Ask the Readers: What was the BEST Investment Decision You Ever Made?

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The path to financial freedom is not an easy one. It takes a lot of effort to get there, and many will fight their entire lives and still not get to the point where their passive income exceeds their expenses each and every month.

We all take our bumps and bruises along the way, and if you’ve invested in the markets for awhile, I’m sure you’ll agree that the journey can feel a lot like riding a rollercoaster on many occasions. Still, rain or shine, highs or lows, regardless, we keep on investing because we have full conviction that we are doing the right thing to better our futures.

Good earnings and an even higher savings rate are just some examples on how to shortcut the time it takes to get to financial nirvana. Also, depending on the investment decisions you make along the way, this can help greatly expedite your progress, or set you back a few years. Whether it be luck or skill, the right moves do make a huge difference in the grand scheme of things.

At this point, I would like to ask everyone, “What was the BEST investment decision you ever made?”

  • Best stock decision.
  • Best real estate decision.
  • Best lending decision.
  • Best business decision.
  • Best knowledge (growth) decision.
  • Etc.

This is a very open-ended question, and can mean more than just a simple transaction event (e.g. buying or selling). For myself, and many other freedom fighters, I’m guessing the decision to actually get started with investing was one of the best investment decisions ever made…

And getting started is tougher than it might sound. When you are new and green, everything seems overwhelming and excessive. I remember when I first decided to start investing in stocks in late 2011 and began researching individual companies… Not only were there a million terms to learn, but just the sheer number of publicly traded companies that are out there is mind-boggling… “Oh boy, this stuff is going to take a lot more time to sink in and marinade than I thought!”

Anyway, if I was going to answer with the best investment transaction decision I’ve made over the last 4 years on the journey to early FI, I’m going to go with the following:

  • Purchasing Rental Property #1
  • Purchasing Rental Property #2

I know that ‘decision’ should be singular and not plural, but I’m electing to go with those two transactions because they were nearly identical, and really just the same move duplicated twice.

  • I purchased Rental Property #1 in August 2012 for $315,000. I put in 25%, or $78,750 to close escrow. It most recently appraised at $435,000.
  • I purchased Rental Property #2 in February 2013 for $290,000. I put in 20%, or $58,000 to close escrow. It most recently appraised at $440,000.

The reason those transactions rank at the top of my list is because they presented a very unique opportunity that rarely occurs in my local real estate market:

  • The ability to generate strong cash flow on Day 1 with typical 20% downpayment.
  • Opportunity to buy at a significant discount relative to previously set all-time highs.

I wasn’t a real estate investor prior to 2012, but from talking to other local investors, I’ve learned that investing for cash flow prior to the subprime market crash of 2008 was a foreign concept. Back then, the only reason to acquire rental properties in the Bay Area was to speculate on future price appreciation… Yes, that’s a risky proposition, and a lot of investors paid the price (literally) when the housing market collapsed and they were unable to support the negative cash flow each month.

Crazy or not, it was the norm back then… and it’s starting to become the norm again today (scary thought). Right now, it’s extremely difficult to find a cash flow positive property in the Bay Area… unless you are willing to force cash flow by putting in a very large downpayment (30%+)… Or, unless you can get lucky enough and lease out to a corporate tenant who is willing to pay a premium for rent + ammenties. In general, when you have single family homes pushing north of $650,000 (even in mediocre locations), and renting for only $2,800/month, the numbers simply don’t work. Townhouses and condos can offer better cash flow potential… but even most of those options will still be cash flow negative on Day 1.

Today, with the benefit of hindsight, I really believe that these two moves were the best financial decisions I’ve made in my life (so far). With two cash out refis completed recently, I’ve now pulled back out all my investment capital (and then some) on each property.

Looking back, I can’t say that I had enough experience back then to know what I was doing; I simply got lucky and found myself caught up in the right place at the right time. In the future, if such a wonderful investing environment presents itself again, I will have the knowledge and experience to know that opportunity is indeed knocking… and pounding loudly on the door! It will be time to capitalize, once again.

Sometimes, it’s better to be lucky than good… Or, as they say, “luck is when opportunity meets preparation”. But you have to play the game to have a shot.


What was the BEST investment decision you ever made?

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14 Comment authors
NazarFI FighterGen Y Finance GuyJoshua MyersA Frugal Family's Journey Recent comment authors
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Gen Y Finance Guy

I don’t know if I have the best investment decision I ever made, but as you pointed out, it would have to be that I started….

