12 Investing Mistakes I’ve Made (and How You Can Learn From Them) Print
Wednesday, 26th September 2007 (by J.D.)This article is about Investing, Real-Life
This is a guest post from Pinyo, author of Moolanomy, a personal finance blog about money, wealth, investing, and more.
I’ve been investing since 1996. In the process, I have learned a lot, mainly from trial and error. I’d like to share my experience with you. Here are some of the mistakes I’ve made:
- Not investing soon enough — I have been working part-time since my first year at college in 1991. If I had known what I know today, I would have invested my money in an IRA from day one. But like many other young adults, I was thrilled to have money and to spend it all on things that I enjoyed — movies, games, electronics, etc. If I had invested just $2,000 per year while I was in college, that $8,000 invested in an S&P 500 index fund would be worth about $36,000 today.
- Not knowing the basics— When I finally began investing, my first move was to give my money to a full brokerage firm to invest for me. I didn’t know anything about stocks or mutual funds. I just knew I should invest money to make more money. This was a big mistake since each trade executed by my broker cost a lot of money. Also, the mutual funds they picked weren’t good, and were very expensive.
- Chasing past performance — Once I got smart enough to switch to a discount broker, I committed another mistake. I chose mutual funds based on their past performance and Morningstar rating. I picked several loaded / high expense-ratio funds that lagged the general market in the subsequent years.
- Experimenting with my IRA — Back then I had tons of ideas. Unfortunately most of my money was in IRA, so I experimented using my retirement money — big mistake! First, money lost in an IRA cannot be replenished. I was allowed to deposit $2,000 per year and that was the limit. Second, I could not claim my losses as tax deductions. Since the IRA was tax-sheltered, the loss was simply a loss. [Learn more about IRAs.]
- Not paying attention to expense ratios — Not until recently did I realize how badly expense ratios can affect investment performance. I always thought “it’s only 1%, what’s the difference,” and went for the investment with better performance. I finally ran some numbers and I was shocked to learn that a difference of 1% can lower my investment performance by 25% over the course of 30 years. Instead of ending up with $1 million, for example, I might only have $750,000.
- Not paying attention to distributions — This is another number that I did not pay attention to back then. I held some funds in my IRA and some in my regular account. For a couple years, I thought high distribution was really cool because I was making more money. How silly was that? Now I realize that I am paying other people’s taxes when I get mutual fund distributions. Now with my regular account, I invest either in low distribution funds or in ETFs. (Distributions do not affect IRAs.)
- Not paying attention to asset allocation — Way back when, my investment was mainly in large-capitalization U.S. stocks and funds. I did not know about asset allocation as a risk management and performance enhancement tool. It wasn’t until 1999 — when I became eligible for a 401k — that I started giving asset allocation serious thought.
- Ignoring diversification — Again, with little experience and little money to invest, I was going after high-flying stocks (at least I thought they were) and did not pay any attention to diversification. Like asset allocation, it took me a long time to realize how diversification helps to reduce risk and enhance performance. The value of diversification became apparent to me at about the same time that asset allocation did.
- Selling winners and keeping losers — This was my all time weakness. I knew the concept of “buy low and sell high.” So with little experience, I ended up selling a lot of my winners like Staples (SPLS), Ameritrade (AMTD), and Microsoft (MSFT) to lock in the gain; but held on to my losers like Flemings (FLMIQ) and eToys (ETYS).
- Cost averaging down — This was another “buy low and sell high” mistake. Not only did I hold on to my losers, I bought more shares in hope of lowering my cost basis and reducing my losses. I did this blindly without additional research to find out why these losing stocks went south.
- Investing without a goal — Not until recently did I define a real goal for my investment — among other things, one of my investment goals today is to build a $1 million investment portfolio by 2017. This is my main retirement portfolio. Other goals, which I am still defining, are investing to subsidize my kids’ college expenses and my parent’s retirement expenses. Without a clear goal, I was chasing short-term performance and was prone to act on market swings.
- Selling on corrections & buying at the top of the market — These are symptoms of not having a clear goal. Since I was chasing short-term performance with the objective of making more money. I occasionally gave in to my emotion and sold my investments during corrections to protect my gains. Occasionally, I did come out ahead, but most of the time I ended up rushing to reinvest my money as the market invariably rose after these corrections.
As you can see, I was not a very good investor, and it took me a long time and too much money to learn from my mistakes. I hope that by sharing these common pitfalls, you can avoid some of them on your journey. Good luck with your investing!

