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Pain & Struggles Of Investing
Old 09-16-2019, 09:46 AM   #1
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Pain & Struggles Of Investing

Hey Everyone!

Thought It might be interesting to hear stories of how you got started investing for yourself and maybe share what problems you've encountered or struggles your currently dealing with when it comes to investing your own money.
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Old 09-16-2019, 09:59 AM   #2
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Hmmm, I find investing entertaining, problem-free, and easy.

I started back in the mid-1970s when I invested my high school job money for future college expenses. Now that I look back on it, I didn't have to tell the out-of-state bank my age, income, or anything about myself. They were happy to pay me a higher interest rate than local places whenever I mailed them a check. I didn't have to get permission or signatures from my parents at all.
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Old 09-16-2019, 10:01 AM   #3
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My first struggle, didn't know the value of a dollar until I was about 22...then didn't think I had the skills to get a good career until I met a good women...finally landed job with 401k but struggled to increase contributions beyond companies match.

FF we are now close to maxing both me and DW 401k 10 years later.

Now it's a new question, how will I struggle to afford college while still ER. while having the assets all in the right buckets. Tough to do 529, Roth, Broker after maxing 401k but we are doing best we can (and likely better than many of our peers but plenty doing as well).

The struggle is real.
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AA (Stock/Bond/Cash ): 97.5/0/2.5% MIX (Small/Mid/Large): 25/25/50% BLEND(US/Foreign): 100/0%, REIT (Real Estate Equity): ~50% of Assets

FIRE in 2031 @ 50yrs old (+/- 2yrs) w/ a hypothetical $2.5mil portfolio, 3 appreciated homes worth $1.0mil and rental income to fund my gap years until RMD. Assets will go to an inherited IRA where I plan on watching the investments grow until I die or the trust gets executed.
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Old 09-16-2019, 10:03 AM   #4
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Another struggle I had was I never knew "what" I was investing in. Once I discovered how to understand what I own, in terms of ETF, Index funds, etc... the fear of "changing anything" the struggling to know WHERE to invest went away. See clear as day now.
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AA (Stock/Bond/Cash ): 97.5/0/2.5% MIX (Small/Mid/Large): 25/25/50% BLEND(US/Foreign): 100/0%, REIT (Real Estate Equity): ~50% of Assets

FIRE in 2031 @ 50yrs old (+/- 2yrs) w/ a hypothetical $2.5mil portfolio, 3 appreciated homes worth $1.0mil and rental income to fund my gap years until RMD. Assets will go to an inherited IRA where I plan on watching the investments grow until I die or the trust gets executed.
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Old 09-16-2019, 10:15 AM   #5
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Well, I started about 45 years ago with a scheme to use Fourier analysis to beat the market. For about 30 years from that point I spent time making all the classic mistakes. Day trading stocks, buying on margin, chasing hot fund managers, believing the stock-picking myth, etc. A number of private placements, most of which worked out pretty well, though I flushed $50K on a restaurant deal that soured pretty quickly. 20 years as a landlord holding duplexes, fours, and small apartment buildings. That went pretty well because I was lucky enough to have a good caretaker/handyman working for me. Did a few options back when DW was a retail broker and could watch the action in real time. (Remember Quotrons?) In general, I made money at all of this.

I finally found and studied the evidence for passive investing and realized I probably could have made more by investing that way. As a result we now have no struggles. We happily accept what the equity market gives us, which over a long term beats 90+% of stock pickers.

We really didn't do bonds until the last ten years or so. I have a very simplistic view of that market: term, yield, risk -- pick any two and the market will tell you what the the third is. We buy long TIPs and take the yield they give us. Again, no struggles at all.

Investing life is good. Watching the market is like watching fish in an aquarium. Detachment.
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Old 09-16-2019, 10:32 AM   #6
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Quote:
Originally Posted by kylewright View Post
Hey Everyone!

Thought It might be interesting to hear stories of how you got started investing for yourself and maybe share what problems you've encountered or struggles your currently dealing with when it comes to investing your own money.
Welcome to the forum, Kylewright. Seeing how you’re interested in stories, why not stop by and share yours here Hi, I am... - Early Retirement & Financial Independence Community
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Old 09-16-2019, 11:38 AM   #7
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I started investing in 1982 when I was starting working.

