2017 just hasn't gotten any easier, has it? After ten months of natural disasters, internet hacks, political tumult, and celebrity scandal, I know I'm not the only one looking forward to the start of the holiday season for some much-needed light at the end of the tunnel.

Hard as it's been sometimes this year, my team at Keen Wealth always keeps its eyes on the big picture when we're managing our clients' money. And just last month, many of us in the financial industry were looking back at an infamous anniversary: October 19, 1987, aka "Black Monday" – the biggest one-day percentage drop in the history of the Dow Jones Industrial Average.

Thirty years later, there's a lot that Black Monday can teach us about market volatility, and long-term retirement planning. So, on today's show, we open up the listener mailbag and apply the lessons of Black Monday to some important retirement questions.