDividends

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Re: Your biggest shoulda/coulda's
« Reply #14 on: November 27, 2017, 05:48:23 PM »
I've never had even close to a 'ten bagger' but this would have been it.
I bought Apple at around $2 (mere weeks before Steve Jobs came back to save it), rode it up to ten-bagger territory (over $20) and sold out a year or so later.  To suggest I exited way too early would be a monumental understatement.
« Last Edit: November 27, 2017, 06:01:56 PM by ILikeDividends »

surfhb

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Re: Your biggest shoulda/coulda's
« Reply #15 on: November 27, 2017, 06:08:21 PM »
Saving at least 30 measly % of my income when I started working and investing in the stock market.    Id have some FU money

firescape

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Re: Your biggest shoulda/coulda's
« Reply #16 on: November 27, 2017, 06:49:31 PM »
I remember telling my wife 10 years ago that we should quit EJ. I didn't actually commit to getting an education and then taking over our investments and moving to Vanguard until several months ago. I'm glad as hell I finally did do it, but can't help but to wonder how much further we'd be ahead had I done it long ago.

Heckler

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Re: Your biggest shoulda/coulda's
« Reply #17 on: November 27, 2017, 08:30:18 PM »
Taking three or four years to get on the couch potato ETF program, wasting time an money in "energy" mutual funds

MrThatsDifferent

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Re: Your biggest shoulda/coulda's
« Reply #18 on: November 28, 2017, 03:49:44 AM »
3 years ago, when I had a $20k windfall, I should have invested it all instead of spending it spoiling my family and self. Bought so much that I donít even use. And had I discovered MMM a year earlier, Iíd probably be $200k richer now. Damn.

BTDretire

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Re: Your biggest shoulda/coulda's
« Reply #19 on: November 28, 2017, 06:43:33 AM »
About 20 years ago I invested(?) $36,000 in the business I worked for.
That money basically paid me, at $14k a year for a few more years before we closed the doors.
 I loved the job, but it was not good for building wealth.

DavidAnnArbor

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Re: Your biggest shoulda/coulda's
« Reply #20 on: November 28, 2017, 07:48:59 AM »
1992 - when I inherited a small amount of money I should have known about passive equity index fund investing. My parents sure didn't as they invested some of that money in a natural gas scheme that went bankrupt.

Back in the late 90's I shouldn't have invested in these high expense actively managed mutual funds that did so poor over the next 2-4 years as the dot com bubble burst.
Fortunately, though most savings were invested in the SP 500 index.

2002-2003 - I shouldn't have purchased $80,000 in I Bonds - I should have just got more SP 500 index.

2004-2016 - I should have just done 100% equity index funds.

If I made those changes I'd be a few hundred thousand dollars richer now.

aboatguy

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Re: Your biggest shoulda/coulda's
« Reply #21 on: November 28, 2017, 10:54:14 AM »
I wish I would have bought all the C2 corvettes, Panteras, 356s and Shelbys when they were easy to find for a couple thousand bucks....

josh4trunks

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Re: Your biggest shoulda/coulda's
« Reply #22 on: November 28, 2017, 12:34:22 PM »
As several others have said, bitcoin. I never actually "invested" since I was a broke college student living on student loans. I only bought ~$400 in computer parts, and spent time to mine it, from 2011-2013.

I made several choices, that if made differently could have given me more, or lost me less bitcoin.
  • Not trust an online wallet service instead of storing my own wallet. I lost me ~7BTC (maybe $10 at the time) due to hacking and learned my lesson.
  • Mine by myself instead of in a consortium. My GPUs actually mined 50 BTC twice, but since I worked in a consortium I only got paid around ~50BTC over my time mining there. This was pure luck though.
  • Hoard BTC instead of using them as I needed to buy stuff. I was skeptical of people saying its price would explode (I only earned it when it was valued anywhere from $1-13).

Even if I had kept my 100BTC I mined, I doubt I would have sold it at the market 'top'. After graduating in 2012 and getting my first job, I bought an engagement ring, a house in 2013, and got married in 2014, put my wife through nursing school in 2015, and am sure I would have liquidated whatever BTC I had kept for any of those events.