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September 26th, 2007 at 5:15 am
Great lessons. Posts like this are why my 401k is entirely in index funds, including a Europe/Australia/Far East (EAFE) index, along with 10% bonds and 10% money market. And one weakness, 5% company stock. But it pays dividends, so by the time I retire it would have to have fallen more than 50% to lose value. Maybe more with the dividends being reinvested… Too much work to do the real math on that one.
Number 6 is a very good point though. Dividends are great for tax-sheltered accounts, but otherwise taxes have their way with them and you get the leftovers.
September 26th, 2007 at 5:53 am
@J.D. - thank you for the opportunity to present my work to your readers. It’s a huge honor.
@Justin - thank you for the comment. I now keep my company stock at 5% as well. Used to have too much and it plunged — the lowest point was at 4.5% of the high point. That really hurts.
September 26th, 2007 at 6:32 am
Great list, thanks! I don’t know anything about distributions, but once I open a non-401k investment account (still on the horizon!), I’ll be sure to learn what they are, and how to avoid them.
Thanks again
September 26th, 2007 at 6:53 am
how would you invest $40,000.00 for a large return?
September 26th, 2007 at 6:57 am
I often say that a mistake is a “philosopher’s” greatest tool for growth…
In response to your insightful blog post, I’ll also say that a good “fee-only” advisor would likely have prevented every one of those “mistakes.”
Finally, emotions can wreck a portfolio…
“A wise man should have money in his head, but not in his heart.” –Jonathan Swift
Thanks for the article…
September 26th, 2007 at 7:41 am
Thanks for sharing those, Pinyo. I’m still young, so hopefully if I learn these the less-hard way, my investment future will be brighter. Great post.
September 26th, 2007 at 8:01 am
@SJean - Thank you. When a mutual fund sell underlying stocks, it generates capital gain tax on these sales. The cumulative capital gain tax is distributed to each fund shareholder once per year.
@Kim - I would start by learning about mutual funds and Exchange-Traded Funds. Many people start out with Vanguard Index Funds.
@The Financial Philosopher - I agree that a good fee-only advisor would have helped. However, I prefer to learn on my own. That said, I would not hessitate to utilize one if I have to work through more complicated financial situations.
@Micah - by visiting and reading GRS everyday, you are already doing better than most people your age.
September 26th, 2007 at 8:11 am
Great post! I am still young (23) and I feel very fortunate to have had this knowledge passed on to me early in life. Thanks Pinyo for the great info, and JD for this blog, and the whole rest of this community for all of the support and knowledge you guys share. If possible, I’d love to see a series on investing that delves into these topics more deeply. Right now, I’m trying to figure out the whole diversification/asset allocation and whether to go with Mutual Funds, ETFs, Individual stocks etc.
September 26th, 2007 at 8:16 am
Sounds like Coffeehouse Portfolios advocated by Bill Schultheis http://coffeehouseinvestor.com/. Ben Stein recommends him too.
- 33.3% in Vanguard Total Stock Market (VTI)
- 33.3% in iShares International MSCI EAFE Value Index (EFV)
- 33.3% in iShares Lehman Aggregate Bond (AGG)
September 26th, 2007 at 8:18 am
Pinyo,
Great post. While I tend to ignore point 8 in favor of a focus on real estate investments, most of these are spot on in any investment approach.
The only thing I might add is to repeat your point No. 1 about 10 more times. I, like you, lament not starting earlier. Here’s to your looking back from 2017 with nothing to lament!
Mike
September 26th, 2007 at 8:56 am
These are all great tips for any newcomer or anyone who has been trading for years. I would also like to add to no underestimate the power of compounding gains when investing. Kudos on the good blog you have here!
September 26th, 2007 at 10:28 am
I hear ya on not starting sooner!
Other than that, this post made me feel a lot better about my own investment strategies.
September 26th, 2007 at 10:31 am
“The only thing I might add is to repeat your point No. 1 about 10 more times. I, like you, lament not starting earlier. Here’s to your looking back from 2017 with nothing to lament!”
That’s crying over spilt milk, though. As the saying goes, investing is like planting a tree, the best time to start is 20 years ago, the second best time is right now.
Your past self probably wouldn’t listen to your current self, even if you could go back in time and impart the wisdom of the ages. Most people probably were told this stuff when they were young, I know I was. But we weren’t ready to listen.