What I did right: dollar cost average into stock index mutual funds, read alot, paid myself first.

What I did wrong: Didn't have a clue what I was doing and was definitely was the victim of whatever pundits I read or heard. Tried to "time the market" including (yikes!) going in strong Friday, October 16, 1987 after the market dropped big that day. Learned my lesson.

I basically had five opportunities to start to build wealth (1982, 1988, 1995, 2002, 2009). Took advantage of all of them but the first four were two steps forward one step back. Really only got the last one right, but that was the big one that got me over the top.
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Old 09-16-2019, 11:41 AM   #8
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Once the internet boomed and opened my eyes to how much $$ Edward Jones was gigging me for. I'm just glad I learned that lesson early in life.
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Old 09-16-2019, 11:48 AM   #9
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90% real estate, since mid-80's. A couple of flips, a couple of rentals but mostly buy a house, upgrade while living there (from cash flow), sell and put zero taxed capital gains into the next property, or into the bank. Rinse, repeat. Housing downturn? Great buying opportunities. Stock market crash? Ho-hum. Learn your local market (take a Realtor to lunch) and live rent free while building your net worth.

Have given my kids the same advice. It still works, even today. (Even better today with crazy cheap interest mortgages!)

Obviously, if you have access to 401-k, you would be stupid not to invest the match minimum.-but then put the rest into your next home.
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Old 09-16-2019, 11:52 AM   #10
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My first job had an employee stock purchase plan. I put the maximum into it (10%) because they offered a minimum of 15% off the market price so I viewed it as an easy way to get an extra 2% salary for nothing.

Eventually I had amassed a large position and followed advice to diversify out of the company stock. I found an ethical stock broker who studied companies and invested his own money when he recommended them. I made a number of big wins and a few losers by following his advice.

I also opened a discount brokerage account because he charged $30/trade. He tended to be buy and hold and many times I unloaded against his advice. So I would split the proceeds 50/50 putting half the gains into my trading account.

When he retired young and rich, I moved the balance to my trading account.

Not any master plan but it did work out OK.
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Old 09-16-2019, 11:54 AM   #11
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Once I got a real job, I saved in a bank account and read Money magazine to "learn to invest". Every month it was a new list of "hot stocks you should buy now!". The next month it was a different list. I dithered and finally started investing in mutual funds because they were diversified. I later got onto Vanguard and low cost index funds and the rest is history.


Save yourself a lot of grief and read up on asset allocation and three fund portfolios at Bogleheads. Re-balance once a year or so then forget about it between re-balancings..
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Old 09-16-2019, 12:14 PM   #12
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Compulsive saver since childhood, a brief foray into options around 1980 (fresh out of college) soured me on market timing and technical analysis forever, muni bonds for a few years (9.5% tax free for 25 years), maxed 401k index funds as soon as I could (1983), then all individual stocks since 1993, using Value Line as a starting point.

Never struggled / had problems. I find investing to be an exercise in math, no emotions involved. The rewards are so high compared to the costs I cannot imagine taking another path.
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Old 09-16-2019, 12:25 PM   #13
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Started in 1994 after high school graduation with a DRIP account buying Janus Fund and Templeton Foreign Fund. Had a decent stash and 1998 comes around and I believe I can get rich overnight. Bought some WCTI, watched it go up a bit, then went all in, only to see it blowup.
Learned a valuable lesson at an early age, and luckily with a smallish amount (not then though!). Got a bit more conservative, invest in BRK/B and ETF's with a small dabble in AMZN and GOOGL to scratch that itch. Compounding and growing quite well now.
With age my focus has changed from picking the right investments, to planning and making sure I have the right accounts. For example, Taxable and Tax Deferred, how much needs to go where, etc. More tax planning and management now than anything else now that I just turned 45.
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Old 09-16-2019, 01:05 PM   #14
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Hurry up and Wait

When I finally got paid enough to have money leftover to save, I got sold a mutual fund with a hefty load, and whole life insurance (before I was 30, with no family yet). Thankfully some other guy started a class action lawsuit against the advisor, and that lawsuit notice was my wake up call. I started seriously educating myself during the "Waiting" in Iraq in 2006-7.