ChpBstrd

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Re: Your biggest shoulda/coulda's
« Reply #23 on: November 28, 2017, 01:59:00 PM »
I think regrets over not buying bitcoin a few years ago for a nickel each don't really count as a "shoulda / woulda". That's like saying you should have bought a lottery ticket with what turned out in hindsight to be the winning numbers. There's nothing to learn from such exercises.

A good "shoulda / woulda" is a bad decision you should have been able to make correctly using the information available at the time. Maybe also include cases when you pursued the wrong objectives, e.g. buying that new sports car to impress everyone when you should have been investing in index funds, getting too greedy/fearful, buying physical gold based on Fox News commercials, etc. A better term for "shoulda / woulda" might be "lessons learned".

Northern gal

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Re: Your biggest shoulda/coulda's
« Reply #24 on: November 28, 2017, 02:34:45 PM »
I think regrets over not buying bitcoin a few years ago for a nickel each don't really count as a "shoulda / woulda". That's like saying you should have bought a lottery ticket with what turned out in hindsight to be the winning numbers. There's nothing to learn from such exercises.

A good "shoulda / woulda" is a bad decision you should have been able to make correctly using the information available at the time. Maybe also include cases when you pursued the wrong objectives, e.g. buying that new sports car to impress everyone when you should have been investing in index funds, getting too greedy/fearful, buying physical gold based on Fox News commercials, etc. A better term for "shoulda / woulda" might be "lessons learned".

I agree.

I went into cash in 2010, worried about markets. My portfolio allocation is still primary residence and cash in 2017. I just got my butt into gear to at least make it term deposits.

I know it is stupid but every time I want to get into ETFs it seems like I just missed a run up and a correction is just ahead.

GardenBaker

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Re: Your biggest shoulda/coulda's
« Reply #25 on: November 28, 2017, 02:57:51 PM »
Wish I would have been maxing out my 401k's and IRAs all along.  Instead I had no idea and just had money sitting in savings accounts for years... deflating.  Of course that gave me the freedom to do (mostly) what I wanted, so it's not bad to have some FU money up your sleeve! =)

^^^This! You just wrote my life story...Oh well, at least I know better now.

caracarn

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Re: Your biggest shoulda/coulda's
« Reply #26 on: November 28, 2017, 03:03:16 PM »
Does marrying my ex count?  If I had not done that I would not have had to split my investments in divorce and would have double my retirement funds right now, so that decision cost me 50%.  In addition to make the separation quick and efficient I also gave away 100% of my equity by fully covering home sale costs while she walked away with her half of the equity, so my overall financial loss exceeded 50%. 

NoStacheOhio

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Re: Your biggest shoulda/coulda's
« Reply #27 on: November 29, 2017, 05:55:29 AM »
I know it is stupid but every time I want to get into ETFs it seems like I just missed a run up and a correction is just ahead.

http://awealthofcommonsense.com/2014/02/worlds-worst-market-timer/

You're welcome. ;-)

J_Stache

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Re: Your biggest shoulda/coulda's
« Reply #28 on: November 29, 2017, 08:13:36 AM »
Thought about buying Bitcoin around $130, but didn't.  The only saving grace is that I probably would have sold it at $300 and would be crying today.

Timodeus

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Re: Your biggest shoulda/coulda's
« Reply #29 on: November 29, 2017, 08:45:01 AM »
I think regrets over not buying bitcoin a few years ago for a nickel each don't really count as a "shoulda / woulda". That's like saying you should have bought a lottery ticket with what turned out in hindsight to be the winning numbers. There's nothing to learn from such exercises.

A good "shoulda / woulda" is a bad decision you should have been able to make correctly using the information available at the time. Maybe also include cases when you pursued the wrong objectives, e.g. buying that new sports car to impress everyone when you should have been investing in index funds, getting too greedy/fearful, buying physical gold based on Fox News commercials, etc. A better term for "shoulda / woulda" might be "lessons learned".

Why shouldn't they count? That's the point of this thread, as the OP said "missed opportunities". I definitely count not buying something for $1 when it now is $10,000 a missed opportunity.  Any speculative investment can be compared to a lottery, but it doesn't mean it's gambling. But using your definition to my own scenario regarding bitcoin-my "lessons learned" is don't be overly dismissive of new financial products and don't let fear of the unknown guide your financial actions. In 2010 I understood what Bitcoin was and heavily suspected it would be the wave of the future but yet due to fear didn't buy it.