Saving for retirement is one of those things that kids don’t care about and adults do. Until you go through the transition to adulthood, no amount of good advice is going to make a difference.
September 26th, 2007 at 10:51 am
Yes, not letting your winners ride is a big one.
September 26th, 2007 at 11:42 am
Great Post! These are excellent tips and will go a long way.
September 26th, 2007 at 12:43 pm
[...] 12 Investing Mistakes I’ve Made (and How You Can Learn From Them) 1. Not investing soon enough 2. Not knowing the basics 3. Chasing past performance 4. Experimenting with my IRA 5. Not paying attention to expense ratios 6. Not paying attention to distributions 7. Not paying attention to asset allocation 8. Ignoring diversification 9. Selling winners and keeping losers 10. Cost averaging down 11. Investing without a goal 12. Selling on corrections & buying at the top of the market 0 comments [...]
September 26th, 2007 at 12:53 pm
Aleks, you remind me of another quote: “Forgiveness means giving up all hope of a better past.” -Landrum Bolling
It’s hard to give up the woulda, coulda, shouldas. But doing so gives you more energy for what you’re doing right now.
September 26th, 2007 at 1:42 pm
@James - Thank you. Only 23, you’ll probably be doing even better than me then!
As for asset allocation, it’s a very personal subject. Right now, I put 20% in large, 20% in mid-cap, 20% in small-cap, 30% in international, 5% in REIT, and 5% in company stock. Some people will think this is a decent allocation for a 33 yrs old; some will think it’s bad portfolio because I am not carrying any bonds.
There’s a lot on the Web about this topic, so I encourage you to look around. The allocation shared by Todd is an option — you just have to find what’s right for you.
@Mike - Thank you. Real estate is one area I wish I can get into, but that’s a whole new level for me. I will have to learn a lot more before I can jump in with confidence. Amen, to number one — time is something none of us can ever get back.
@Bunk - Thank you. Good point about compounding gains. I discussed this on my blog, compounding gains make a drastic difference in performance.
@Maitresse - Glad to make you feel better
@Aleks - Intereting. I can make a whole post around that. I bet my younger self won’t listen either.
@David, AskProfit, and JenK - Thank you for your comments.
September 26th, 2007 at 2:03 pm
[...] 09/26 - Please visit Get Rich Slowly for my article 12 Investing Mistakes I’ve Made (and How You Can Learn From Them). [...]
September 26th, 2007 at 6:04 pm
These are great points and very helpful for anyone out there trying to invest their money. It can be very intimidating to the average person. I think the major point is having a clear goal to work towards. Thanks!
September 26th, 2007 at 6:53 pm
I think “not starting early enough” is one of the biggest factors. People are automatically handicapped if you don’t have a family member or high school teacher who clues you into the power of compounding interest at an early age.
September 26th, 2007 at 9:17 pm
Pinyo, I hear you about wishing you had begun investing earlier. Better late then never though, eh?
September 26th, 2007 at 11:40 pm
Very Nice insights drawn from mistakes on investing. I am also young and just starting to look for opportunities to invest. Getrichslowly is something that many youngsters wont understand, we usually want to getrichnow
However, tomorrow I will be a day older and understand why I cant just get rich now.
September 27th, 2007 at 12:37 am
I wish I read this post 3 years ago.
September 27th, 2007 at 4:01 am
[...] Read about what 12 investment mistakes JD has made and what you can learn from them. [...]
September 27th, 2007 at 5:59 am
@InvestEveryMonth - Great point. I was handicapped as well. On my blog, I have a post where I advocate teaching money management in high school. I think it’s absolutely critical since we can’t count on ALL parents to pass on good financial advice.
@Mariette - yes, the fact that I got started was a good thing. Even if I made my fair share of mistakes.
September 27th, 2007 at 6:30 am
[...] 12 Investing Mistakes I’ve Made (And How You Can Learn From Them) Some excellent thoughts on mistakes made - and how they can be used to choose a better path later on. (@ get rich slowly) [...]
September 27th, 2007 at 8:09 am
Just invest in ASTI and you’ll be fine!
September 27th, 2007 at 10:19 am
This is just a bunch of platitudes and not a method.
September 27th, 2007 at 11:58 am
Why should we listen to you now? Show me the money!. Your blog seems absolutely crammed with various advice about how we should do this and that about investing, but I don’t see you sharing your portfolio or investing decisions with us. What is your actual rate of return?