So if my comments are jaded against advisors, that's the big reason why. The other reason is that their compensation model is all wrong to me (commission and % of AUM). When I need one, I'll go find a fee only RIA with an independent practice.
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Old 09-16-2019, 01:33 PM   #15
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My first employer out of college shared a floor with a Dean Witter office. I had a "guy" who gave me some leads on individual stocks.... some winners and some losers but certainly didn't beat the index. I got into index investing in the early 1980s and pretty much was 100% equity index funds until I was in my mid 40s. I was a consistent saver/investor and was too busy to watch it too much so investing came easy to me.

Also, see my last tag line.

The biggest investing mistake was investing in my 401k in the Evergreen Core Bond Fund thinking that it was a core bond fund similar to Total Bond... when the SHTF during the financial crisis it tanked a lot more than Total Bond.... come to find out the managers had made some significant bets on mortgage backed securities and lost.
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Old 09-16-2019, 02:14 PM   #16
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I started investing around 1984, age 23. But all savings were consumed when I went back to grad school at 26. Started over at 29. Eventually I retired at 52 in 2013. I made plenty of mistakes along the way, the two main ones being: market timing and holding too much Megacorp stock.

The timing strategy yielded mixed results... usually quite good when I was paying attention. But the career and parenting became all-consuming and I would regularly miss buy/sell signals. I went to a buy-and-hold strategy around 2005 following one such missed signal. One exception was when I moved from 100/0 to ~50/50 (cash) in mid 2008. Then back to 100/0 mid 2009. That worked out very well. I had subscribed to a newsletter starting about 2006 that talked nonstop about the real estate bubble. I finally took their advice and sold when foreclosures were on the nightly news every day.

Megacorp offered ESPP and I also got option grants and RSUs. I often held on to ESPP shares and even invested in Megacorp stock in my 401K. Megacorp took a beating in the dot-com disaster. And so did I. I later sold lots of ESPP shares for significantly less than the payroll deduction. Options that had been in the money early on, expired after 10 years. After that, I sold ESPP shares immediately and exercised/sold options and RSUs every year, although there was still some market timing involved with that. The proceeds went into low-cost equity index funds.

On the positive side, DW and I saved consistently, always maxing out both 401Ks. Later in our 40s when income was rising fast, we plowed the extra money into our taxable brokerage account. By the time we retired at 52, the taxable account was almost as big as tax-deferred. That worked out well for ER.
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WR: 2.7% SI: 2 pensions, some rental income, SS later
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Old 09-16-2019, 03:07 PM   #17
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Was blessed to have made decent money in late 80's living in a very small depressed town where investing was NEVER spoke of or engaged in. Working towards retirement meant working 100 hrs a week and sticking it in the bank. Moved out west @26yo which is where I first learned of investing. Still took until I was 30 before we got involved investing. Then proceeded to lose half of our 401k TWICE never fully recovering it all. Went back to working 100 hrs a week and retired @ 45 with a broke down, wore out body full of pain!
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Old 09-16-2019, 03:36 PM   #18
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In order to graduate from high school, we had to write a research paper on any subject. At that time, purchasing gold bullion just became legal again. So, my paper was about investing in gold bullion, or gold mining stocks. Gold stocks won out, and Engelhardt Mining and Manufacturing was the stock I picked out, and it was trading at $16 at the time. I was expecting my very first income tax refund check of $320. I was so excited when I cashed it and went downtown to open my brokerage account. That's when I found out that the price fell that day to ~$12. I was mortified and left without depositing any money. It never looked back after that; it rose to triple digits and split and did it a couple more times. One that got away....
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Old 09-16-2019, 04:37 PM   #19
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Maybe I'm being too cynical, but the OP reads like someone fishing for answers for an article or a homework assignment, rather than genuinely being interested in the experiences of people here. There was no personal info provided, or specific questions asked. A quick Google search shows that OP did a copy/paste of the post at another forum (that appears not that active) about 15 minutes later. I could be wrong and, if so, I apologize.

There's nothing wrong with wanting info for an article or homework, as long as the purpose is revealed.
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Old 09-16-2019, 05:00 PM   #20
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Or could be fishing for clients... market research, who knows
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