Kroaler

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Re: Your biggest shoulda/coulda's
« Reply #30 on: November 29, 2017, 09:12:29 AM »
Does marrying my ex count?  If I had not done that I would not have had to split my investments in divorce and would have double my retirement funds right now, so that decision cost me 50%.  In addition to make the separation quick and efficient I also gave away 100% of my equity by fully covering home sale costs while she walked away with her half of the equity, so my overall financial loss exceeded 50%.

I feel like this post assumes your ex didnt contribute.   As someone potentially about to go through the process of splitting all assets 50%, I feel comfortable saying that my wife earned 50% of those assets.

ZiziPB

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Re: Your biggest shoulda/coulda's
« Reply #31 on: November 29, 2017, 09:22:24 AM »
Allowing my husband to deal with all of our investments while we were married instead of learning the basics myself.  He's a market time and made some big mistakes with our money.  I've fixed it after we divorced - I'm very comfortable handling my own portfolio now.

ChpBstrd

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Re: Your biggest shoulda/coulda's
« Reply #32 on: November 29, 2017, 12:01:04 PM »
I think regrets over not buying bitcoin a few years ago for a nickel each don't really count as a "shoulda / woulda". That's like saying you should have bought a lottery ticket with what turned out in hindsight to be the winning numbers. There's nothing to learn from such exercises.

A good "shoulda / woulda" is a bad decision you should have been able to make correctly using the information available at the time. Maybe also include cases when you pursued the wrong objectives, e.g. buying that new sports car to impress everyone when you should have been investing in index funds, getting too greedy/fearful, buying physical gold based on Fox News commercials, etc. A better term for "shoulda / woulda" might be "lessons learned".

Why shouldn't they count? That's the point of this thread, as the OP said "missed opportunities". I definitely count not buying something for $1 when it now is $10,000 a missed opportunity.  Any speculative investment can be compared to a lottery, but it doesn't mean it's gambling. But using your definition to my own scenario regarding bitcoin-my "lessons learned" is don't be overly dismissive of new financial products and don't let fear of the unknown guide your financial actions. In 2010 I understood what Bitcoin was and heavily suspected it would be the wave of the future but yet due to fear didn't buy it.
Would this post be educational if 500 people all chimed in to observe that e-currencies have been the highest returning "investment" of the past several years?

Timodeus

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Re: Your biggest shoulda/coulda's
« Reply #33 on: November 29, 2017, 02:08:19 PM »
I think regrets over not buying bitcoin a few years ago for a nickel each don't really count as a "shoulda / woulda". That's like saying you should have bought a lottery ticket with what turned out in hindsight to be the winning numbers. There's nothing to learn from such exercises.

A good "shoulda / woulda" is a bad decision you should have been able to make correctly using the information available at the time. Maybe also include cases when you pursued the wrong objectives, e.g. buying that new sports car to impress everyone when you should have been investing in index funds, getting too greedy/fearful, buying physical gold based on Fox News commercials, etc. A better term for "shoulda / woulda" might be "lessons learned".

Why shouldn't they count? That's the point of this thread, as the OP said "missed opportunities". I definitely count not buying something for $1 when it now is $10,000 a missed opportunity.  Any speculative investment can be compared to a lottery, but it doesn't mean it's gambling. But using your definition to my own scenario regarding bitcoin-my "lessons learned" is don't be overly dismissive of new financial products and don't let fear of the unknown guide your financial actions. In 2010 I understood what Bitcoin was and heavily suspected it would be the wave of the future but yet due to fear didn't buy it.
Would this post be educational if 500 people all chimed in to observe that e-currencies have been the highest returning "investment" of the past several years?

Educational?-No, probably not. But it would be cathartic. This is a forum, let people with similar stories commiserate. 

surfhb

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Re: Your biggest shoulda/coulda's
« Reply #34 on: November 29, 2017, 04:30:28 PM »
Wasting my time in college would be a big one.    Learning a trade or going for a gov. job would have been a good thing for me in hindsight. 

