What are the best and worst things you’ve ever done financially? Doesn’t necessarily have to be about the money made or lost, could be a titling or trust mistake or win. Trying to build out different wealth strategies and pitfalls to avoid, thanks!

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Best - got married to someone that shares my financial goals and attitudes.
Close second best - taking a year off work to travel the world with my spouse.

Worst - buying things because of FOMO.
Second worst - working in public accounting with lots of independence restrictions.

likesmarthelpful

No, actually, he found it was a great way to connect with the interviewer on a non-technical subject. People generally seem to like traveling and discussing travel!

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I don’t know if I would call it worst, but I was extremely conservative in allocating money until about a year ago. Paid off student loans instead of buying multi family RE in 2014 in a market that has subsequently 3-5x’d, didn’t put any money into crypto and just did a steady three fund strategy, etc. I did fine but some of my friends absolutely crushed it. My income is pretty high now so my risk tolerance has gone up and I don’t regret the past conservative investing or increasing my risk tolerance now but it does seem that I’ve been unlucky in timing.

likesmart

That’s awesome P1 hopefully you get there!

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Worst financial decision - bought a boat.

Best experience decision - bought a boat.

likefunny

I also grew up on a boat every summer during my younger childhood. Loved it. Also taught my why I don’t want to own one. 🤣

likefunny

Worst - tithing

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I just don't support churches anymore.

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Bought a house with 20% down in 2016. Sold it in 2020. Made $300k profit on a $115k investment.

This was my primary home so not a real investment, but definitely learned what Leverage meant.

likeupliftingsmart

worst: took out full loans to attend law school
didn’t invest or contribute to retirement accounts until well after 30
didn’t get born into a family with more financial savvy to share

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worst thing i’ve done-
1. graduate a non target public school with a general studies degree
2. was an idiot in my early twenties and spent/overspent my paychecks living a high roller life in a VHCOL city (Boston)
3. didn’t max out my 401K asap
4. spent too much on rent for 2 years

best financial things-
1. did not pick my dream undergrad so that i graduated with a reasonable amount of debt
2. i have a saved up 6 months emergency fund
3. max out my 403b
4. marry an anesthesiologist 🙃💅🏾

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Don’t invest in ARKK might be a good strategy. Cant think of any big mistakes I have made. I think the best thing I have done is ignore my balances and just invest whenever I have the money into diversified funds.

likefunny

Don’t we all…

But now that we’re here, forgetting the past. What would you do going forward?

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32year old SE
Worst: not buying a house when I could and was living with roommates.
Didn’t change jobs and stagnated near 100k for 7years as a cloud software engineer who had lot more opportunities, blamed immigration but I could have still changed.
Not investing my savings into stocks sooner to take advantage of the boom cycle.
Started investing significantly in last two years at the peak of the economic cycle and now sitting on high losses.
Pretty stressed for my financial future and paranoid about impact of the economic cycle as I missed out on best decade and now entering a down decade if I read news right.

Good: explicitly asking for raise and promotion and pushing my salary to 150 in last two years from 105.

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BTW, “somehow holding” (or even buying in) isn’t the most pleasant, but when you have a long time horizon, the company is good, thee is extreme fear, and the outlook is binary (either the system will collapse or it won’t and things will eventually recover), it’s easier to pay $5 for something that during booms times can be worth $100 over buying something “during” boom periods at $100 and hoping to sell it for $200…

Best - I married someone who’s grandfather paid for my Bachelors degree. We’re divorced now lmao

Worst - dogecoin lol

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Ugh biggest mistake was not starting sooner with saving and investing.

I started working at 14 in retail (lied about my age lol) and by the time I was 18, I also added part time gymnastics coaching at 21$/hour. If only I had started saving then instead of wasting it buying stupid teenage things...the difference time makes and how you can't get it back 🥲

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same, friend. same.

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Best: started funding my 401k from day one and increased my contribution with every raise until hitting the max.
Worst: traded a leased car in early to buy a different new one instead of just buying the leased car at the end. (Bonus points: I now live in Manhattan and never drive the dang thing)

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Best - bought AAPL at an average price of 18, many years ago

Worst - waited until 2018 to buy an apartment when I easily could have as far back as 2012-13. Missed a pretty sweet run up in prices in my area

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Worst - taking out 150k in student loans for a fine arts degree.

Best - living way below our means (saving/investing 60+% of our HHI)

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Uhhhhg I’ve always thought about doing a MFA but sooooo expensive

Best (completely by chance) : bought a house in early Covid for 650k that has doubled in price.
Best (by design): hardly ever falling into to FOMO and hype as it relates to investments. Mostly stuck to stuff I understand clearly.
Worst: sold a few rental properties in 2019 which could have fetched me another 150k easy.

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Add another Best - core philosophy, thankfully shared by my wife: living way within our mean. Typically, 50% of take him goes to savings. This after contributing to 401k etc.

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Best: joined military as an officer. 4 yrs of service led to two bachelor degrees, masters, and MBA from top tier schools, all paid for. Free in state public tuition for kids and utilized VA jumbo mortgage at 2.25% with nothing down on a $1.25M+ house.

Worst: too risk adverse on investments. Value strategy is working now, but missed out on a lot of momentum

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Put my sizeable sign on bonus into Crypto in December 2021 🙃

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Worst financial decision was to have children.. Currently in toddler stage. Paying dividends in love..

likefunny

Best: bought house at bottom of market in 2012; married someone good with money; spent less than $3k on wedding

Worst: didn't invest in stocks in 20s; tech tilt/arkk in 2021

Coast fire now in early 40s

likeuplifting

My worst decisions have been purchasing new vehicles. The last vehicle I purchased was used with 20k miles and I saved considerably. No more new cars just good used vehicles 2-3 years old!

likesmart

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