Mine’s been an annualized 40+ percent since the beginning of 2005. Every single one of those investments has been recorded online as I made it.
September 27th, 2007 at 12:23 pm
@Irfan - thank you. Get rich slowly is the best way to do it. There is no such thing as get rich quick for common folks — very few individuals manage this feat.
@Mick - from your perspective, it might be obvious to you and some people, but this is not true for everyone. If you are looking for a method, it will take more than a blog post to accomplish this and you are probably looking at the wrong place.
@Mark - I am not sure if you addressed me or J.D. I can’t speak for J.D., but my blog is not about picking amazing stocks. I am an ordinary person and I only share what I believe to be practical financial decisions or guidelines that I live by.
I don’t own any fancy stocks, but I did manage to beat the S&P500 for the past 7 years. It does not compare to your 40+ return, but good nonetheless.
September 27th, 2007 at 1:03 pm
Great! Thanks the kind of info I was looking for. It would be nice to see your buy decisions from beforehand, though. That way we could see how you evaluated your investments (and maybe even pick out some of the same ones next time you buy).
September 27th, 2007 at 1:28 pm
“I don’t own any fancy stocks, but I did manage to beat the S&P500 for the past 7 years. ”
Now adjust your % return against the commodities price index, printed weekly in The Economist.
The CPI for the dollar went from 100 in the year 2000 to 205 in September 2007.
That would mean your investments would have to at least doubled for the purchasing power to be equal. That is doubtful.
The Fed itself said that a moving average of CPI is a better indicator of inflation.
http://www.newyorkfed.org/research/staff_reports/sr236.html
The problem with investing right now is its a distraction to the real problem, the debasing of the dollar.
Since all of your investments are likely indexed in dollar, pay dividends in dollars, and everything being tied to the dollar, the DOW would need to be 26,000 today per the CPI to equal what it was in 2000.
Many people can attet they they arent where they were in 2000 even to this day.
September 27th, 2007 at 1:47 pm
Great story. I’d like to recommend to anyone out there looking for wise ways to invest first read “The Intelligent Investor” (1949 or any of the replubishing dates) by Benjamin Graham - take the slow approach to investing, read, learn, and take your first footstep in the market with a plan containing real knowledge.
It’s well worth it.
September 27th, 2007 at 2:01 pm
@Mick - you are obviously a lot more knowledgeable than I am because I don’t know anything about economy. I can only measure my performance against what I know, and if I can beat S&P500, I am happy. However, I will try to read up on the information you posted and see if I can learn it.
Secondly, I am aware that USD is going down the toilet in term of value. I have relatives that live in other countries and I travel internationally, so I am painfully aware of this.
September 27th, 2007 at 2:11 pm
You’re childish. No, you are. No. You….
I was looking at some of the reaction to that “bed-wetter” article we saw in yesterday’s Clicked and saw an unexpected theme: defining maturity. I’m thinking the cultural context for the question is that we typically think of diplomacy and negotiat…
September 27th, 2007 at 2:27 pm
@eric: I second your recommendation of Graham’s The Intelligent Investor. Along with Peter Lynch’s One up on Wall Street, it’s my all-time favorite.
September 27th, 2007 at 3:12 pm
@Pinyo
I understand. People need to investigate the purchasing power of dollars when they get paid in dollars and accept risk to get more dollars. The M3 is no longer tracked by the Fed, but it is a vital indication of much the money supply is expanding. Expanding money supply means inflation. The M3 is now being tracked by others as the M3b, here:
http://www.nowandfutures.com/key_stats.html
Please also keep the CPI in mind, The Economist has that here:
http://www.economist.com/markets/indicators/
And this weeks CPI:
http://www.economist.com/images/20070929/TAB3.gif
Oh man I just looked. Its 216 this week. This is really bad news.
All investors really, really need to be reading The Ecomonomist before jumping in.
September 27th, 2007 at 7:32 pm
um, #9 Selling winners and keeping losers. When did you actually determine they were winners or loosers - after you sold? You have no way to predict if either will continue to go up or down
September 27th, 2007 at 8:31 pm
No one under 50ish should have any bonds. the return is too low, and can be more or less matched with a money market with none of the holding time penalties.
And if you live in the US, there’s no need to index your gains against the falling dollar, because even if the dollar falls, Purchasing Power Parity remains. Diversifying into foreign stocks is a good idea, and would be even if the dollar were rising.
