If you are over the age of 40 and have some history to look back on,...what was the best and worse financial decisions you have made in your life?

In 1994, my best decision was to quit being a Tenant and buy my first house. I remember how scared and nervous I was at the closing table of that first house. Now, closings are a breeze and are a welcomed event!

In 1996, my worse decision was to allow a Morgan Stanley stockbroker to convince me to invest in his company's mutual funds. My broker made money,...I lost money.

Best decision: take control & responsibility of my finances instead of outsource this to someone else.

I wanted to buy a house in my track for $58K. My wife thought it was too close to ours. Worth close to $800K today. Worst

Best decision has easily been investing in real estate. Although some of the decisions within that have been better than others, from a long-term viewpoint there are no bad ones within that.

Best,

Opening a Bank Account at age 12.

Along with:

Having a Paper Route. (No bike. Had to walk it)

Push mowing several Neighborhood Lawns,

and Pulling Weeds.

( Lesson, Self-Reliance )

Worst :

Sid,

ROY

Roy...42 but can out run most 20-somethings. I credit consumption of modest amounts of micro-brewed suds and Coors for my svelt figure and youthful good looks. (wink)

I'm not the kind to look back and say: "what if".

After buying my first rental and getting it rented, I bought a second one...on the same block.

Best decision, not buying myself a new car at age 16 and instead saving towards a down payment to buy a house. At 18 I did make an accepted offer and purchased my first house.

Best - getting involved in rentals. It's a job that I love. Find something you love and you'll never work, well I haven't worked a day at the rentals. Had to fight the first wife to make every purchase, but it's been worth it.

No Marriage, No Kids ?

Best financial decision: marrying my third husband (31+ years ago.) And yes, I mean that financially that was the best thing I've done.

I just asked him. He said marrying me was his best financial decision too, so we are on the same page there.

Best: maxing out my husbands 401k and forgetting about it. There have been many years where we could have used that money, which is a significant amount for us. He’s coming on 30 years of working and it gives us comfort that if the real estate market crashed we will still be ok.

Best and worst, all rolled up into one. My rental homes.

They cost me a wife that I loved, a 'home', and sleepily read, nighttime literature, w my amazing kids. Then again, here I am, after 20-ish years of practicing this craft, and they've finally begun to deliver the late night promises that Carleton H. Sheets, said they would. ;)

Best was stepping up to save my dad's rental business after he passed and mom couldn't handle it.

Well only 37 but been on my own since the week after I graduated high school so almost 20 years hope that’s good enough.

Best: Getting into the rental business. Wish I would have done it at 18 when I had a chance to buy a duplex to live in.

I find it interesting that the best or worse financial decisions seem to revolve around who you chose to marry.

@REMAVEN [PA]) - same here for the worst - sold it at a loss of 90K after 10 years

@Roy - Marriage is the riskiest financial decision you will ever make. Its just that no one tells you that up front.

To answer your question....

Worst decision: listening to DH and investing with a "good friend" of his who was a financial planner. When the market dropped 50% in 2008-2009, our investments dropped 65%. At least I had only agreed to let him invest half of our savings.

I have two bests and a worst.

Best: Buying my beach house on what became one of the most expensive residential blocks in the world. And selling after 15 years with enough equity to never have to work again.

2nd best: Switching my apts to 62 plus senior living. Went from constant headaches to nearly hands off. And a tenant cooked us dinner tonight!

@ 1Gr81/NC, just curious how your rental business cost you your first marriage (your first response above)...if it's not too personal?

@ Otis/IL, keep it up...your still on track. Nice work.

There seems to be a great disparity for sure: Either your marriage (or a previous marriage) was the worst choice you ever made...or your spouse may have been an inspiration and helper along the way. Luckily for me it was the latter.

Best decision: learning all I could about investing and real estate when I was young.

Worst Financial Decision: thinking my education gave me the ability to be a stock picker during the dot.com era. My naivety lead me into buying/selling options, shorting, and other things best left to Goldman Sachs. I lost probably $200K at a time when I was in my 30's, and needing to establish a foundation for our economic future

JB, As you can imagine, that very long conversation, with it's many nuances, would take many nights of darts and beers in a garage of a good friend, to unpack. Even longer to spend w the thoughts that stay with you, long past when the conversation is no longer appropriate. Trust me.

That being said, the short version....She hated the homes, they triggered her always present anxiety, she was a pathological liar, who regrettably was in charge of the Post office, books, and the deposits. She had this funny quirk of not telling me when a tenant had stopped paying....for months. So yeah...problems. I, in no way am blameless, but that conversation will need to be in your garage. :)

Best decision - multi family housing.

I noticed that some of the worst decisions are missed opportunities.

I'm turning that around: my best financial decision is I never buy lottery tickets, or help out a Nigerian prince on the internet.

Best decision: marrying sweetie. 38 wonderful years together this week.

Oh, you meant financial...

Choosing the right spouse IS a financial decision. And one of the best I've ever made.

Best strictly financial decision: listening to my father's financial advice. It was very simple: 1. Give the first 10 percent to God. 2. Invest the second 10 in long term savings. 3. Live on LESS than the remaining 80 percent. 4. Never use credit for anything that loses value (car, vacation, furniture, etc.)

Hmmm. Best was the very risky decision to promise an old lady that we could buy the tri-plex she bought for her dead son and have her back to Oregon by Christmas. We did that on December 19 - with no bank loans, no $$ and the knowledge of about 40 library books on how not to be broke. That led to me making about 20 phone calls to banks - whose loan officers were already on Christmas vacation, and so, all 20 said "no." Ended up putting the $45,000 triplex on a deck of credit cards (all with credit limits of around $1,500-$2,000) at a local bank. Added another $8,000 on credit cards to have a foundation poured beneath the building in the next 2 weeks. Closed on the tri-plex December 23, and then made an astonishing number of phone calls to bankers who laughed - yes, laughed - when I explained what I did. I continued to make calls, and finally got to speak to a bank president who listened patiently, believed in us, and agreed to loan on the tri-plex on the condition that I NEVER do that again. (This was back before cash-advance fees, by the way.) With a new foundation, the place was completely lend-able, and we made a lot of money on it.

Roy,

Best: getting myself to Convention

Worst: waiting so long to go there.

Best: building like a crazy person on fire because Inhad a burn for FREEDOM!!!

Worst: letting years slip away, just piddling with the biz before I got the burn.

Well I’m not 40 but hubby is 53 so I’ll answer for him. WORST decision was not wanting another house payment so we stopped paying credit card to have the cash and still can’t “catch up” talk about STUPID. But you live , you learn right? (We acquired unexpected properties too quickly).

Best decision: investing in real estate

Best: marrying my wife

Best decision was to become a landlord.

Ain't that the truth, Mike (PA).