But the best decision I have ever made that will effect my path to financial freedom and expedite that path would be moving our of Orange County about an hour where the cost of living was much cheaper.

The move alone allowed me to buy a house for half the money that was 4X’s the size of anything I could buy in the OC. This allowed me to reduce my expenses by $1,500/month…which goes right back into investments. Now I am looking at where I might have more fat to trim without lowing my standard of living.



Best real estate investment – Rental property #2 in summer 2011 for $115K with 20% down. Worth approximately $200K. Monthly mortgage (including taxes and insurance) is $700. Renting for $1500.

Best stock investment – BAC at $6.55/share. I wish I bought double the quantity.

Best business decision – Marrying my husband! LOL Always good to find someone with the same financial ideals.

J. Money

Interestingly enough, 10 of us bloggers just answered this exact question over at Daily Finance! 🙂

My answer:

My best investment I ever made was listening to my father 10 years ago and finally investing into my 401(k). It was the first time in my life I saw money actually pile up, and once I realized employers then give you money on top of what you put in, I was hooked. My pot grew from $500, to $5,000, to $50,000 and right on up to $200,000 before I left to go work for myself. Compounding is no joke with investing, and especially when you get free matches on top of it!


My best investment is probably start RRSP contribution and taking the work’s RRSP matching policy. Free money is always good right?

My Dividend Pipeline

FI Fighter,

Making the decision to pay off my house in 2009 was my best decision. I will never forget the feeling walking into the bank in October of 2010 when I made the final payment. The tellers and bank manager gave me a round of applause as they handed me my receipt. In the years since, I have been able to focus on building my passive income.



kudos to you MDP. Thats awesome!


My best investment decision was near the end of 2010 I sold three quarters of all my investments (I was 100% invested in Canada) and transferred the cash from CAD to USD and used it to buy US stocks. At that time the CAD was worth $1.05 versus the USD. Now the CAD is work about $0.80 which is 25% profit just on the cash. Since I invested that money in stocks, I have almost tripled my money in a bit over four years.

I was lucky enough to get into companies that took off like BAC, MCK, GILD, MA and DIS to name a few. It’s easy to look back and say it was a good idea, but at the time there was a decent amount of risk.


I’m young, and working with little as far as investing, but I want to learn, and slowly but surely, become a wise investor.

The best single investment I think I made? I bought 1.081 shares of BP on 1/5/15. I used my old sharebuilder account as I found a promo code to get a free trade. (One of the reasons I don’t use sharebuilder much anymore is commission simply isn’t worth it most of the time.)
It is up by over 16%, and I know BP has a great dividend.

Other moves I’ve made that I know were smart, were reducing fees. I switched from this to using Lendingclub, Loyal3 and Betterment.

I even changed from betterment to Wisebanyan once I could, because zero fees. Moving some AT&T stock I received from my uncle out of computershares and to Ameritrade stopped them from cutting themselves 5% of the dividend I received when it got reinvested.

No Nonsense Landlord

Not jumping in on investment properties in 2006/2007 when prices were too high. I made offers, but they were way too low for the ultimate sale price.

Then, in 2008, purchasing properties that met my investment objectives, and exceeded them. Today, they are producing a solid 6-figure profit, and have been for a few years.


best decision made was to put away $X a year into a ‘Wealth Fund’ and building a sound investment process.

I wouldn’t call any of my investment success of 100-200% gains as my decision. a rising tide tend to lift all boats so i attribute more to luck than talent in the equation success = luck + talent

A Frugal Family's Journey

The best investment decision I ever made was increasing my 457K contribution following the 2009 market collapse. I went from contributing 3-6% simply to get the company match to contributing 15-20% and maxing out my annual contribution for 3 straight years. Since then, my 457K portfolio has triple in value!! AFFJ

Joshua Myers
Joshua Myers

Paying off all consumer debt and getting on a budget. Hands down the best money decision I’ve made so for. I’m starting to think about paying off my real estate loans too.

Gen Y Finance Guy

Second that Joshua Myers. We just paid off my wife’s car loan and only have our mortgage left. Which we are working to pay off within the next 7 years.


My best decision was knowing when not to buy. In 2006, stocks started getting overvalued, so I put extra funds into mortgage prepayments and paid it off in full. When I was laid off in 2008 during the great recession, I had zero debt and my only concern was finding a new job, which happened a few months later. At that point, Stock prices were an excellent value and I used my severance funds to buy various securities at a discount. I wouldn’t have been able to do that if my funds were spent servicing debt during that period of unemployment.