How did you invest it ? (Stocks, saving accounts, startup, house...)
What went wrong ? What would you do instead today ?
What were your best decisions ?
Given that the timing for this investment was the last four years, I have of course been clobbered.
Had I been less aggressive at both of those plans, I would have mid five-figures extra to put into my business. I would not mind having the extra cushion, and it would ease cash flow issues this summer, but I don't think the presence of it would make a major difference in my life.
I do not have any regrets. Part of the discipline of investing in index funds is that we don't know when we're going to get clobbered, so we invest regularly and over long periods of time will get very close to the market's average return.
(I also don't regret paying my student loans early: I have a burning, passionate hatred of indebtedness. Even a comparatively small amount of money at a subsidized interest rate makes me feel like I'm owned.)
Had I rolled it directly into an IRA, my retirement savings would be about 2x what they are now, and working for companies too cheap to offer 401k plans to employees for almost all of my 30s means that I have to put the max into 401k and IRA (for the rest of my working life) in order to avoid living under a bridge when I get too old to work.