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I'm really struggling psychologically with investing concerns and need to get some perspective. The problems are the Past and the Future, and both effective our financial sense of well-being.

The Past

Other than some employer-contributed investments, my wife and didn't invest so far in our life other than CDs and other guaranteed small returns (though at one point CDs were at 5%). But during this time we sat on a large amount of cash, hundreds of thousands of dollars, almost all of which was earned through working, year by year, and scrimping. Lots of self denial, bargain shopping, etc.

But during those years, obviously, we missed out on an incredible bull market. For various odd/complex psychological reasons, I didn't "wake up" to that fact until fairly recently, and the realization has made me sick. We're middle aged, and based on our current cash savings, some future inheritance, and what we would have made in the market we could have:

  • retired by now.
  • not scrimped so much all those years (including living in some questionable homes!).

Further, My wife is now entertaining taking a job that she truly doesn't want to do because it pays so well. Again, had we invested, she very likely would not have to ever consider taking any job, let alone one that she is doing mostly under protest. Likewise, I am going to have to look for work I don't really want to do, either. She also is an international person and so we also could have had two (small, humble) homes, one in each of our countries, by now, had we invested.

Up until fairly recently, I thought we had done quite well, having saved up so much. But now I realize we have been complete abject idiots! She's taking it in stride, but I get these waves of regret and sort of anxiety over it.

Any perspective that can help?

The Future

Of course, now it seems I want to stop the bleeding and get into the market. I opened an IRA and put a small amount in it from last year's earnings, just about $9k...but as I started considering the market I talked to a friend who pulled out of the market around the last election, thinking the market would go down because of Shiller's high CAPE warning, Trump's policies, etc. He is well aware that he lost out on double digit % returns since even then. I wasn't even "awake" yet until well after that but have still misssed out on good returns, but now I am fearful:

I am fearful that, having waited out this amazing bull market, I'm going to dump our life savings into an index fund...only to have the market "correct" or pull a 2008 or 2001 or whatever.

I feel that would feel far worse than a person who had made tons of returns during this runup and then it got pulled back--because at least he would have made some money to lose. I'd be losing all earned income that was saved through scrimping.

And yet I'm also aware of "time in market beats timing the market", that doom and gloom predictions are commonly wrong, maybe the Shiller CAPE isn't as applicable this time, etc., etc. And so I'd hate to stay out even more and just continue to miss out.

We also may--not sure--by a home or two (small, each) in our countries in the next 1-5 years, and so wouldn't want to have to be waiting for a recovery to access our cash. But again, I'm not sure. Otherwise, we have no particular spending needs: my parents are dead, hers are alive in a socialized medicine country, we have and will have no children, and we're frugal.

So: Any advice for a person in my boat?

[And I know I shouldn't complain, in that we do have cash savings, whereas many people have $0 or are in debt. But we got it the hard way]

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    You need specific goals, because how you move forward will depend on how many years you plan to be working and what your retirement spending will look like. With specific goals you can develop a plan and explore different scenarios based on different levels of risk. Maybe at this point it's best to buy your real-estate and CD's until you start drawing from your retirement accounts, maybe it's worth going all-in on the market, who knows. It depends on too many things to answer adequately here. – Hart CO May 8 '17 at 5:33
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You're being too hard on yourself. You've managed to save quite a bit, which is more than most people ever do. You're in a wonderful position, actually -- you have savings and time! You don't mention how long you want/need to continue working, but I'll assume 20 years or so?

You don't have to invest it all at once. Like Pete B says, index funds (just read what Mr. Buffett said in recent news: he'd tell his widow to invest in the S&P 500 Index and not Berkshire Hathaway!) should be a decent percentage. You can also pick a target fund from any of the major investment firms (fees are higher than an Index, but it will take care of any asset allocation decisions). Put some in each.

Also look at retirement accounts to take advantage of tax-deferred or tax-free growth, but that's another question and country-specific.

In any case, don't even blink when the market goes down. And it will go down. If you're still working, earning, and saving, it'll just be another opportunity to buy more at lower prices.

As for the house, no reason you can't invest and save for a house. Invest some for the long term and set aside the rest for the house in 1-5 years. If you don't think you'll ever really buy the house, though, invest the majority of it for the long-term: I have a feeling from the tone of your question that you tend to put off the big financial decisions. So if you won't really buy the house, just admit it to yourself now!

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I would read any and all of the John Bogle books. Essentially: We know the market will rise and fall. We just don't know when specifically. For the most part it is impossible to time the market.

He would advocate an asset allocation approach to investing. So much to bonds, tbills, S&P500 index, NASDAQ index. In your case you could start out with 10% of your portfolio each in S&P500 and NASDAQ. Had you done that, you would have achieved growth of 17% and 27% respectively. The growth on either one of those funds would have probably dwarfed the growth on the entire rest of your portfolio. BTW 2013 and 2014 were also very good years, with 2015 being mostly flat.

In the past you have avoided risk in the market to achieve the detrimental effects of inflation and stagnant money. Don't make the same mistakes going forward.

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As an investor you must remember to forgive yourself. However, you must not only forgive but make it up to yourself by putting in the hours of study necessary to ensure that what you are forgiving yourself for will not happen again.

Studying (finance, fundamental analysis, statistics, etc.)will also help you to worry less. Once you have put in the hours of study necessary, you can turn to any of a number of still relatively conservative strategies, such as seeking out undervalued blue-chip stocks to purchase or selling covered call options. Good luck.

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