SnackDog

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Re: Your biggest shoulda/coulda's
« Reply #35 on: November 29, 2017, 05:48:16 PM »
My father strongly recommended I buy AAPL in ..... 1981! The CAGR since then is about 25%.

ILikeDividends

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Re: Your biggest shoulda/coulda's
« Reply #36 on: November 29, 2017, 07:59:25 PM »
My father strongly recommended I buy AAPL in ..... 1981! The CAGR since then is about 25%.
You would have had to have a pretty strong constitution to ride that stock down to ~$2.00 in the mid '90s.

Scully wrecked that company, until Jobs came back to rescue it.

I was in that stock in the '80s, and got out when Scully pulled his coup.  What could the ex-CEO of Pepsi know about selling computers, eh?

But, obviously, your dad turned out to be correct, in the end.
« Last Edit: November 29, 2017, 08:12:57 PM by ILikeDividends »

talltexan

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Re: Your biggest shoulda/coulda's
« Reply #37 on: November 30, 2017, 10:00:15 AM »
I'm disappointed in myself for holding too much cash during 2009-2013 (my wife and I were DINK during the first four years). Would have

Kroaler

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Re: Your biggest shoulda/coulda's
« Reply #38 on: November 30, 2017, 10:04:50 AM »
I'm disappointed in myself for holding too much cash during 2009-2013 (my wife and I were DINK during the first four years). Would have

I got my first real job in 2010 making about 50K at 19 with only an associates degree.      I didnt invest a single dime, not so much as a tiny 401k contribution until 2013... So I feel your pain....    Man if I could go back just a few short years and have a chat with myself...

Dicey

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Re: Your biggest shoulda/coulda's
« Reply #39 on: November 30, 2017, 12:09:28 PM »
I could write a long list, but I got to FIRE eventually, so fuck it. It all worked out fine in the end. My five-year FIREversary is next week.

ChpBstrd

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Re: Your biggest shoulda/coulda's
« Reply #40 on: November 30, 2017, 08:55:29 PM »
I could write a long list, but I got to FIRE eventually, so fuck it. It all worked out fine in the end. My five-year FIREversary is next week.

I wrote myself a list at one point, to confront my regrets and get over them. This might seem like strange behavior from a post-FIRE perspective, but there's a certain bitterness you have to choke back when you're facing a 7 year sentence in cubicle prison and you know your own boneheaded choices put you there. Mine included things like:

-picking a low-pay college major
-prioritizing the purchase of a house
-trading up to a bigger house
-driving a truck for years
-buying a fixer-upper investment property and pouring my energy into it instead of getting a master's degree 5 years earlier than I did. (I earned minimum wage or less on that adventure)
-buying high-dividend stocks instead of growth stocks
-buying a boat
-sticking with a relatively conservative stock allocation from 2009-2015 (cost estimate: $250k).
-I once bet, and lost, $5k on gold puts before I understood much about how options worked.
-I sold an AMZN $1,000 strike call option last summer because I was down 25% on a $5k investment (trying to avoid my earlier mistake with gold). Had I held I would have quadrupled my money.
-I was sitting in a master's-level economics classroom in late 2008, learning about monetary velocity and how the great depression occurred, realizing that the government was doing all the correct things to avoid a depression right at that moment, and STILL failed to go all-in and stay all-in in the midst of the SECOND crash of my investing career.

The net value of these mistakes? Probably millions. Yet, the satisfying part - maybe only to me - is knowing the following: You had to learn these lessons, you'll never make those specific mistakes again, and the universe of mistakes you are vulnerable to has shrunken by that many. Learning and chicken pox are a lot alike.

