Based on your financial expertise, provide your response or viewpoint on the given financial question or topic. The response format is open.

Need help with the psychology of investing: past failures and future fears
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.