September 27th, 2007 at 8:34 pm
and the ’selling winners and holding loosers’ sounds dangerously like attempting to time the market. you should have sell points and buy points, and sell or buy when they are met.
They can be variable and time based, say up 30% in a year, or down 10% in a month, but you shouldn’t try to guess when a gain is gonna turn on you, or you will probably get burned and angry more often than you win.
September 27th, 2007 at 8:48 pm
@beanspants
“Purchasing Power Parity remains”
Wrong. Check out the price of gas since 2003. Houses since 2003 (then normalize against gold). Check out the prices of food since 2003.
Your PPP bull only works with Core inflation (the walmart chinese plastic index).
But for everyday Items, look to the big mac index and the commodities price index, the price of gas and foods, and oh wait, your Purchasing Power Parity turns out to be a simple lie. Its a lie. you cant tell me its not a lie because prices are rising.
QED, proved PPP with “core” inflation numbers is a lie.
September 27th, 2007 at 10:25 pm
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September 28th, 2007 at 3:20 am
Star Money Articles for the Week of September 24…
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September 28th, 2007 at 7:44 am
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September 29th, 2007 at 2:28 pm
oh please. so the price of a few things are up since 2003 (what an odd date to pick, and currently, housing seems to be diving, so does that mean we are in a period of deflation?), so therefore, inflation is higher than what the gov’t posts. Is that correct? people, please don’t listen to this craziness.
The simple story is that inflation (yes, the gov’t calculation) is the basis for the risk free rate, or the short rate. You know, that 5ish percent value right now that Bernake just cut. Large investors and corporations need their return right around the risk free rate, because they can’t invest in speculative investments. So they are ok with the inflation rate being 2.5-3%, and the risk free rate slightly above that. But whoa, weren’t they aware that the government is lying on the inflation rate, so their investments are returning less than inflation?
Wow, it’s weird that only the few people who read the Economist know this, and don’t accept 5% as the risk free rate. Everyone else must be asleep like in the Matrix. Sure. That makes sense. Let me guess. You also feel we need to tie our currency to the price of gold again too. Of course.
September 29th, 2007 at 2:43 pm
beanspants1 just declared a “few items” went up.
Energy went up
food went up
gold
oil
metals
all other currencies
What items can you buy that are not made from these commodities?
None.
Housing is diving because of the fact that not even the Fed lowering rates and discount window is enough liquidity for now nervous underwriters to provide loans for idiotically overpriced houses. You are trying to use housing and say there is an overall deflationary trend? Idiotic.
You second paragraph is bunkum. The fed itself says so here:
http://www.newyorkfed.org/research/staff_reports/sr236.html
I never said to tie the currency to gold. The usual attack vector for corrupted minions like you that can understand aggregate money supply issues.
If we aren’t inflating horribly, why stop printing M3 stats?
http://www.federalreserve.gov/releases/h6/discm3.htm
Why since then has the M3 gone from 9 trillion to 12.25 trillion?
http://www.nowandfutures.com/key_stats.html
beanspants1, you really are a know-nothing, or a shill for some brokerage who wants to continue to make money off the broken backs of taxpayers while the Fed continues to inject liquidity costing us all.
September 30th, 2007 at 6:01 am
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October 4th, 2007 at 2:38 pm
I have really loved learning from your mistakes. As an investor, I am always willing to learn from other people who have experienced the market.
October 8th, 2007 at 7:00 am
[...] good financial goals, I was prone to make mistakes as I have written in my guest post “12 Investing Mistakes I’ve Made (and How You Can Learn From Them)” at Get Rich [...]
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June 11th, 2008 at 5:29 pm
Gas, nationwide $4.00 and rising.
Like I said before, the costs of living will rise far quicker than your ability out make money on investments …
I only wish that I had been wrong … Time will continue to prove me correct until either sane policy or a collapse occurs.
See:
George Soros: ‘We face the most serious recession of our lifetime’
http://tinyurl.com/6yfuqm
See:
It’s going to be much worse - Famed investor Jim Rogers sees hard times ahead for the United States
http://tinyurl.com/27×93m
“Jim Rogers says the Fed, and Fed Chairman Ben Bernanke, are out of control.”
July 15th, 2008 at 5:02 am
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January 18th, 2009 at 1:44 am
uABoms hi! how you doin?