It wasn't all a self-beatdown. I also wrote a contrasting list of things that I did well, especially if I went against trends to do so. E.g. maintaining full-ride scholarship at a state school, doing my own house and auto repairs, always earning the 401k match even when my pay sucked, marrying a relatively high earner who's also frugal, etc. The exercise was worth it.

talltexan

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Re: Your biggest shoulda/coulda's
« Reply #41 on: December 01, 2017, 08:11:51 AM »
I honestly think marrying the right person--all on its own--probably cancels out about all of those bad decisions. Before you get to any of the other smart moves you listed.

caracarn

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Re: Your biggest shoulda/coulda's
« Reply #42 on: December 01, 2017, 10:50:13 AM »
I honestly think marrying the right person--all on its own--probably cancels out about all of those bad decisions. Before you get to any of the other smart moves you listed.
+1

soccerluvof4

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Re: Your biggest shoulda/coulda's
« Reply #43 on: December 09, 2017, 05:02:27 AM »
Shoulda stayed in the first house I ever bought it was plenty big and could of remodeled 10xs over for money I lost on real estate

Shoulda not believed the words " I cant get pragnents" got married because thought was right thing to do , divorced and lost ton of money and paid out a fortune over years

Shoulda sold my business years before I fired with the big offer I got because would have double my fire account but didnt know things would go the way they did in my defens.

Shoulda invested and saved all along over the years I worked if not at least 15%  instead of having the mentality I will always make a ton of money and played catchup last 8 or so.

But at least I turned it around thanks to MMM and was still able to pull a rabbit out of my hat and be fire'd at 50!

RedmondStash

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Re: Your biggest shoulda/coulda's
« Reply #44 on: December 09, 2017, 10:19:38 AM »
Putting my trust in investment advisors when I was younger, thinking that they had magical stock or fund picking powers. Now I know to stick with index funds on my own and that no advisor should ever attempt to beat the indexes.

This. I actually had some small index-fund investments that I let our financial advisor talk me into putting into her hands to reinvest. If we'd gone the full index-fund route 10 years sooner, we probably could have FIREd 5 years sooner, and with a bigger cushion. Ah, well, live and learn. At least we're managing our own investments and in index funds now.

tallen

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Re: Your biggest shoulda/coulda's
« Reply #45 on: December 10, 2017, 03:04:14 PM »
I wanted to buy a bitcoin (at the time I was unaware you could invest how much you wanted and I thought you had to buy the whole thing) and found out they had just passed $500. Decided to wait and see if the price dropped. Should have just bought it :(

BudgetSlasher

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Re: Your biggest shoulda/coulda's
« Reply #46 on: December 10, 2017, 03:39:53 PM »
I remember in 2009 thinking I could spare a couple hundred to a thousand dollars in bitcoin, but then I convinced myself I was just being geeky and bitcoin would be gone in a year or two . . . so  that month I put that grand, plus 2 more, into T. Rowe Price Capital Appreciation Fund.

I could drive you 5 hours away walk you up the hill and point to the exact spot in the road I was walking over when I had the thought.

waltworks

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Re: Your biggest shoulda/coulda's
« Reply #47 on: December 10, 2017, 06:49:29 PM »
I think regrets over not buying bitcoin a few years ago for a nickel each don't really count as a "shoulda / woulda". That's like saying you should have bought a lottery ticket with what turned out in hindsight to be the winning numbers. There's nothing to learn from such exercises.

A good "shoulda / woulda" is a bad decision you should have been able to make correctly using the information available at the time. Maybe also include cases when you pursued the wrong objectives, e.g. buying that new sports car to impress everyone when you should have been investing in index funds, getting too greedy/fearful, buying physical gold based on Fox News commercials, etc. A better term for "shoulda / woulda" might be "lessons learned".

Indeed.

I paid off a 5.5% mortgage in 2009 when my wife was halfway through grad school. Had enough money to put ~$200k into the stock market but I knew *nothing* about the stock market at the time. If I'd done just a little bit of homework (and I was a statistician at the time!) I would be much richer than I am now.

I mean, I'm glad I didn't spend it on hookers and blow or something. But we sold the house 3 years later anyway, so that 5.5% interest... not such a big deal.

-W

RedmondStash

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Re: Your biggest shoulda/coulda's
« Reply #48 on: December 10, 2017, 06:53:12 PM »
I mean, I'm glad I didn't spend it on hookers and blow or something.

Well, that puts it into perspective, lol. I am similarly glad. We could be way worse off than we are.

talltexan

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Re: Your biggest shoulda/coulda's
« Reply #49 on: December 11, 2017, 08:47:11 AM »
I actually regret spending exactly $0 on hookers/blow. Some positive amount in my frivolous youth might have been nice ;-)